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FUNDAMENTALS OF
GENERAL ORGANIC
AND BIOLOGICAL
CHEMISTRY
Textmap McMurry et al.

Map: Fundamentals of General Organic and
Biological Chemistry (McMurry et al.)
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TABLE OF CONTENTS
Licensing
1: Matter and Measurements

1.1: Chemistry - The Central Science
1.2: States of Matter
1.3: Classification of Matter
1.4: Chemical Elements and Symbols
1.5: Chemical Reactions - Examples of Chemical Change
1.6: Physical Quantities - Units and Scientific Notation
1.7: Measuring Mass, Length, and Volume
1.8: Measurement and Significant Figures
1.9: Rounding Off Numbers
1.10: Problem Solving - Unit Conversions and Estimating Answers
1.11: Temperature, Heat, and Energy
1.12: Density and Specific Gravity
2: Atoms and the Periodic Table

2.1: Atomic Theory and the Structure of Atoms
2.2: Elements and Atomic Number
2.3: Isotopes and Atomic Weight
2.4: The Periodic Table
2.5: Some Characteristics of Different Groups
2.6: Electronic Structure of Atoms
2.7: Electron Configurations
2.8: Electron Configurations and the Periodic Table
2.9: Electron-Dot Symbols
3: Ionic Compounds
3.1: Ions
3.2: Ions and the Octet Rule
3.3: Ions of Some Common Elements
3.4: Periodic Properties and Ion Formation
3.5: Naming Monoatomic Ions
3.6: Polyatomic Ions
3.7: Ionic Bonds
3.8: Formulas of Ionic Compounds
3.9: Naming Ionic Compounds
3.10: Some Properties of Ionic Compounds
3.11: H⁺ and OH⁻ Ions - An Introduction to Acids and Bases
4: Molecular Compounds
4.1: Covalent Bonds
4.2: Covalent Bonds and the Periodic Table
4.3: Multiple Covalent Bonds
4.4: Coordinate Covalent Bonds
4.5: Characteristics of Molecular Compounds
1 https://chem.libretexts.org/@go/page/271986
4.6: Molecular Formulas and Lewis Structures
4.7: Drawing Lewis Structures
4.8: The Shapes of Molecules
4.9: Polar Covalent Bonds and Electronegativity
4.10: Polar Molecules
4.11: Naming Binary Molecular Compounds
5: Classification and Balancing of Chemical Reactions

5.1: Chemical Equations
5.2: Balancing Chemical Equations
5.3: Precipitation Reactions and Solubility Guidelines
5.4: Acids, Bases, and Neutralization Reactions
5.5: Redox Reactions
5.6: Recognizing Redox Reactions
5.7: Net Ionic Equations
6: Chemical Reactions - Mole and Mass Relationships

6.1: The Mole and Avogadro’s Number
6.2: Gram-Mole Conversions
6.3: Mole Relationships and Chemical Equations
6.4: Mass Relationships and Chemical Equations
6.5: Limiting Reagent and Percent Yield
7: Chemical Reactions - Energy, Rates, and Equilibrium

7.1: Energy and Chemical Bonds
7.2: Heat Changes during Chemical Reactions
7.3: Exothermic and Endothermic Reactions
7.4: Why Do Chemical Reactions Occur? Free Energy
7.5: How Do Chemical Reactions Occur? Reaction Rates
7.6: Effects of Temperature, Concentration, and Catalysts on Reaction Rates
7.7: Reversible Reactions and Chemical Equilibrium
7.8: Equilibrium Equations and Equilibrium Constants
7.9: Le Chatelier’s Principle- The Effect of Changing Conditions on Equilibria
8: Gases, Liquids, and Solids

8.1: States of Matter and Their Changes
8.2: Intermolecular Forces
8.3: Gases and the Kinetic-Molecular Theory
8.4: Pressure
8.5: Boyle’s Law - The Relation between Volume and Pressure
8.6: Charles’s Law- The Relation between Volume and Temperature
8.7: Gay-Lussac's Law- The Relationship Between Pressure and Temperature
8.8: The Combined Gas Law
8.9: Avogadro’s Law - The Relation between Volume and Molar Amount
8.10: The Ideal Gas Law
8.11: Partial Pressure and Dalton's Law
8.12: Liquids
8.13: Solids
8.14: Changes of State Calculations
9: Solutions
9.1: Mixtures and Solutions
9.2: The Solution Process
9.3: Solubility
9.4: The Effect of Temperature on Solubility
9.5: The Effect of Pressure on Solubility - Henry’s Law
9.6: Units of Concentration
9.7: Dilution
9.8: Ions in Solution - Electrolytes
9.9: Properties of Solutions
9.10: Osmosis and Osmotic Pressure
9.11: Dialysis
10: Acids and Bases

10.1: Acids and Bases Definitions
10.2: Acid and Base Strength
10.3: Acid Dissociation Constants
10.4: Water as Both an Acid and a Base
10.5: Measuring Acidity in Aqueous Solutions- The pH Scale
10.6: Working with pH
10.7: Acid and Base Equivalents
10.8: Some Common Acid-Base Reactions
10.9: Acidity and Basicity of Salt Solutions
10.10: Buffer Solutions
10.11: Titration
11: Nuclear Chemistry

11.1: Nuclear Reactions
11.2: The Discovery and Nature of Radioactivity
11.3: Stable and Unstable Isotopes
11.4: Nuclear Decay
11.5: Radioactive Half-Life
11.6: Ionizing Radiation
11.7: Detecting and Measuring Radiation
11.8: Artificial Transmutation
11.9: Nuclear Fission and Nuclear Fusion
12: Introduction to Organic Chemistry - Alkanes

12.1: The Nature of Organic Molecules
12.2: Families of Organic Molecules - Functional Groups
12.3: The Structure of Organic Molecules - Alkanes and Their Isomers
12.4: Drawing Organic Structures
12.5: The Shapes of Organic Molecules
12.6: Naming Alkanes
12.7: Properties of Alkanes
12.8: Reactions of Alkanes
12.9: Cycloalkanes
12.10: Drawing and Naming Cycloalkanes
13: Alkenes, Alkynes, and Aromatic Compounds
13.1: Alkenes and Alkynes
13.2: Naming Alkenes and Alkynes
13.3: The Structure of Alkenes- Cis-Trans Isomerism
13.4: Properties of Alkenes and Alkynes
13.5: Types of Organic Reactions
13.6: Addition Reactions of Alkenes
13.7: Alkene Polymers
13.8: Aromatic Compounds and the Structure of Benzene
13.9: Naming Aromatic Compounds
13.10: Reactions of Aromatic Compounds
14: Some Compounds with Oxygen, Sulfur, or a Halogen

14.1: Alcohols, Phenols, and Ethers
14.2: Naming Alcohols
14.3: Properties of Alcohols
14.4: Reactions of Alcohols
14.5: Phenols
14.6: Acidity of Alcohols and Phenols
14.7: Ethers
14.8: Thiols and Disulfides
14.9: Halogen-Containing Compounds
14.10: Stereochemistry and Chirality
15: Aldehydes and Ketones

15.1: The Carbonyl Group
15.2: Naming Aldehydes and Ketones
15.3: Properties of Aldehydes and Ketones
15.4: Some Common Aldehydes and Ketones
15.5: Oxidation of Aldehydes
15.6: Reduction of Aldehydes and Ketones
15.7: Addition of Alcohols - Hemiacetals and Acetals
16: Amines
16.1: Classifying Amines
16.2: Naming and Drawing Amines
16.3: Properties of Amines
16.4: Heterocyclic Nitrogen Compounds
16.5: Basicity of Amines
16.6: Amine Salts
16.7: Amines in Plants- Alkaloids
17: Carboxylic Acids and their Derivatives

17.1: Carboxylic Acids and Their Derivatives- Properties and Names
17.2: Acidity of Carboxylic Acids
17.3: Reactions of Carboxylic Acids - Ester and Amide Formation
17.4: Hydrolysis of Esters and Amides
17.5: Polyamides and Polyesters
17.6: Phosphoric Acid Derivatives
18: Amino Acids and Proteins
18.1: An Introduction to Biochemistry
18.2: Proteins and Their Functions- An Overview
18.3: Amino Acids
18.4: Acid-Base Properties of Amino Acids
18.5: Peptides
18.6: Protein Structure- An Overview and Primary Protein Structure
18.7: Secondary Protein Structure
18.8: Tertiary Protein Structure
18.9: Quaternary Protein Structure
18.10: Chemical Properties of Proteins
19: Enzymes and Vitamins

19.1: Catalysis by Enzymes
19.2: Enzyme Cofactors
19.3: Enzyme Classification
19.4: How Enzymes Work
19.5: Factors Affecting Enzyme Activity
19.6: Enzyme Regulation - Inhibition
19.7: Enzyme Regulation- Allosteric Control and Feedback Inhibition
19.8: Enzyme Regulation - Covalent Modification and Genetic Control
19.9: Vitamins, Antioxidants, and Minerals
20: Carbohydrates
20.1: An Introduction to Carbohydrates
20.2: Handedness of Carbohydrates
20.3: Structure of Glucose and Other Monosaccharides
20.4: Some Important Monosaccharides
20.5: Reactions of Monosaccharides
20.6: Common Disaccharides
20.7: Some Important Polysaccharides Based on Glucose
21: The Generation of Biochemical Energy

21.1: Energy, Life, and Biochemical Reactions
21.2: Cells and Their Structure
21.3: An Overview of Metabolism and Energy Production
21.4: Strategies of Metabolism - ATP and Energy Transfer
21.5: Strategies of Metabolism - Metabolic Pathways and Coupled Reactions
21.6: Strategies of Metabolism- Oxidized and Reduced Coenzymes
21.7: The Citric Acid Cycle
21.8: The Electron-Transport Chain and ATP Production
22: Carbohydrate Metabolism

22.1: Digestion of Carbohydrates
22.2: Glucose Metabolism - An Overview
22.3: Glycolysis
22.4: Entry of Other Sugars into Glycolysis
22.5: The Fate of Pyruvate
22.6: Energy Output in Complete Glucose Catabolism
22.7: Regulation of Glucose Metabolism and Metabolism During Stress
22.8: Glycogen Metabolism- Glycogenesis and Glycogenolysis
22.9: Gluconeogenesis- Glucose Synthesis from Noncarbohydrates
23: Lipids
23.1: Structure and Classification of Lipids
23.2: Fatty Acids and Their Esters
23.3: Properties of Fats and Oils
23.4: Chemical Reactions of Triacylglycerols
23.5: Phospholipids and Glycolipids
23.6: Steroids
23.7: Cell Membranes- Structure and Transport
24: Lipid Metabolism

24.1: Digestion of Triacylglycerols
24.2: Lipoproteins for Lipid Transport
24.3: Triacylglycerol Metabolism - An Overview
24.4: Storage and Mobilization of Triacylglycerols
24.5: Oxidation of Fatty Acids
24.6: Ketone Bodies and Ketoacidosis
24.7: Biosynthesis of Fatty Acids
25: Protein and Amino Acid Metabolism

25.1: Digestion of Proteins
25.2: Amino Acid Metabolism - An Overview
25.3: Amino Acid Catabolism - The Amino Group
25.4: The Urea Cycle
25.5: Amino Acid Catabolism - The Carbon Atoms
25.6: Biosynthesis of Nonessential Amino Acids
26: Nucleic Acids and Protein Synthesis

26.1: DNA, Chromosomes, and Genes
26.2: Composition of Nucleic Acids
26.3: The Structure of Nucleic Acid Chains
26.4: Base Pairing in DNA- The Watson-Crick Model
26.5: Nucleic Acids and Heredity
26.6: Replication of DNA
26.7: Structure and Function of RNA
26.8: Transcription - RNA Synthesis
26.9: The Genetic Code
26.10: Translation- tRNA and Protein Synthesis
27: Genomics
27.1: Mapping the Human Genome
27.2: DNA and Chromosomes
27.3: Mutations and Polymorphisms
27.4: Recombinant DNA
27.5: Genomics- Using What We Know
28: Chemical Messengers- Hormones, Neurotransmitters, and Drugs
28.1: Messenger Molecules
28.2: Hormones and the Endocrine System
28.3: How Hormones Work - Epinephrine and Fight-or-Flight
28.4: Amino Acid Derivatives and Polypeptides as Hormones
28.5: Neurotransmitters
28.6: How Neurotransmitters Work- Acetylcholine, Its Agonists and Antagonists
28.7: Histamines, Antihistamines, and Important Neurotransmitters
29: Body Fluids

29.1: Body Water and Its Solutes
29.2: Fluid Balance
29.3: Blood
29.4: Plasma Proteins, White Blood Cells, and Immunity
29.5: Blood Clotting
29.6: Red Blood Cells and Blood Gases
29.7: The Kidney and Urine Formation
29.8: Urine Composition and Function
Index
Glossary
Detailed Licensing
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CHAPTER OVERVIEW
1: Matter and Measurements

What is chemistry? Simply put, chemistry is the study of the interactions of matter with other matter and with energy. This seems
straightforward enough. However, the definition of chemistry includes a wide range of topics that must be understood to gain a
mastery of the topic or even take additional courses in chemistry. In this book, we will lay the foundations of chemistry in a topic-
by-topic fashion to provide you with the background you need to successfully understand chemistry.
1: Matter and Measurements is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
1
 Learning Objectives
Define chemistry in relation to other sciences.
Use physical and chemical properties, including phase, to describe matter.
Chemistry is the study of matter—what it consists of, what its properties are, and how it changes. Being able to describe the
ingredients in a cake and how they change when the cake is baked is called chemistry. Matter is anything that has mass and takes
up space—that is, anything that is physically real. Some things are easily identified as matter—this book, for example. Others are
not so obvious. Because we move so easily through air, we sometimes forget that it, too, is matter.
Chemistry is one branch of science. Science is the process by which we learn about the natural universe by observing, testing, and
then generating models that explain our observations. Because the physical universe is so vast, there are many different branches of
science (Figure 1.1.1). Thus, chemistry is the study of matter, biology is the study of living things, and geology is the study of
rocks and the earth. Mathematics is the language of science, and we will use it to communicate some of the ideas of chemistry.
Figure 1.1.1 : The Relationships between Some of the Major Branches of Science. Chemistry lies more or less in the middle, which
emphasizes its importance to many branches of science. (CC BY-SA-NC; anonymous)
Although we divide science into different fields, there is much overlap among them. For example, some biologists and chemists
work in both fields so much that their work is called biochemistry. Similarly, geology and chemistry overlap in the field called
geochemistry. Figure 1.1.1 shows how many of the individual fields of science are related; there are many other fields of science in
addition to the ones listed here.
How do scientists work? Generally, they follow a process called the scientific method. The scientific method is an organized
procedure for learning answers to questions and making explanations for observations. The steps of the scientific method may not
be as clear-cut in real life as described here, but most scientific work follows this general outline.
1. Propose a hypothesis. A scientist generates a testable idea, or hypothesis, to try to answer a question or explain an observation
about how the natural universe works. Some people use the word theory in place of hypothesis, but the word hypothesis is the
proper word in science. For scientific applications, the word theory is a general statement that describes a large set of
observations and data. A theory represents the highest level of scientific understanding.
2. Test the hypothesis. A scientist evaluates the hypothesis by devising and carrying out experiments to test it. If the hypothesis
passes the test, it may be a proper answer to the question. If the hypothesis does not pass the test, it may not be a good answer.
3. Refine the hypothesis if necessary. Depending on the results of experiments, a scientist may want to modify the hypothesis
and then test it again. Sometimes the results show the original hypothesis to be completely wrong, in which case a scientist will
1.1.1 https://chem.libretexts.org/@go/page/86181
have to devise a new hypothesis.
Not all scientific investigations are simple enough to be separated into these three discrete steps. But these steps represent the
general method by which scientists learn about our natural universe.
Physical and Chemical Properties and Changes

The properties that chemists use to describe matter fall into two general categories. Physical properties are characteristics that
describe matter. They include characteristics such as size, shape, color, and mass. These characteristics can be observed or
measured without changing the identity of the matter in question. Chemical properties are characteristics that describe how matter
changes its chemical structure or composition. An example of a chemical property is flammability—a material’s ability to burn—
because burning (also known as combustion) changes the chemical composition of a material. The observation of chemical
properties involves a chemical change of the matter in question, resulting in matter with a different identity and different physical
and chemical properties. Part of understanding matter is being able to describe it. One way chemists describe matter is to assign
different kinds of properties to different categories.
Figure 1.1.1 : (left) Ice Melting is a physical change. When liquid water (H O ) freezes into a solid state (ice), it appears changed;
2
However, this change is only physical as the the composition of the constituent molecules is the same: 11.19% hydrogen and
88.81% oxygen by mass. (right) Burning of wax to generate water and carbon dioxide is a chemical reaction. (CC SA-BY-3.0;
Andrikkos)
We know from our experience with water that substances can change from one phase to another if the conditions are right.
Typically, varying the temperature of a substance (and, less commonly, the pressure exerted on it) can cause a physical process in
which a substance changes from one phase to another. Examples are summarized in Table 1.1.1.
Table 1.1.1 : Physical Changes
Change Name
solid to liquid melting, fusion
solid to gas sublimation
liquid to gas boiling, evaporation
liquid to solid solidification, freezing
gas to liquid condensation
gas to solid deposition
The difference between a physical reaction and a chemical reaction is composition. In a chemical reaction, there is a change in the
composition of the substances in question; in a physical change there is a difference in the appearance, smell, or simple display of
a sample of matter without a change in composition. Although we call them physical "reactions," no reaction is actually occurring.
In order for a reaction to take place, there must be a change in the elemental composition of the substance in question. Thus, we
shall simply refer to "physical reactions" as physical changes from now on.
 Example 1.1.1
Classify each of the following changes as physical or chemical:

a. condensation of steam
b. burning of gasoline
c. souring of milk
d. dissolving of sugar in water
e. melting of gold
Solution
The best way to determine whether a change is physical or chemical is to determine if the substance identity has changed or
not.
a. Steam is water in the gas phase. When it condenses, changes from gas to liquid, it remains water. Therefore, this is a
physical change.
b. When gasoline burns, it changes into different substances. This is a chemical change.
c. When milk becomes sour, several chemical changes have occured; proteins denature, sugars break down, and acid is
produced. The milk is now made up of different substances.
d. Sugar dissolves easily into water but it still remains sugar. If the water is evaporated, the sugar will recrystalize as a solid
again. Dissolving is a physical change, the substance does not change identity.
e. Melting solid gold into liquid gold is a physical change much like melting solid water (an ice cube) into liquid water is a
physical change.
 Exercise 1.1.1
Classify each of the following changes as physical or chemical:

a. coal burning
b. ice melting
c. mixing chocolate syrup with milk
d. explosion of a firecracker
e. magnetizing of a screwdriver
Answer a:
chemical
Answer b:
physical
Answer c:
physical
Answer d:
chemical
Answer e:
physical
Key Takeaways
Chemistry is the study of matter and how it behaves.
The scientific method is the general process by which we learn about the natural universe.
When a substance changes from one state to another, this is a physical change.
If a substance undergoes a change into one or more different substances, this is a chemical change.
1.1: Chemistry - The Central Science is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
Describe the different physical states of matter; solid, liquid, and gas.
Understand how external conditions can affect the states of matter.
Water can take many forms. At low temperatures (below 0 C), it is a solid. When at "normal" temperatures (between 0 C and
o o
100 C), it is a liquid. While at temperatures above 100 C, water is a gas (steam). The state the water is in depends upon the
o o
temperature. Each state (solid, liquid, and gas) has its own unique set of physical properties.
Figure 1.2.1 : Matter is usually classified into three classical states. From left to right: quartz (solid), water (liquid), nitrogen
dioxide (gas).
Matter typically exists in one of three states: solid, liquid, or gas and these different states of matter have different properties
(Table 1.2.1):
A gas is a state of matter in which atoms or molecules have enough energy to move freely. The molecules come into contact
with one another only when they randomly collide. Forces between atoms or molecules are not strong enough to hold them
together.
A liquid is a state of matter in which atoms or molecules are constantly in contact but have enough energy to keep changing
positions relative to one another. Forces between atoms or molecules are strong enough to keep the molecules relatively close
together but not strong enough to prevent them from moving past one another.
A solid is a state of matter in which atoms or molecules do not have enough energy to move. They are constantly in contact and
in fixed positions relative to one another. Forces between atoms or molecules are strong enough to keep the molecules together
and to prevent them from moving past one another.
The state a given substance exhibits is a physical property. Some substances exist as gases at room temperature (oxygen and carbon
dioxide), while others, like water and mercury metal, exist as liquids. Most metals exist as solids at room temperature. All
substances can exist in any of these three states. Figure 1.2.2 shows the differences among solids, liquids, and gases at the
molecular level. A solid has definite volume and shape, a liquid has a definite volume but no definite shape, and a gas has neither a
definite volume nor shape (Table 1.2.1).
Figure 1.2.2 : The three most common states or phases of matter are solid, liquid, and gas. (CC BY-4.0; OpenStax)
A beaker labeled solid contains a cube of red matter and says has fixed shape and volume. A beaker labeled liquid contains a
brownish-red colored liquid. This beaker says takes shape of container, forms horizontal surfaces, has fixed volume. The beaker
labeled gas is filled with a light brown gas. This beaker says expands to fill container.
These three descriptions each imply that the matter has certain physical properties when in these states. A solid has a definite shape
and a definite volume. Liquids ordinarily have a definite volume but not a definite shape; they take the shape of their containers.
Gases have neither a definite shape nor a definite volume, and they expand to fill their containers. We encounter matter in each
phase every day; in fact, we regularly encounter water in all three phases: ice (solid), water (liquid), and steam (gas).
Table 1.2.1 : Characteristics of each Phase of Matter
Gas Liquid Solid
no definite shape (takes the shape no definite shape (takes the shape
Shape definite shape (rigid)
of its container) of its container)
particles move in random motion

Volume with little or no attraction to each has definite volume definite volume
other
particles move in random motion particles are free to move over

Mobility with little or no attraction to each each other, but are still attracted to particles vibrate around fixed axes
other each other
Compressibility highly compressible weakly compressible weakly compressible
Adding energy to matter gives its atoms or molecules the ability to resist some of the forces holding them together. For example,
heating ice to its melting point gives its molecules enough energy to move. The ice melts and becomes liquid water. Similarly,
heating liquid water to its boiling point gives its molecules enough energy to pull apart from one another so they no longer have
contact. The liquid water vaporizes and becomes water vapor.
State of Matter Depends on the External Conditions

The temperature of the melting and boiling points depend on the identity of the substance and the atmospheric pressure. Each
substance has its own boiling and melting points that depend on the properties of the substance. As an example, the values for
water are given in Table 1.2.2. Note how the boiling point of water varies greatly with pressure.
Table 1.2.1 : Boiling point of water as a function of pressure
Altitude (ft) Pressure (atm) Boiling Point (oC)
-500 1.05 100.5
0 1.00 100
4000 0.892 96
7000 0.797 93
 Example 1.2.1
Isopropyl alcohol is a colorless, flammable chemical compound with a strong odor. Its melting point is –89°C and it boiling
point is 82.5°C. Is isopropyl alcohol a solid, liquid or gas at room temperature (25°C)?
Solution
Room temperature (25°C) is above the melting point of isopropyl alcohol (–89°C), but lower than its boiling point (82.5°C),
therefore, it is a liquid at room temperature.
 Exercise 1.2.1
Freon-12 is used as a refrigerant and aerosol spray propellant. Its melting point is –157.7°C and it boiling point is –29.8 °C. Is
Freon-12 a solid, liquid or gas at room temperature (25°C).
Answer
Freon-12 is a gas at room temperature
Key Takeaways
Matter exists in different physical states.
Changes in conditions such as temperature and pressure can allow matter to change state.
Contributors and Attributions
Allison Soult, Ph.D. (Department of Chemistry, University of Kentucky)
1.2: States of Matter is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
Categorize different types of matter as a pure substances or mixtures.
Explain the difference between an element and a compound.
Explain the difference between a homogeneous mixture and a heterogeneous mixture.
One useful way of organizing our understanding of matter is to think of a hierarchy that extends down from the most general and
complex substances to the simplest and most fundamental (Figure 1.3.1). At the top of this hierarchy is two broad categories into
which all matter can be classified: pure substances and mixtures. A pure substance is a form of matter that has a constant
composition (meaning that all samples of this substance have uniform composition) and properties that are constant throughout the
sample (meaning that there is only one set of properties such as melting point, color, boiling point, etc. throughout the matter). If
we take two or more pure substances and physically mix them together, we refer to this as a mixture. A mixture does not have
constant composition or properties throughout.
Figure 1.3.1 : The Classification of Matter. Matter can be classified in a variety of ways, depending on its properties.
Elements and compounds are both examples of pure substances. A substance that cannot be broken down into chemically simpler
components is an element. Oxygen, O, and hydrogen, H, are each examples of elements. A pure substance that can be broken
down into chemically simpler components (because it made up of more than one element) is a compound. For example, the
compound water, H2O, is formed when hydrogen and oxygen chemically combine in a fixed ratio of 2 hydrogen atoms for every 1
oxygen atom.
Compounds may have different chemical and physical properties from the individual elements that they are composed of. Mixtures,
on the other hand, are physical blends of two or more components, each of which retains its own identity and properties. Mixtures
can always be separated again into the component pure substances, because bonding among the atoms of the constituent substances
does not occur. For example sodium is a soft shiny metal and chlorine is a pungent green gas. These two elements chemically
combine to form the compound, sodium chloride (table salt) which is a white, crystalline solid having none of the properties of
either sodium or chlorine. If, however, you mixed table salt with ground pepper, you would still be able to see the individual grains
of each of them and, if you were patient, you could take tweezers and carefully separate them back into pure salt and pure pepper.
Mixtures fall into two categories, based on the uniformity of their composition (Figure 1.3.1). The first, called a heterogeneous
mixture, is distinguished by the fact that different samples of the mixture may have a different composition. For example, if you
open a container of mixed nuts and pull out a series of small samples and examine them, the exact ratio of peanuts-to-almonds in
the samples will always be slightly different, no matter how carefully you mix them. Common examples of heterogeneous mixtures
include dirt, gravel, and vegetable soup.
In a homogeneous mixture, on the other hand, any sample that you examine will have exactly the same composition as any other
sample. Within chemistry, the most common type of homogeneous mixture is a solution which is one substance dissolved
completely within another. Think of a solution of pure sugar dissolved in pure water. Any sample of the solution that you examine
will have exactly the same ratio of sugar-to-water, which means that it is a homogeneous mixture. Even in a homogeneous mixture,
the properties of the components are generally recognizable. Thus, sugar-water tastes sweet (like sugar) and is wet (like water).
Unlike a compound, which has a fixed, definite ratio, in a mixture the amounts of each component can vary. For example, when
you add a little sugar to one cup of tea and a lot of sugar to another, each cup will contain a homogeneous mixture of tea and sugar
but they will have a different ratio of sugar-to-tea and a different taste. If you add so much sugar that some does not dissolve and
stays on the bottom, however, the mixture is no longer homogeneous, it is heterogeneous; you could easily separate the two
components (Figure 1.3.1).
 Example 1.3.1
Identify each substance as a compound, an element, a heterogeneous mixture, or a homogeneous mixture (solution).
a. filtered tea
b. freshly squeezed orange juice
c. a compact disc
d. aluminum oxide, a white powder that contains a 2:3 ratio of aluminum and oxygen atoms
e. selenium
Given: a chemical substance
Asked for: its classification
Strategy:
I. Decide whether a substance is chemically pure. If it is pure, the substance is either an element or a compound. If a
substance can be separated into its elements, it is a compound.
II. If a substance is not chemically pure, it is either a heterogeneous mixture or a homogeneous mixture. If its composition is
uniform throughout, it is a homogeneous mixture.
Solution
a. I. Tea is a solution of compounds in water, so it is not chemically pure. It is usually separated from tea leaves by filtration.
II. Because the composition of the solution is uniform throughout, it is a homogeneous mixture.
b. I. Orange juice contains particles of solid (pulp) as well as liquid; it is not chemically pure.
II. Because its composition is not uniform throughout, orange juice is a heterogeneous mixture.
c. I. A compact disc is a solid material that contains more than one element, with regions of different compositions visible
along its edge. Hence a compact disc is not chemically pure.
II. The regions of different composition indicate that a compact disc is a heterogeneous mixture.
d. I. Aluminum oxide is a single, chemically pure compound.
e. I. Selenium is one of the known elements.
 Exercise 1.3.1
Identify each substance as a compound, an element, a heterogeneous mixture, or a homogeneous mixture (solution).
a. white wine
b. mercury
c. ranch-style salad dressing
d. table sugar (sucrose)
Answer a:
homogeneous mixture (solution)
Answer b:
element
Answer c:
heterogeneous mixture
Answer d:
compound
 Example 1.3.2
How would a chemist categorize each example of matter?

a. saltwater
b. soil
c. water
d. oxygen
Solution
a. Saltwater acts as if it were a single substance even though it contains two substances—salt and water. Saltwater is a
homogeneous mixture, or a solution.
b. Soil is composed of small pieces of a variety of different materials, so it is a heterogeneous mixture.
c. Water is a substance; more specifically, because water is composed of a fixed ratio hydrogen and oxygen atoms, it is a
compound.
d. Oxygen, a substance, is an element.
 Exercise 1.3.2
How would a chemist categorize each example of matter?

a. coffee
b. hydrogen
c. an egg
Answer a:
Coffee, assuming it is filtered, is a variety of substances dissolved in water, therefore, it is a homogeneous mixture, or a
solution.
Answer b:
Hydrogen is a known element.
Answer c:
An egg is composed of many different substances with different compositions between the yolk and white, it is a
heterogeneous mixture.
Summary
Matter can be classified into two broad categories: pure substances and mixtures. A pure substance is a form of matter that has a
constant composition and properties that are constant throughout the sample. Mixtures are physical combinations of two or more
elements and/or compounds. Mixtures can be classified as homogeneous or heterogeneous. Elements and compounds are both
examples of pure substances. Compounds are substances that are made up of more than one type of atom. Elements are the simplest
substances made up of only one type of atom.

This page was constructed from content via the following contributor(s) and edited (topically or extensively) by the LibreTexts
development team to meet platform style, presentation, and quality:
Marisa Alviar-Agnew (Sacramento City College)
Henry Agnew (UC Davis)
Paul R. Young, Professor of Chemistry, University of Illinois at Chicago, Wiki: AskTheNerd; PRY askthenerd.com - pyoung
uic.edu; ChemistryOnline.com
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Identify names and symbols of common chemical elements.
Represent a chemical compound with a chemical formula.
As described in the previous section, an element is a pure substance that cannot be broken down into simpler chemical substances.
There are about 90 naturally occurring elements known on Earth. Using technology, scientists have been able to create nearly 30
additional elements that do not occur in nature. Today, chemistry recognizes 118 elements—some of which were created an atom at
a time. Figure 1.4.1 shows some of the chemical elements.
Figure 1.4.1 : Samples of Elements. Gold is a yellowish solid, iron is a silvery solid, while mercury is a silvery liquid at room
temperature. © Thinkstock
Elemental Names and Symbols

Each element has a name. Some of these names date from antiquity, while others are quite new. Today, the names for new elements
are proposed by their discoverers but must be approved by the International Union of Pure and Applied Chemistry, an international
organization that makes recommendations concerning all kinds of chemical terminology.
Today, new elements are usually named after famous scientists.

The names of the elements can be cumbersome to write in full, especially when combined to form the names of compounds.
Therefore, each element name is abbreviated as a one- or two-letter chemical symbol. By convention, the first letter of a chemical
symbol is a capital letter, while the second letter (if there is one) is a lowercase letter. The first letter of the symbol is usually the
first letter of the element’s name, while the second letter is some other letter from the name. Some elements have symbols that
derive from earlier, mostly Latin names, so the symbols may not contain any letters from the English name. Table 1.4.1 lists the
names and symbols of some of the most familiar elements.
Table 1.4.1 : Element Names and Symbols
Element Name Element Symbol Element Name Element Symbol
aluminum Al magnesium Mg
argon Ar manganese Mn
arsenic As mercury Hg*
barium Ba neon Ne
bismuth Bi nickel Ni
boron B nitrogen N
bromine Br oxygen O
calcium Ca phosphorus P
carbon C platinum Pt
chlorine Cl potassium K*
chromium Cr silicon Si
Element Name Element Symbol Element Name Element Symbol
copper Cu* silver Ag*
fluorine F sodium Na*
gold Au* strontium Sr
helium He sulfur S
hydrogen H tin Sn*
iron Fe tungsten W†
iodine I uranium U
lead Pb* zinc Zn
lithium Li zirconium Zr
*The symbol comes from the Latin name of element. †The symbol for tungsten comes from its German name—wolfram.
Element names in languages other than English are often close to their Latin names. For example, gold is oro in Spanish and
or in French (close to the Latin aurum), tin is estaño in Spanish (compare to stannum), lead is plomo in Spanish and plomb in
French (compare to plumbum), silver is argent in French (compare to argentum), and iron is fer in French and hierro in
Spanish (compare to ferrum). The closeness is even more apparent in pronunciation than in spelling.
Elements in Nature and the Human Body

The elements vary widely in abundance. In the universe as a whole, the most common element is hydrogen (about 90% of atoms),
followed by helium (most of the remaining 10%). All other elements are present in relatively minuscule amounts, as far as we can
detect. On the planet Earth, however, the situation is rather different (Table 1.4.2). Oxygen makes up 46.1% of the mass of Earth’s
crust (the relatively thin layer of rock forming Earth’s surface), mostly in combination with other elements, while silicon makes up
28.2%. Hydrogen, the most abundant element in the universe, makes up only 0.14% of Earth’s crust.
Table 1.4.2 : Elemental Composition of Earth and the Human Body
Earth’s Crust Human Body
Element Percentage Element Percentage
oxygen 46.1 oxygen 61
silicon 28.2 carbon 23
aluminum 8.23 hydrogen 10
iron 5.53 nitrogen 2.6
calcium 4.15 calcium 1.4
sodium 2.36 phosphorus 1.1
magnesium 2.33 sulfur 0.20
potassium 2.09 potassium 0.20
titanium 0.565 sodium 0.14
hydrogen 0.14 chlorine 0.12
phosphorus 0.105 magnesium 0.027
all others 0.174 silicon 0.026
Source: D. R. Lide, ed. CRC Handbook of Chemistry and Physics, 89th ed. (Boca Raton, FL: CRC Press, 2008–9), 14–17.
Table 1.4.2 also lists the relative abundances of elements in the human body. If you compare both compositions, you will find
disparities between the percentage of each element in the human body and on Earth. Oxygen has the highest percentage in both
cases, but carbon, the element with the second highest percentage in the body, is relatively rare on Earth and does not even appear
as a separate entry; carbon is part of the 0.174% representing “other” elements.
How does the human body concentrate so many apparently rare elements? The relative amounts of elements in the body have less
to do with their abundances on Earth than with their availability in a form we can assimilate. We obtain oxygen from the air we
breathe and the water we drink. We also obtain hydrogen from water. On the other hand, although carbon is present in the
atmosphere as carbon dioxide, and about 80% of the atmosphere is nitrogen, we obtain those two elements from the food we eat,
not the air we breathe.
 Looking Closer: The Phosphorous Bottleneck
There is an element that we need more of in our bodies than is proportionately present in Earth’s crust, and this element is not
easily accessible. Phosphorus makes up 1.1% of the human body but only 0.105% of Earth’s crust. We need phosphorus for our
bones and teeth, and it is a crucial component of all living cells. Unlike carbon, which can be obtained from carbon dioxide,
there is no phosphorus compound present in our surroundings that can serve as a convenient source. Phosphorus, then, is
nature’s bottleneck. Its availability limits the amount of life our planet can sustain.
Higher forms of life, such as humans, can obtain phosphorus by selecting a proper diet (plenty of protein); but lower forms of
life, such as algae, must absorb it from the environment. When phosphorus-containing detergents were introduced in the 1950s,
wastewater from normal household activities greatly increased the amount of phosphorus available to algae and other plant life.
Lakes receiving this wastewater experienced sudden increases in growth of algae. When the algae died, concentrations of
bacteria that ate the dead algae increased. Because of the large bacterial concentrations, the oxygen content of the water
dropped, causing fish to die in large numbers. This process, called eutrophication, is considered a negative environmental
impact.
Figure 1.4.2 : The eutrophication of the Potomac River is evident from the bright green water, caused by a dense bloom of
cyanobacteria. (CC BY-SA 3.0; Alexandr Trubetskoy via Wikipedia)
Today, many detergents are made without phosphorus so the detrimental effects of eutrophication are minimized. You may
even see statements to that effect on detergent boxes. It can be sobering to realize how much impact a single element can have
on life—or the ease with which human activity can affect the environment.
 Example 1.4.1
Write the chemical symbol for each element without consulting the above tables.
a. bromine
b. boron
c. carbon
d. calcium
e. gold
Strategy: The symbol for some of the more common elements is the first one or two letters of the element name. Test yourself
to see if you know the symbol, then check your answer in the above tables. You will learn the element symbols as you practice.
Solution
a. Br
b. B
c. C
d. Ca
e. Au
 Exercise 1.4.1
Write the chemical symbol for each element without consulting the above tables.
a. manganese
b. magnesium
c. neon
d. nitrogen
e. silver
Answer a
Mn
Answer b
Mg
Answer c
Ne
Answer d
N
Answer e
Ag
 Example 1.4.2
What element is represented by each chemical symbol?

a. Na
b. Hg
c. P
d. K
e. I
a. sodium
b.
c. mercury
d.
e. phosphorus
f.
g. potassium
h. iodine
i.
 Exercise 1.4.2
What element is represented by each chemical symbol?

a. Pb
b. Sn
c. U
d. O
e. F
Answer a
lead
Answer b
tin
Answer c
uranium
Answer d
oxygen
Answer e
fluorine
Chemical Formulas
A chemical formula is an expression that shows each of the elements in a compound and the relative proportions of those
elements. Water is composed of hydrogen and oxygen in a 2:1 ratio and its chemical formula is H O . Sulfuric acid is one of the
2
most widely produced chemicals in the United States and is composed of the elements hydrogen, sulfur, and oxygen; the chemical
formula for sulfuric acid is H SO . Sucrose (table sugar) consists of carbon, hydrogen, and oxygen in a 12:22:11 ratio. The
2 4
chemical formula of these are:

H O H SO C H O
2 2 4 12 22 11
  
2 H atoms 2 H atoms 12 H atoms
1 O atom 1 S atom 22 C atoms
4 O atoms 11 O atoms
Notice that the oxygen and sulfur in water and sulfuric acid, respectively, do not have a "1" subscripts - this is assumed.
Sometimes certain groups of atoms are bonded together within the chemical and act as a single unit. Polyatomic ions will be
discussed later and are enclosed in parenthesis followed by a subscript if more than one of the same ion exist in a chemical formula.
For example, the formula Ca (PO ) represents a compound with:
3 4 2
3 Ca atoms and
2 PO polyatomic ions
3 −
4
To count the total number of atoms for formulas with polyatomic ions enclosed in parenthesis, use the subscript as a multiplier for
each atom or number of atoms.
Ca (PO )
3 4 2
and decomposing this to elements gives

3 Ca atoms
2 × 1 P atoms
2 × 4 O atoms
That is, 3 Ca atoms, 2 P atoms, and 8 O atoms
Chemical formula can be used in chemical equations. For example, the reaction of hydrogen gas (H ) burning with oxygen gas (
2
O ) to form water (H O ) is written as:

2 2
2H +O → 2H O
2 2 2
 Exercise 1.4.3
Identify the elements in each of the following chemical formulas and what is the ratio of different elements in the chemical
formulas:
a. NaOH
b. NaCl
c. CaCl 2
d. CH COOH
3
Answer a
Sodium Na, oxygen O , and hydrogen H are present. This is sodium hydroxide and is also known as lye or caustic soda.
This is a 1:1:1 ratio of sodium, oxygen, and hydrogen, respectively.
Answer b
Sodium Na and chlorine O are present. This is sodium chloride and is also known as table salt.
This is a 1:1 ratio of sodium and chlorine, respectively.
Answer c
Calcium Ca and Chlorine Cl are present. This is calcium chloride and is a different type of salt than sodium chloride.
This is a 1:2 ratio of calcium and chlorine, respectively.
Answer d
Carbon C , Oxygen O , and Hydrogen H are present. This is acetic acid and is also known as vinegar.
This is a 2:2:4 (or 1:1:2) ratio of carbon, oxygen, and hydrogen, respectively.
Key Takeaways
All matter is composed of elements, which are represented by one- or two-letter symbols.
Chemical compounds are represented by formulas using element symbols and numerical subscripts to represent the ratio of each
element in the compound.

Anonymous
1.4: Chemical Elements and Symbols is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
Chemical reactions are the processes by which chemicals interact to form new chemicals with different compositions. Simply
stated, a chemical reaction is the process where reactants are transformed into products. How chemicals react is dictated by the
chemical properties of the element or compound- the ways in which a compound or element undergoes changes in composition.
Chemical reactions are constantly occurring in the world around us; everything from the rusting of an iron fence to the metabolic
pathways of a human cell are all examples of chemical reactions. Chemistry is an attempt to classify and better understand these
reactions. One key reaction in modern civilization is combustion
Figure 1.5.1 : An ignited lighter showing the combustion of butane. (Public Domain; Kimmo Palosaari via Wikipedia)
A chemical reaction is typically represented by a chemical equation, which represents the change from reactants to products. The
left hand side of the equation represents the reactants, while the right hand side represents the products. A typical chemical
reaction is written with stoichiometric coefficients, which show the relative amounts of products and reactants involved in the
reaction. Each compound is followed by a parenthetical note of the compound’s physical state: (l) for liquid, (s) for solid, (g) for
gas. The symbol (aq) is also commonly used in order to represent an aqueous solution, in which compounds are dissolved in water.
Butane is a gas at room temperature and atmospheric pressure and is highly flammable, colorless, easily liquefied gas (under light
pressure). Butane can be used for gasoline blending, as a fuel gas, fragrance extraction solvent, either alone or in a mixture with
propane, and as a feedstock for the manufacture of ethylene and butadiene, a key ingredient of synthetic rubber. The chemical
formula of butane if C H . When oxygen is plentiful, butane burns to form carbon dioxide and water vapor as observed in modern
4 10
lighters (Figure 1.5.1).

This reaction in words is:
butane + oxygen → carbon dioxide + water (1.5.1)
and the corresponding chemical equation for this reaction is:

2C H (g) + 13 O (g) → 8 CO (g) + 10 H O(g) (1.5.2)
4 10 2 2 2
In the above chemical equation, C 4

H
10
and O are the reactants that reacted to form the products: CO and H
2 2 2
O ,
 Writing Chemical Equations
To write an accurate chemical equation, two things must occur:

1. Each product and reactant must be written using its chemical formula
2. Coefficients are used in front of the chemical formulas to reflect the ratio species (discussed further in a later chapter)
3. Adding the phase of each chemical in parentheses (although this is often dropped for convenience)
Key Takeaways
Chemical reactions are written to represent chemical changes.
Chemical formulas are used to represent the reactants (starting substance) and the products (the new substances).
1.5: Chemical Reactions - Examples of Chemical Change is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated
by LibreTexts.
Express quantities properly using a number and a unit.
Recognize the different measurement systems used in chemistry.
Describe how prefixes are used in the metric system and identify how the prefixes milli-, centi-, and kilo- compare to the
base unit.
Understand when and how to use scientific notation to represent measurements.
Measurements
A coffee maker’s instructions tell you to fill the coffeepot with 4 cups of water and use 3 scoops of coffee. When you follow these
instructions, you are measuring. When you visit a doctor’s office, a nurse checks your temperature, height, weight, and perhaps
blood pressure (Figure 1.6.1); the nurse is also measuring.
Figure 1.6.1 : Measuring Blood Pressure. A nurse or a doctor measuring a patient’s blood pressure is taking a measurement. (GNU
Free Documentation License; Pia von Lützau via Wikipedia).
Chemists measure the properties of matter using a variety of devices or measuring tools, many of which are similar to those used in
everyday life. Rulers are used to measure length, balances (scales) are used to measure mass (weight), and graduated cylinders or
pipettes are used to measure volume. Measurements made using these devices are expressed as quantities. A quantity is an amount
of something and consists of a number and a unit. The number tells us how many (or how much), and the unit tells us what the
scale of measurement is. For example, when a distance is reported as “5.2 kilometers,” we know that the quantity has been
expressed in units of kilometers and that the number of kilometers is 5.2.
5.2 kilometers
 
number unit
If you ask a friend how far he or she walks from home to school, and the friend answers “12” without specifying a unit, you do not
know whether your friend walks—for example, 12 miles, 12 kilometers, 12 furlongs, or 12 yards.
Without units, a number can be meaningless, confusing, or possibly life threatening. Suppose a doctor prescribes phenobarbital to
control a patient’s seizures and states a dosage of “100” without specifying units. Not only will this be confusing to the medical
professional giving the dose, but the consequences can be dire: 100 mg given three times per day can be effective as an
anticonvulsant, but a single dose of 100 g is more than 10 times the lethal amount.
Both a number and a unit must be included to express a quantity properly.

To understand chemistry, we need a clear understanding of the units chemists work with and the rules they follow for expressing
numbers.
 Example 1.6.1
Identify the number and the unit in each quantity.

a. one dozen eggs
b. 2.54 centimeters
c. a box of pencils
d. 88 meters per second
Answers
a. The number is one, and the unit is dozen.
b. The number is 2.54, and the unit is centimeter.
c. The number 1 is implied because the quantity is only a box. The unit is box of pencils.
d. The number is 88, and the unit is meters per second. Note that in this case the unit is actually a combination of two units:
meters and seconds.
 Exercise 1.6.2
Identify the number and the unit in each quantity.

a. 99 bottles of soda
b. 60 miles per hour
c. 32 fluid ounces
d. 98.6 degrees Fahrenheit
Answer a
The number is 99, and the unit is bottles of soda.
Answer b
The number is 60, and the unit is miles per hour.
Answer c
The number 32, and the unit is fluid ounces
Answer d
The number is 98.6, and the unit is degrees Fahrenheit
The International System of Units

How long is a yard? It depends on whom you ask and when you asked the question. Today we have a standard definition of the
yard, which you can see marked on every football field. If you move the ball ten yards, you get a first down and it doesn't matter
whether you are playing in Los Angeles, Dallas, or Green Bay. But at one time that yard was arbitrarily defined as the distance
from the tip of the king's nose to the end of his outstretched hand. Of course, the problem there is simple: new king, new distance
(and then you have to remark all those football fields).
Figure 1.6.2 : Meter standard (left) and Kilogram standard (right).
SI Base Units
All measurements depend on the use of units that are well known and understood. The English system of measurement units
(inches, feet, ounces, etc.) are not used in science because of the difficulty in converting from one unit to another. The metric
system is used because all metric units are based on multiples of 10, making conversions very simple. The metric system was
originally established in France in 1795. The International System of Units is a system of measurement based on the metric
system. The acronym SI is commonly used to refer to this system and stands for the French term, Le Système International
d'Unités. The SI was adopted by international agreement in 1960 and is composed of seven base units in Table 1.6.1.
Table 1.6.1 : SI Base Units of Measurement
Quantity SI Base Unit Symbol
Length meter m
Mass kilogram kg
Temperature kelvin K
Time second s
Amount of a Substance mole mol
Electric Current ampere A
Luminous Intensity candela cd
The first units are frequently encountered in chemistry. All other measurement quantities, such as volume, force, and energy, can be
derived from these seven base units.
 The Metric System is Not Ubiquitously Adopted
The map below shows the adoption of the SI units in countries around the world. The United States has legally adopted the
metric system for measurements, but does not use it in everyday practice. Great Britain and much of Canada use a combination
of metric and imperial units.
Figure 1.6.2 : Areas of world using metric system (in green). Only a few countries are slow or resistant to adoption including
the United States.
Metric Prefixes
Conversions between metric system units are straightforward because the system is based on powers of ten. For example, meters,
centimeters, and millimeters are all metric units of length. There are 10 millimeters in 1 centimeter and 100 centimeters in 1 meter.
Metric prefixes are used to distinguish between units of different size. These prefixes all derive from either Latin or Greek terms.
For example, mega comes from the Greek word μεγας , meaning "great". Table 1.6.2 lists the most common metric prefixes and
their relationship to the central unit that has no prefix. Length is used as an example to demonstrate the relative size of each
prefixed unit.
Table 1.6.2 : SI Prefixes. Commonly used prefixes are bolded.
Prefix Unit Abbreviation Meaning Example
giga G 1,000,000,000 1 gigameter (Gm) = 10 9

m
mega M 1,000,000 1 megameter (Mm) = 10 6

m
kilo k 1,000 1 kilometer (km) = 1, 000 m
hecto h 100 1 hectometer (hm) = 100 m
deka da 10 1 dekameter (dam) = 10 m
1 1 meter (m)
deci d 1/10 1 decimeter (dm) = 0.1 m
centi c 1/100 1 centimeter (cm) = 0.01 m
milli m 1/1,000 1 millimeter (mm) = 0.001 m
micro μ 1/1,000,000 1 micrometer (μm) = 10 −6

m
nano n 1/1,000,000,000 1 nanometer (nm) = 10 −9

m
pico p 1/1,000,000,000,000 1 picometer (pm) = 10 −12

m
Just as expressing a quantity without a unit is meaningless, so is using the incorrect format for units and prefixes. As you may have
noticed, most metric abbreviations are lowercase. We use "m" for meter and not "M ", which you will see later to represent solution
concentration, something very different from length. However, when it comes to volume, the base unit "liter" is abbreviated as "L"
and not "l". So we would write 3.5 milliliters as 3.5 mL.
As a practical matter, whenever possible you should express the units in a small and manageable number. If you are measuring the
weight of a material that weighs 6.5 kg, this is easier than saying it weighs 6500 g or 0.65 dag. All three are correct, but the kg
units in this case make for a small and easily managed number. However, if a specific problem needs grams instead of kilograms,
go with the grams for consistency.
 Example 1.6.2: Unit Abbreviations
Give the abbreviation for each unit and define the abbreviation in terms of the base unit.
a. kiloliter
b. microsecond
c. decimeter
d. nanogram
Solutions
Solutions to example explaining unit abbreviations.
Explanation Answer
The prefix kilo means “1,000 ×,” so 1 kL

a kL
equals 1,000 L
The prefix micro implies 1/1,000,000th of a

b µs
unit, so 1 µs equals 0.000001 s.
The prefix deci means 1/10th, so 1 dm equals

c dm
0.1 m.
The prefix nano means 1/1000000000, so a

d ng
nanogram is equal to 0.000000001 g
 Exercise 1.6.2
Give the abbreviation for each unit and define the abbreviation in terms of the base unit.
a. kilometer
b. milligram
c. nanosecond
d. centiliter
Answer a
km
Answer b
mg
Answer c
ns
Answer d
cL
Scientific Notation
Chemists often work with numbers that are exceedingly large or small. For example, entering the mass in grams of a hydrogen
scientific notation avoids
atom into a calculator would require a display with at least 24 decimal places. A system called
much of the tedium and awkwardness of manipulating numbers with large or small magnitudes. In
scientific notation, these numbers are expressed in the form
n
N × 10 (1.6.1)
0
where N is a number greater than or equal to 1 and less than 10 (1 ≤ N < 10), and n is a positive or negative integer (10 = 1). The
number 10 is called the base because it is this number that is raised to the power n . Although a base number may have values other
than 10, the base number in scientific notation is always 10.
A simple way to convert numbers to scientific notation is to move the decimal point as many places to the left or right as needed to
give a number from 1 to 10 (N). The magnitude of n is then determined as follows:
If the decimal point is moved to the left n places, n is positive.
If the decimal point is moved to the right n places, n is negative.
Another way to remember this is to recognize that as the number N decreases in magnitude, the exponent increases and vice versa.
The application of this rule is illustrated in Example 1.6.1.
 Example 1.6.1: Expressing Numbers in Scientific Notation
Convert each number to scientific notation.

a. 637.8
b. 0.0479
c. 7.86
d. 12,378
e. 0.00032
f. 61.06700
g. 2002.080
h. 0.01020
Solution
Solutions to example explaining how numbers look in scientific notation.
Explanation Answer
To convert 637.8 to a number from 1 to 10,

we move the decimal point two places to the
a left: 637.8 6.378 × 10
2
Because the decimal point was moved two

places to the left, n = 2.
To convert 0.0479 to a number from 1 to 10,

we move the decimal point two places to the
b right: 0.0479 4.79 × 10
−2

places to the right, n = −2.
This is usually expressed simply as 7.86.

c 7.86 × 10
0
(Recall that 100 = 1.)
Because the decimal point was moved four

d 1.2378 × 10
4
Because the decimal point was moved four

e 3.2 × 10
−4
places to the right, n = −4.
Because the decimal point was moved one

f 6.106700 × 10
1
place to the left, n = 1.
Because the decimal point was moved three

g 2.002080 × 10
3

h 1.020 × 10
−2
places to the right, n = -2.
Scientific Notation: Addition and Subtraction

Before numbers expressed in scientific notation can be added or subtracted, they must be converted to a form in which all the
exponents have the same value. The appropriate operation is then carried out on the values of N. Example 1.6.2 illustrates how to
do this.
 Example 1.6.2: Expressing Sums and Differences in Scientific Notation

Carry out the appropriate operation and then express the answer in scientific notation.
a. (1.36 × 10 ) + (4.73 × 10 )
2 3
b. (6.923 × 10 ) − (8.756 × 10
−3 −4
)
Solution
Solution to example explaining how sums and differences look in scientific notation.
Explanation Answer
Explanation Answer
Both exponents must have the same value, so

these numbers are converted to either
2 2 2 2
(1.36 × 10 ) + (47.3 × 10 ) = (1.36 + 47.3) × 10 = 48.66 × 10
or
3 3 3 3
(0.136 × 10 ) + (4.73 × 10 ) = (0.136 + 4.73) × 10 ) = 4.87 × 10
a . 4.87 × 10
3
Choosing either alternative gives the same

answer, reported to two decimal places:
In converting 48.66 × 102 to scientific
notation, n has become more positive by 1
because the value of N has decreased.
Converting the exponents to the same value

gives either
−3 −3 −3
(6.923 × 10 ) − (0.8756 × 10 ) = (6.923 − 0.8756) × 10
or
b (69.23 × 10
−4
) − (8.756 × 10
−4
) = (69.23 − 8.756) × 10
−4
6.047
= 60.474
× 10× 10
−3 −4
.
In converting 60.474 × 10-4 to scientific
Scientific Notation: Multiplication and Division

When multiplying numbers expressed in scientific notation, we multiply the values of N and add together the values of n .
Conversely, when dividing, we divide N in the dividend (the number being divided) by N in the divisor (the number by which we
are dividing) and then subtract n in the divisor from n in the dividend. In contrast to addition and subtraction, the exponents do not
have to be the same in multiplication and division. Examples of problems involving multiplication and division are shown in
Example 1.6.3.
 Example 1.6.3: Expressing Products and Quotients in Scientific Notation
Perform the appropriate operation and express your answer in scientific notation.
a. [(6.022 × 10
23
)(6.42 × 10
−2
)
−24
1.67 × 10
b. −28
9.12 × 10
−34
(6.63 × 10 )(6.0 × 10)
c. −2
8.52 × 10
Solution
Solutions to example explaining how products and quotients look in scientific notation.
Explanation Answer
In multiplication, we add the exponents:

23 −2 [23+(−2)] 21
(6.022 × 10 )(6.42 × 10 ) = (6.022)(6.42) × 10 = 38.7 × 10
a 3.87 × 10
22

21

Explanation Answer
In division, we subtract the exponents:

−24
1.67 × 10 1.67
[−24−(−28)] 4
= × 10 = 0.183 × 10
−28
9.12 × 10 9.12
b 1.83 × 10
3

4
notation, n has become more negative by 1

because the value of N has increased.
This problem has both multiplication and

division:
c −34 4.7 × 10
−31
(6.63 × 10 )(6.0 × 10) 39.78

[−34+1−(−2)]
= × 10
−2 8.52
(8.52 × 10 )
Key Takeaways
Identifying a quantity properly requires both a number and a unit.
Metric prefixes derive from Latin or Greek terms. The prefixes are used to make the units manageable.
The SI system is based on multiples of ten. There are seven basic units in the SI system. Five of these units are commonly used
in chemistry.
1.6: Physical Quantities - Units and Scientific Notation is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by
Marisa Alviar-Agnew & Henry Agnew.
 Learning Objective
Describe the units (and abbreviations) that go with various quantities.
Derive new units by combining numerical prefixes with units.
Mass vs. Weight

One of the many interesting things about travel in outer space is the idea of weightlessness. If something is not fastened down, it
will float in mid-air. Early astronauts learned that weightlessness had bad effects on bone structure. If there was no pressure on the
legs, those bones would begin to lose mass. Weight provided by gravity is needed to maintain healthy bones. Specially designed
equipment is now a part of every space mission so the astronauts can maintain good body fitness.
Mass is a measure of the amount of matter that an object contains. The mass of an object is made in comparison to the standard
mass of 1 kilogram. The kilogram was originally defined as the mass of 1 L of liquid water at 4 C (volume of a liquid changes
o
slightly with temperature). In the laboratory, mass is measured with a balance (see below), which must be calibrated with a
standard mass so that its measurements are accurate.
Figure 1.7.1 : An analytical balance makes very sensitive mass measurements in a laboratory, usually in grams.
Other common units of mass are the gram and the milligram. A gram is 1/1000th of a kilogram, meaning that there are 1000 g in
1 kg. A milligram is 1/1000th of a gram, so there are 1000 mg in 1 g.
 The Difference Between Mass and Weight

The mass of a body is a measure of its inertial property or how much matter it contains. The weight of a body is a measure of
the force exerted on it by gravity or the force needed to support it. Gravity on earth gives a body a downward acceleration of
about 9.8 m/s2. In common parlance, weight is often used as a synonym for mass in weights and measures. For instance, the
verb “to weigh” means “to determine the mass of” or “to have a mass of.” The incorrect use of weight in place of mass should
be phased out, and the term mass used when mass is meant. The SI unit of mass is the kilogram (kg). In science and
technology, the weight of a body in a particular reference frame is defined as the force that gives the body an acceleration equal
to the local acceleration of free fall in that reference frame. Thus, the SI unit of the quantity weight defined in this way (force)
is the newton (N).
Length
Length is the measurement of the extent of something along its greatest dimension. The SI basic unit of length, or linear measure,
is the meter (m). All measurements of length may be made in meters, though the prefixes listed in various tables will often be
more convenient. The width of a room may be expressed as about 5 meters (m), whereas a large distance, such as the distance
between New York City and Chicago, is better expressed as 1150 kilometers (km) . Very small distances can be expressed in units
such as the millimeter or the micrometer. The width of a typical human hair is about 10 micrometers (μm).
Figure 1.7.2 : The relative lengths of 1 m, 1 yd, 1 cm, and 1 in. are shown (not actual size), as well as comparisons of 2.54 cm and 1
in., and of 1 m and 1.094 yd. (CC BY 4.0; OpenStax)
Volume
In addition to the fundamental units, SI also allows for derived units based on a fundamental unit or units. There are many derived
units used in science. For example, the derived unit for area comes from the idea that area is defined as width times height.
Because both width and height are lengths, they both have the fundamental unit of meter, so the unit of area is meter × meter, or
meter2 (m2). This is sometimes spoken as "square meters." A unit with a prefix can also be used to derive a unit for area, so we can
also have cm2, mm2, or km2 as acceptable units for area.
Volume is the amount of space occupied by a sample of matter. The volume of a regular object can be calculated by multiplying its
length by its width and its height. Since each of those is a linear measurement, we say that units of volume are derived from units
of length. One unit of volume is the cubic meter (m ), which is the volume occupied by a cube that measures 1 m on each side.
3
This very large volume is not very convenient for typical use in a chemistry laboratory. A liter (L) is the volume of a cube that
measures 10 cm (1 dm) on each side. A liter is thus equal to both 1000 cm (10 cm × 10 cm × 10 cm) and to 1 dm . A smaller
3 3
unit of volume that is commonly used is the milliliter (mL - note the capital L which is a standard practice). A milliliter is the
volume of a cube that measures 1 cm on each side. Therefore, a milliliter is equal to a cubic centimeter (cm ). There are 1000 mL
3
in 1 L, which is the same as saying that there are 1000 cm in 1 dm .

3 3
Another definition of a liter is one-tenth of a meter cubed. Because one-tenth of a meter is 10 cm, then a liter is equal to 1,000 cm3
(Figure 1.7.3). Because 1 L equals 1,000 mL, we conclude that 1 mL equals 1 cm3; thus, these units are interchangeable.
Figure 1.7.3 : Units of Volume. (a) The relative volumes are shown for cubes of 1 m3, 1 dm3 (1 L), and 1 cm3 (1 mL) (not to scale).
A liter (L) is defined as a cube 1 dm (1/10th of a meter) on a side. A milliliter (mL), 1/1,000th of a liter, is equal to 1 cubic
centimeter. (b) The diameter of a dime is compared relative to the edge length of a 1-cm3 (1-mL) cube. (CC BY 4.0; OpenStax)
Units not only are multiplied together but also can be divided. For example, if you are traveling at one meter for every second of
time elapsed, your velocity is 1 meter per second, or 1 m/s. The word per implies division, so velocity is determined by dividing a
distance quantity by a time quantity. Other units for velocity include kilometers per hour (km/h) or even micrometers per
nanosecond (μm/ns). Later, we will see other derived units that can be expressed as fractions.
Key Takeaways
Mass is a measure of the amount of matter that an object contains. Mass is independent of location.
Weight is a measure of force that is equal to the gravitational pull on an object. Weight depends on location.
Units can be multiplied and divided to generate new units for quantities like the liter for volume.
1.7: Measuring Mass, Length, and Volume is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
Identify the number of significant figures in a reported value.
Apply the concept of significant figures to report a measurement with the proper number of digits.
Scientists have established certain conventions for communicating the degree of precision of a measurement, which is dependent
on the measuring device used (See Figure 1.8.1). Imagine, for example, that you are using a meterstick to measure the width of a
table. The centimeters (cm) marked on the meterstick, tell you how many centimeters wide the table is. Many metersticks also have
markings for millimeters (mm), so we can measure the table to the nearest millimeter. The measurement made using millimeters is
more precise, it is closer to the actual length of the table. Most metersticks do not have any smaller (or more precise) markings
indicated, so you cannot report the measured width of the table any more precise than to the nearest millimeter.
Figure 1.8.1 : Different measuring devices have different degrees of precision. The ruler on the left has centimeter markings and
the measurement of the box is 2.3 cm. Here, the first digit is certain, and the second digit is estimated, there are two digits reported
for this measurement. The ruler on the right has millimeter markings (1/10 of a centimeter) and the measurement of the box is 2.36
cm. Here, the first two digits are certain, and the third digit is estimated, there are three digits reported for this measurement. The
ruler on the right is more precise than the ruler on the left because more digits are reported. (Figure: Lisa Sharpe Elles)
The concept of significant figures takes the limitation of measuring devices into account. The significant figures of a measured
quantity are defined as all the digits known with certainty (those indicated by the markings on the measuring device) and the first
uncertain, or estimated, digit (one digit past the smallest marking on the measuring device). It makes no sense to estimate and
report any digits after the first uncertain one, so it is the last significant digit reported in a measurement. Zeros are used when
needed to place the significant figures in their correct positions. Thus, zeros are sometimes counted as significant figures but are
sometimes only used as placeholders (see the rules for significant figures below for more details).
“Sig figs” is a common abbreviation for significant figures.

Rules for Determination of Significant Figures
Consider the earlier example of measuring the width of a table with a meterstick. If the table is measured and reported as being
1,357 mm wide, the number 1,357 has four significant figures. The 1 (thousands place), the 3 (hundreds place), and the 5 (tens
place) are certain; the 7 (ones place) is assumed to have been estimated. It would make no sense to report such a measurement as
1,357.0 (five Sig Figs) or 1,357.00 (six Sig Figs) because that would suggest the measuring device was able to determine the width
to the nearest tenth or hundredth of a millimeter, when in fact it shows only tens of millimeters and therefore the ones place was
estimated.
On the other hand, if a measurement is reported as 150 mm, the 1 (hundreds) and the 5 (tens) are known to be significant, but how
do we know whether the zero is or is not significant? The measuring device could have had marks indicating every 100 mm or
marks indicating every 10 mm. How can you determine if the zero is significant (the estimated digit), or if the 5 is significant and
the zero a value placeholder?
The rules for deciding which digits in a measurement are significant are as follows:
Rule 1: All nonzero digits in a measurement are significant.
237 has three significant figures.
1.897 has four significant figures.
Rule 2: Zeros that appear between other nonzero digits (i.e., "middle zeros") are always significant.
39,004 has five significant figures.
5.02 has three significant figures.
Rule 3: Zeros that appear in front of all of the nonzero digits are called leading zeros. Leading zeros are never significant.
0.008 has one significant figure.
0.000416 has three significant figures.
Rule 4: Zeros that appear after all nonzero digits are called trailing zeros. A number with trailing zeros that lacks a decimal point
may or may not be significant.
1400 is ambiguous.
1.4 × 10 has two significant figures.
3
1.40 × 10 three significant figures.

3
1.400 × 10 has four significant figures.

3
Rule 5: Trailing zeros in a number with a decimal point are significant. This is true whether the zeros occur before or after the
decimal point.
620.0 has four significant figures.
19.000 has five significant figures.
It needs to be emphasized that just because a certain digit is not significant does not mean that it is not important or that it can be
left out. Though the zero in a measurement of 140 may not be significant, the value cannot simply be reported as 14. An
insignificant zero functions as a placeholder for the decimal point. When numbers are written in scientific notation, this becomes
more apparent. The measurement 140 can be written as 1.4 × 10 , with two significant figures in the coefficient or as 1.40 × 10 ,
2 3
with three significant figures. A number less than one, such as 0.000416, can be written in scientific notation as 4.16 × 10 , −4
which has 3 significant figures. In some cases, scientific notation is the only way to correctly indicate the correct number of
significant figures. In order to report a value of 15,000,00 with four significant figures, it would need to be written as 1.500 × 10 . 7
Exact Quantities
When numbers are known exactly, the significant figure rules do not apply. This occurs when objects are counted rather than
measured. For example, a carton of eggs has 12 eggs. The actual value cannot be 11.8 eggs, since we count eggs in whole number
quantities. So the 12 is an exact quantity. Exact quantities are considered to have an infinite number of significant figures; the
importance of this concept will be seen later when we begin looking at how significant figures are dealt with during calculations.
Numbers in many conversion factors, especially for simple unit conversions, are also exact quantities and have infinite significant
figures. There are exactly 100 centimeters in 1 meter and exactly 60 seconds in 1 minute. Those values are definitions and are not
the result of a measurement.
 Example 1.8.2
Give the number of significant figures in each. Identify the rule for each.
a. 5.87
b. 0.031
c. 52.90
d. 00.2001
e. 500
f. 6 atoms
Solution
Solution to example explaining how many significant figures are in each number.
Explanation Answer
a. All three numbers are significant (rule 1). 5.87 , three significant figures
b. The leading zeros are not significant (rule 3). The 3 and the 1 are
0.031, two significant figures
significant (rule 1)
c. The 5, the 2 and the 9 are significant (rule 1). The trailing zero is
52.90, four significant figures
also significant (rule 5).
Explanation Answer
d. The leading zeros are not significant (rule 3). The 2 and the 1 are
00.2001, four significant figures
significant (rule 1) and the middle zeros are also significant (rule 2).
e. The number is ambiguous. It could have one, two or three

500, ambiguous
significant figures.
f. The 6 is a counting number. A counting number is an exact

6, infinite
number.
 Exercise 1.8.2
Give the number of significant figures in each.

a. 36.7 m
b. 0.006606 s
c. 2,002 kg
d. 306,490,000 people
e. 3,800 g
Answer a:
three significant figures.
Answer b:
four significant figures.
Answer c:
four significant figures.
Answer d:
Infinite (Exact number)
Answer e:
Ambiguous, could be two, three or four significant figure.
Summary
Uncertainty exists in all measurements. The degree of uncertainty is affected in part by the quality of the measuring tool.
Significant figures give an indication of the certainty of a measurement. Rules allow decisions to be made about how many digits to
use in any given situation.
1.8: Measurement and Significant Figures is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by Marisa
Alviar-Agnew, Henry Agnew, Sridhar Budhi, & Sridhar Budhi.
1.5: Expressing Numbers - Significant Figures by Anonymous is licensed CC BY-NC-SA 4.0. Original source:
https://2012books.lardbucket.org/books/introduction-to-chemistry-general-organic-and-biological.
Use significant figures correctly in arithmetical operations.
Rounding
Before dealing with the specifics of the rules for determining the significant figures in a calculated result, we need to be able to
round numbers correctly. To round a number, first decide how many significant figures the number should have. Once you know
that, round to that many digits, starting from the left. If the number immediately to the right of the last significant digit is less than
5, it is dropped and the value of the last significant digit remains the same. If the number immediately to the right of the last
significant digit is greater than or equal to 5, the last significant digit is increased by 1.
Consider the measurement 207.518 m. Right now, the measurement contains six significant figures. How would we successively
round it to fewer and fewer significant figures? Follow the process as outlined in Table 1.9.1.
Table 1.9.1 : Rounding examples
Number of Significant Figures Rounded Value Reasoning
6 207.518 All digits are significant
5 207.52 8 rounds the 1 up to 2
4 207.5 2 is dropped
3 208 5 rounds the 7 up to 8
2 210 8 is replaced by a 0 and rounds the 0 up to 1
1 200 1 is replaced by a 0
Notice that the more rounding that is done, the less reliable the figure is. An approximate value may be sufficient for some
purposes, but scientific work requires a much higher level of detail.
It is important to be aware of significant figures when you are mathematically manipulating numbers. For example, dividing 125 by
307 on a calculator gives 0.4071661238… to an infinite number of digits. But do the digits in this answer have any practical
meaning, especially when you are starting with numbers that have only three significant figures each? When performing
mathematical operations, there are two rules for limiting the number of significant figures in an answer—one rule is for addition
and subtraction, and one rule is for multiplication and division.
In operations involving significant figures, the answer is reported in such a way that it
reflects the reliability of the least precise operation. An answer is no more precise than
the least precise number used to get the answer.
Rules for Calculations With Measured Numbers

How are significant figures handled in calculations? It depends on what type of calculation is being performed.
Multiplication and Division

For multiplication or division, the rule is to count the number of significant figures in each number being multiplied or divided and
then limit the significant figures in the answer to the lowest count. An example is as follows:
38.65 times 105.93 equals 4094.1954, which should be rounded to 4 sig figs since the lowest count in the numbers being multiplied
is 4 sig figs
The final answer, limited to four significant figures, is 4,094. The first digit dropped is 1, so we do not round up.
Scientific notation provides a way of communicating significant figures without ambiguity. You simply include all the significant
figures in the leading number. For example, the number 450 has two significant figures and would be written in scientific notation
as 4.5 × 102, whereas 450.0 has four significant figures and would be written as 4.500 × 102. In scientific notation, all significant
figures are listed explicitly.
 Example 1.9.1
Write the answer for each expression using scientific notation with the appropriate number of significant figures.
a. 23.096 × 90.300
b. 125 × 9.000
Solution
a
Solution to (a) in example question.
Explanation Answer
The calculator answer is 2,085.5688, but we need to round it to five

significant figures. Because the first digit to be dropped (in the tenths 2.0856 × 10
3
place) is greater than 5, we round up to 2,085.6.
b
Solution to (b) in example question.
Explanation Answer
The calculator gives 1,125 as the answer, but we limit it to three 3

1.13 × 10
Addition and Subtraction

If the calculation is an addition or a subtraction, the rule is as follows: limit the reported answer to the rightmost column that all
numbers have significant figures in common. For example, if you were to add 1.2 and 4.71, we note that the first number stops its
significant figures in the tenths column, while the second number stops its significant figures in the hundredths column. We
therefore limit our answer to the tenths column.
We drop the last digit—the 1—because it is not significant to the final answer.
The dropping of positions in sums and differences brings up the topic of rounding. Although there are several conventions, in this
text we will adopt the following rule: the final answer should be rounded up if the first dropped digit is 5 or greater and rounded
down if the first dropped digit is less than 5.
 Example 1.9.2
a. 13.77 + 908.226
b. 1,027 + 611 + 363.06
Solution
a
Explanation Answer
The calculator answer is 921.996, but because 13.77 has its farthest-
right significant figure in the hundredths place we need to round the
final answer to the hundredths position. Because the first digit to be 922.00 = 9.2200 × 10
2
dropped (in the thousandths place) is greater than 5, we round up to

922.00
b
Explanation Answer
The calculator gives 2,001.06 as the answer, but because 611 and
1027 has its farthest-right significant figure in the ones place, the 2, 001.06 = 2.001 × 10
3
final answer must be limited to the ones position.
 Exercise 1.9.2
Write the answer for each expression using scientific notation with the appropriate number of significant figures.
a. 217 ÷ 903
b. 13.77 + 908.226 + 515
c. 255.0 − 99
d. 0.00666 × 321
Answer a:
−1
0.240 = 2.40 × 10
Answer b:
3
1, 437 = 1.437 × 10
Answer c:
2
156 = 1.56 × 10
Answer d:
0
2.14 = 2.14 × 10
Remember that calculators do not understand significant figures. You are the one who must apply the rules of significant
figures to a result from your calculator
 Example 1.9.3
a. 2(1.008g) + 15.99 g
b. 137.3 s + 2(35.45 s)
118.7g
c. 2
− 35.5g
Solution
a
Explanation Answer
2(1.008g) + 15.99 g =
Perform multiplication first.
2 (1.008g 4 sig figs) = 2.016 g 4 sig figs
The number with the least number of significant figures is 1.008g;
the number 2 is an exact number and therefore has infinite number of
Then, perform the addition. 18.01 g (rounding up)
2.016 g thousandths place + 15.99 g hundredths place (least precise)
= 18.006 g
Round the final answer.
Round the final answer to the hundredths place since 15.99 has its
farthest right significant figure in the hundredths place (least
precise).
b
Explanation Answer
137.3 s + 2 (35.45 s) =
Perform multiplication first.
2 (35.45 s 4 sig figs) = 70.90 s 4 sig figs
The number with the least number of significant figures is 35.45; the
number 2 is an exact number and therefore has infinite number of
significant figures. 208.2 s
Then, perform the addition.
137.3 s tenths place (least precise) + 70.90 s hundredths place =
208.20 s
Round the final answer to the tenths place based on 137.3 s.
c
Solution to (c) in example question.
Explanation Answer
118.7g
2
− 35.5g =
Perform division first.
118.7g
2
4 sig figs = 59.35 g 4 sig figs
The number with the least number of significant figures is 118.7g;
the number 2 is an exact number and therefore has infinite number of
significant figures. 23.9 g (rounding up)
Perform subtraction next.
59.35 g hundredths place − 35.5 g tenths place (least precise) =
23.85 g
Round the final answer to the tenths place based on 35.5 g.
 Exercise 1.9.3
Complete the calculations and report your answers using the correct number of significant figures.
a. 5(1.008s) - 10.66 s
b. 99.0 cm+ 2(5.56 cm)
Answer a
-5.62 s
Answer b
110.2 cm
Summary
Rounding
If the number to be dropped is greater than or equal to 5, increase the number to its left by 1. e.g. 2.9699 rounded to three
significant figures is 2.97
If the number to be dropped is less than 5, there is no change. e.g. 4.00443 rounded to four sig. figs. is 4.004
The rule in multiplication and division is that the final answer should have the same number of significant figures as there are in
the number with the fewest significant figures.
The rule in addition and subtraction is that the answer is given the same number of decimal places as the term with the fewest
decimal places.
Contributions & Attributions


1.9: Rounding Off Numbers is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
Convert a value reported in one unit to a corresponding value in a different unit.
The ability to convert from one unit to another is an important skill. For example, a nurse with 50 mg aspirin tablets who must
administer 0.2 g of aspirin to a patient needs to know that 0.2 g equals 200 mg, so 4 tablets are needed. Fortunately, there is a
simple way to convert from one unit to another.
Conversion Factors
If you learned the SI units and prefixes described previously, then you know that 1 cm is 1/100th of a meter.
1
1 cm = m
100
or
100 cm = 1 m
Suppose we divide both sides of the equation by 1 m (both the number and the unit):
100 cm 1 m
=
1 m 1 m
As long as we perform the same operation on both sides of the equals sign, the expression remains an equality. Look at the right
side of the equation; it now has the same quantity in the numerator (the top) as it has in the denominator (the bottom). Any fraction
that has the same quantity in the numerator and the denominator has a value of 1:
We know that 100 cm is 1 m, so we have the same quantity on the top and the bottom of our fraction, although it is expressed in
different units. A fraction that has equivalent quantities in the numerator and the denominator but expressed in different units is
called a conversion factor.
Here is a simple example. How many centimeters are there in 3.55 m? Perhaps you can determine the answer in your head. If there
are 100 cm in every meter, then 3.55 m equals 355 cm. To solve the problem more formally with a conversion factor, we first write
the quantity we are given, 3.55 m. Then we multiply this quantity by a conversion factor, which is the same as multiplying it by 1.
We can write 1 as 100 cm
1 m
and multiply:
100 cm
3.55 m ×
1 m
The 3.55 m can be thought of as a fraction with a 1 in the denominator. Because m, the abbreviation for meters, occurs in both the
numerator and the denominator of our expression, they cancel out:
3.55 m 100 cm
×
1 1 m
The final step is to perform the calculation that remains once the units have been canceled:
3.55 100 cm
× = 355 cm (1.10.1)
1 1
In the final answer, we omit the 1 in the denominator. Thus, by a more formal procedure, we find that 3.55 m equals 355 cm. A
generalized description of this process is as follows:
quantity (in old units) × conversion factor = quantity (in new units)
You may be wondering why we use a seemingly complicated procedure for a straightforward conversion. In later studies, the
conversion problems you will encounter will not always be so simple. If you can master the technique of applying conversion
factors, you will be able to solve a large variety of problems.
In the previous example (Equation 1.10.1), we used the fraction as a conversion factor. Does the conversion factor
100 cm
1 m
1 m
100 cm
also equal 1? Yes, it does; it has the same quantity in the numerator as in the denominator (except that they are expressed in
different units). Why did we not use that conversion factor? If we had used the second conversion factor, the original unit would
not have canceled, and the result would have been meaningless. Here is what we would have gotten:
2
1 m m
3.55 m × = 0.0355
100 cm cm
For the answer to be meaningful, we have to construct the conversion factor in a form that causes the original unit to cancel out.
Figure 1.10.1 shows a concept map for constructing a proper conversion.
Figure 1.10.1 : A Concept Map for Conversions. This is how you construct a conversion factor to convert from one unit to another.
Meters converted to centimeters. A fraction showing 100 cm over 1 m. The unit you convert to is on top, and the unit you convert
from is on bottom.
Significant Figures in Conversions

How do conversion factors affect the determination of significant figures? Numbers in conversion factors based on prefix changes,
such as kilograms to grams, are not considered in the determination of significant figures in a calculation because the numbers in
such conversion factors are exact. Exact numbers are defined or counted numbers, not measured numbers, and can be considered
as having an infinite number of significant figures. (In other words, 1 kg is exactly 1,000 g, by the definition of kilo-.) Counted
numbers are also exact. If there are 16 students in a classroom, the number 16 is exact. In contrast, conversion factors that come
from measurements (such as density, as we will see shortly) or are approximations have a limited number of significant figures and
should be considered in determining the significant figures of the final answer.
 Example 1.10.1
a. The average volume of blood in an adult male is 4.7 L. What is this volume in milliliters?
b. A hummingbird can flap its wings once in 18 ms. How many seconds are in 18 ms?
Solution
a. We start with what we are given, 4.7 L. We want to change the unit from liters to milliliters. There are 1,000 mL in 1 L.
From this relationship, we can construct two conversion factors:
1 L 1, 000 mL
or
1, 000 mL 1 L
We use the conversion factor that will cancel out the original unit, liters, and introduce the unit we are converting to,
which is milliliters. The conversion factor that does this is the one on the right.
1, 000 mL
4.7 L × = 4, 700 mL
1 L
Because the numbers in the conversion factor are exact, we do not consider them when determining the number of
significant figures in the final answer. Thus, we report two significant figures in the final answer.
b. We can construct two conversion factors from the relationships between milliseconds and seconds:
1, 000 ms 1 s
or
1 s 1, 000 ms
To convert 18 ms to seconds, we choose the conversion factor that will cancel out milliseconds and introduce seconds.
The conversion factor on the right is the appropriate one. We set up the conversion as follows:
1 s
18 ms × = 0.018 s
1, 000 ms
The conversion factor’s numerical values do not affect our determination of the number of significant figures in the final
answer.
 Exercise 1.10.1
Perform each conversion.

a. 101,000 ns to seconds
b. 32.08 kg to grams
Answer a
1 s
101, 000 ns × = 0.000101 s
1, 000, 000, 000 ns
Answer b
1, 000 g
32.08 kg × = 32, 080 g
1 kg
Conversion Factors From Different Units

Conversion factors can also be constructed for converting between different kinds of units. For example, density can be used to
convert between the mass and the volume of a substance. Consider mercury, which is a liquid at room temperature and has a
density of 13.6 g/mL. The density tells us that 13.6 g of mercury have a volume of 1 mL. We can write that relationship as follows:
13.6 g mercury = 1 mL mercury
This relationship can be used to construct two conversion factors:
13.6 g 1 mL
and
1 mL 13.6 g
Which one do we use? It depends, as usual, on the units we need to cancel and introduce. For example, suppose we want to know
the mass of 16 mL of mercury. We would use the conversion factor that has milliliters on the bottom (so that the milliliter unit
cancels) and grams on top so that our final answer has a unit of mass:
13.6 g
16 mL × = 217.6 g
1 mL
≈ 220 g
In the last step, we limit our final answer to two significant figures because the volume quantity has only two significant figures;
the 1 in the volume unit is considered an exact number, so it does not affect the number of significant figures. The other conversion
factor would be useful if we were given a mass and asked to find volume, as the following example illustrates.
Density can be used as a conversion factor between mass and volume.
 Example 1.10.2: Mercury Thermometer
A mercury thermometer for measuring a patient’s temperature contains 0.750 g of mercury. What is the volume of this mass of
mercury?
Solution
Because we are starting with grams, we want to use the conversion factor that has grams in the denominator. The gram unit
will cancel algebraically, and milliliters will be introduced in the numerator.
1 mL
0.750 g × = 0.055147 … mL
13.6 g
≈ 0.0551 mL
We have limited the final answer to three significant figures.
 Exercise 1.10.2
What is the volume of 100.0 g of air if its density is 1.3 g/L?
Answer
1 L
100.0 g × = 76.92307692 L ≈ 77L
1.3 g
Because the density (1.3 g/L) has only 2 significant figures, we are rounding off the final answer to 2 significant figures.
Problem Solving With Multiple Conversions

Sometimes you will have to perform more than one conversion to obtain the desired unit. For example, suppose you want to
convert 54.7 km into millimeters. You can either memorize the relationship between kilometers and millimeters, or you can do the
conversion in two steps. Most people prefer to convert in steps.
To do a stepwise conversion, we first convert the given amount to the base unit. In this example, the base unit is meters. We know
that there are 1,000 m in 1 km:
1, 000 m
54.7 km × = 54, 700 m
1 km
Then we take the result (54,700 m) and convert it to millimeters, remembering that there are 1, 000 mm for every 1 m :
1, 000 mm
54, 700 m × = 54, 700, 000 mm
1 m
7
= 5.47 × 10 mm
We have expressed the final answer in scientific notation.

As a shortcut, both steps in the conversion can be combined into a single, multistep expression:
Concept Map
Calculation
1, 000 m 1, 000 mm
54.7 km × × = 54, 700, 000 mm
1 km 1 m
7
= 5.47 × 10 mm
In each step, the previous unit is canceled and the next unit in the sequence is produced, each successive unit canceling out until
only the unit needed in the answer is left.
Either method—one step at a time or all the steps together—is acceptable. If you do all the steps together, the restriction for the
proper number of significant figures should be done after the last step. As long as the math is performed correctly, you should get
the same answer no matter which method you use.
 Example 1.10.3
Convert 58.2 ms to megaseconds in one multistep calculation.
Solution
First, convert the given unit (ms) to the base unit—in this case, seconds—and then convert seconds to the final unit,
megaseconds:
Concept Map
To convert ms to s, put 1 s over 1000 ms in a fraction. To convert s to Ms, put 1 Ms over 1,000,000 s in a fraction.
Calculation
1s 1 Ms
58.2 ms × × = 0.0000000582 Ms
1, 000 ms 1, 000, 000 s
−8
= 5.82 × 10 Ms
Neither conversion factor affects the number of significant figures in the final answer.
 Exercise 1.10.3
Convert 43.007 mg to kilograms in one multistep calculation.
Answer
1g
1 kg
43.007 mg × × = 0.000043007 kg
1, 000 mg 1, 000 g
−5
= 4.3007 × 10 kg
.
Neither conversion factor affects the number of significant figures in the final answer.
 Career Focus: Pharmacist
A pharmacist dispenses drugs that have been prescribed by a doctor. Although that may sound straightforward, pharmacists in
the United States must hold a doctorate in pharmacy and be licensed by the state in which they work. Most pharmacy programs
require four years of education in a specialty pharmacy school.
Pharmacists must know a lot of chemistry and biology so they can understand the effects that drugs (which are chemicals, after
all) have on the body. Pharmacists can advise physicians on the selection, dosage, interactions, and side effects of drugs. They
can also advise patients on the proper use of their medications, including when and how to take specific drugs properly.
Pharmacists can be found in drugstores, hospitals, and other medical facilities.
Curiously, an outdated name for pharmacist is chemist, which was used when pharmacists formerly did a lot of drug
preparation, or compounding. In modern times, pharmacists rarely compound their own drugs, but their knowledge of the
sciences, including chemistry, helps them provide valuable services in support of everyone’s health.
Key Takeaway
A unit can be converted to another unit of the same type with a conversion factor.
Concept Review Exercises

1. How do you determine which quantity in a conversion factor goes in the denominator of the fraction?
2. State the guidelines for determining significant figures when using a conversion factor.
3. Write a concept map (a plan) for how you would convert 1.0 × 10 nanoliters (nL) to kiloliters (kL).
12
Answers
1. The unit you want to cancel from the numerator goes in the denominator of the conversion factor.
2. Exact numbers that appear in many conversion factors do not affect the number of significant figures; otherwise, the normal
rules of multiplication and division for significant figures apply.
3. Concept Map: Convert the given (nanoliters, nL) to liters; then convert liters to kiloliters.
1.0 times 10 to the 12th nL converts to 1000 Liters converts to 1 kiloLiter. One Liter is 1.0 times 10 to the 9th nL. One kiloLiter is
1000 Liters.
1.10: Problem Solving - Unit Conversions and Estimating Answers is shared under a CC BY-NC-SA 3.0 license and was authored, remixed,
and/or curated by LibreTexts.
1.7: Converting Units by Anonymous is licensed CC BY-NC-SA 4.0. Original source: https://2012books.lardbucket.org/books/introduction-
to-chemistry-general-organic-and-biological.
To identify the different between temperature and heat
To recognize the different scales used to measuring temperature
Temperature
Temperature is a measure of the average kinetic energy of the particles in matter. In everyday usage, temperature indicates a
measure of how hot or cold an object is. Temperature is an important parameter in chemistry. When a substance changes from solid
to liquid, it is because there was in increase in the temperature of the material. Chemical reactions usually proceed faster if the
temperature is increased. Many unstable materials (such as enzymes) will be viable longer at lower temperatures.
Figure 1.11.1 : The glowing charcoal on the left represents high kinetic energy, while the snow and ice on the right are of much
lower kinetic energy.
Three different scales are commonly used to measure temperature: Fahrenheit (expressed as °F), Celsius (°C), and Kelvin (K).
Thermometers measure temperature by using materials that expand or contract when heated or cooled. Mercury or alcohol
thermometers, for example, have a reservoir of liquid that expands when heated and contracts when cooled, so the liquid column
lengthens or shortens as the temperature of the liquid changes.
Figure 1.11.2 : Daniel Gabriel Fahrenheit (left), Anders Celsius (center), and Lord Kelvin (right)
The Fahrenheit Temperature Scale

The first thermometers were glass and contained alcohol, which expanded and contracted as the temperature changed. The German
scientist, Daniel Gabriel Fahrenheit used mercury in the tube, an idea put forth by Ismael Boulliau. The Fahrenheit scale was first
developed in 1724 and tinkered with for some time after that. The main problem with this scale is the arbitrary definitions of
temperature. The freezing point of water was defined as 32 F and the boiling point as 212 F. The Fahrenheit scale is typically not
o o
used for scientific purposes.
The Celsius Temperature Scale

The Celsius scale of the metric system is named after Swedish astronomer Anders Celsius (1701 - 1744). The Celsius scale sets the
freezing point and boiling point of water at 0 C and 100 C respectively. The distance between those two points is divided into 100
o o
equal intervals, each of which is one degree. Another term sometimes used for the Celsius scale is "centigrade" because there are
100 degrees between the freezing and boiling points of water on this scale. However, the preferred term is "Celsius".
The Kelvin Temperature Scale

The Kelvin temperature scale is named after Scottish physicist and mathematician Lord Kelvin (1824 - 1907). It is based on
molecular motion, with the temperature of 0 K, also known as absolute zero, being the point where all molecular motion ceases.
The freezing point of water on the Kelvin scale is 273.15 K, while the boiling point is 373.15 K. Notice that there is no "degree"
used in the temperature designation. Unlike the Fahrenheit and Celsius scales where temperatures are referred to as "degrees F " or
"degrees C", we simply designated temperatures in the Kelvin scale as kelvin.
Figure 1.11.3 : A Comparison of the Fahrenheit, Celsius, and Kelvin Temperature Scales. Because the difference between the
freezing point of water and the boiling point of water is 100° on both the Celsius and Kelvin scales, the size of a degree Celsius
(°C) and a kelvin (K) are precisely the same. In contrast, both a degree Celsius and a kelvin are 9/5 the size of a degree Fahrenheit
(°F). (CC BY-SA-NC 3.0; anonymous)
The Kelvin is the same size as the Celsius degree, so measurements are easily converted from one to the other. The freezing point
of water is 0°C = 273.15 K; the boiling point of water is 100°C = 373.15 K. The Kelvin and Celsius scales are related as follows:
T (in °C) + 273.15 = T (in K) (3.10.1)
T (in K) − 273.15 = T (in °C) (3.10.2)
Degrees on the Fahrenheit scale, however, are based on an English tradition of using 12 divisions, just as 1 ft = 12 in. The
relationship between degrees Fahrenheit and degrees Celsius is as follows: where the coefficient for degrees Fahrenheit is exact.
(Some calculators have a function that allows you to convert directly between °F and °C.) There is only one temperature for which
the numerical value is the same on both the Fahrenheit and Celsius scales: −40°C = −40°F. The relationship between the scales are
as follows:
5
°C = × (°F − 32) (3.10.3)
9
9
°F = × (°C ) + 32 (3.10.4)
5
 Example 1.11.1: Temperature Conversions
A student is ill with a temperature of 103.5°F. What is her temperature in °C and K?
Solution
Converting from Fahrenheit to Celsius requires the use of Equation 3.10.3:
5
°C = × (103.5°F − 32)
9
= 39.7 °C
Converting from Celsius to Kelvin requires the use of Equation 3.10.1:

K = 39.7 °C + 273.15
= 312.9 K
 Exercise 1.11.1
Convert each temperature to °C and °F.

a. the temperature of the surface of the sun (5800 K)
b. the boiling point of gold (3080 K)
c. the boiling point of liquid nitrogen (77.36 K)
Answer (a)
5527 K, 9980 °F
Answer (b)
2807 K, 5084 °F
Answer (c)
-195.79 K, -320.42 °F
Heat
While the concept of temperature may seem familiar to you, many people confuse temperature with heat. as discussed above,
Temperature is a measure of how hot or cold an object is relative to another object (its thermal energy content), whereas heat is
the flow of thermal energy between objects with different temperatures.
When scientists speak of heat, they are referring to energy that is transferred from an object with a higher temperature to an object
with a lower temperature as a result of the temperature difference. Heat will "flow" from the hot object to the cold object until both
end up at the same temperature. When you cook with a metal pot, you witness energy being transferred in the form of heat.
Initially, only the stove element is hot – the pot and the food inside the pot are cold. As a result, heat moves from the hot stove
element to the cold pot. After a while, enough heat is transferred from the stove to the pot, raising the temperature of the pot and all
of its contents.
Energy
Just like matter, energy is a term that we are all familiar with and use on a daily basis. Before you go on a long hike, you eat an
energy bar; every month, the energy bill is paid; on TV, politicians argue about the energy crisis. But what is energy? If you stop to
think about it, energy is very complicated. When you plug a lamp into an electric socket, you see energy in the form of light, but
when you plug a heating pad into that same socket, you only feel warmth. Without energy, we couldn't turn on lights, we couldn't
brush our teeth, we couldn't make our lunch, and we couldn't travel to school. In fact, without energy, we couldn't even wake up
because our bodies require energy to function. We use energy for every single thing that we do, whether we're awake or asleep.
Energy is measured in one of two common units: the calorie and the joule. The joule (J) is the SI unit of energy. The calorie is
familiar because it is commonly used when referring to the amount of energy contained within food. A calorie (cal) is the quantity
of heat required to raise the temperature of 1 gram of water by 1 C. For example, raising the temperature of 100 g of water from
o
20 C to 22 C would require 100 × 2 = 200 cal.

o o
Calories contained within food are actually kilocalories (kcal). In other words, if a certain snack contains 85 food calories, it
actually contains 85 kcal or 85, 000 cal. In order to make the distinction, the dietary calorie is written with a capital C.
1 kilocalorie = 1 Calorie = 1000 calories (1.11.1)
To say that the snack "contains" 85 Calories means that 85 kcal of energy are released when that snack is processed by your body.
Heat changes in chemical reactions are typically measured in joules rather than calories. The conversion between a joule and a
calorie is shown below.
1 J = 0.2390 cal or 1 cal = 4.184 J (1.11.2)
We can calculate the amount of heat released in kilojoules when a 400. Calorie hamburger is digested.
4.184 kJ
3
400 Cal = 400 kcal × = 1.67 × 10 kJ (1.11.3)
1 kcal
Heat Capacity and Specific Heat
If a swimming pool and wading pool, both full of water at the same temperature, were subjected to the same input of heat energy,
the wading pool would certainly rise in temperature more quickly than the swimming pool. Because of its much larger mass, the
swimming pool of water has a larger "heat capacity" than the wading pool. Similarly, different substances respond to heat in
different ways. If a metal chair sits in the bright sun on a hot day, it may become quite hot to the touch. An equal mass of water in
the same sun will not become nearly as hot.
We would say that water has a high heat capacity (the amount of heat required to raise the temperature of an object by 1 C). Water o
is very resistant to changes in temperature, while metals in general are not. The specific heat of a substance is the amount of
energy required to raise the temperature of 1 gram of the substance by 1 C. The symbol for specific heat is c , with the p subscript
o
p
referring to the fact that specific heats are measured at constant pressure. The units for specific heat can either be joules per gram
per degree (J/g C) or calories per gram per degree (cal/g C) (Table 1.11.1). This text will use J/g C for specific heat.
o o o
heat
specific heat = (1.11.4)
o
mass × cal/g C
Notice that water has a very high specific heat compared to most other substances.
Table 1.11.1 : Specific Heat Capacities
Specific Heat Capacity Specific Heat Capacity
Substance Substance
at 25oC in J/g oC at 25oC in J/g oC
H
2
gas 14.267 steam @ 100oC 2.010
He gas 5.300 vegetable oil 2.000
H O(l)
2
4.184 sodium 1.23
lithium 3.56 air 1.020
ethyl alcohol 2.460 magnesium 1.020
ethylene glycol 2.200 aluminum 0.900
ice @ 0oC 2.010 Concrete 0.880
steam @ 100oC 2.010 glass 0.840
Water is commonly used as a coolant for machinery because it is able to absorb large quantities of heat (see table above). Coastal
climates are much more moderate than inland climates because of the presence of the ocean. Water in lakes or oceans absorbs heat
from the air on hot days and releases it back into the air on cool days.
Figure 1.11.4 : This power plant in West Virginia, like many others, is located next to a large lake so that the water from the lake
can be used as a coolant. Cool water from the lake is pumped into the plant, while warmer water is pumped out of the plant and
back into the lake.
 Example 1.11.1: Measuring Heat
A flask containing 8.0 × 10 2

g of water is heated, and the temperature of the water increases from 21 °C to 85 °C. How much
heat did the water absorb?
Solution
To answer this question, consider these factors:
the specific heat of the substance being heated (in this case, water)
the amount of substance being heated (in this case, 800 g)
the magnitude of the temperature change (in this case, from 21 °C to 85 °C).
The specific heat of water is 4.184 J/g °C, so to heat 1 g of water by 1 °C requires 4.184 J. We note that since 4.184 J is
required to heat 1 g of water by 1 °C, we will need 800 times as much to heat 800 g of water by 1 °C. Finally, we observe that
since 4.184 J are required to heat 1 g of water by 1 °C, we will need 64 times as much to heat it by 64 °C (that is, from 21 °C to
85 °C).
This can be summarized using the equation:
q = c × m × ΔT
= c × m × (Tfinal − Tinitial)
= (4.184 J/ g °C) × (800 g ) × (85 − 21)°C
= (4.184 J/ g ° C ) × (800 g ) × (64)° C
= 210, 000 J(= 210 kJ)
Because the temperature increased, the water absorbed heat and q is positive
 Exercise 1.11.1
How much heat, in joules, must be added to a 5.00 × 10 2

g iron skillet to increase its temperature from 25 °C to 250 °C? The
specific heat of iron is 0.451 J/g °C.
Answer
4
5.05 × 10 J
Summary
Three different scales are commonly used to measure temperature: Fahrenheit (expressed as °F), Celsius (°C), and Kelvin (K).
Heat capacity is the amount of heat required to raise the temperature of an object by 1 C). o
The specific heat of a substance is the amount of energy required to raise the temperature of 1 gram of the substance by 1 C. o

Template:OpenStax
1.11: Temperature, Heat, and Energy is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
Define density and specific gravity.
Perform calculations involving both density and specific gravity.
After trees are cut, logging companies often move these materials down a river to a sawmill where they can be shaped into building
materials or other products. The logs float on the water because they are less dense than the water they are in. Knowledge of
density is important in the characterization and separation of materials. Information about density allows us to make predictions
about the behavior of matter.
Density
A golf ball and a table tennis ball are about the same size. However, the golf ball is much heavier than the table tennis ball. Now
imagine a similar size ball made out of lead. That would be very heavy indeed! What are we comparing? By comparing the mass of
an object relative to its size, we are studying a property called density. Density is the ratio of the mass of an object to its volume.
mass
density = (1.12.1)
volume
m
D = (1.12.2)
V
Density is usually a measured property of a substance, so its numerical value affects the significant figures in a calculation. Notice
that density is defined in terms of two dissimilar units, mass and volume. That means that density overall has derived units, just like
velocity. Common units for density include g/mL, g/cm3, g/L, kg/L, and even kg/m3. Densities for some common substances are
listed in Table 1.12.1.
Table 1.12.1 : Densities of Some Common Substances
Liquids and Solids Density at 20o
C (g/mL) Gases Density at 20o
C (g/L)
Ethanol 0.79 Hydrogen 0.084
Ice (0
o
C) 0.917 Helium 0.166
Corn oil 0.922 Air 1.20
Water 0.998 Oxygen 1.33
Water (4 o
C) 1.000 Carbon dioxide 1.83
Corn syrup 1.36 Radon 9.23
Aluminum 2.70
Copper 8.92
Lead 11.35
Mercury 13.6
Gold 19.3
The SI units of density are kilograms per cubic meter (kg/m )

3
, since the kg and the m are the SI units for mass and length
respectively. In everyday usage in a laboratory, this unit is awkwardly large. Most solids and liquids have densities that are
3
conveniently expressed in grams per cubic centimeter (g/cm ) . Since a cubic centimeter is equal to a milliliter, density units can
also be expressed as g/mL. Gases are much less dense than solids and liquids, so their densities are often reported in g/L . Water
has a density of 1.0 g/mL.
File:Separatory_funnel_with_oil_and_colored_water.jpgfile
File:Separatory_funnel_with_oil_and_colored_water.jpg
Figure 1.12.1 : Separatory Funnel containing oil and colored water to display density differences. (CC BY-SA 3.0; PRHaney vai
Wikipedia).
Because of how it is defined, density can act as a conversion factor for switching between units of mass and volume. For example,
suppose you have a sample of aluminum that has a volume of 7.88 cm3. How can you determine what mass of aluminum you have
without measuring it? You can use the volume to calculate it. If you multiply the given volume by the known density (from Table
1.12.1), the volume units will cancel and leave you with mass units, telling you the mass of the sample:
Start with Equation 1.12.1

m
density =
V
and insert the relavant numbers

2.7g m
=
3 3
cm 7.88 cm
Cross multiplying both sides (right numerator x left denominator = left numerator x right denominator), we get the following
expression with answer and appropriate unit.
2.7 g
3
7.88 cm × = 21g of aluminum
3
cm
Since most materials expand as temperature increases, the density of a substance is temperature dependent and usually decreases as
temperature increases. You known that ice floats in water and it can be seen from the table that ice is less dense. Alternatively, corn
syrup, being denser, would sink if placed in water.
 Example 1.12.1
An 18.2 g sample of zinc metal has a volume of 2.55 cm . Calculate the density of zinc.
3
Solution
Step 1: List the known quantities and plan the problem.
Known
Mass = 18.2 g
Volume = 2.55 cm 3
Unknown
3
Density =? g/cm
Use Equation 1.12.1 to solve the problem.
Step 2: Calculate
m 18.2 g 3
D = = = 7.14 g/cm (1.12.3)
3
V 2.55 cm
Step 3: Think about your result.

If 1 cm of zinc has a mass of about 7 grams, then 2 and a half cm will have a mass about 2 and a half times as great. Metals
3 3
are expected to have a density greater than that of water and zinc's density falls within the range of the other metals listed
above.
Since density values are known for many substances, density can be used to determine an unknown mass or an unknown volume.
Dimensional analysis will be used to ensure that units cancel appropriately.
 Example 1.12.2
1. What is he mass of 2.49 cm of aluminum?
3
2. What is the volume of 50.0 g of aluminum?
Solution
Known
3
Density = 2.70 g/cm
1. Volume = 2.49 cm 3
2. Mass = 50.0 g
Unknown
1. Mass =? g
2. Volume =? cm 3
Use the equation for density, D = m
V
, and dimensional analysis to solve each problem.
Step 2: Calculate
2.70 g
3
1. 2.49 cm × = 6.72 g (1.12.4)
3
1 cm
3
1 cm 3
2. 50.0 g × = 18.5 cm (1.12.5)
2.70 g
In problem 1, the mass is equal to the density multiplied by the volume. In problem 2, the volume is equal to the mass divided
by the density.
Step 3: Think about your results.
Because a mass of 1 cm of aluminum is 2.70 g, the mass of about 2.5 cm should be about 2.5 times larger. The
3 3
50 g of
aluminum is substantially more than its density, so that amount should occupy a relatively large volume.
Specific Gravity
Specific gravity is the ratio of the density (mass of a unit volume) of a substance to the density of a given reference material, often
a liquid.
Density of a substance( g/mL )
specific gravity = (1.12.6)

Density of the water at the same temperature( g/mL )
If a substance's relative density is less than one then it is less dense than water and similarly, if greater than 1 then it is denser than
water. If the relative density is exactly 1 then the densities are equal. For example, an ice cube, with a relative density of about 0.91,
will float on water and a substance with a relative density greater than 1 will sink.
A hydrometer is an instrument used for measuring the specific density of liquids based on the concept of buoyancy (Figure 1.12.2).
A hydrometer usually consists of a sealed hollow glass tube with a wider bottom portion for buoyancy, a ballast such as lead or
mercury for stability, and a narrow stem with graduations for measuring. The liquid to test is poured into a tall container, often a
graduated cylinder, and the hydrometer is gently lowered into the liquid until it floats freely. The point at which the surface of the
liquid touches the stem of the hydrometer correlates to relative density. Hydrometers can contain any number of scales along the
stem corresponding to properties correlating to the density.
Figure 1.12.2 : A US Navy Aviation Boatswain's Mate tests the specific gravity of JP-5 fuel. (Public Domain; U.S. Navy via
Wikipedia)
Summary
Density is the ratio of the mass of an object to its volume.
Gases are less dense than either solids or liquids.
Both liquid and solid materials can have a variety of densities.
For liquids and gases, the temperature will affect the density to some extent.
Elizabeth R. Gordon (Furman University)
1.12: Density and Specific Gravity is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
CHAPTER OVERVIEW
2: Atoms and the Periodic Table

2: Atoms and the Periodic Table is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
1
State the modern atomic theory.
Describe how atoms are constructed.
The smallest piece of an element that maintains the identity of that element is called an atom. Individual atoms are extremely small.
It would take about fifty million atoms in a row to make a line that is 1 cm long. The period at the end of a printed sentence has
several million atoms in it. Atoms are so small that it is difficult to believe that all matter is made from atoms-but it is.
The modern atomic theory, proposed about 1803 by the English chemist John Dalton, is a fundamental concept that states that all
elements are composed of atoms. Previously, we defined an atom as the smallest part of an element that maintains the identity of
that element. Individual atoms are extremely small; even the largest atom has an approximate diameter of only 5.4 × 10−10 m. With
that size, it takes over 18 million of these atoms, lined up side by side, to equal the width of your little finger (about 1 cm).
Dalton studied the weights of various elements and compounds. He noticed that matter always combined in fixed ratios based on
weight, or volume in the case of gases. Chemical compounds always contain the same proportion of elements by mass, regardless
of amount, which provided further support for Proust's law of definite proportions. Dalton also observed that there could be more
than one combination of two elements.
From his experiments and observations, as well as the work from peers of his time, Dalton proposed a new theory of the atom. This
later became known as Dalton's atomic theory. The general tenets of this theory were as follows:
All matter is composed of extremely small particles called atoms.
Atoms of a given element are identical in size, mass, and other properties. Atoms of different elements differ in size, mass, and
other properties.
Atoms cannot be subdivided, created, or destroyed.
Atoms of different elements can combine in simple whole number ratios to form chemical compounds.
In chemical reactions, atoms are combined, separated, or rearranged.
Dalton's atomic theory has been largely accepted by the scientific community, with the
exception of three changes. We know now that (1) an atom can be further subdivided, (2)
all atoms of an element are not identical in mass, and (3) using nuclear fission and fusion
techniques, we can create or destroy atoms by changing them into other atoms.
These concepts form the basis of chemistry. Although the word atom comes from a Greek word that means "indivisible," we
understand now that atoms themselves are composed of smaller parts called subatomic particles. The first part to be discovered
was the electron, a tiny subatomic particle with a negative charge. It is often represented as e−, with the right superscript showing
the negative charge. Later, two larger particles were discovered. The proton, a subatomic particle with a positive charge. is a more
massive (but still tiny) subatomic particle with a positive charge, represented as p+. The neutron is a subatomic particle with about
the same mass as a proton but no charge. It is represented as either n or n0. We now know that all atoms of all elements are
composed of electrons, protons, and (with one exception) neutrons. Table 2.1.1 summarizes the properties of these three subatomic
particles.
Table 2.1.1 : Properties of the Three Subatomic Particles
Name Symbol Mass (approx.; g) Mass (approx.; amu) Charge
Proton p+ 1.673 × 10−24 1.0073 +1
Neutron n, n0 1.675 × 10−24 1.0087 none
Electron e− 9.109 × 10−28 5.486 × 10−4 –1
Atoms and subatomic particles are so small that it doesn't quite make sense to measure their masses in grams. A more useful unit to
measure atomic mass is the atomic mass unit (amu), where 1 amu = 1.660539 × 10−24 g or one-twelfth of the mass of a carbon-12
atom. As you can see in the table above, the mass of 1 proton and 1 neutron are each 1 amu in this system. Carbon-12 contains six
protons and six neutrons and is assigned a mass of exactly 12 amu.
Figure 2.1.1 : Electrons are much smaller than protons or neutrons. If an electron was the mass of a penny (right), a proton or a
neutron would have the mass of a large bowling ball (left)!
How are these subatomic particles arranged in atoms? They are not arranged at random. Experiments by Ernest Rutherford in
England in the 1910's pointed to a nuclear model with atoms that has the protons and neutrons in a central nucleus with the
electrons in orbit about the nucleus. The relatively massive protons and neutrons are collected in the center of an atom, in a region
called the nucleus of the atom (plural nuclei). The electrons are outside the nucleus and spend their time orbiting in space about the
nucleus. (Figure 2.1.2). Because protons and neutrons are so massive compared to electrons, Table 2.1.1, nearly all of the mass of
an atom is contained in the nucleus.
Figure 2.1.2 : The Structure of the Atom. Atoms have protons and neutrons in the center, making the nucleus, while the electrons
orbit the nucleus.
 Note Atoms In Action
The evidence for atoms is so great that few doubt their existence. In fact, individual atoms are now routinely observed with
state-of-the art technologies. Moreover, they can even be used for making pretty images or as IBM research demonstrate in
Video 2.1.1, control of individual atoms can be use used create animations.
A Boy And His Atom: The World's Sma…
Sma…
Video 2.1.1: A Boy And His Atom - The World's Smallest Movie. A Boy and His Atom is a 2012 stop-motion animated short
film released by IBM Research. The movie tells the story of a boy and a wayward atom who meet and become friends. It
depicts a boy playing with an atom that takes various forms. It was made by moving carbon monoxide molecules viewed with
a scanning tunneling microscope, a device that magnifies them 100 million times. These molecules were moved to create
images, which were then saved as individual frames to make the film.
Key Takeaways
Chemistry is based on the modern atomic theory, which states that all matter is composed of atoms.
Atoms themselves are composed of protons, neutrons, and electrons.
Each element has its own atomic number, which is equal to the number of protons in its nucleus.
2.1: Atomic Theory and the Structure of Atoms is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by
LibreTexts.
Use the atomic number and mass number to describe an atom.
The modern atomic theory states that atoms of one element are the same, while atoms of different elements are different. What
makes atoms of different elements different? The fundamental characteristic that all atoms of the same element share is the number
of protons. All atoms of hydrogen have one and only one proton in the nucleus; all atoms of iron have 26 protons in the nucleus.
This number of protons is so important to the identity of an atom that it is called the atomic number (Z). The number of protons in
an atom is the atomic number of the element. Thus, hydrogen has an atomic number of 1, while iron has an atomic number of 26.
Each element has its own characteristic atomic number.
Atoms are electrically neutral, meaning that the overall electric charge is zero. This is because the number of protons (positive
charge) equals the number of electrons (negative charge). Therefore, the atomic number also provides the number of electrons. For
example, helium has Z = 2, which tells us that there are 2 protons in the nucleus and 2 electrons outside of the nucleus. Sometimes
atoms will gain or lose electrons resulting in a difference in the number of protons and electrons, which means the charge is no
longer zero. Atoms that have a charge are called ions and will be discussed further in later chapters.
+ –1
atomic number = Z = p =e (2.2.1)
As we learned previously, protons and neutrons, which are found in the nucleus of an atom, each have a mass of ~1 amu. Because
an electron has negligible mass relative to that of a proton or a neutron, the majority of an atom's mass is in the nucleus. The mass
number (A) is defined as the total number of protons (p ) and neutrons (n ) in an atom:
+
+
mass number = A = p +n (2.2.2)
Atoms of the same element always have the same number of protons, same Z, but often have different numbers of neutrons,
therefore, different mass numbers. These atoms are called isotopes and will be discussed in more detail in the next chapter.
 Example 2.2.1
a. The most common carbon atoms have six protons and six neutrons in their nuclei. What are the atomic number and the
mass number of these carbon atoms?
b. An isotope of uranium has an atomic number of 92 and a mass number of 235. What are the number of protons and
neutrons in the nucleus of this atom?
Solution
a. If a carbon atom has six protons in its nucleus, its atomic number is 6. If it also has six neutrons in the nucleus, then the
mass number is 6 + 6, or 12.
b. If the atomic number of uranium is 92, then that is the number of protons in the nucleus. Because the mass number is 235,
then the number of neutrons in the nucleus is 235 − 92, or 143.
 Exercise 2.2.1
The number of protons in the nucleus of a tin atom is 50, while the number of neutrons in the nucleus is 68. What are the
atomic number and the mass number of this isotope?
Answer
Atomic number = 50, mass number = 118
 Example 2.2.2:
a. What is the symbol for an isotope of uranium that has an atomic number of 92 and a mass number of 235?
b. How many protons and neutrons are in Fe 56
26
Solution
a. The symbol for this isotope is U 235
92
b. This iron atom has 26 protons and 56 − 26 = 30 neutrons.
 Exercise 2.2.2
How many protons are in 23

11
Na
Answer
11 protons
Key Takeaways
Atoms themselves are composed of protons, neutrons, and electrons.
Each element has its own atomic number, which is equal to the number of protons in its nucleus.
Isotopes of an element contain different numbers of neutrons.
Elements are represented by an atomic symbol.
Contributors
Lisa Sharpe Elles, University of Kansas
2.2: Elements and Atomic Number is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
Explain how isotopes differ from one another.
Calculate the atomic mass of an element from the masses and relative percentages of the isotopes of the element.
Isotopes
As introduced previously, atoms of a specific element are distinguished from other elements by their atomic number, (the number
of protons). Atoms of the same element always have the same number of protons, however, the number of neutrons can vary.
Isotopes are atoms of the same element that contain different numbers of neutrons. This difference in neutron amount affects the
mass number (A) but not the atomic number (Z). In a chemical laboratory, isotopes of an element appear and react the same. For
this reason, it is difficult to distinguish between different isotopes. In contrast, nuclear scientists can identify and separate different
types of atomic nuclei. The technology required for this process is more sophisticated that what could be found in a typical
chemical laboratory.
Figure 2.3.1 shows an easy way to represent isotopes with a nuclear symbol, which includes the atomic or element symbol
(represented by X), the mass number, A , and the atomic number, Z . Thus, for the isotope of carbon that has 6 protons and 6
neutrons, the symbol is:
12
C
6
where C is the symbol for carbon, 6 represents the atomic number, and 12 represents the mass number.
It is also common to state the mass number after the name of an element to indicate a particular isotope. Carbon-12 represents an
isotope of carbon with 6 protons and 6 neutrons, while uranium-238 is an isotope of uranium that has 92 protons and 146 neutrons.
Figure 2.3.1 : Nuclear Symbol. Unlike protons, the number of neutrons is not absolutely fixed for most elements. Atoms that have
the same number of protons, and hence the same atomic number, but different numbers of neutrons are called isotopes. All isotopes
of an element have the same number of protons and electrons, which means they exhibit the same chemistry. The isotopes of an
element differ only in their atomic mass, which is given by the mass number (A), the sum of the numbers of protons and neutrons.
(CC BY-NC-SA 4.0; anonymous by request)
Most elements on the periodic table have at least two stable isotopes. For example, in addition to C, a typical sample of carbon
12
contains 1.11% C, with 7 neutrons and 6 protons, and a trace of C, with 8 neutrons and 6 protons. The nucleus of C is not
13
6
14
6
14
6
stable, however, but undergoes a slow radioactive decay that is the basis of the carbon-14 dating technique used in archeology.
Many elements other than carbon have more than one stable isotope; tin, for example, has 10 isotopes. There are about twenty
elements that exist in only one isotopic form (sodium and fluorine are examples of these).
An important series of isotopes is found with hydrogen atoms. Most hydrogen atoms have a nucleus with only a single proton.
About 1 in 10,000 hydrogen nuclei, however, also has a neutron; this particular isotope is called deuterium. An extremely rare
hydrogen isotope, tritium, has 1 proton and 2 neutrons in its nucleus. Figure 2.3.2 compares the three isotopes of hydrogen.
Figure 2.3.2 : Isotopes of Hydrogen. Most hydrogen atoms have only a proton in the nucleus (a). A small amount of hydrogen
exists as the isotope deuterium, which has one proton and one neutron in its nucleus (b). A tiny amount of the hydrogen isotope
tritium, with one proton and two neutrons in its nucleus, also exists on Earth (c). The nuclei and electrons are proportionately much
smaller than depicted here.
There are currently over 3,500 isotopes known for all the elements. When scientists discuss individual isotopes, they need an
efficient way to specify the number of neutrons in any particular nucleus. A/Z and symbol-mass formats can be used to display
periodic table information. When viewing either of these two notations, isotopic differences can be obtained.
The discovery of isotopes required a minor change in Dalton’s atomic theory. Dalton
thought that all atoms of the same element were exactly the same.
Look at the A/Z formats for the three isotopes of hydrogen in Table 2.3.1. Note how the atomic number (bottom value) remains
the same while the atomic masses (top number) are varied. All isotopes of a particular element will vary in neutrons and mass. This
variance in mass will be visible in the symbol-mass format of same isotopes as well.
Table 2.3.1
Common Name A/Z formats symbol-mass format Expanded Name
Hydrogen 1
1
H H-1 hydrogen-1
Deuterium 2
1
H H-2 hydrogen-2
Tritium 3
1
H H-3 hydrogen-3
Both A/Z or symbol-mass formats can be utilized to determine the amount of subatomic particles (protons, neutrons, and electrons)
contained inside an isotope. When given either format, these mass values should be used to calculate the number of neutrons in the
nucleus.
Atomic Weight
Since most naturally occurring elements samples are mixtures of isotopes, it is useful to use an average weight of an element. The
atomic mass of an element is the weighted mass of all the naturally presented isotopes (on earth). To determine the most abundant
isotopic form of an element, compare given isotopes to the weighted average on the periodic table. For example, the three hydrogen
isotopes in Figure 2.3.2 are H-1, H-2, and H-3. The atomic mass or weighted average of hydrogen is around 1.008 amu ( look
again to the periodic table). Of the three hydrogen isotopes, H-1 is closest in mass to the weighted average; therefore, it is the most
abundant. The other two isotopes of hydrogen are quite rare, but are very exciting in the world of nuclear science.
You can calculate the atomic mass (or average mass) of an element provided you know the relative abundances (the fraction of an
element that is a given isotope), the element's naturally occurring isotopes, and the masses of those different isotopes. We can
calculate this by the following equation:
Atomic mass = (%1 ) (mass1 ) + (%2 ) (mass2 ) + ⋯ (2.3.1)
Averages like Equation 1 are known as weighted averages. An element's atomic mass can be calculated provided the relative
abundances of the element's naturally occurring isotopes and the masses of those isotopes are known. If all the abundances are not
provided, it is safe to assume that all numbers should add up to 100%.
For example, Boron has two naturally occurring isotopes. In a sample of boron, 20% of the atoms are B-10 , which is an isotope of
boron with 5 neutrons and mass of 10 amu. The other 80% of the atoms are B-11 , which is an isotope of boron with 6 neutrons
and a mass of 11 amu. How do we calculate the atomic mass of boron?
Boron has two isotopes so we will use the Equation 2.3.1 and substitute the relative abundances and atomic masses of Boron into
Equation 2.3.1:
Atomic mass = (0.20) (10) + (0.80) (11)
= 10.8 amu
The mass of an average boron atom, and thus boron's atomic mass, is 10.8 amu.
 Example 2.3.1: Atomic Weight of Neon
Neon has three naturally occurring isotopes. In a sample of neon, 90.92% of the atoms are Ne-20, which is an isotope of neon
with 10 neutrons and a mass of 19.99 amu. Another 0.3% of the atoms are Ne-21, which is an isotope of neon with 11
neutrons and a mass of 20.99 amu. The final 8.85% of the atoms are Ne-22, which is an isotope of neon with 12 neutrons and
a mass of 21.99 amu. What is the atomic mass of neon?
Solution
Neon has three isotopes. We will use the equation:
Atomic mass = (%1 ) (mass1 ) + (%2 ) (mass2 ) + ⋯
Substitute these into the equation, and we get:
Atomic mass = (0.9092) (19.99) + (0.003) (20.99) + (0.0885) (21.99)
= 20.17 amu
The mass of an average neon atom is 20.17 amu
 Exercise 2.3.1
Magnesium has the three isotopes listed in the following table:

Table showing the 3 isotopes of magnesium, the exact mass of each, and the percent abundance of each.
Isotope Exact Mass (amu) Percent Abundance (%)
24Mg 23.98504 78.70
25Mg 24.98584 10.13
26Mg 25.98259 11.17
Use these data to calculate the atomic mass of magnesium.
Answer
24.31 amu
 Applications of Isotopes
During the Manhattan project, the majority of federal funding was dedicated the separation of uranium isotopes. The two most
common isotopes of uranium are U-238 and U-235. About 99.3% of uranium is of the U-238 variety, this form is not
fissionable and will not work in a nuclear weapon or reaction. The remaining 0.7% is U-235 which is fissionable, but first had
to be separated from U-238. This separation process is called enrichment. During World War II, a nuclear facility was built in
Oak Ridge, Tennessee to accomplish this project. At the time, the enrichment process only produced enough U-235 for one
nuclear weapon. This fuel was placed inside the smaller of the two atomic bombs (Little Boy) dropped over Japan.
Figure 2.3.3 : A billet of highly enriched uranium that was recovered from scrap processed at the Y-12 National Security
Complex Plant. Original and unrotated.
A billet of highly enriched uranium that was recovered from scrap processed at the Y-12 National Security Complex Plant.
Uranium is a natural element that can be found in several different countries. Countries that do not have natural uranium
supplies would need to obtain it from one of the countries below. Most nuclear reactors that provide energy rely on U-235 as a
source of fuel. Fortunately, reactors only need 2-5% U-235 for the production of megawatts or even gigawatts of power. If the
purification process exceeds this level, than it is likely a country is focusing on making nuclear weapons. For example,
Manhattan Project scientists enriched U-235 up to 90% in order to produce the Little Boy weapon.
Abbreviations like HEU (highly enriched uranium) and LEU (low-enriched uranium) are used frequently by nuclear scientists
and groups. HEU is defined as being over 20% pure U-235 and would not be used in most commercial nuclear reactors. This
type of material is used to fuel larger submarines and aircraft carriers. If the purification of U-235 reaches 90%, then the HEU
is further classified as being weapons grade material. This type of U-235 could be used to make a nuclear weapon (fission or
even fusion based). As for LEU, its U-235 level would be below this 20% mark. LEU would be used for commercial nuclear
reactors and smaller, nuclear powered submarines. LEU is not pure enough to be used in a conventional nuclear weapon, but
could be used in a dirty bomb. This type of weapon uses conventional explosives like dynamite to spread nuclear material.
Unlike a nuclear weapon, dirty bombs are not powerful enough to affect large groups of buildings or people. Unfortunately, the
spread of nuclear material would cause massive chaos for a community and would result in casualties.
Summary
The isotopes of an element have different masses and are identified by their mass numbers.
An element's atomic mass is the weighted average of the masses of the isotopes of an element
An element's atomic mass can be calculated provided the relative abundances of the element's naturally occurring isotopes and
the masses of those isotopes are known. If all the abundances are not provided, it is safe to assume that all numbers should add
up to 100%.

1. Why is the atomic number so important to the identity of an atom?
2. What is the relationship between the number of protons and the number of electrons in an atom?
3. How do isotopes of an element differ from each other?
4. What is the mass number of an element?
Answers
1. The atomic number defines the identity of an element. It describes the number of protons in the nucleus.
2. In an electrically neutral atom, the number of protons equals the number of electrons.
3. Isotopes of an element have the same number of protons but have different numbers of neutrons in their nuclei.
4. The mass number is the sum of the numbers of protons and neutrons in the nucleus of an atom.
Elizabeth R. Gordon (Furman University)
2.3: Isotopes and Atomic Weight is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
Explain how elements are organized into the periodic table.
Describe how some characteristics of elements relate to their positions on the periodic table.
In the 19th century, many previously unknown elements were discovered, and scientists noted that certain sets of elements had
similar chemical properties. For example, chlorine, bromine, and iodine react with other elements (such as sodium) to make similar
compounds. Likewise, lithium, sodium, and potassium react with other elements (such as oxygen) to make similar compounds.
Why is this so?
In 1864, Julius Lothar Meyer, a German chemist, organized the elements by atomic mass and grouped them according to their
chemical properties. Later that decade, Dmitri Mendeleev, a Russian chemist, organized all the known elements according to
similar properties. He left gaps in his table for what he thought were undiscovered elements, and he made some bold predictions
regarding the properties of those undiscovered elements. When elements were later discovered whose properties closely matched
Mendeleev’s predictions, his version of the table gained favor in the scientific community. Because certain properties of the
elements repeat on a regular basis throughout the table (that is, they are periodic), it became known as the periodic table.
Mendeleev had to list some elements out of the order of their atomic masses to group them
with other elements that had similar properties.
The periodic table is one of the cornerstones of chemistry because it organizes all the known elements on the basis of their
chemical properties. A modern version is shown in Figure 2.4.1. Most periodic tables provide additional data (such as atomic
mass) in a box that contains each element’s symbol. The elements are listed in order of atomic number.
Figure 2.4.1 : Modern Periodic Table. (Public Domain; PubChem modified Leticia Colmenares). An interactive Periodic table can
be found here.
Elements that have similar chemical properties are grouped in columns called groups (or families). As well as being numbered,
some of these groups have names—for example, alkali metals (the first column of elements), alkaline earth metals (the second
column of elements), halogens (the next-to-last column of elements), and noble gases (the last column of elements).
Each row of elements on the periodic table is called a period. Periods have different lengths; the first period has only 2 elements
(hydrogen and helium), while the second and third periods have 8 elements each. The fourth and fifth periods have 18 elements
each, and later periods are so long that a segment from each is removed and placed beneath the main body of the table.
Metals, Nonmetals, and Metalloids

Certain elemental properties become apparent in a survey of the periodic table as a whole. Every element can be classified as either
a metal, a nonmetal, or a semimetal, as shown in Figure 2.4.2. A metal is a substance that is shiny, typically (but not always)
silvery in color, and an excellent conductor of electricity and heat. Metals are also malleable (they can be beaten into thin sheets)
and ductile (they can be drawn into thin wires). A nonmetal is typically dull and a poor conductor of electricity and heat. Solid
nonmetals are also very brittle. As shown in Figure 2.4.2, metals occupy the left three-fourths of the periodic table, while
nonmetals (except for hydrogen) are clustered in the upper right-hand corner of the periodic table. The elements with properties
intermediate between those of metals and nonmetals are called semimetals (or metalloids). Elements adjacent to the bold zigzag
line in the right-hand portion of the periodic table have semimetal properties.
Figure 2.4.2 : Types of Elements. Elements are either metals, nonmetals, or semimetals. Each group is located in a different part of
the periodic table.
 Example 2.4.1
Based on its position in the periodic table, classify each element below as metal, a nonmetal, or a metalloid.
a. Se
b. Mg
c. Ge
Solution
a. The atomic number of selenium is 34, which places it in period 4 and group 16. In Figure 2.4.2, selenium lies above and to
the right of the diagonal line marking the boundary between metals and nonmetals, so it should be a nonmetal. Note,
however, that because selenium is close to the metal-nonmetal dividing line, it would not be surprising if selenium were
similar to a semimetal in some of its properties.
b. Magnesium lies to the left of the diagonal line marking the boundary between metals and nonmetals, so it should be a
metal.
c. Germanium lies within the diagonal line marking the boundary between metals and nonmetals, so it should be a metalloid.
 Exercise 2.4.1
Based on its location in the periodic table, do you expect indium (In) to be a nonmetal, a metal, or a semimetal?
Answer
metal
Representative, Transition, and Inner-transition
Another way to categorize the elements of the periodic table is shown in Figure 2.4.3. The first two columns on the left (groups 1
and 2) and the last six columns on the right (groups 13-19) are called the main group or representative elements. The ten-column
block between these columns (groups 3-12) contains the transition metals. The two rows beneath the main body of the periodic
table contain the inner transition metals. The elements in these two rows are also referred to as, respectively, the lanthanide
metals and the actinide metals.
Figure 2.4.3 : Special Names for Sections of the Periodic Table. Some sections of the periodic table have special names. The
elements lithium, sodium, potassium, rubidium, cesium, and francium are collectively known as alkali metals.
 To Your Health: Transition Metals in the Body
Most of the elemental composition of the human body consists of main group elements. The most abundant non-main group
element is iron, at 0.006 percentage by mass. Because iron has relatively massive atoms, it would appear even lower on a list
organized in terms of percent by atoms rather than percent by mass.
Iron is a transition metal and the chemistry of iron makes it a key component in the proper functioning of red blood cells.
Red blood cells are cells that transport oxygen from the lungs to cells of the body and then transport carbon dioxide from the
cells to the lungs. Without red blood cells, animal respiration as we know it would not exist. The critical part of the red blood
cell is a protein called hemoglobin. Hemoglobin combines with oxygen and carbon dioxide, transporting these gases from one
location to another in the body. Hemoglobin is a relatively large molecule, with a mass of about 65,000 u.
The crucial atom in the hemoglobin protein is iron. Each hemoglobin molecule has four iron atoms, which act as binding sites
for oxygen. It is the presence of this particular transition metal in your red blood cells that allows you to use the oxygen you
inhale.
Other transition metals have important functions in the body, despite being present in low amounts. Zinc is needed for the
body’s immune system to function properly, as well as for protein synthesis and tissue and cell growth. Copper is also needed
for several proteins to function properly in the body. Manganese is needed for the body to metabolize oxygen properly. Cobalt
is a necessary component of vitamin B-12, a vital nutrient. These last three metals are present in the body in very small
quantities. However, even these small quantities are required for the body to function properly.

2.4: The Periodic Table is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
Describe how some characteristics of elements relate to their positions on the periodic table.
The periodic table is useful for understanding atomic properties that show periodic trends. Periodic trends are specific patterns
that are present in the periodic table that illustrate different aspects of a certain element, including its size and its electronic
properties. Major periodic trends include atomic radius, melting point, among many other properties as we will discuss. Periodic
trends, arising from the arrangement of the periodic table, provide chemists with an invaluable tool to quickly predict an element's
properties. These trends exist because of the similar atomic structure of the elements within their respective group families or
periods, and because of the periodic nature of the elements.
One important atomic property is the atomic radius, which is a measure of the atomic size, usually the distance from the nucleus to
the out electron shell. However, since this boundary is not well-defined, there are multiple definitions of atomic radius. Irrespective
of the definition used, a clear periodic trend can be observed when atomic radius is plotted vs. atomic number (Figure 2.5.1). The
radii generally decrease along each row of the table and increase down each group. The radius increases sharply between the noble
gas at the end of each period and the alkali metal at the beginning of the next period. The largest atoms are found in the lower left
corner of the periodic table and the smallest are found in the upper right corner
Figure : A Plot of Periodic Variation of Atomic Radius with Atomic Number for the First
2.5.1
Six Rows of the Periodic Table.

The melting point is a metric of the energy required to transform the solid phase of a substance into a liquid. Generally, the stronger
the bond between the atoms of an element, the more energy required to break that bond. The melting points exhibit comparable,
albeit more complex, periodic trends as observed in the atomic radii (Figure 2.5.2). Key feature of these trends are:
Metals generally possess a high melting point.
Most non-metals possess low melting points.
The non-metal carbon possesses the highest melting point of all the elements. The semi-metal boron also possesses a high
melting point.
Figure 2.5.2 : A plot of melting point vs. atomic number show a periodic trend.
The trends of the atomic radii and melting points (and other chemical and physical properties of the elements) can be explained by
the electron shell theory of the atom discussed in the following sections.
Element Characteristics By Group

The periodic table is arranged so that elements with similar chemical behaviors are in the same group. Chemists often make general
statements about the properties of the elements in a group using descriptive names with historical origins. For example, the
elements of Group 1 are known as the alkali metals, Group 2 are the alkaline earth metals, Group 17 are the halogens, and Group
18 are the noble gases.
Group 1: The Alkali Metals – lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), and francium (Fr) are
soft, shiny, and highly reactive metals. The compounds of the alkali metals are common in nature and daily life. One example is
table salt (sodium chloride); lithium compounds are used in greases, in batteries, and as drugs to treat patients who exhibit
manic-depressive, or bipolar, behavior. Although lithium, rubidium, and cesium are relatively rare in nature, and francium is so
unstable and highly radioactive that it exists in only trace amounts, sodium and potassium are the seventh and eighth most
abundant elements in Earth’s crust, respectively. Hydrogen is unique in that it is generally placed in Group 1, but it is not a
metal.
Group 2: The Alkaline Earth Metals – beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), and
radium (Ra) are shiny, slivery-white, somewhat reactive metals. Beryllium, strontium, and barium are rare, and radium is
unstable and highly radioactive. In contrast, calcium and magnesium are the fifth and sixth most abundant elements on Earth,
respectively; they are found in huge deposits of limestone and other minerals.
Group 17: The Halogens – fluorine (F), chlorine (Cl), bromine (Br), iodine (I), and astatine (At) are nonmetals. The name
halogen is derived from the Greek words for “salt forming,” which reflects that all the halogens react readily with metals to
form compounds, such as sodium chloride and calcium chloride (used in some areas as road salt).
Group 18: The Noble Gases – helium (He), neon (Ne), argon (Ar), krypton (Kr), xenon (Xe), and radon (Rn) are gases at room
temperature and pressure. Because the noble gases are composed of only single atoms, they are called monatomic. Because of
their lack of reactivity, for many years they were called inert gases or rare gases. However, the first chemical compounds
containing the noble gases were prepared in 1962. Although the noble gases are relatively minor constituents of the atmosphere,
natural gas contains substantial amounts of helium. Because of its low reactivity, argon is often used as an unreactive (inert)
atmosphere for welding and in light bulbs. The red light emitted by neon in a gas discharge tube is used in neon lights.
 To Your Health: Radon

Radon is an invisible, odorless noble gas that is slowly released from the ground, particularly from rocks and soils whose
uranium content is high. Because it is a noble gas, radon is not chemically reactive. Unfortunately, it is radioactive, and
increased exposure to it has been correlated with an increased lung cancer risk.
Because radon comes from the ground, we cannot avoid it entirely. Moreover, because it is denser than air, radon tends to
accumulate in basements, which if improperly ventilated can be hazardous to a building’s inhabitants. Fortunately, specialized
ventilation minimizes the amount of radon that might collect. Special fan-and-vent systems are available that draw air from
below the basement floor, before it can enter the living space, and vent it above the roof of a house.
After smoking, radon is thought to be the second-biggest preventable cause of lung cancer in the United States. The American
Cancer Society estimates that 10% of all lung cancers are related to radon exposure. There is uncertainty regarding what levels
of exposure cause cancer, as well as what the exact causal agent might be (either radon or one of its breakdown products, many
of which are also radioactive and, unlike radon, not gases). The US Environmental Protection Agency recommends testing
every floor below the third floor for radon levels to guard against long-term health effects.
 Example 2.5.1: Groups
Provide the family/group names and period numbers (horizontal values) of each element.
a. Li
b. Ar
c. Ra
Solution:
a. Lithium is an alkali metal. It is located in period two.
b. Argon is a noble gas. It is located in period three.
c. Radium is an alkaline metal. It is located in period seven.
 Example 2.5.2: Classification of Elements
Provide elemental names for the following combinations:

a. The alkali metal in period three.
b. The halogen in period two
c. A metalloid in period four
d. A transition metal in period three
Solution:
a. Sodium
b. Fluorine
c. Germanium or Arsenic
d. There are no transition metals in period three (gotcha!)
Key Takeaways
The chemical elements are arranged in a chart called the periodic table.
Some characteristics of the elements are related to their position on the periodic table.
The number of valence electrons of an element can be determined by the group (vertical column) number in the Periodic Table.
Elements with the same number of valence electrons have similar chemical properties.
2.5: Some Characteristics of Different Groups is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by
LibreTexts.
Describe how electrons are grouped within atoms into shells, subshells, and orbitals using quantum numbers.
You now know that the periodic table is arranged in groups and periods (columns and rows) based on chemical and physical
properties of the different elements. The first element, hydrogen (Z=1) has one proton and one electron and as you move right
across the rows, each subsequent element has one additional proton and electron. You may have asked yourself, why are periodic
trends observed across the rows and down the groups? Or, why do the rows have different numbers of elements, giving the table a
unique shape?
These questions can be answered by learning more about the electrons in atoms. Although we have discussed the general
arrangement of subatomic particles in atoms, we have said little about how electrons occupy the space around the nucleus. Do they
move around the nucleus at random, or do they exist in some ordered arrangement?
In 1913, the Danish scientist Niels Bohr suggested that the electron in a hydrogen atom could not have any random energy, having
only certain fixed values of energy that were indexed by the number n (now called a quantum number). Bohr suggested that the
energy of the electron in hydrogen was quantized because it was in a specific orbit; much like the steps on a staircase does not
have half or quarter stairs or the keys on a piano don't have notes in between, there are no energy levels in between each orbit.
Figure 2.6.1 shows a model of the hydrogen atom based on Bohr's ideas.
Figure 2.6.1 : Bohr's Model of the Hydrogen Atom. Bohr's description of the hydrogen atom had specific orbits for the electron,
which had quantized energies.
Bohr's ideas were useful, but were applicable only to the hydrogen atom. However, later researchers generalized Bohr's ideas into a
new theory called quantum mechanics, which explains the behavior of electrons as if they were acting as a wave, not as particles.
Quantum mechanics predicts two major things: quantized energies for electrons of all atoms (not just hydrogen) and an
organization of electrons within atoms. Electrons are no longer thought of as being randomly distributed around a nucleus or
restricted to certain orbits (in that regard, Bohr was wrong). Instead, electrons are collected into groups (shells) and subgroups
(subshells) that explain much about the chemical behavior of the atom.
In the quantum-mechanical model of an atom, which is the modern and currently accepted model, the location of electrons in the
atom are described by four quantum numbers, not just the one predicted by Bohr. Much like your home address can be used to
locate you in a specific state, city, street, and house number, the first three quantum numbers identify approximately where
electrons are in an atom. The fourth quantum number describes the electron and whether it is spin up or down (clockwise or
counterclockwise). The theory and mathematics behind these four quantum numbers are well beyond the scope of this textbook,
however, it is useful to learn some of the basics in order to understand how atoms behave and interact with (react) with other atoms.
Electron Arrangements: Shells, Subshells, and Orbitals

Electrons are organized according to their energies into sets called shells (labeled by the principle quantum number, n). Generally
the higher the energy of a shell, the farther it is (on average) from the nucleus. Shells do not have specific, fixed distances from the
nucleus, but an electron in a higher-energy shell will spend more time farther from the nucleus than does an electron in a lower-
energy shell.
Shells are further divided into subsets of electrons called subshells, labeled by type as s, p, d, or f. The first shell has only one
subshell, s. The second shell has two subshells, s and p; the third shell has three subshells, s, p, and d, and the fourth shell has four
subshells, s, p, d, and f. Within each subshell, electrons are arranged into different numbers of orbitals, an s subshell is made up of
one s orbital, a p subshell has two p orbitals, a d subshell, five d orbitals, and an f subshell, seven f orbitals. Each orbital has a
different shape and orientation around the nucleus (Figure 2.6.1, however, rather than representing an orbit, as the name suggests,
orbitals define a boundary for the region of space where a given electron is most likely to be found. Lastly, a single orbital can hold
up to two electrons each with a different spin.
Figure 2.6.1 : Electron Orbitals. (a) The lone s orbital in an s subshell is spherical in distribution. (b) The three p orbitals have two
lobes, shaped kind of like dumbbells, each is oriented around the nucleus along a different axis. (c) The five d orbitals have four
lobes, except for the d orbital, which is a "dumbbell + torus" combination. They are all oriented in different directions.
z
2
It is important to note that according to quantum theory, there are specific allowed combinations of quantum numbers and others
that are not allowed. For example, shell two can only have two subshells, s with one orbital and p with 3 orbitals, therefore, this
shell can hold a maximum of eight electrons (four orbitals times two electrons each). It takes practice to learn the allowed
combinations as shown in Table \(\PageIndex{1}\ but it is helpful to visualize the atom as a sphere with the nucleus in the center.
Close to the nucleus, there is a smaller amount of space for electrons – a smaller shell. As the number of electrons increases, the
shells that hold the electrons get larger and thus further away from the nucleus.
Table 2.6.1: Shells and Subshells

Number of Number of
Number of Names of Total Electrons
Shell Orbitals (per Electrons (per
Subshells Subshells (per Shell)
Subshell) Subshell)
1 1 1s 1 2 2
2 2 2s and 2p 1, 3 2, 6 8
3 3 3s, 3p, and 3d 1, 3, 5 2, 6, 10 18
4s, 4p, 4d, and

4 4 1, 3, 5, 7 2, 6, 10, 14 32
4f
All of this information about the shell, subshell, and orbital is put together to make up the "address" for an electron and all of the
addresses for all the electrons in an atom make up the electron configuration, which is described more later.
2.6: Electronic Structure of Atoms is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
2.6: Arrangements of Electrons by Anonymous is licensed CC BY-NC-SA 4.0. Original source:
8.3: Quantum Numbers for Electrons by Anonymous is licensed CC BY-NC-SA 3.0. Original source:
https://2012books.lardbucket.org/books/beginning-chemistry.
Describe how electrons are arranged in an atom using electron configurations.
Previously we discussed the concept of electron shells, subshells, orbitals, and electron spin. It is the arrangement of electrons into
shells and subshells that most concerns us here, so we will focus on that.
We use numbers to indicate which shell an electron is in. The first shell, closest to the nucleus and with the lowest-energy electrons,
is shell 1. This first shell has only one subshell, which is labeled 1s and can hold a maximum of 2 electrons. We combine the shell
and subshell labels when referring to the organization of electrons about a nucleus and use a superscript to indicate how many
electrons are in a subshell. Thus, because a hydrogen atom has its single electron in the s subshell of the first shell, we use 1s1
(spoken as “one-ess-one”) to describe the electron arrangement or distribution of electrons in hydrogen. This structure is called an
electron configuration and is unique to hydrogen.
Helium atoms have 2 electrons. Both electrons fit into the 1s subshell because s subshells contain one s orbital which can hold up
to 2 electrons; therefore, the electron configuration for helium atoms is 1s2 (spoken as “one-ess-two”).
The 1s subshell can hold a maximum of 2 electrons, so the electron configuration for a lithium atom, which has three electrons,
cannot be 1s3. Two of the lithium electrons can fit into the 1s subshell, but the third electron must go into the second shell and the
lower energy orbital, which is the 2s orbital. Therefore, we write the electron configuration of a lithium atom as 1s22s1 (spoken as
“one-ess-two two-ess-one”).
The shell diagram for a lithium atom (Figure 2.7.1). The shell closest to the nucleus (first shell) has 2 dots representing the 2
electrons in 1s, while the outermost shell (2s) has 1 electron.
Figure 2.7.1 : Shell diagrams of hydrogen (H), helium (He), lithium (Li), and Berryellium (Be) atoms. (CC BY-SA 2.0 UK; Greg
Robson modified by Pumbaa via Wikipedia)
There are a set of general rules that are used to figure out the electron configuration of an atomic species: Aufbau Principle,
Hund's Rule and the Pauli-Exclusion Principle.
Rule 1 (Aufbau Principle): Electrons occupy the lowest-energy orbitals (closest to the nucleus) possible, starting with 1s, then
2s, 2p, and continuing on to higher energy (further away from the nucleus). Shells increase in energy in order from 1 to 2 to 3,
and so on. Within these shells, an s subshell is the lowest energy followed by p, then d, then f.
Rule 2 (Hund's Rule): When electrons occupy degenerate orbitals (i.e. same shell and subshell), they must first singly occupy
(half-fill) each empty orbital in a subshell before double occupying (completely filling) them. Furthermore, the most stable
configuration results when the spins are parallel (i.e. all spin up or all spin down). For example, all three p orbitals in a p
subshell will have one electron before a single p orbital contains two electrons.
Rule 3 (Pauli-Exclusion Principle): Each electron is described with a unique set of four quantum numbers (a unique address).
Therefore, if two electrons occupy the same orbital, they must have different spins. This is the reason all orbitals can hold a
maximum of two electrons.
Continuing on the periodic table to the next largest atom, beryllium, with 4 electrons, the electron configuration is 1s22s2. Now that
the 2s subshell is filled, electrons in larger atoms, starting with boron, begin filling the 2p subshell, which can hold a maximum of
six electrons. The next six elements progressively fill up the 2p subshell:
B: 1s22s22p1
C: 1s22s22p2
N: 1s22s22p3
O: 1s22s22p4
F: 1s22s22p5
Ne: 1s22s22p6
At the end of the period the element neon, has filled the 2s, and 2p subshells, which completes the second shell. Now atoms with
more electrons now must begin the third shell starting with the 3s subshell. The first two subshells of the third shell are filled in
order—for example, the electron configuration of aluminum, with 13 electrons, is 1s22s22p63s23p1. However, a curious thing
happens after the 3p subshell is filled: the 4s subshell begins to fill before the 3d subshell does. In fact, the exact ordering of
subshells becomes more complicated at this point (after argon, with its 18 electrons), so we will not consider the electron
configurations of larger atoms.
Table 2.7.1 : Electron Configurations of the First 20 Elements
Atomic Number Element Symbol Outermost Shell Electron Configuration Noble Gas Configuration
1 H 1 1s 1 1s 1
2 He 1 1s 2 1s 2
3 Li 2 1s 2 2s 1 [He] 2s 1
4 Be 2 1s 2 2s 2 [He] 2s 2
5 B 2 1s 2 2s 2 2p1 [He] 2s 2 2p1
6 C 2 1s 2 2s 2 2p2 [He] 2s 2 2p2
7 N 2 1s 2 2s 2 2p3 [He] 2s 2 2p3
8 O 2 1s 2 2s 2 2p4 [He] 2s 2 2p4
9 F 2 1s 2 2s 2 2p5 [He] 2s 2 2p5
10 Ne 2 1s 2 2s 2 2p6 [He] 2s 2 2p6
11 Na 3 1s 2 2s 2 2p6 3s 1 [Ne] 3s 1
12 Mg 3 1s 2 2s 2 2p6 3s 2 [Ne] 3s 2
13 Al 3 1s 2 2s 2 2p6 3s 2 3p1 [Ne] 3s 2 3p1
14 Si 3 1s 2 2s 2 2p6 3s 2 3p2 [Ne]3s 2 3p2
15 P 3 1s 2 2s 2 2p6 3s 2 3p3 [Ne] 3s 2 3p3
16 S 3 1s 2 2s 2 2p6 3s 2 3p4 [Ne] 3s 2 3p4
17 Cl 3 1s 2 2s 2 2p6 3s 2 3p5 [Ne] 3s 2 3p5
18 Ar 3 1s 2 2s 2 2p6 3s 2 3p6 [Ne] 3s 2 3p6
19 K 4 1s 2 2s 2 2p6 3s 2 3p6 4s 1 [Ar] 4s 1
20 Ca 4 1s 2 2s 2 2p6 3s 2 3p6 4s 2 [Ar] 4s 2
 Noble Gas Configuration
The electron configuration of sodium is 1s 2s 2p 3s (Table 2.7.1). The first ten electrons of the sodium atom are the inner-
2 2 6 1
shell electrons and the configuration of just those ten electrons is exactly the same as the configuration of the element neon
(Z = 10) . This provides the basis for a shorthand notation for electron configurations called the noble gas configuration,
which atom consists of the elemental symbol of the last noble gas prior to that atom, followed by the configuration of the
remaining electrons. So for sodium, we make the substitution of [Ne] for the 1s 2s 2p part of the configuration. Sodium's
2 2 6
noble gas configuration becomes [Ne] 3s . 1
The electron filling diagram shown below in Figure 2.7.2 is useful in remembering the order for electrons to occupy shells and
subshells. Although it is much easier to use the periodic table as a guide for electron filling as you will see in the next section.
Figure 2.7.2 : The order of electron filling in an atom. Follow each arrow in order from top to bottom. The subshells you reach
along each arrow give the ordering of filling of subshells in larger atoms.
 Example 2.7.1: Electronic Configuration of Phosphorus Atoms
Using Figure 2.7.2 as your guide, write the electron configuration of a neutral phosphorus atom. The atomic number of P is 15.
Solution
A neutral phosphorus atom has 15 electrons. Two electrons can go into the 1s subshell, 2 can go into the 2s subshell, and 6 can
go into the 2p subshell. That leaves 5 electrons. Of those 5 electrons, 2 can go into the 3s subshell, and the remaining 3
electrons can go into the 3p subshell. Thus, the electron configuration of neutral phosphorus atoms is 1s22s22p63s23p3.
 Exercise 2.7.1: Electronic Configuration of Chlorine Atoms
Using Figure 2.7.2 as your guide, write the electron configuration of a neutral chlorine atom. The atomic number of Cl is 17.
Answer
A neutral chlorine atom has 17 electrons. Two electrons can go into the 1s subshell, 2 can go into the 2s subshell, and 6 can
go into the 2p subshell. That leaves 7 electrons. Of those 7 electrons, 2 can go into the 3s subshell, and the remaining 5
electrons can go into the 3p subshell. Thus, the electron configuration of neutral chlorine atoms is 1s22s22p63s23p5.
Orbital Diagrams
An orbital diagram is the more visual way to represent the arrangement of all the electrons in a particular atom. In an orbital
diagram, the individual orbitals are shown as squares and orbitals within a sublevel are drawn next to each other horizontally. Each
sublevel is labeled by its shell and sublevel. Electrons are indicated by arrows inside of the squares. An arrow pointing upwards
indicates one spin direction, while a downward pointing arrow indicates the other direction. The orbital filling diagrams for
hydrogen, helium, and lithium are shown in the figure below.
Figure 2.7.3 : Orbital diagrams for hydrogen, helium, and lithium.

According to the Aufbau Principle, sublevels and orbitals are filled with electrons in order of increasing energy. Since the s
sublevel consists of just one orbital, the second electron simply pairs up with the first electron as in helium. The next element is
lithium and necessitates the use of the next available sublevel, the 2s.
The orbital diagram for carbon is shown in Figure 2.7.10 . There are two 2p electrons for carbon and each occupies its own 2p
orbital (Hund's Rule).
Figure 2.7.4 : Orbital diagram for carbon.

Oxygen has four 2p electrons. After each 2p orbital has one electron in it, the fourth electron can be placed in the first 2p orbital
with a spin opposite that of the other electron in that orbital.
Figure 2.7.5 : Orbital diagram for oxygen.

If you keep your papers in manila folders, you can pick up a folder and see how much it weighs. If you want to know how many
different papers (articles, bank records, or whatever else you keep in a folder), you have to take everything out and count. A
computer directory, on the other hand, tells you exactly how much you have in each file. We can get the same information on
atoms. If we use an orbital filling diagram, we have to count arrows. When we look at electron configuration data, we simply add
up the numbers.
 Example 2.7.3: Carbon Atoms
Draw the orbital filling diagram for carbon and write its electron configuration.
Solution
Known
Atomic number of carbon, Z=6
Use the order of fill diagram to draw an orbital filling diagram with a total of six electrons. Follow Hund's rule. Write the
electron configuration.
Step 2: Construct the diagram.
Orbital filling diagram for carbon.

Electron configuration 1s22s22p2
Following the 2s sublevel is the 2p, and p sublevels always consist of three orbitals. All three orbitals need to be drawn
even if one or more is unoccupied. According to Hund's rule, the sixth electron enters the second of those p orbitals and
has the same spin as the fifth electron.
2.7: Electron Configurations is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
8.4: Organization of Electrons in Atoms by Anonymous is licensed CC BY-NC-SA 3.0. Original source:
9.6: Quantum-Mechanical Orbitals and Electron Configurations by Henry Agnew, Marisa Alviar-Agnew is licensed CK-12. Original
source: https://www.ck12.org/c/chemistry/.
Relate the electron configurations of the elements to the shape of the periodic table.
Determine the expected electron configuration of an element by its place on the periodic table.
Remember, that the periodic table as a tool for organizing the known chemical elements(Figure 2.8.1). The elements are listed by
atomic number (the number of protons in the nucleus), and elements with similar chemical properties are grouped together in
columns. Why does the periodic table have the structure it does? The answer is rather simple, if you understand electron
configurations: the shape of the periodic table mimics the filling of the subshells with electrons.
The shape of the periodic table mimics the filling of the subshells with electrons.
Let us start with H and He. Their electron configurations are 1s1 and 1s2, respectively; with He, the n = 1 shell is filled. These two
elements make up the first row of the periodic table (Figure 2.8.1)
Figure 2.8.1 : The 1s Subshell. H and He represent the filling of the 1s subshell.
The next two electrons, for Li and Be, would go into the 2s subshell. Figure 2.8.2 shows that these two elements are adjacent on
the periodic table.
Figure 2.8.2 : The 2s Subshell. In Li and Be, the 2s subshell is being filled.
For the next six elements, the 2p subshell is being occupied with electrons. On the right side of the periodic table, these six
elements (B through Ne) are grouped together (Figure 2.8.3).
Figure 2.8.3 : The 2p Subshell. For B through Ne, the 2p subshell is being occupied.
The next subshell to be filled is the 3s subshell. The elements when this subshell is being filled, Na and Mg, are back on the left
side of the periodic table (Figure 2.8.4).
Figure 2.8.4 : The 3s Subshell. Now the 3s subshell is being occupied.

Next, the 3p subshell is filled with the next six elements (Figure 2.8.5).
Figure 2.8.5 : The 3p Subshell. Next, the 3p subshell is filled with electrons.
Instead of filling the 3d subshell next, electrons go into the 4s subshell (Figure 2.8.6).
Figure 2.8.6 : The 4s Subshell. The 4s subshell is filled before the 3d subshell. This is reflected in the structure of the periodic table.
After the 4s subshell is filled, the 3d subshell is filled with up to 10 electrons. This explains the section of 10 elements in the
middle of the periodic table (Figure 2.8.7).
Figure 2.8.7 : The 3d Subshell. The 3d subshell is filled in the middle section of the periodic table.
And so forth. As we go across the columns of the periodic table, the overall shape of the table outlines how the electrons are
occupying the shells and subshells.
The first two columns on the left side of the periodic table are where the s subshells are being occupied. Because of this, the first
two rows of the periodic table are labeled the s block. Similarly, the p block are the right-most six columns of the periodic table,
the d block is the middle 10 columns of the periodic table, while the f block is the 14-column section that is normally depicted as
detached from the main body of the periodic table. It could be part of the main body, but then the periodic table would be rather
long and cumbersome. Figure 2.8.8 shows the blocks of the periodic table.
Figure 2.8.8 : Blocks on the Periodic Table. The periodic table is separated into blocks depending on which subshell is being filled
for the atoms that belong in that section.
The electrons in the highest-numbered shell, plus any electrons in the last unfilled subshell, are called valence electrons; the
highest-numbered shell is called the valence shell. (The inner electrons are called core electrons.) The valence electrons largely
control the chemistry of an atom. If we look at just the valence shell's electron configuration, we find that in each column, the
valence shell's electron configuration is the same. For example, take the elements in the first column of the periodic table: H, Li,
Na, K, Rb, and Cs. Their electron configurations (abbreviated for the larger atoms) are as follows, with the valence shell electron
configuration highlighted:
Table shows first column of the periodic table and their electron configurations.
H: 1s1
Li: 1s22s1
Na: [Ne]3s1
K: [Ar]4s1
Rb: [Kr]5s1
Cs: [Xe]6s1
They all have a similar electron configuration in their valence shells: a single s electron. Because much of the chemistry of an
element is influenced by valence electrons, we would expect that these elements would have similar chemistry-and they do. The
organization of electrons in atoms explains not only the shape of the periodic table but also the fact that elements in the same
column of the periodic table have similar chemistry.
The same concept applies to the other columns of the periodic table. Elements in each column have the same valence shell electron
configurations, and the elements have some similar chemical properties. This is strictly true for all elements in the s and p blocks.
In the d and f blocks, because there are exceptions to the order of filling of subshells with electrons, similar valence shells are not
absolute in these blocks. However, many similarities do exist in these blocks, so a similarity in chemical properties is expected.
Similarity of valence shell electron configuration implies that we can determine the electron configuration of an atom solely by its
position on the periodic table. Consider Se, as shown in Figure 2.8.9. It is in the fourth column of the p block. This means that its
electron configuration should end in a p4 electron configuration. Indeed, the electron configuration of Se is [Ar]4s23d104p4, as
expected.
Figure 2.8.9 : Selenium on the Periodic Table
 Example 2.8.1
From the element's position on the periodic table, predict the valence shell electron configuration for each atom (Figure
2.8.10).
Figure 2.8.10 : Various Elements on the Periodic Table
1. Ca
2. Sn
Solution
1. Ca is located in the second column of the s block. We would expect that its electron configuration should end with s2.
Calcium's electron configuration is [Ar]4s2.
2. Sn is located in the second column of the p block, so we expect that its electron configuration would end in p2. Tin's
electron configuration is [Kr]5s24d105p2.
 Exercise 2.8.1
From the element's position on the periodic table, predict the valence shell electron configuration for each atom. Figure 2.8.10.
a. Ti
b. Cl
Answer a
[Ar]4s23d2
Answer b
[Ne]3s23p5
 Example 2.8.2: Aluminum
Write the electron configuration of neutral aluminum atom. The atomic number of Al is 13.
Solution
Aluminum has 13 electrons.
Start at Period 1 of the periodic table, Figure 2.8.2. Place two electrons in the 1s subshell (1s2).
Proceed to Period 2 (left to right direction). Place the next two electrons in the 2s subshell (2s2) and the next six electrons in
the 2p subshell (2p6).
Proceed to Period 3 (left to right direction). Place the next two electrons in the 3s subshell (3s2) and the last one electron in the
3p subshell (3p1).
The electron configuration of Aluminum is 1s22s22p63s23p1
 Exercise 2.8.2
Using Figure 2.8.2 as your guide, write the electron configuration of the atom that has 20 electrons
Answer
Start at Period 1 of Figure 2.8.2. Place two electrons in the 1s subshell (1s2).
Proceed to Period 2 (left to right direction). Place the next two electrons in the 2s subshell (2s2) and the next six electrons
in the 2p subshell (2p6).
Proceed to Period 3 (left to right direction). Place the next two electrons in the 3s subshell (3s2) and the next six electron in
the 3p subshell (3p6).
Proceed to Period 4. Place the remaining two electrons in the 4s subshell (4s2).
The electron configuration is 1s22s22p63s23p64s2
Summary
The arrangement of electrons in atoms is responsible for the shape of the periodic table. Electron configurations can be predicted
by the position of an atom on the periodic table
2.8: Electron Configurations and the Periodic Table is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by
LibreTexts.
Draw a Lewis electron dot symbol for a given atom.
In almost all cases, chemical bonds are formed by interactions of valence electrons in atoms. To facilitate our understanding of how
valence electrons interact, a simple way of representing those valence electrons would be useful.
A Lewis electron-dot symbol (or electron-dot symbol or a Lewis symbol) is a representation of the valence electrons of an atom
that uses dots around the symbol of the element. The number of dots equals the number of valence electrons in the atom. These
dots are arranged to the right and left and above and below the symbol, with no more than two dots on a side. (It does not matter
what order the positions are used.) For example, the electron-dot symbol for hydrogen is simply
H⋅ (2.9.1)
Because the side is not important, the electron-dot symbol could also be drawn as follows:
˙
H or ⋅H or H (2.9.2)
.
The electron-dot symbol for helium, with two valence electrons, is as follows:
He: (2.9.3)
By putting the two electrons together on the same side, we emphasize the fact that these two electrons are both in the 1s subshell;
this is the common convention we will adopt, although there will be exceptions later. The next atom, lithium, has an electron
configuration of 1s22s1, so it has only one electron in its valence shell. Its electron dot diagram resembles that of hydrogen, except
the symbol for lithium is used:
Li⋅ (2.9.4)
Beryllium has two valence electrons in its 2s shell, so its eelectron-dot symbol is like that of helium:
Be: (2.9.5)
The next atom is boron. Its valence electron shell is 2s22p1, so it has three valence electrons. The third electron will go on another
side of the symbol:
˙
Be: (2.9.6)
Again, it does not matter on which sides of the symbol the electron dots are positioned.
For carbon, there are four valence electrons, two in the 2s subshell and two in the 2p subshell. As usual, we will draw two dots
together on one side, to represent the 2s electrons. However, conventionally, we draw the dots for the two p electrons on different
sides. As such, the electron-dot symbol for carbon is as follows:
˙
⋅ C: (2.9.7)
With N, which has three p electrons, we put a single dot on each of the three remaining sides:
˙
⋅ N: (2.9.8)
.
For oxygen, which has four p electrons, we now have to start doubling up on the dots on one other side of the symbol. When
doubling up electrons, make sure that a side has no more than two electrons.
¨
⋅ O: (2.9.9)
.
Fluorine and neon have seven and eight dots, respectively:

¨:
:F (2.9.10)
.
¨
:Ne: (2.9.11)
. .
With the next element, sodium, the process starts over with a single electron because sodium has a single electron in its highest-
numbered shell, the n = 3 shell. By going through the periodic table, we see that the electron-dot symbol of atoms will never have
more than eight dots around the atomic symbol.
 Example 2.9.1:
What is the electron-dot symbol for each element?

a. aluminum
b. selenium
Solution
a. The valence electron configuration for aluminum is 3s23p1. So it would have three dots around the symbol for aluminum,
two of them paired to represent the 3s electrons:
˙
Al :
2. The valence electron configuration for selenium is 4s24p4. In the highest-numbered shell, the n = 4 shell, there are six
electrons. Its electron dot diagram is as follows:
˙
⋅ S e:
. .
 Exercise 2.9.1
What is the electron-dot symbol for each element?

a. phosphorus
b. argon
Answer
˙
⋅ P:
.
¨
:Ar:
. .
Summary
Lewis electron-dot symbols use dots to represent valence electrons around an atomic symbol.
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CHAPTER OVERVIEW
3: Ionic Compounds
When you think of bonding, you may not think of ions or molecules. Like most of us, you probably think of bonding between
people. Like people, molecules bond — and some bonds are stronger than others. It's hard to break up a mother and baby, or a
molecule made up of one oxygen and two hydrogen atoms! A chemical bond is a force of attraction between atoms or ions. Bonds
form when atoms share or transfer valence electrons. Valence electrons are the electrons in the outer energy level of an atom that
may be involved in chemical interactions. Valence electrons are the basis of all chemical bonds.
3.1: Ions
3.7: Ionic Bonds
3: Ionic Compounds is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
1
3.1: Ions
Describe how an ion is formed.
Distinguish the difference between the two types of ions.
Ions
As introduced previously, atoms contain a nucleus with neutrons and positively charged protons, surrounded by negatively charged
electrons. In an atom, the total number of electrons, negative charge, equals the total number of protons, positive charge, and
therefore, atoms are electrically neutral or uncharged. If an atom loses or gains electrons, it will become a positively or negatively
charged particle, called an ion. The loss of one or more electrons results in more protons than electrons and an overall positively
charged ion, called a cation. For example, a sodium atom with one less electron is a cation, Na+, with a +1 charge (Figure 3.1.1).
Figure 3.1.1 : A sodium atom (Na) has equal numbers of protons and electrons (11) and is uncharged. When it loses an electron, the
resulting sodium cation has one more proton (11) than electrons (10), giving it an overall positive one charge, Na+.
When an atom gains one or more electrons, it becomes a negatively charged anion, because there are more electrons than protons.
When chlorine gains one electron it forms a chloride ion, Cl–, with a –1 charge (Figures 3.1.2)
The names for positive and negative ions are pronounced CAT-eye-ons (cations) and ANN-eye-ons (anions), respectively.
Figure 3.1.2 : A chlorine atom (Cl) has equal numbers of protons and electrons (17) and is uncharged. When it gains an electron,
the resulting chlorine anion has one more electron (18) than protons (17), giving it an overall negative one charge, Cl–.
 Note Naming Ions
Cations are named using the element name plus "ion" to indicate it is charged. Anions are named by changing the element
name ending to "ide". For example, a magnesium ion is formed when neutral magnesium loses electrons and a fluoride ion is
formed when neutral fluorine gains electrons.
 Example 3.1.1
A calcium (Ca) atom loses two electrons and a sulfur (S) atom gains two electrons. Determine if the resulting ions are cations
or anions? Write the ion symbols for each.
Solution
When calcium (Z = 20) gains two electrons the resulting ion will have 18 electrons and 20 protons and therefore a charge of +2
(there are two more positive protons than negative electrons), it is a cation. The symbol for a calcium ion is Ca2+.
When sulfur (Z = 16) gains two electrons the resulting ion will have 18 electrons and 16 protons and therefore a charge of –2
(there are two more negative electrons than positive protons), it is an anion. The symbol for a sulfide ion is S2–.
Key Takeaways
Ions are formed when atoms gain or lose electrons.
Ions can be positively charged (cations) or negatively charged (anions).
Contributors
Lisa Sharpe Elles, University of Kansas
This page titled 3.1: Ions is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by Lisa Sharpe Elles.
Use the octet rule and electron configurations to determine if an atom will gain or lose electrons forming anions or cations.
Ions are formed when an atom, usually on the left side of the periodic table, reacts with and transfers one or more electrons to
another atom, usually on the right side of the periodic table. These electrons are usually lost from or gained into the valence shell,
or outermost energy level (shell). Why do some atoms lose electrons and others gain electrons? How can we predict the number of
electrons lost or gained? Which ions are stable and which ions do not form at all? These questions are best answered by looking at
electron configurations and considering what is called the octet rule, which states that atoms gain or lose electrons to form a stable,
noble gas configuration, i.e., a filled subshell containing eight electrons. Therefore, it is useful to take a closer look at electron
configurations to further illustrate ion formation and electron transfer between atoms.
The electron configuration for sodium shows that there are ten core electrons and one valence electron in the third energy level.
When sodium loses the single valence electron, forming the cation Na+, the electron configuration is now identical to that of neon,
a stable noble gas with eight valence electrons.
+ −
Na → Na +e
(3.2.1)
2 2 6 1 2 2 6
1s 2s 2p 3s 1s 2s 2p
Chlorine also has ten core electrons and valence electrons in the third energy level. However, chlorine has seven valence electrons,
one less than the noble gas argon, which has eight valence electrons. Thus, chlorine will gain one electron, forming the anion, Cl–,
and achieving a stable noble gas configuration.
− −
Cl + e → Cl
(3.2.2)
2 2 6 2 5 2 2 6 2 6
1s 2s 2p 3s 3p 1s 2s 2p 3s 3p
The octet rule and the periodic table can be used to predict what ions will form; main group elements on the left side of the periodic
table (metals in groups 1, 2, and 13) tend to lose electrons (form cations) to achieve the same electron configuration as the noble
gas just before them in the table. The number of electrons the atom will lose depends on what group the atom is in, i.e., how many
valence electrons it has. Main group elements on the right side of the periodic table (nonmetals in groups 15-17) will gain electrons
to achieve the same electron configuration as the noble gas just after them in the table. Again, the number of electrons the atom
will gain depends on the number of valence electrons it has and how many are needed to reach the filled subshell, eight electrons.
 Note Violation of the Octet Rule
It is not impossible to violate the octet rule. Consider sodium: in its elemental form, it has one valence electron and is stable. It
is rather reactive, however, and does not require a lot of energy to remove that electron to make the Na+ ion. We could remove
another electron by adding even more energy to the ion, to make the Na2+ ion. However, that requires much more energy than
is normally available in chemical reactions, so sodium stops at a 1+ charge after losing a single electron. It turns out that the
Na+ ion has a complete octet in its new valence shell, the n = 2 shell, which satisfies the octet rule. The octet rule is a result of
trends in energies and is useful in explaining why atoms form the ions that they do.
 Example 3.2.1
Write the electron configuration of aluminum atom (Z = 13) and underline the valence electrons. How many electrons are
gained/lost to form an aluminum ion? Write the symbol and the electron configuration for an aluminum ion.
Solution
The electron configuration of Al atom is 1s22s22p63s23p1. Aluminum has three valence electrons in the third energy level,
(3s23p1). The cation, Al3+, is formed when these three valence electrons are lost, leaving the configuration for the noble gas
neon, 1s22s22p6.
 Exercise 3.2.1
Write the electron configuration of oxygen atom (Z = 8) and underline the valence electrons. How many electrons are
gained/lost to form an oxide ion? Write the symbol and electron configuration for oxide ion.
Answer
The electron configuration of O atom is 1s22s22p4. Oxygen has six valence electrons in the second energy level, (2s22p4).
The anion O2− is formed when two electrons are gained in the valence shell. The resulting electron configuration,
1s22s22p6, which is also identical to the configuration for the noble gas neon.
This page titled 3.2: Ions and the Octet Rule is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by Lisa
Sharpe Elles.
Learning Objectives
Become familiar with the charge of some common ions.
Use the periodic table to predict ion charge.
In many cases, elements that belong to the same group (vertical column) on the periodic table form ions with the same charge
because they have the same number of valence electrons. Thus, as introduced previously, the periodic table becomes a tool for
remembering the charges on many ions. For example, all ions made from alkali metals, the first column on the periodic table, have
a +1 charge. Ions made from alkaline earth metals, the second group on the periodic table, have a +2 charge. On the other side of
the periodic table, the next-to-last column, the halogens, form ions having a −1 charge. Figure 3.3.1 shows how the charge on
many ions can be predicted by the location of an element on the periodic table.
Some elements, especially transition metals, can form ions with variable charges. Figure 3.3.1 shows the characteristic charges for
some of these ions. Notice that there is no simple pattern for transition metal ions (or for the larger main group elements) as there is
with the main group ions. This is because the transition metals have electrons in d subshell and do not follow the octet rule. In order
for an element such as iron (Fe) to achieve the same noble gas configuration of argon (Ar), it would need to lose 6 electrons in the
3d subshell and 2 electrons in the 4s subshell. An iron ion with a charge of +8 is not very likely, therefore, the octet rule is not
applicable to transition elements.
 Note
For a multiply-charged ion, the correct convention is to write the charge number first followed by the sign. For example, the
barium cation is written Ba2+, not Ba+2.
Figure 3.3.1 : Common ions formed by specific elements on the periodic table. The charge that a representative (main group
element) acquires when it becomes an ion is related to the location on the periodic table. Note that some metal atoms, specifically
the transition elements, commonly form ions with variable charges.
Example
Which of these ions is not likely to form?

a. Mg+
b. K+
Solution
(a) Mg is in Group 2A and has two valence electrons. It achieves octet by losing two electrons to form Mg2+ cation. Losing
only one electron to form Mg+ does not make an octet, hence, Mg+ is not likely to form.
Exercise
Which of these ions is not likely to form?
a. S3−
b. N3−
Answer
(a) S is in Group 6A and has six valence electrons. It achieves octet by gaining two electrons to form S2− anion. Gaining
three electrons to form S3−does not make it octet, hence, S3− is not likely to form.
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Describe ionization energy and electron affinity and how this relates to ion formation trends.
We have seen that elements often gain or lose enough electrons to achieve the valence electron configuration of the nearest noble
gas. Why is this so? In this section, we develop a more quantitative approach to predicting such reactions by examining periodic
trends in the energy changes that accompany ion formation.
Ionization Energy
Because atoms do not spontaneously lose electrons, energy is required to remove an electron from an atom to form a cation.
Chemists define the ionization energy (I E ) of an element as the amount of energy needed to remove an electron from the gaseous
atom A in its ground state. I E is therefore the energy required for the reaction:
+ −
A(g) → A (g) + e energy required=IE (3.4.1)
Because an input of energy is required, the ionization energy is always positive (I E > 0 ) for the reaction as written in Equation
3.4.1. Larger values of (I E ) mean that the electron is more tightly bound to the atom and thus, harder to remove. Typical units for
ionization energies are kilojoules/mole (kJ/mol) or electron volts (eV):
1 eV /atom = 96.49 kJ/mol (3.4.2)
As you move across a row on the periodic table, the ionization energies generally tend to increase. This means that elements on the
left side of the periodic table lose electrons more easily (requires less energy to remove an electron) than those on the right side of
the periodic table. The trend in ionization energy can be explained by considering the trend in atomic radius (explained in an earlier
chapter). As you move from left to right on the periodic table, the atomic size decreases and the electrostatic interactions between
the nucleus and valence electrons increases, which increases the energy required to remove electrons, thus the (I E ) increases.
Figure 3.4.1 : Ionization Energy Trends on the Periodic Table. (Left Figure) A Plot of Periodic Variation of First Ionization Energy
with Atomic Number for the First Six Rows of the Periodic Table. There is a decrease in ionization energy within a group (most
easily seen here for groups 1 and 18). (Right Figure) First Ionization Energies of the s-, p-, d-, and f-Block Elements
If you look closely at the trends in ionization energy, you will notice that there are some "exceptions" where you see a decrease in
energy rather than an increase. In periods 1 and 2, you can see this decrease in (I E ) between groups 2 and 3 and again between
groups 5 and 6. These variations in the trend can be further explained by looking closely at the electron configurations of the atoms
in question. As you move from magnesium to aluminum, one electron is added to the 3p subshell. This 3p electron is slightly
further from the nucleus (higher in energy) and is therefore, more easy to remove compared to the 3s electrons. The decrease
between phosphorous and sulfur occurs because the added electron in sulfur is the first to be paired in the p subshell. These two
electrons in the same p orbital repel each other, making the sulfur atom slightly less stable than would otherwise be expected, as is
true of all the group 16 elements. This electron is easier to remove because it will lead to more stability.
 Example 3.4.1: Lowest First Ionization Energy
Use their locations in the periodic table to predict which element has the lowest first ionization energy: Ca, K, Mg, Na, Rb, or
Sr.
Given: six elements
Asked for: element with lowest first ionization energy
Strategy:
Locate the elements in the periodic table. Based on trends in ionization energies across a row and down a column, identify the
element with the lowest first ionization energy.
Solution:
These six elements form a rectangle in the two far-left columns of the periodic table. Because we know that ionization energies
increase from left to right in a row and from bottom to top of a column, we can predict that the element at the bottom left of the
rectangle will have the lowest first ionization energy: Rb.
 Exercise 3.4.1: Highest First Ionization Energy
Use their locations in the periodic table to predict which element has the highest first ionization energy: As, Bi, Ge, Pb, Sb, or
Sn.
Answer
As
Electron Affinity
The electron affinity (EA) of an element A is defined as the energy change that occurs when an electron is added to a gaseous
atom or ion:
− −
A(g) + e → A (g) energy change=EA (3.4.3)
Unlike ionization energies, which are always positive for a neutral atom because energy is required to remove an electron, electron
affinities can be negative (energy is released when an electron is added), positive (energy must be added to the system to produce
an anion), or zero (the process is energetically neutral). This sign convention is consistent with a negative value corresponded to the
energy change for an exothermic process, which is one in which heat is released (Figure 3.4.2).
Figure 3.4.2 : Electron Affinity Trends. (Left) A Plot of Periodic Variation of Electron Affinity with Atomic Number for the First
Six Rows of the Periodic Table. Notice that electron affinities can be both negative and positive. from Robert J. Lancashire
(University of the West Indies). (Right) Electron Affinities (in kJ/mol) of the s-, p-, and d-Block Elements.
The chlorine atom has the most negative electron affinity of any element, which means that more energy is released when an
electron is added to a gaseous chlorine atom than to an atom of any other element:
− −
Cl(g) + e → Cl (g) EA = −346 kJ/mol (3.4.4)
In contrast, beryllium does not form a stable anion, so its effective electron affinity is
− −
Be(g) + e → Be (g) EA ≥ 0 (3.4.5)
In general, electron affinities of the main-group elements become less negative as we proceed down a column. This is because as
the energy level increases, the extra electrons enter orbitals that are increasingly far from the nucleus, and it is less easy to gain
extra electrons forming anions.
 Example 3.4.2: Contrasting Electron Affinities of Sb, Se, and Te
Based on their positions in the periodic table, which of Sb, Se, or Te would you predict to have the most negative electron
affinity?
Given: three elements
Asked for: element with most negative electron affinity
Strategy:
A. Locate the elements in the periodic table. Use the trends in electron affinities going down a column for elements in the
same group. Similarly, use the trends in electron affinities from left to right for elements in the same row.
B. Place the elements in order, listing the element with the most negative electron affinity first.
Solution:
We know that electron affinities become less negative going down a column (except for the anomalously low electron affinities
of the elements of the second row), so we can predict that the electron affinity of Se is more negative than that of Te. We also
know that electron affinities become more negative from left to right across a row, and that the group 15 elements tend to have
values that are less negative than expected. Because Sb is located to the left of Te and belongs to group 15, we predict that the
electron affinity of Te is more negative than that of Sb. The overall order is Se < Te < Sb, so Se has the most negative electron
affinity among the three elements.
 Exercise 3.4.2: Contrasting Electron Affinities of Rb, Sr, and Xe
Based on their positions in the periodic table, which of Rb, Sr, or Xe would you predict to most likely form a gaseous anion?
Answer
Rb
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Name monoatomic ions using the defined nomenclature rules.
After learning a few more details about the names of individual ions, you will be a step away from knowing how to name ionic
compounds. This section begins the formal study of nomenclature, the systematic naming of chemical compounds.
Naming Cations
The name of a monatomic cation is simply the name of the element followed by the word ion. Thus, Na+ is the sodium ion, Al3+ is
the aluminum ion, Ca2+ is the calcium ion, and so forth.
We have seen that some elements lose different numbers of electrons, producing ions of different charges. Iron, for example, can
form two cations, each of which, when combined with the same anion, makes a different ionic compound with unique physical and
chemical properties. Thus, we need a different name for each iron ion to distinguish Fe2+ from Fe3+. The same issue arises for other
ions with more than one possible charge.
There are two ways to make this distinction. In the simpler, more modern approach, called the stock system, an ion’s positive
charge is indicated by a roman numeral in parentheses after the element name, followed by the word ion. Thus, Fe2+ is called the
iron(II) ion, while Fe3+ is called the iron(III) ion. This system is used only for elements that form more than one common positive
ion. We do not call the Na+ ion the sodium(I) ion because (I) is unnecessary. Sodium forms only a 1+ ion, so there is no ambiguity
about the name sodium ion.
The second system, called the common system, is not conventional but is still prevalent and used in the health sciences. This
system recognizes that many metals have two common cations. The common system uses two suffixes (-ic and -ous) that are
appended to the stem of the element name. The -ic suffix represents the greater of the two cation charges, and the -ous suffix
represents the lower one. In many cases, the stem of the element name comes from the Latin name of the element. Table 3.5.1 lists
the elements that use the common system, along with their respective cation names.
Table 3.5.1 : Names of Some Cations
Element Charge Symbol Common System Name Stock System Name
2+ Cr2+ chromous ion chromium(II) ion

chromium
3+ Cr3+ chromic ion chromium(III) ion
1+ Cu+ cuprous ion copper(I) ion

copper
2+ Cu2+ cupric ion copper(II) ion
2+ Fe2+ ferrous ion iron(II) ion

iron
3+ Fe3+ ferric ion iron(III) ion
2+ Pb2+ plumbous ion lead(II) ion

lead
4+ Pb3+ plumbic ion lead(IV) ion
2+ Sn2+ stannous ion tin(II) ion

tin
4+ Sn4+ stannic ion tin(IV) ion
Naming Anions
The name of a monatomic anion consists of the stem of the element name, the suffix -ide, and then the word ion. Thus, as we have
already seen, Cl− is “chlor-” + “-ide ion,” or the chloride ion. Similarly, O2− is the oxide ion, Se2− is the selenide ion, and so forth.
Table 3.5.2 lists the names of some common monatomic ions.
Table 3.5.2 : Some Monatomic Anions
Element Charge Symbol Name
fluorine 1– F− fluoride ion
Element Charge Symbol Name
chlorine 1– Cl− chloride ion
bromine 1– Br− bromide ion
iodine 1– I− iodide ion
oxygen 2– O2− oxide ion
sulfur 2– S2− sulfide ion
phosphorous 3– P3− phosphide ion
nitrogen 3– N3− nitride ion
 Example 3.5.1
Name each ion.

a. Ca2+
b. S2−
c. SO32−
d. NH4+
e. Cu+
Answer a
the calcium ion
Answer b
the sulfide ion (from Table 3.5.2)
Answer c
the sulfite ion
Answer d
the ammonium ion
Answer e
the copper(I) ion or the cuprous ion (copper can form cations with either a 1+ or 2+ charge, so we have to specify which
charge this ion has
 Exercise 3.5.1
Name each ion.
a. Fe2+
b. Fe3+
c. SO42−
d. Ba2+
e. HCO3−
Answer a
the iron (II) or ferrous ion
Answer b
the iron (III) or ferric ion
Answer c
the sulfate ion
Answer d
the barium ion
Answer e
the bicarbonate ion or hydrogen carbonate ion
 Example 3.5.2
Write the formula for each ion.

a. the bromide ion
b. the phosphate ion
c. the cupric ion
d. the magnesium ion
Answer a
Br−
Answer b
PO43−
Answer c
Cu2+
Answer d
Mg2+
 Exercise 3.5.2
Write the formula for each ion.

a. the fluoride ion
b. the carbonate ion
c. the ferrous ion
d. the potassium ion
Answer a
F−
Answer b
CO32-
Answer c
Fe2+
Answer d
K+
 Note Chemistry Is Everywhere: Salt
The element sodium (part [a] in the accompanying figure) is a very reactive metal; given the opportunity, it will react with the
sweat on your hands and form sodium hydroxide, which is a very corrosive substance. The element chlorine (part [b] in the
accompanying figure) is a pale yellow, corrosive gas that should not be inhaled due to its poisonous nature. Bring these two
hazardous substances together, however, and they react to make the ionic compound sodium chloride (part [c] in the
accompanying figure), known simply as salt.
Figure 3.5.1 : Sodium + Chlorine = Sodium Chloride (a) Sodium is a very reactive metal. (b) Chlorine is a pale yellow, noxious
gas. (c) Together, sodium and chlorine make sodium chloride-salt-which is necessary for our survival. Source: Photo(opens in
new window) on the left courtesy of Greenhorn1. Photo(opens in new window) in the center courtesy of Benjah-bmm27, .
Photo on the right © Thinkstock.
Salt is necessary for life. Na+ ions are one of the main ions in the human body and are necessary to regulate the fluid balance
in the body. Cl− ions are necessary for proper nerve function and respiration. Both of these ions are supplied by salt. The taste
of salt is one of the fundamental tastes; salt is probably the most ancient flavoring known, and one of the few rocks we eat.
The health effects of too much salt are still under debate, although a 2010 report by the US Department of Agriculture
concluded that "excessive sodium intake…raises blood pressure, a well-accepted and extraordinarily common risk factor for
stroke, coronary heart disease, and kidney disease."US Department of Agriculture Committee for Nutrition Policy and
Promotion, Report of the Dietary Guidelines Advisory Committee on the Dietary Guidelines for Americans, accessed January
5, 2010. It is clear that most people ingest more salt than their bodies need, and most nutritionists recommend curbing salt
intake. Curiously, people who suffer from low salt (called hyponatria) do so not because they ingest too little salt but because
they drink too much water. Endurance athletes and others involved in extended strenuous exercise need to watch their water
intake so their body's salt content is not diluted to dangerous levels.
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Learning Objectives
To identify and name polyatomic ions.
Some ions consist of groups of atoms covalently bonded together and have an overall electric charge. Because these ions contain
more than one atom, they are called polyatomic ions. The structures, names, and formulas of some polyatomic ions are found in
the below figure and table.
Figure 3.6.1 : Polyatomic Ions Infographic

Polyatomic ions have defined formulas, names, and charges that cannot be modified in any way. Table 3.6.1 lists the ion names and
ion formulas of the most common polyatomic ions. For example, NO is the nitrate ion; it has one nitrogen atom and three oxygen
−
atoms and an overall −1 charge.

Table 3.6.1 : Common Polyatomic Ion Names and Formulas
Ion Name Ion Formula
hyddronium ion H3O+
ammonium ion NH4+
hydroxide ion OH−
cyanide ion CN−
carbonate ion CO32−
bicarbonate or hydrogen carbonate HCO3−
acetate ion C2H3O2− or CH3CO2−
Ion Name Ion Formula
nitrate ion NO3−
nitrite ion NO2−
sulfate ion SO42−
sulfite ion SO32−
phosphate ion PO43−
phosphite ion PO33−
Note that only two polyatomic ions in this table are cations, hydronium ion (H3O+) and ammonium ion (NH4+), the remaining
polyatomic ions are all negatively-charged and, therefore, are classified as anions. However, only two of these, the hydroxide ion
and the cyanide ion, are named using the "-ide" suffix that is typically indicative of negatively-charged ions. The remaining
polyatomic anions, which all contain oxygen, in combination with another non-metal, exist as part of a series in which the number
of oxygens within the polyatomic unit can vary. A single suffix, "-ide," is insufficient for distinguishing the names of the anions in
a related polyatomic series. Therefore, "-ate" and "-ite" suffixes are employed, in order to denote that the corresponding
polyatomic ions are part of a series. Additionally, these suffixes also indicate the relative number of oxygens that are contained
within the polyatomic ions. Note that all of the polyatomic ions whose names end in "-ate" contain one more oxygen than those
polyatomic anions whose names end in "-ite." Unfortunately, much like the common system for naming transition metals, these
suffixes only indicate the relative number of oxygens that are contained within the polyatomic ions. For example, both the nitrate
ion, symbolized as NO3−, and the sulfate ion, symbolized as SO42−, share an "-ate" suffix, however, the former contains three
oxygens, and the latter contains four. Additionally, both the nitrate ion and the sulfite ion contain three oxygens, but these
polyatomic ions do not share a common suffix. Unfortunately, the relative nature of these suffixes mandates that the ion
formula/ion name combinations of the polyatomic ions must simply be memorized.
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3.7: Ionic Bonds
Define an ionic bond, ionic compound, and electrostatic force
Recognize the complexity of three-dimensional ionic bond interactions involved in ionic compounds
Oppositely charged particles attract each other. This attractive force is often referred to as an electrostatic attraction. An ionic
bond is the electrostatic electrostatic attraction that holds ions together in an ionic compound. The strength of the ionic bond is
directly dependent upon the quantity of the charges and inversely dependent on the distance between the charged particles. A cation
with a 2+ charge will make a stronger ionic bond than a cation with a 1+ charge. A larger ion makes a weaker ionic bond because
of the greater distance between its electrons and the nucleus of the oppositely charged ion.
We will use sodium chloride as an example to demonstrate the nature of the ionic bond and how it forms. As you know, sodium is a
metal and loses its one valence electron to become a cation. Chlorine is a nonmetal and gains one electron in becoming an anion.
However, electrons cannot be simply "lost" to nowhere in particular. A more accurate way to describe what is happening is that a
single electron is transferred from the sodium atom to the chlorine atom as shown below.
The ionic bond is the attraction of the Na ion for the Cl ion. It is conventional to show show the cation without dots around the
+ −
symbol to emphasize that the original energy level that contained the valence electron is now empty. The anion is now shown with
a complete octet of electrons.
Ionic compounds are held together by attractive electrostatic interactions between cations and anions. In contrast to the simplified
electron transfer depicted above for sodium and chlorine, the cations and anions in ionic compounds are arranged in space to form
an extended three-dimensional array that maximizes the number of attractive electrostatic interactions and minimizes the number of
repulsive electrostatic interactions (Figure 3.7.1). In other words, each ion is attracted to many of its neighboring ions forming a
sodium chloride crystal or ionic solid.
Figure 3.7.1 : Ionic Bonding. The ionic compound NaCl forms when electrons from sodium atoms are transferred to chlorine
atoms. The resulting Na+ and Cl− ions form a three-dimensional solid that is held together by attractive electrostatic interactions.
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Write the chemical formula for a simple ionic compound based on the charges of the cations and anions in the compound.
In every ionic compound, the total number of positive charges of the cations equals the total number of negative charges of the
anions. Thus, ionic compounds are electrically neutral overall, even though they contain positive and negative ions. We can use this
observation to help us write the formula of an ionic compound. The formula of an ionic compound must have a ratio of ions such
that the numbers of positive and negative charges are equal.
Ionic Compounds Formed From Monoatomic Ions

Consider an Na atom in the presence of a Cl atom. The two atoms have these Lewis electron dot diagrams and electron
configurations:
¨
Na ⋅ ⋅ Cl :
. .
1 2 5
[N e] 3 s [N e] 3 s 3 p
For the Na atom to obtain an octet, it must lose an electron; for the Cl atom to obtain an octet, it must gain an electron. An electron
transfers from the Na atom to the Cl atom:
¨
Na ⋅ ↷ ⋅ Cl :
. .
resulting in two ions—the Na+ ion and the Cl− ion:

+ ¨ −
Na ⋅ :Cl :
. .
2 6
[N e] [N e] 3 s 3 p
Both species now have complete octets, and the electron shells are energetically stable. From basic physics, we know that opposite
charges attract. This is what happens to the Na+ and Cl− ions:
+ ¨ − + −
Na ⋅ + :Cl : → N a Cl or N aC l
. .
where we have written the final formula (the formula for sodium chloride) as per the convention for ionic compounds, without
listing the charges explicitly. As explained previously, the attraction between oppositely charged ions is called an ionic bond.
In electron transfer, the number of electrons lost must equal the number of electrons gained. We saw this in the formation of NaCl.
A similar process occurs between Mg atoms and O atoms, except in this case two electrons are transferred:
Magnesium donates two electrons to oxygen to empty its own orbital and fill oxygens, thus creating Mg2+ and O2-.
The two ions each have octets as their valence shell, and the two oppositely charged particles attract, making an ionic bond:
2+ ¨ 2− 2+ 2−
Mg + :O : Mg O or M gO
. .
What about when an Na atom interacts with an O atom? The O atom needs two electrons to complete its valence octet, but the Na
atom supplies only one electron:
¨
Na ⋅ ↷ ⋅ O :
.
The O atom still does not have an octet of electrons. What we need is a second Na atom to donate a second electron to the O atom:
Two sodium atoms donate one electron each to oxygen to empty their orbitals and fill oxygen's, thus creating 2 Na+ and O2-.
These three ions attract each other to form an overall neutrally charged ionic compound, which we write as Na2O. The need for the
number of electrons lost to be equal to the number of electrons gained explains why ionic compounds have the ratio of cations to
anions that they do. This is also required by the law of conservation of matter.
Example
3.8.1
With arrows, illustrate the transfer of electrons to form calcium chloride from Ca atoms and Cl atoms.
Solution
A Ca atom has two valence electrons, while a Cl atom has seven electrons. A Cl atom needs only one more to complete its
octet, while Ca atoms have two electrons to lose. We need two Cl atoms to accept the two electrons from one Ca atom. The
transfer process is as follows:
Calcium donates two electrons, one each going to a chlorine. This empties calcium's orbital and fills both of the chlorines'. This
creates Ca2+ and two Cl-.
The oppositely charged ions attract one another to make CaCl2.
Exercise
3.8.1
With arrows, illustrate the transfer of electrons to form potassium sulfide from K atoms and S atoms.
Answer
Two potassium atoms donate an electron to sulphur to fill sulphur's orbital and empty their own, thus creating two K+ and
one S2-. They ionically bond to form K2S.
For compounds in which the ratio of ions is not as obvious, the subscripts in the formula can be obtained by crossing charges: use
the absolute value of the charge on one ion as the subscript for the other ion. This method is shown schematically in Figure 3.3.2.
Figure 3.8.1 : Crossing charges. One method for obtaining subscripts in the empirical formula is by crossing charges.
When crossing charges, it is sometimes necessary to reduce the subscripts to their simplest ratio to write the empirical formula.
Consider, for example, the compound formed by Pb4+ and O2−. Using the absolute values of the charges on the ions as subscripts
gives the formula Pb2O4. This simplifies to its correct empirical formula PbO2. The empirical formula has one Pb4+ ion and two
O2− ions.
 Example 3.8.2: Predicting the Formula of an Ionic Compound
The gemstone sapphire (Figure 3.8.2) is mostly a compound of aluminum and oxygen that contains aluminum cations, Al3+,
and oxygen anions, O2−. What is the formula of this compound?
Figure 3.8.2 : Although pure aluminum oxide is colorless, trace amounts of iron and titanium give blue sapphire its
characteristic color. (credit: modification of work by Stanislav Doronenko)
Solution
Because the ionic compound must be electrically neutral, it must have the same number of positive and negative charges. Two
aluminum ions, each with a charge of 3+, would give us six positive charges, and three oxide ions, each with a charge of 2−,
would give us six negative charges. The formula would be Al2O3.
 Exercise 3.8.2
Predict the formula of the ionic compound formed between the sodium cation, Na+, and the sulfide anion, S2−.
Answer
Na2S
Ionic Compounds Formed From Polyatomic Ions

Many ionic compounds contain polyatomic ions as the cation, the anion, or both. As with simple ionic compounds, these
compounds must also be electrically neutral, so their formulas can be predicted by treating the polyatomic ions as discrete units.
We use parentheses in a formula to indicate a group of atoms that behave as a unit. For example, the formula for calcium
phosphate, one of the minerals in our bones, is Ca3(PO4)2. This formula indicates that there are three calcium ions (Ca2+) for every
two phosphate (PO ) groups. The PO
3 −
4
3 −
4
groups are discrete units, each consisting of one phosphorus atom and four oxygen
atoms, and having an overall charge of 3−. The compound is electrically neutral, and its formula shows a total count of three Ca,
two P, and eight O atoms.
 Example 3.8.3: Predicting the Formula of a Compound with a Polyatomic Anion
Baking powder contains calcium dihydrogen phosphate, an ionic compound composed of the ions Ca2+ and H 2
−
PO4 . What is
the formula of this compound?
Solution
The positive and negative charges must balance, and this ionic compound must be electrically neutral. Thus, we must have two
negative charges to balance the 2+ charge of the calcium ion. This requires a ratio of one Ca2+ ion to two H PO ions. We
2
−
4
designate this by enclosing the formula for the dihydrogen phosphate ion in parentheses and adding a subscript 2. The formula
is Ca(H2PO4)2.
 Exercise 3.8.3
Write the chemical formula for an ionic compound composed of each pair of ions.
a. the magnesium ion and the carbonate ion
b. the aluminum ion and the acetate ion
Answer a:
Mg2+ and CO32- = MgCO3
Answer b:
Al3+ and C2H3O2- = Al(C2H3O2)3
Formula Unit
Ionic compounds exist as alternating positive and negative ions in regular, three-dimensional arrays called crystals (Figure 3.8.3).
As you can see, there are no individual NaCl “particles” in the array; instead, there is a continuous lattice of alternating sodium
and chloride ions. However, we can use the ratio of sodium ions to chloride ions, expressed in the lowest possible whole numbers
or simplest formula, as a way of describing the compound. In the case of sodium chloride, the ratio of sodium ions to chloride ions,
expressed in lowest whole numbers, is 1:1, so we use NaCl (one Na symbol and one Cl symbol) to represent the compound. Thus,
NaCl is the chemical formula for sodium chloride, which is a concise way of describing the relative number of different ions in the
compound. A macroscopic sample is composed of myriads of NaCl pairs; each individual pair called a formula unit. Although it is
convenient to think that NaCl crystals are composed of individual NaCl units, Figure 3.8.3 shows that no single ion is exclusively
associated with any other single ion. Each ion is surrounded by ions of opposite charge.
Figure 3.8.3 : A Sodium Chloride Crystal. A crystal contains a three-dimensional array of alternating positive and negative ions.
The precise pattern depends on the compound. A crystal of sodium chloride, shown here, is a collection of alternating sodium and
chlorine ions.
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Write the names for ionic compounds by recognizing and naming the ions in the formula unit.
Ionic compounds are named using the formula unit and by following some important conventions. First, the name of the cation is
written first followed by the name of the anion. Because most metals form cations and most nonmetals form anions, formulas
typically list the metal first and then the nonmetal. Second, charges are not included in the name (or the formula). Remember that
in an ionic compound, the component species are ions, not neutral atoms, even though the formula does not contain charges. The
proper formula for an ionic compound will show how many of each ion is needed to balance the total positive and negative
charges; the name does not need to include indication of this ratio.
There are two main types of ionic compound with different naming rules for each; Type I: compounds containing cations of main
group elements and Type II: compounds containing cations of variable charge (generally transition metals). Below we will look at
examples of each type to learn the rules for naming.
Type I Ionic Compounds

Cations of main group elements do not have variable charges and are the simply named by placing the name of the cation first,
followed by the name of the anion, and dropping the word ion from both parts. For example, what is the name of the compound
whose formula is Ba(NO ) ?3 2
The compound’s name does not need to indicate that there are two nitrate ions for every barium ion. You must determine the ratio
of ions in the formula unit by balancing the positive and negative charges.
Type II Ionic Compounds

Some metals can form cations with variable charges. When naming a formula for an ionic compound whose cation can have more
than one possible charge, you must first determine the charge on the cation before identifying its correct name. For example,
consider FeCl and FeCl . In the first compound, the iron ion has a 2+ charge because there are two Cl ions in the formula (1−
2 3
−
charge on each chloride ion). In the second compound, the iron ion has a 3+ charge, as indicated by the three Cl ions in the −
formula. These are two different compounds that need two different names. By the stock system, the names are iron(II) chloride and
iron(III) chloride. If we were to use the stems and suffixes of the common system, the names would be ferrous chloride and ferric
chloride, respectively.
 Ionic Compounds in Your Cabinets
Every day you encounter and use a large number of ionic compounds. Some of these compounds, where they are found, and
what they are used for are listed in Table 3.9.1. Look at the label or ingredients list on the various products that you use during
the next few days, and see if you run into any of those in this table, or find other ionic compounds that you could now name or
write as a formula.
Table 3.9.1 : Everyday Ionic Compounds
Ionic Compound Name Use
NaCl sodium chloride ordinary table salt
KI potassium iodide added to “iodized” salt for thyroid health
NaF sodium fluoride ingredient in toothpaste
baking soda; used in cooking (and in

NaHCO3 sodium bicarbonate
antacids)
Na2CO3 sodium carbonate washing soda; used in cleaning agents
NaOCl sodium hypochlorite active ingredient in household bleach
CaCO3 calcium carbonate ingredient in antacids
Mg(OH)2 magnesium hydroxide ingredient in antacids
Al(OH)3 aluminum hydroxide ingredient in antacids
NaOH sodium hydroxide lye; used as drain cleaner
K3PO4 potassium phosphate food additive (many purposes)
MgSO4 magnesium sulfate added to purified water
Na2HPO4 sodium hydrogen phosphate anti-caking agent; used in powdered products
Na2SO3 sodium sulfite preservative
As you practice naming compounds, use Figure 3.9.1 as a guide.
Figure 3.9.1 : A Guide to Naming Simple Ionic Compounds. Follow these steps to name a simple ionic compound.
Identify the cation name and the anion name. If the cation can have more than one possible charge, either use the Stock system
name of the cation and name of the anion, or use the stem of the cation name and -ic/-ous and the name of the anion. Examples of
this would be FeCl2, which is iron(II) chloride of ferrous chloride, CuSO4, which is copper(II) sulfate or cupric sulfate, and
Cr2O3, which is chromium(III) oxide or chromic oxide. If the cation can not have more than one possible charge, use the name of
the cation and the name of the anion. Examples of this would be KBr, which is potassium bromide, NaNO3, which is sodium
nitrate, and (NH4)2S, which is ammonium sulfide.
 Example 3.9.3
Name each ionic compound, using both Stock and common systems if necessary.
a. Ca3(PO4)2
b. (NH4)2Cr2O7
c. KCl
d. CuCl
e. SnF2
Answer a
calcium phosphate
Answer b
ammonium dichromate (the prefix di- is part of the name of the anion)
Answer c
potassium chloride
Answer d
copper(I) chloride or cuprous chloride
Answer e
tin(II) fluoride or stannous fluoride
 Exercise 3.9.3
Name each ionic compound, using both Stock and common systems if necessary.
a. ZnBr2
b. Fe(NO3)3
c. Al2O3
d. CuF2
e. AgF
Answer a
zinc bromide
Answer b
iron (III) nitrate or ferric nitrate
Answer c
aluminum oxide
Answer d
copper (II) fluoride or cupric fluoride
Answer e
silver fluoride
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Describe the basic physical properties of ionic compounds.
The figure below shows just a few examples of the color and brilliance of naturally occurring ionic crystals. The regular and
orderly arrangement of ions in the crystal lattice is responsible for the various shapes of these crystals, while transition metal ions
give rise to the colors.
Figure 3.10.1 : In nature, the ordered arrangement of ionic solids gives rise to beautiful crystals. (A) Amethyst - a form of quartz,
SiO2, whose purple color comes from iron ions. (B) Cinnabar - the primary ore of mercury is mercury (II) sulfide, HgS (C) Azurite -
a copper mineral, Cu3(CO3)2(OH)2. (D) Vanadinite - the primary ore of vanadium, Pb3(VO4)3Cl.
Melting Points
Because of the many simultaneous attractions between cations and anions that occur, ionic crystal lattices are very strong. The
process of melting an ionic compound requires the addition of large amounts of energy in order to break all of the ionic bonds in
the crystal. For example, sodium chloride has a melting temperature of about 800 oC. As a comparison, the molecular compound
water melts at 0 °C.
Shattering
Ionic compounds are generally hard, but brittle. Why? It takes a large amount of mechanical force, such as striking a crystal with a
hammer, to force one layer of ions to shift relative to its neighbor. However, when that happens, it brings ions of the same charge
next to each other (see below). The repulsive forces between like-charged ions cause the crystal to shatter. When an ionic crystal
breaks, it tends to do so along smooth planes because of the regular arrangement of the ions.
Figure 3.10.2 : (A) The sodium chloride crystal is shown in two dimensions. (B) When struck by a hammer, the negatively-charged
chloride ions are forced near each other and the repulsive force causes the crystal to shatter.
Conductivity
Another characteristic property of ionic compounds is their electrical conductivity. The figure below shows three experiments in
which two electrodes that are connected to a light bulb are placed in beakers containing three different substances.
Figure 3.10.3 : (A) Distilled water does not conduct electricity. (B) A solid ionic compound also does not conduct. (C) A water
solution of an ionic compound conducts electricity well.
In the first beaker, distilled water does not conduct a current because water is a molecular compound. In the second beaker, solid
sodium chloride also does not conduct a current. Despite being ionic and thus composed of charged particles, the solid crystal
lattice does not allow the ions to move between the electrodes. Mobile charged particles are required for the circuit to be complete
and the light bulb to light up. In the third beaker, the NaCl has been dissolved into the distilled water. Now the crystal lattice has
been broken apart and the individual positive and negative ions can move.
 Example 3.10.1
Write the dissociation equation of solid NaCl in water.
Solution
NaCl(s) → Na+(aq) + Cl–(aq)
 Exercise 3.10.1
Write the dissociation equation of solid NH4NO3 in water.
Answer
NH4NO3(s) → NH4+(aq) + NO3–(aq)
Key Takeaways
Ionic compounds have high melting points.
Ionic compounds are hard and brittle.
Ionic compounds dissociate into ions when dissolved in water.
Solutions of ionic compounds and melted ionic compounds conduct electricity, but solid materials do not.
An ionic compound can be identified by its chemical formula: metal + nonmetal or polyatomic ions.
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To identify H+ as an acid and OH– as a base.
You may have some idea, from your day-to-day experiences, of some chemical substances that are considered acids or bases.
Generally, a compound that is sour is recognized as being an acid. Some familiar acids may include citric acid, which is a molecule
found in citrus fruits such as lemons and limes, and acetic acid, the molecule that makes up vinegar. Bases, on the other hand,
include chemicals such as sodium bicarbonate (baking soda), which is bitter-tasting, and sodium hydroxide, which is found in
cleaning substances and is not recommended for ingestion.
More details about acids, bases, and the reactions they undergo will be discussed later in this text. However, because you have just
learned about ions and ionic compounds, it is worth pointing out two important ions that are used to identify and distinguish if a
substance is acidic or basic; hydrogen ions, H , and hydroxide ions, OH . In fact, one definition of acids and bases states that an
+ −
acid will produce H when dissolved in water and a base will produce a OH when dissolved in water.
+ −
Ionic compounds that are basic are easily recognized because the hydroxide ion is part of the formula and name. Some common
examples are sodium hydroxide, NaOH, and calcium hydroxide, Ca(OH) . When dissolved in water, sodium hydroxide will split
2
into its constituent ions, sodium ions (Na ) and hydroxide ions (OH ) in a 1:1 ratio. However, according to it's chemical formula,
+ −
calcium hydroxide will produce two hydroxide ions for every one calcium ion, a 1:2 ratio.
Compounds that produce hydrogen ions in water contain one or more hydrogen ions in the chemical formula and usually have
special names to help recognize them as acids. Hydrochloric acid (HCl), nitric acid (HNO ), and carbonic acid (H CO ) are all
3 2 3
acids. HCl and HNO each dissolve in water producing a H and an anion (chloride and nitrate respectively). As indicated by the
3
+
formula for carbonic acid there are two H for every one carbonate ion. The below table lists some common acids. See if you can
+
determine the ratio of H to anions produced when these compounds are dissolved in water.
+
Table 3.11.1 Common Acids and Their Anions

Acid Name Acid Formula Anion Name Anion Formula
acetic acid CH COOH

3
acetate ion CH COO
3
−
carbonic acid H CO
2 3
bicarbonate ion HCO
−
3
carbonate ion CO
2 −
3
hydrobromic acid HBr bromide ion Br

−
nitric acid HNO

3
nitrate ion NO
−
3
nitrous acid HNO

2
nitrous ion NO
−
2
phosphoric acid H PO
3 4
dihydrogen phosphate ion H PO
2
−
4
hydrogen phosphate ion HPO

2 −
4
phosphate ion PO
3 −
4
sulfuric acid H SO
2 4
hydrogen sulfate ion HSO
−
4
sulfate ion SO
2 −
4
sulfurous acid H SO
2 3
hydrogen sulfite ion HSO
−
3
sulfite ion SO
2 −
3
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CHAPTER OVERVIEW
4: Molecular Compounds
4.1: Covalent Bonds
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1
4.1: Covalent Bonds
Describe how covalent bonds form using the octet rule.
Formation of Covalent Bonds

Nonmetal atoms frequently form covalent bonds with other nonmetal atoms. Covalent bonds are formed between two atoms when
both have similar tendencies to attract electrons to themselves (i.e., when both atoms have identical or fairly similar ionization
energies and electron affinities). For example, two hydrogen atoms bond covalently to form an H2 molecule; each hydrogen atom
in the H2 molecule has two electrons stabilizing it, giving each atom the same number of valence electrons as the noble gas He.
The bond in a hydrogen molecule, measured as the distance between the two nuclei, is about 7.4 × 10−11 m, or 74 picometers (pm;
1 pm = 1 × 10−12 m). This particular bond length represents the lowest potential energy state of two hydrogen atoms and is a
balance between several forces: the attractions between oppositely charged electrons and nuclei, the repulsion between two
negatively charged electrons, and the repulsion between two positively charged nuclei.
Figure 4.1.1 : Attractive and Repulsive Interactions between Electrons and Nuclei in the Hydrogen Molecule. Electron–electron and
proton–proton interactions are repulsive; electron–proton interactions are attractive. At the observed bond distance, the repulsive
and attractive interactions are balanced.
A plot of the potential energy of the system as a function of the internuclear distance (Figure 4.1.2) shows that energy decreases as
two hydrogen atoms move toward each other. Starting on the far right, we have two separate hydrogen atoms with a particular
potential energy, indicated by the red line. Along the x-axis is the distance between the two atoms. As the two atoms approach each
other (moving left along the x-axis), their valence orbitals (1s) begin to overlap. The single electrons on each hydrogen atom then
interact with both atomic nuclei, occupying the space around both atoms. The strong attraction of each shared electron to both
nuclei stabilizes the system, and the potential energy decreases as the bond distance decreases. If the atoms continue to approach
each other, the positive charges in the two nuclei begin to repel each other, and the potential energy increases.
Figure 4.1.2 : The interaction of two hydrogen atoms changes as a function of distance. The energy of the system changes as the
atoms interact. The lowest (most stable) energy occurs at a distance of 74 pm, which is the bond length observed for the H2
molecule.
Lewis Structures
Chemists frequently use Lewis structures to represent covalent bonding in molecular substances. For example, the Lewis symbols
of two separate hydrogen atoms are as follows:
The Lewis structures of two hydrogen atoms sharing electrons looks like this:
We can use circles to show that each H atom has two electrons around the nucleus, completely filling each atom’s valence shell:
Because each H atom has a filled valence shell, this bond is stable, and we have made a diatomic hydrogen molecule. For
simplicity’s sake, it is common to represent the covalent bond with a dash, instead of with two dots:
Because two atoms are sharing one pair of electrons, this covalent bond is called a single bond. As another example, consider
fluorine. F atoms have seven electrons in their valence shell:
These two atoms can do the same thing that the H atoms did; they share their unpaired electrons to make a covalent bond.
Note that each F atom has a complete octet around it now:
We can also write this using a dash to represent the shared electron pair:
You will notice that there are two different types of electrons in the fluorine diatomic molecule. The bonding electron pair makes
the covalent bond. Each F atom has three other pairs of electrons that do not participate in the bonding; they are called lone pair
electrons. Each F atom has one bonding pair and three lone pairs of electrons.
Diatomic Molecules
Hydrogen (H ) and fluorine (F ) are both described as diatomic molecules. These elements and others (see Table 4.1.1) exist
2 2
naturally as molecules rather than as individual atoms. It is important to note that the names of these elements represent molecules
and not individual atoms. When describing a single atom rather than a molecule, the word atom is used.
Table 4.1.1 : Elements That Exist as Diatomic Molecules
Hydrogen (H )
2
Oxygen (O )2
Nitrogen (N ) 2
Fluorine (F ) 2
Chlorine (Cl )
2
Bromine (Br )
2
Iodine (I )
2
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Learning Objectives
Predict the number of covalent bonds formed based on the elements involved and their position on the periodic table.
Describe the important exceptions to the octet rule.
Diatomic molecules such as hydrogen (H ), chlorine (Cl ), fluorine (F ), etc. containing covalent bonds between two of the same
2 2 2
type of atom are only a few examples of the vast number of molecules that can form. Two different atoms can also share electrons
and form covalent bonds. For example, water, (H O ), has two covalent bonds between a single oxygen atom and two hydrogen
2
atoms. Ammonia, (NH , is a central nitrogen atom bonded to three hydrogen atoms. Methane, (CH , is a single carbon atom
3 4
covalently bonded to four hydrogen atoms. In these examples the central atoms form different numbers of bonds to hydrogen atoms
in order to complete their valence subshell and form octets.
Figure 4.2.4 : 3D molecule examples. From left to right: water molecule, ammonia molecule, and methane molecule
How Many Covalent Bonds Are Formed?

The number of bonds that an atom can form can often be predicted from the number of electrons needed to reach an octet (eight
valence electrons); this is especially true of the nonmetals of the second period of the periodic table (C, N, O, and F). For example,
each atom of a group 14 element has four electrons in its outermost shell and therefore requires four more electrons to reach an
octet. These four electrons can be gained by forming four covalent bonds, as illustrated here for carbon in CCl4 (carbon
tetrachloride) and silicon in SiH4 (silane). Because hydrogen only needs two electrons to fill its valence shell, it is an exception to
the octet rule and only needs to form one bond. The transition elements and inner transition elements also do not follow the octet
rule since they have d and f electrons involved in their valence shells.
Group 15 elements such as nitrogen have five valence electrons in the atomic Lewis symbol: one lone pair and three unpaired
electrons. To obtain an octet, these atoms form three covalent bonds, as in NH3 (ammonia). Oxygen and other atoms in group 16
obtain an octet by forming two covalent bonds:
The number of electrons required to obtain an octet determines the number of covalent bonds an atom can form. This is
summarized in the table below. In each case, the sum of the number of bonds and the number of lone pairs is 4, which is equivalent
to eight (octet) electrons.
Table showing 4 different atoms, each of their number of bonds, and each of their number of lone pairs.
Atom (Group number) Number of Bonds Number of Lone Pairs
Carbon (Group 14) 4 0
Atom (Group number) Number of Bonds Number of Lone Pairs
Nitrogen (Group 15) 3 1
Oxygen (Group 16) 2 2
Fluorine (Group 17) 1 3
Because hydrogen only needs two electrons to fill its valence shell, it follows the duet rule. Hydrogen only needs to form one bond
to complete a duet of electrons. This is the reason why H is always a terminal atom and never a central atom.
 Example 4.2.1
Examine the Lewis structure of OF2 below. Count the number of bonds formed by each element. Based on the element's
location in the periodic table, does it correspond to the expected number of bonds shown in Table 4.1? Does the Lewis
structure below follow the octet rule?
Solution
Yes. F (group 7A) forms one bond and O (group 6A) forms 2 bonds. Each atom is surrounded by 8 electrons. This structure
satisfies the octet rule.
 Exercise 4.2.1
Examine the Lewis structure of NCl3 below. Count the number of bonds formed by each element. Based on the element's
location in the periodic table, does it correspond to the expected number of bonds shown in Table 4.1? Does the Lewis
structure below follow the octet rule?
Answer
Both Cl and N form the expected number of bonds. Cl (group 7A) has one bond and 3 lone pairs. The central atom N
(group 5A) has 3 bonds and one lone pair. Yes, the Lewis structure of NCl3 follows the octet rule.
Octet Rule Exceptions

As important and useful as the octet rule is in chemical bonding, there are many covalent molecules with central atoms that do not
have eight electrons in their Lewis structures. This does not mean that the octet rule is useless—quite the contrary. As with many
rules, there are exceptions, or violations. These molecules fall into three categories:
Odd-electron molecules have an odd number of valence electrons, and therefore have an unpaired electron.
Electron-deficient (diminished octet) molecules have a central atom that has fewer electrons than needed for a noble gas
configuration.
Expanded octet (hypervalent) molecules have a central atom that has more electrons than needed for a noble gas configuration.
Odd-electron molecules
Although they are few, some stable compounds, often called free radicals, have an odd number of electrons in their valence shells.
With an odd number of electrons, at least one atom in the molecule will have to violate the octet rule. Examples of stable, odd-
electron molecules are NO, NO , and ClO . The Lewis electron dot diagram for NO, a compound produced in internal
2 2
combustion engines when oxygen and nitrogen react at high temperatures, is as follows:
As you can see, the nitrogen and oxygen share four electrons between them. The oxygen atom has an octet of electrons but the
nitrogen atom has only seven valence electrons, two electrons in the double bond, one lone pair, and one additional lone electron.
Although NO is a stable compound, it is very chemically reactive, as are most other odd-electron compounds.
Electron-deficient molecules
These stable compounds have less than eight electrons around an atom in the molecule, i.e. they have less than an octet. The most
common examples are the covalent compounds of beryllium and boron. For example, beryllium can form two covalent bonds,
resulting in only four electrons in its valence shell:
Boron commonly makes only three covalent bonds, resulting in only six valence electrons around the B atom. A well-known
example is BF :3
Expanded Octet Molecules

Elements in the second period of the periodic table (n = 2) can accommodate only eight electrons in their valence shell orbitals
because they have only four valence orbitals (one 2s and three 2p orbitals). Elements in the third and higher periods (n ≥ 3) have
more than four valence orbitals and can share more than four pairs of electrons with other atoms because they have empty d orbitals
in the same shell. Molecules formed from these elements have expanded octets and are sometimes called hypervalent molecules.
Phosphorous pentachloride shares five pairs of electrons for a total of ten electrons in the valence shell.
In some expanded octet molecules, such as IF5 and XeF4, some of the electrons in the outer shell of the central atom are lone pairs:
 Example 4.2.2
Identify each violation to the octet rule by drawing a Lewis electron dot diagram.
a. ClO
b. SF 6
Solution
1. With one Cl atom and one O atom, this molecule has 6 + 7 = 13 valence electrons, so it is an odd-electron molecule. A
Lewis electron dot diagram for this molecule is as follows:
2. In SF , the central S atom makes six covalent bonds to the six surrounding F atoms, so it is an expanded valence shell
6
molecule. Its Lewis electron dot diagram is as follows:
 Exercise 4.2.2: Xenon Difluoride
Identify the violation to the octet rule in XeF by drawing a Lewis electron dot diagram.
2
Answer
The Xe atom has an expanded valence shell with more than eight electrons around it.

1. How is a covalent bond formed between two atoms?
2. How does covalent bonding allow atoms in group 6A to satisfy the octet rule?
Answers
1. Covalent bonds are formed by two atoms sharing electrons.
2. The atoms in group 6A make two covalent bonds.
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7.3: Lewis Symbols and Structures by OpenStax is licensed CC BY 4.0. Original source: https://openstax.org/details/books/chemistry-2e.
9.6: Violations of the Octet Rule by Anonymous is licensed CC BY-NC-SA 3.0. Original source:
Identify when a multiple bond (double or triple) is needed to complete an octet.
The sharing of a pair of electrons represents a single covalent bond, usually just referred to as a single bond. However, in many
molecules atoms attain complete octets by sharing more than one pair of electrons between them:
Two electron pairs shared a double bond
Three electron pairs shared a triple bond
Because each nitrogen contains 5 valence electrons, they need to share 3 pairs to each achieve a valence octet. N2 is fairly inert, due
to the strong triple bond between the two nitrogen atoms.
In addition to nitrogen and oxygen, carbon will also commonly form multiple bonds to complete valence octets. Additional
examples involving these three atoms are shown below.
A double bond is formed between the carbon and oxygen atoms in CH2O (formaldehyde) and between the two carbon atoms in
C2H4 (ethylene):
A triple bond is formed between carbon and oxygen in carbon monoxide (CO) and between carbon and nitrogen in the cyanide ion
(CN–):
 Example 4.3.1: Writing Lewis Structures

NASA’s Cassini-Huygens mission detected a large cloud of toxic hydrogen cyanide (HCN) on Titan, one of Saturn’s moons.
Titan also contains ethane (H3CCH3), acetylene (HCCH), and ammonia (NH3). What are the Lewis structures of these
molecules?
Solution
Calculate the number of valence electrons.
HCN: (1 × 1) + (4 × 1) + (5 × 1) = 10
H3CCH3: (1 × 3) + (2 × 4) + (1 × 3) = 14
HCCH: (1 × 1) + (2 × 4) + (1 × 1) = 10
NH3: (5 × 1) + (3 × 1) = 8
Draw a skeleton and connect the atoms with single bonds. Remember that H is never a central atom:
Where needed, distribute electrons to the terminal atoms:
HCN: six electrons placed on N

H3CCH3: no electrons remain
HCCH: no terminal atoms capable of accepting electrons
NH3: no terminal atoms capable of accepting electrons
Where needed, place remaining electrons on the central atom:
HCN: no electrons remain

H3CCH3: no electrons remain
HCCH: four electrons placed on carbon
NH3: two electrons placed on nitrogen
Where needed, rearrange electrons to form multiple bonds in order to obtain an octet on each atom:
HCN: form two more C–N bonds
H3CCH3: all atoms have the correct number of electrons
HCCH: form a triple bond between the two carbon atoms
NH3: all atoms have the correct number of electrons
 Exercise 4.3.1
Both carbon monoxide, CO, and carbon dioxide, CO2, are products of the combustion of fossil fuels. Both of these gases also
cause problems: CO is toxic and CO2 has been implicated in global climate change. What are the Lewis structures of these two
molecules?
Answer
4.3: Multiple Covalent Bonds is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
4.6: Covalent Bonds- Shared Electron Pairs is licensed CC BY-NC-SA 4.0.
Describe the difference between a covalent bond and a coordinate covalent bond.
Identify molecules that form coordinate covalent bonds.
Remember when you were younger, and were told to share your favorite toy with your brother, sister, or friend? You probably
didn't want to share, but did anyway. It likely turned out that you had more fun playing with the toy together than if you had kept it
to yourself. Atoms often share electrons with other atoms that have nothing to contribute to the situation forming a coordinate
covalent bond; the end result is a new structure.
Coordinate Covalent Bonds

Each of the covalent bonds that we have looked at so far has involved each of the atoms that are bonding contributing one of the
electrons to the shared pair. There is an alternate type of covalent bond in which one of the atoms provides both of the electrons in a
shared pair. Carbon monoxide, CO, is a toxic gas that is released as a byproduct during the burning of fossil fuels. The bonding
between the C atom and the O atom can be thought of in the following procession:
Figure 4.4.2 : Formation of a CO double bond (incorrect structure). (Credit: Joy Sheng; Source: CK-12 Foundation; License: CC
BY-NC 3.0(opens in new window))
At this point, a double bond has formed between the two atoms, with each atom providing one of the electrons to each bond. The
oxygen atom now has a stable octet of electrons, but the carbon atom only has six electrons and is unstable. This situation is
resolved if the oxygen atom contributes one of its lone pairs in order to make a third bond with the carbon atom.
Figure 4.4.3 : Correct CO structure. (Credit: Joy Sheng; Source: CK-12 Foundation; License: CC BY-NC 3.0(opens in new
window))
The carbon monoxide molecule is correctly represented by a triple covalent bond between the carbon and oxygen atoms. One of the
bonds formed is a coordinate covalent bond, a covalent bond in which one of the atoms contributes both of the electrons in the
shared pair. Once formed, a coordinate covalent bond is the same as any other covalent bond. It is not as if the two conventional
bonds in the CO molecule are stronger or different in any other way than the coordinate covalent bond.
Electron-deficient molecules, like BF , are very reactive and will often combine with other molecules forming coordinate covalent
3
bonds. The central boron atom in BF does not have eight electrons, and is therefore very reactive. It can readily combine with a
3
molecule containing a central atom with a lone pair of electrons. For example, NH reacts with BF because the lone pair on
3 3
nitrogen can be shared with the boron atom:
Summary
Coordinate covalent bonds can form when one atom provides a lone pair of electrons to the bond.
Coordinate covalent bonds are as strong as other covalent bonds.
Review
1. Where does the third covalent bond in the CO molecule come from?
2. Why is the incorrect structure for CO above wrong?
3. Are coordinate covalent bonds stronger or weaker than regular covalent bonds?
4.4: Coordinate Covalent Bonds is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
9.8: Coordinate Covalent Bond by CK-12 Foundation is licensed CK-12. Original source: https://flexbooks.ck12.org/cbook/ck-12-
chemistry-flexbook-2.0/.
Compare the properties of ionic and molecular compounds.
The physical state and properties of a particular compound depend in large part on the type of chemical bonding it displays.
Molecular compounds, sometimes called covalent compounds, display a wide range of physical properties due to the different
types of intermolecular attractions such as different kinds of polar interactions. The melting and boiling points of molecular
compounds are generally quite low compared to those of ionic compounds. This is because the energy required to disrupt the
intermolecular forces (discussed further in a later chapter) between molecules is far less than the energy required to break the ionic
bonds in a crystalline ionic compound. Since molecular compounds are composed of neutral molecules, their electrical conductivity
is generally quite poor, whether in the solid or liquid state. Ionic compounds do not conduct electricity in the solid state because of
their rigid structure, but conduct well when either molten or dissolved into a solution. The water solubility of molecular compounds
is variable and depends primarily on the type of intermolecular forces involved. Substances that exhibit hydrogen bonding or
dipole-dipole forces are generally water soluble, whereas those that exhibit only London dispersion forces are generally insoluble.
Most, but not all, ionic compounds are quite soluble in water. The table below summarizes some of the differences between ionic
and molecular compounds.
Table 4.5.1 : Comparison of Ionic and Molecular Compounds
Property Ionic Compounds Molecular Compounds
Type of elements Metal and nonmetal Nonmetals only
Covalent - sharing of pair(s) of electrons

Bonding Ionic - transfer of electron(s) between atoms
between atoms
Representative unit Formula unit Molecule
Physical state at room temperature Solid Gas, liquid, or solid
Water solubility Usually high Variable
Melting and boiling temperatures Generally high Generally low
Electrical conductivity Good when molten or in solution Poor
In summary, covalent compounds are softer, have lower boiling and melting points, are more flammable, are less soluble in water
and do not conduct electricity compared to ionic compounds. The individual melting and boiling points, solubility and other
physical properties of molecular compounds depend on molecular polarity.
4.5: Characteristics of Molecular Compounds is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by
LibreTexts.
Understand the different ways to represent molecules.
There are many "universal languages" in the world. Musicians of every culture recognize music embodied in a series of notes on a
staff. This passage from a Bach cello suite could be played by any trained musician from any country, because there is an
agreement as to what the symbols on the page mean. In the same way, molecules are represented using symbols and a language that
all chemists agree upon.
Figure 4.6.1 (Credit: J. S. Bach; Source: http://commons.wikimedia.org/wiki/File:Bach_cello_harmony.JPG(opens in new

window); License: Public Domain)
Molecular Formulas
A molecular formula is a chemical formula of a molecular compound that shows the kinds and numbers of atoms present in a
molecule of the compound. Ammonia is a compound of nitrogen and hydrogen as shown below:
Figure 4.6.2 : The molecular formula for ammonia. (Credit: Joy Sheng; Source: CK-12 Foundation; License: CC BY-NC 3.0(opens
in new window))
Note from the example that there are some standard rules to follow in writing molecular formulas. The number of atoms of each
kind is indicated by a subscript following the atom. If there is only one atom, no number is written. If there is more than one atom
of a specific kind, the number is written as a subscript following the atom. We would not write N H for ammonia, because that
3
would mean that there are three nitrogen atoms and one hydrogen atom in the molecule, which is incorrect.
Although it is useful for describing a molecule, the molecular formula does not tell us anything about the shape of the molecule,
where the different atoms are, or what kinds of bonds are formed. Structural formulas are much more useful to communicate
more detailed information about a molecule because they show which atoms are bonded to one another and, in some cases, the
approximate arrangement of the atoms in space. Knowing the structural formula of a compound enables chemists to create a three-
dimensional model, which provides information about how that compound will behave physically and chemically.
Figure 4.6.3 shows some of the different ways to portray the structure of a slightly more complex molecule: methanol. These
representations differ greatly in their information content. For example, the molecular formula for methanol (Figure 4.6.3a) gives
only the number of each kind of atom; writing methanol as CH4O tells nothing about its structure. In contrast, the structural
formula (Figure 4.6.3b) indicates how the atoms are connected, but it makes methanol look as if it is planar (which it is not). Both
the ball-and-stick model (part (c) in Figure 4.6.3) and the perspective drawing (Figure 4.6.3d) show the three-dimensional
structure of the molecule. The latter (also called a wedge-and-dash representation) is the easiest way to sketch the structure of a
molecule in three dimensions. It shows which atoms are above and below the plane of the paper by using wedges and dashes,
respectively; the central atom is always assumed to be in the plane of the paper. The space-filling model (part (e) in Figure 4.6.3)
illustrates the approximate relative sizes of the atoms in the molecule, but it does not show the bonds between the atoms. In
addition, in a space-filling model, atoms at the “front” of the molecule may obscure atoms at the “back.”
Figure 4.6.3 : Different Ways of Representing the Structure of a Molecule. (a) The molecular formula for methanol gives only the
number of each kind of atom present. (b) The structural formula shows which atoms are connected. (c) The ball-and-stick model
shows the atoms as spheres and the bonds as sticks. (d) A perspective drawing (also called a wedge-and-dash representation)
attempts to show the three-dimensional structure of the molecule. (e) The space-filling model shows the atoms in the molecule but
not the bonds. (f) The condensed structural formula is by far the easiest and most common way to represent a molecule.
Although a structural formula, a ball-and-stick model, a perspective drawing, and a space-filling model provide a significant
amount of information about the structure of a molecule, each requires time and effort. Consequently, chemists often use a
condensed structural formula (part (f) in Figure 4.6.3), which omits the lines representing bonds between atoms and simply lists the
atoms bonded to a given atom next to it. Multiple groups attached to the same atom are shown in parentheses, followed by a
subscript that indicates the number of such groups. For example, the condensed structural formula for methanol is CH3OH, which
indicates that the molecule contains a CH3 unit that looks like a fragment of methane (CH4). Methanol can therefore be viewed
either as a methane molecule in which one hydrogen atom has been replaced by an –OH group or as a water molecule in which one
hydrogen atom has been replaced by a –CH3 fragment. Because of their ease of use and information content, we use condensed
structural formulas for molecules throughout this text. Ball-and-stick models are used when needed to illustrate the three-
dimensional structure of molecules, and space-filling models are used only when it is necessary to visualize the relative sizes of
atoms or molecules to understand an important point.
 Example 4.6.1: Molecular Formulas
Write the molecular formula for each compound. The condensed structural formula is given.
a. Sulfur monochloride (also called disulfur dichloride) is a vile-smelling, corrosive yellow liquid used in the production of
synthetic rubber. Its condensed structural formula is ClSSCl.
b. Ethylene glycol is the major ingredient in antifreeze. Its condensed structural formula is HOCH2CH2OH.
c. Trimethylamine is one of the substances responsible for the smell of spoiled fish. Its condensed structural formula is
(CH3)3N.
Given: condensed structural formula
Asked for: molecular formula
Strategy:
A. Identify every element in the condensed structural formula and then determine whether the compound is organic or
inorganic.
B. As appropriate, use either organic or inorganic convention to list the elements. Then add appropriate subscripts to indicate
the number of atoms of each element present in the molecular formula.
Solution:
The molecular formula lists the elements in the molecule and the number of atoms of each.
a. A Each molecule of sulfur monochloride has two sulfur atoms and two chlorine atoms. Because it does not contain mostly
carbon and hydrogen, it is an inorganic compound. B Sulfur lies to the left of chlorine in the periodic table, so it is written
first in the formula. Adding subscripts gives the molecular formula S2Cl2.
b. A Counting the atoms in ethylene glycol, we get six hydrogen atoms, two carbon atoms, and two oxygen atoms per
molecule. The compound consists mostly of carbon and hydrogen atoms, so it is organic. B As with all organic compounds,
C and H are written first in the molecular formula. Adding appropriate subscripts gives the molecular formula C2H6O2.
c. A The condensed structural formula shows that trimethylamine contains three CH3 units, so we have one nitrogen atom,
three carbon atoms, and nine hydrogen atoms per molecule. Because trimethylamine contains mostly carbon and hydrogen,
it is an organic compound. B According to the convention for organic compounds, C and H are written first, giving the
molecular formula C3H9N.
 Exercise 4.6.1: Molecular Formulas
Write the molecular formula for each molecule.

a. Chloroform, which was one of the first anesthetics and was used in many cough syrups until recently, contains one carbon
atom, one hydrogen atom, and three chlorine atoms. Its condensed structural formula is CHCl . 3
b. Hydrazine is used as a propellant in the attitude jets of the space shuttle. Its condensed structural formula is H NNH .
2 2
c. Putrescine is a pungent-smelling compound first isolated from extracts of rotting meat. Its condensed structural formula is
H2NCH2CH2CH2CH2NH2. This is often written as H N(CH ) NH to indicate that there are four CH2 fragments linked
2 2 4 2
together.
Answer a
CHCl3
Answer b
N2H4
Answer c
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Draw Lewis structures for molecules.
For very simple molecules and molecular ions, we can write the Lewis structures by merely pairing up the unpaired electrons on
the constituent atoms. See these examples:
For more complicated molecules, it is helpful to follow the step-by-step procedure outlined here:
1. Arrange the atoms to show specific connections. When there is a central atom, it is usually the least electronegative element
in the compound. Chemists usually list this central atom first in the chemical formula (as in CCl4 and CO32−, which both have C
as the central atom), which is another clue to the compound’s structure. Hydrogen and the halogens are almost always
connected to only one other atom, so they are usually terminal rather than central.
2. Determine the total number of valence electrons in the molecule or ion. Add together the valence electrons from each atom.
(Recall that the number of valence electrons is indicated by the position of the element in the periodic table.) If the species is a
polyatomic ion, remember to add or subtract the number of electrons necessary to give the total charge on the ion. For CO32−,
for example, we add two electrons to the total because of the −2 charge.
3. Place a bonding pair of electrons between each pair of adjacent atoms to give a single bond. In H2O, for example, there is
a bonding pair of electrons between oxygen and each hydrogen.
4. Beginning with the terminal atoms, add enough electrons to each atom to give each atom an octet (two for hydrogen).
These electrons will usually be lone pairs.
5. If any electrons are left over, place them on the central atom. We will explain later that some atoms are able to
accommodate more than eight electrons.
6. If the central atom has fewer electrons than an octet, use lone pairs from terminal atoms to form multiple (double or
triple) bonds to the central atom to achieve an octet. This will not change the number of electrons on the terminal atoms.
Now let’s apply this procedure to some particular compounds.
The central atom is usually the least electronegative element in the molecule or ion; hydrogen and the halogens are usually
terminal.
The H O Molecule
2
1. Because H atoms are almost always terminal, the arrangement within the molecule must be HOH.
2. Each H atom (group 1) has 1 valence electron, and the O atom (group 16) has 6 valence electrons, for a total of 8 valence
electrons.
3. Placing one bonding pair of electrons between the O atom and each H atom gives H:O:H, with 4 electrons left over.
4. Each H atom has a full valence shell of 2 electrons.
5. Adding the remaining 4 electrons to the oxygen (as two lone pairs) gives the following structure:
Because this structure gives oxygen an octet and each hydrogen two electrons, we do not need to use step 6.
The OCl Ion
−
1. With only two atoms in the molecule, there is no central atom.

2. Oxygen (group 16) has 6 valence electrons, and chlorine (group 17) has 7 valence electrons; we must add one more for the
negative charge on the ion, giving a total of 14 valence electrons.
3. Placing a bonding pair of electrons between O and Cl gives O:Cl, with 12 electrons left over.
4. If we place six electrons (as three lone pairs) on each atom, we obtain the following structure:
Both the oxygen and chlorine have 3 electron pairs drawn around them with a bond drawn between them. The molecule has square
brackets placed around it and has a negative charge.
Each atom now has an octet of electrons, so steps 5 and 6 are not needed. The Lewis electron structure is drawn within brackets as
is customary for a molecular ion, with the overall charge indicated outside the brackets, and the bonding pair of electrons is
indicated by a solid line. OCl− is the hypochlorite ion, the active ingredient in chlorine laundry bleach and swimming pool
disinfectant.
The C H 2O Molecule
1. Because carbon is less electronegative than oxygen and hydrogen is normally terminal, C must be the central atom. One possible
arrangement is as follows:
2. Each hydrogen atom (group 1) has one valence electron, carbon (group 14) has 4 valence electrons, and oxygen (group 16) has 6
valence electrons, for a total of [(2)(1) + 4 + 6] = 12 valence electrons.
3. Placing a bonding pair of electrons between each pair of bonded atoms gives the following:
Six electrons are used, and 6 are left over.

4. Adding all 6 remaining electrons to oxygen (as three lone pairs) gives the following:
Although oxygen now has an octet and each hydrogen has 2 electrons, carbon has only 6 electrons.
5. There are no electrons left to place on the central atom.
6. To give carbon an octet of electrons, we use one of the lone pairs of electrons on oxygen to form a carbon–oxygen double bond:
The bond between the oxygen and carbon is replaced with a double bond. The oxygen also has two lone pairs drawn.
Both the oxygen and the carbon now have an octet of electrons, so this is an acceptable Lewis electron structure. The O has two
bonding pairs and two lone pairs, and C has four bonding pairs. This is the structure of formaldehyde, which is used in embalming
fluid.
 Example 4.7.1
Write the Lewis electron structure for each species.
a. NCl3
b. S22−
c. NOCl
Given: chemical species
Asked for: Lewis electron structures
Strategy:
Use the six-step procedure to write the Lewis electron structure for each species.
Solution:
a. Nitrogen is less electronegative than chlorine, and halogen atoms are usually terminal, so nitrogen is the central atom. The
nitrogen atom (group 15) has 5 valence electrons and each chlorine atom (group 17) has 7 valence electrons, for a total of
26 valence electrons. Using 2 electrons for each N–Cl bond and adding three lone pairs to each Cl account for (3 × 2) + (3
× 2 × 3) = 24 electrons. Rule 5 leads us to place the remaining 2 electrons on the central N:
Nitrogen trichloride is an unstable oily liquid once used to bleach flour; this use is now prohibited in the United States.
b. In a diatomic molecule or ion, we do not need to worry about a central atom. Each sulfur atom (group 16) contains 6
valence electrons, and we need to add 2 electrons for the −2 charge, giving a total of 14 valence electrons. Using 2 electrons
for the S–S bond, we arrange the remaining 12 electrons as three lone pairs on each sulfur, giving each S atom an octet of
electrons:
c. Because nitrogen is less electronegative than oxygen or chlorine, it is the central atom. The N atom (group 15) has 5
valence electrons, the O atom (group 16) has 6 valence electrons, and the Cl atom (group 17) has 7 valence electrons,
giving a total of 18 valence electrons. Placing one bonding pair of electrons between each pair of bonded atoms uses 4
electrons and gives the following:
Adding three lone pairs each to oxygen and to chlorine uses 12 more electrons, leaving 2 electrons to place as a lone pair on
nitrogen:
Because this Lewis structure has only 6 electrons around the central nitrogen, a lone pair of electrons on a terminal atom
must be used to form a bonding pair. We could use a lone pair on either O or Cl. Because we have seen many structures in
which O forms a double bond but none with a double bond to Cl, it is reasonable to select a lone pair from O to give the
following:
All atoms now have octet configurations. This is the Lewis electron structure of nitrosyl chloride, a highly corrosive,
reddish-orange gas.
 Exercise 4.7.1
Write Lewis electron structures for CO2 and SCl2, a vile-smelling, unstable red liquid that is used in the manufacture of rubber.
Answer
1.
2.
Two chlorines are bonded to a sulfur. The sulfur has 2 lone pairs while the chlorines have 3 lone pairs each.
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Predict the structures of small molecules using valence shell electron pair repulsion (VSEPR) theory.
The Lewis electron-pair approach can be used to predict the number and types of bonds between the atoms in a substance, and it
indicates which atoms have lone pairs of electrons. This approach gives no information about the actual arrangement of atoms in
space, however. We continue our discussion of structure and bonding by introducing the valence-shell electron-pair repulsion
(VSEPR) model (pronounced “vesper”), which can be used to predict the shapes of many molecules and polyatomic ions. Keep in
mind, however, that the VSEPR model, like any model, is a limited representation of reality; the model provides no information
about bond lengths or the presence of multiple bonds.
The VSEPR Model

The VSEPR model can predict the structure of nearly any molecule or polyatomic ion in which the central atom is a nonmetal, as
well as the structures of many molecules and polyatomic ions with a central metal atom. The premise of the VSEPR theory is that
electron pairs located in bonds and lone pairs repel each other and will therefore adopt the geometry that places electron pairs as far
apart from each other as possible. This theory is very simplistic and does not account for the subtleties of orbital interactions that
influence molecular shapes; however, the simple VSEPR counting procedure accurately predicts the three-dimensional structures of
a large number of compounds, which cannot be predicted using the Lewis electron-pair approach.
Figure 4.8.1 : Common Structures for Molecules and Polyatomic Ions That Consist of a Central Atom Bonded to Two or Three
Other Atoms. (CC BY-NC-SA; anonymous)
We can use the VSEPR model to predict the geometry of most polyatomic molecules and ions by focusing only on the number of
electron pairs around the central atom, ignoring all other valence electrons present. According to this model, valence electrons in
the Lewis structure form electron groups (regions of electron density), which may consist of a single bond, a double bond, a triple
bond, a lone pair of electrons, or even a single unpaired electron, which in the VSEPR model is counted as a lone pair. Because
electrons repel each other electrostatically, the most stable arrangement of electron groups (i.e., the one with the lowest energy) is
the one that minimizes repulsions. Groups are positioned around the central atom in a way that produces the molecular structure
with the lowest energy, as illustrated in Figure 4.8.1.
It is important to note that electron group geometry around a central atom is not the same thing as its molecular structure. Electron
group geometries describe all regions where electrons are located, bonds as well as lone pairs. Molecular structure describes the
location of the atoms alone, not including the lone pair electrons.
We differentiate between these two situations by naming the geometry that includes all electron pairs the electron group
geometry. The structure that includes only the placement of the atoms in the molecule is called the molecular structure (or
molecular shape). The electron group geometries will be the same as the molecular structures when there are no lone electron pairs
around the central atom, but they will be different when there are lone pairs present on the central atom.
 Predicting Electron Group Geometry and Molecular Structure

The following procedure uses VSEPR theory to determine electron group geometry and molecular structures (molecular
shape):
1. Draw the Lewis structure of the molecule or polyatomic ion.
2. Count the number of electron groups or regions of electron density (lone pairs and bonds) around the central atom. A
single, double, or triple bond counts as one electron group.
3. Determine the electron group geometry by placing the groups as far apart as possible.
4. Determine the molecular structure (looking at the bonded groups only).
Table 4.8.1 summarizes the shapes of molecules based on the number of electron groups and surrounding atoms.
Table 4.8.1 : Summary of Electron Group Geometries and Molecular Structures
Number of Electron Number of Bonding
Number of Lone Pairs Electron Group Geometry Molecular Structure
Groups on Central Atom Groups
2 2 0 linear linear
3 3 0 trigonal planar trigonal planar
3 2 1 trigonal planar bent 120°
4 4 0 tetrahedral tetrahedral
4 3 1 tetrahedral trigonal pyramidal
4 2 2 tetrahedral bent 109°
Two Electron Groups

Any molecule with only two atoms is linear. A molecule whose central atom contains only two electron groups orients those two
groups as far apart from each other as possible, which is 180° apart. When the two electron groups are 180° apart, the atoms
attached to those electron groups are also 180° apart, so the overall molecular structure is linear. Examples include BeH2 and CO2:
Figure 4.8.2 : Beryllium hydride and carbon dioxide bonding.
Three Electron Groups

A molecule with three electron groups orients the three groups as far apart as possible. They adopt the positions of an equilateral
triangle, 120° apart and in a plane. The shape of such molecules is trigonal planar. An example is BF3:
Figure 4.8.3 : Boron trifluoride bonding. (CK12 Licence)

Some substances have a trigonal planar electron group distribution but have atoms bonded to only two of the three electron groups.
An example is GeF2:
Figure 4.8.4 : Germanium difluoride bonding.

From an electron group geometry perspective, GeF2 has a trigonal planar shape, but its real shape is dictated by the positions of the
atoms. This molecular structure is called bent 120° or angular.
Four Electron Groups

A molecule with four electron groups about the central atom orients the four groups in the direction of a tetrahedron with bond
angles of approximately 109.5°. If there are four atoms attached to these electron groups, then the molecular structure is also
tetrahedral. Methane (CH4) is an example.
Figure 4.8.5 : Tetrahedral structure of methane. (CK12 Licence)

This diagram of CH4 illustrates the standard convention of displaying a three-dimensional molecule on a two-dimensional surface.
The straight lines are in the plane of the page, the solid wedged line is coming out of the plane toward the reader, and the dashed
wedged line is going out of the plane away from the reader.
Figure 4.8.6 : Methane bonding. (CK12 Licence)

NH3 is an example of a molecule whose central atom has four electron groups, but only three of them are bonded to surrounding
atoms.
Figure 4.8.7 : Ammonia bonding. (CK12 Licence)

Although the electron groups are oriented in the shape of a tetrahedron, from a molecular geometry perspective, the shape of NH3
is trigonal pyramidal.
H2O is an example of a molecule whose central atom has four electron groups, but only two of them are bonded to surrounding
atoms.
Figure 4.8.8 : Water bonding.

Although the electron groups are oriented in the shape of a tetrahedron, the shape of the molecule is bent 109° or angular. A
molecule with four electron groups about the central atom, but only one electron group bonded to another atom, is linear because
there are only two atoms in the molecule.
Shapes of Molecules with Double or Triple Bonds

Double or triple bonds count as a single electron group. The Lewis electron dot diagram of formaldehyde (CH2O) is shown in
Figure 4.8.9.
Figure 4.8.9 : Lewis Electron Dot Diagram of Formaldehyde.

The central C atom has three electron groups around it because the double bond counts as one electron group. The three electron
groups repel each other to adopt a trigonal planar shape.
Figure 4.8.10 : Formaldehyde bonding.

(The lone electron pairs on the O atom are omitted for clarity.) The molecule will not be a perfect equilateral triangle because the
C–O double bond is different from the two C–H bonds, but both planar and triangular describe the appropriate approximate shape
of this molecule.
 Example 4.8.1
What is the approximate shape of each molecule?
a. PCl3
b. NOF
Solution
The first step is to draw the Lewis structure of the molecule.
For PCl , the electron dot diagram is as follows:
3
The lone electron pairs on the Cl atoms are omitted for clarity. The P atom has four electron groups with three of them bonded
to surrounding atoms, so the molecular shape is trigonal pyramidal.
The electron dot diagram for NOF is as follows:
The N atom has three electron groups on it, two of which are bonded to other atoms. The molecular shape is bent.
 Exercise 4.8.1
What is the approximate molecular shape of CH 2

Cl
2
?
Answer
Tetrahedral
 Exercise 4.8.2
Ethylene (C H ) has two central atoms. Determine the geometry around each central atom and the shape of the overall
2 4
molecule. (Hint: hydrogen is a terminal atom.)
Answer
Trigonal planar about both central C atoms.
Molecules With Multiple Central Atoms

The VSEPR model can be used to predict the structure of somewhat more complex molecules with more than one central atom by
using VSEPR as described above for each central atom individually. We will demonstrate with methyl isocyanate (CH3–N=C=O), a
volatile and highly toxic molecule that is used to produce the pesticide Sevin.
Start by looking at the electron groups around the first carbon atom at the left, which is connected to three H atoms and one N atom
by single bonds. There are four groups or electrons or four bonds around the carbon. We can therefore predict the CH3–N portion
of the molecule to be roughly tetrahedral, similar to methane:
The nitrogen atom is connected to one carbon by a single bond and to the other carbon by a double bond, producing a total of three
bonds, C–N=C. For nitrogen to have an octet of electrons, it must also have a lone pair:
One carbon bonded to nitrogen and another carbon double bonded to the nitrogen. The nitrogen has one lone pair.
Because multiple bonds are not shown in the VSEPR model, the nitrogen is effectively surrounded by three electron groups. Thus
according to the VSEPR model, the C–N=C fragment should be bent with an angle ~120°.
The carbon in the –N=C=O fragment is doubly bonded to both nitrogen and oxygen, which in the VSEPR model gives carbon a
total of two electron pairs. The N=C=O angle should therefore be 180°, or linear. The three fragments combine to give the
following structure:
Figure 4.8.11 ). The Lewis Structure of Methyl Isocyanate

Three hydrogens are bonded to a carbon. The carbon is also bonded to a nitrogen. The nitrogen is double bonded to another carbon.
The second carbon is double bonded to an oxygen. The nitrogen has one lone pair. The oxygen has two lone pairs.
Figure 4.8.12 : The Experimentally Determined Structure of Methyl Isocyanate

Certain patterns are seen in the structures of moderately complex molecules. For example, carbon atoms with four bonds (such as
the carbon on the left in methyl isocyanate) are generally tetrahedral. Similarly, the carbon atom on the right has two double bonds
that are similar to those in CO2, so its geometry, like that of CO2, is linear. Recognizing similarities to simpler molecules will help
you predict the molecular geometries of more complex molecules.
 Example 4.8.3
Use the VSEPR model to predict the molecular geometry of propyne (H3C–C≡CH), a gas with some anesthetic properties.
Given: chemical compound
Asked for: molecular geometry
Strategy:
Count the number of electron groups around each carbon, recognizing that in the VSEPR model, a multiple bond counts as a
single group. Use Figure 4.8.3 to determine the molecular geometry around each carbon atom and then deduce the structure of
the molecule as a whole.
Solution:
Because the carbon atom on the left is bonded to four other atoms, we know that it is approximately tetrahedral. The next two
carbon atoms share a triple bond, and each has an additional single bond. Because a multiple bond is counted as a single bond
in the VSEPR model, each carbon atom behaves as if it had two electron groups. This means that both of these carbons are
linear, with C–C≡C and C≡C–H angles of 180°.
 Exercise 4.8.3
Predict the geometry of allene (H2C=C=CH2), a compound with narcotic properties that is used to make more complex organic
molecules.
Answer
The terminal carbon atoms are trigonal planar, the central carbon is linear, and the C–C–C angle is 180°.
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Describe electronegativity and polarity.
Use electronegativity values to predict bond polarity.
Our discussions of bonding thus far have focused on two types, ionic and covalent. In ionic bonds, like N aC l, electrons are
transferred; the 3s electron is stripped from the Na atom and is incorporated into the electronic structure of the Cl atom, and the
compound is most accurately described as consisting of individual N a and C l ions. In covalent bonding, unpaired electrons
+ −
from individual atoms are shared in order to fill the valence shell of each atom. When a covalent bond is formed between the same
type of atoms, such as C l , the electrons are shared equally between the two. However, when a covalent bond is formed between
2
different types of atoms, the electrons are not necessarily shared equally. In these compounds their bond character falls between the
two extremes: transferred and shared equally.
Bond Polarity
As demonstrated below, bond polarity is a useful concept for describing the sharing of electrons between atoms, within a covalent
bond:
A nonpolar covalent bond (Figure 4.9.1a)is one in which the electrons are shared equally between two atoms.
A polar covalent bond (Figure 4.9.1b) is one in which one atom has a greater attraction for the electrons than the other atom.
If the relative attraction of an atom for electrons is great enough, then the bond is an ionic bond (Figure 4.9.1c).
Electron density in a polar bond is distributed unevenly and is greater around the atom that attracts the electrons more than the
other. For example, the electrons in the H–Cl bond of a hydrogen chloride molecule spend more time near the chlorine atom than
near the hydrogen atom. Note that the shaded area around Cl in Figure 4.9.1b is much larger than it is around H. This imbalance in
electron density results in a buildup of partial negative charge (designated as δ−) on one side of the bond (Cl) and a partial positive
charge (designated δ+) on the other side of the bond (H).
Figure 4.9.1 : The Electron Distribution in a Nonpolar Covalent Bond, a Polar Covalent Bond, and an Ionic Bond Using Lewis
Electron Structures. In a purely covalent bond (a), the bonding electrons are shared equally between the atoms. In a purely ionic
bond (c), an electron has been transferred completely from one atom to the other. A polar covalent bond (b) is intermediate between
the two extremes: the bonding electrons are shared unequally between the two atoms, and the electron distribution is asymmetrical
with the electron density being greater around the more electronegative atom. Electron-rich (negatively charged) regions are shown
in blue; electron-poor (positively charged) regions are shown in red.
Any covalent bond between atoms of different elements is a polar bond, but the degree of polarity varies widely. Some bonds
between different elements are only minimally polar, while others are strongly polar. Ionic bonds can be considered the ultimate in
polarity, with electrons being transferred rather than shared. To judge the relative polarity of a covalent bond, chemists use
electronegativity, which is a relative measure of how strongly an atom attracts electrons when it forms a covalent bond.
Electronegativity
Because the tendency of an element to gain or lose electrons is so important in determining its chemistry, various methods have
been developed to quantitatively describe this tendency. The most important method uses a measurement called electronegativity,
defined as the relative ability of an atom to attract electrons to itself in a chemical compound. Elements with high
electronegativities tend to acquire electrons in chemical reactions and are found in the upper right corner of the periodic table.
Elements with low electronegativities tend to lose electrons in chemical reactions and are found in the lower left corner of the
periodic table.
Unlike ionization energy or electron affinity, the electronegativity of an atom is not a simple, fixed property that can be directly
measured in a single experiment. In fact, an atom’s electronegativity should depend to some extent on its chemical environment
because the properties of an atom are influenced by its neighbors in a chemical compound. Nevertheless, when different methods
for measuring the electronegativity of an atom are compared, they all tend to assign similar relative values to a given element. For
example, all scales predict that fluorine has the highest electronegativity and cesium the lowest of the stable elements, which
suggests that all the methods are measuring the same fundamental property.
Electronegativity is a function of:
1. the atom's ionization energy (how strongly the atom holds on to its own electrons) and
2. the atom's electron affinity (how strongly the atom attracts other electrons).
Both of these are properties of the isolated atom. An element will be highly electronegative if it has a large (negative) electron
affinity and a high ionization energy (always positive for neutral atoms). Thus, it will attract electrons from other atoms and resist
having its own electrons attracted away.
Electronegativity is defined as the ability of an atom in a particular molecule to attract

electrons to itself. The greater the value, the greater the attractiveness for electrons.
The Pauling Electronegativity Scale
The original electronegativity scale, developed in the 1930s by Linus Pauling (1901– 1994) was based on measurements of the
strengths of covalent bonds between different elements. Pauling arbitrarily set the electronegativity of fluorine at 4.0 (although
today it has been refined to 3.98), thereby creating a scale in which all elements have values between 0 and 4.0.
Figure 4.9.2 : A Plot of Periodic Variation of Electronegativity with Atomic Number for the First Six Rows of the Periodic Table
The main groups 1 and 2 are purple, the main groups 13 through 18 are green, the transition metals are red, and the lanthanides are
blue.
Periodic variations (trends) in Pauling’s electronegativity values are illustrated in Figures 4.9.2 and 4.9.3. If we ignore the inert
gases and elements for which no stable isotopes are known, we see that fluorine is the most electronegative element and cesium is
the least electronegative nonradioactive element. Because electronegativities generally increase diagonally from the lower left to
the upper right of the periodic table, elements lying on diagonal lines running from upper left to lower right tend to have
comparable values (e.g., O and Cl, and N, S, and Br).
Figure 4.9.3 : Pauling Electronegativity Values of the s-, p-, d-, and f-Block Elements. Values for most of the actinides are
approximate. Elements for which no data are available are shown in gray. Source: Data from L. Pauling, The Nature of the
Chemical Bond, 3rd ed. (1960).
The s blocks are purple, the p blocks are green, the d blocks are red, and the f blocks are blue. Electronegativity increase from
bottom to top and left to right.
The polarity of a covalent bond can be judged by determining the difference in the electronegativities of the two atoms making the
bond. The greater the difference in electronegativities, the greater the imbalance of electron sharing in the bond. Although there are
no hard and fast rules, the general rule, (see Figure 4.9.5), is if the difference in electronegativities is less than about 0.4, the bond
is considered nonpolar; if the difference is greater than 0.4, the bond is considered polar. If the difference in electronegativities is
large enough (generally greater than about 1.8), the resulting compound is considered ionic rather than covalent. An
electronegativity difference of zero, of course, indicates a nonpolar covalent bond.
Figure 4.9.4 The electronegativity values derived by Pauling follow predictable periodic trends with the higher electronegativities
toward the upper right of the periodic table. Fluorine has the highest value (4.0).
Figure 4.9.5 : As the electronegativity difference increases between two atoms, the bond becomes more ionic.
 Example 4.9.1
Describe the electronegativity difference between each pair of atoms and the resulting polarity (or bond type).
a. C and H
b. H and H
c. Na and Cl
d. O and H
Solution
a. Carbon has an electronegativity of 2.5, while the value for hydrogen is 2.1. The difference is 0.4, which is rather small. The
C–H bond is therefore considered nonpolar.
b. Both hydrogen atoms have the same electronegativity value—2.1. The difference is zero, so the bond is nonpolar.
c. Sodium’s electronegativity is 0.9, while chlorine’s is 3.0. The difference is 2.1, which is rather high, and so sodium and
chlorine form an ionic compound.
d. With 2.1 for hydrogen and 3.5 for oxygen, the electronegativity difference is 1.4. We would expect a very polar bond. The
sharing of electrons between O and H is unequal with the electrons more strongly drawn towards O.
 Exercise 4.9.1
Describe the electronegativity (EN) difference between each pair of atoms and the resulting polarity (or bond type).
a. C and O
b. K and Br
c. N and N
d. Cs and F
Answer a:
The EN difference is 1.0 , hence polar. The sharing of electrons between C and O is unequal with the electrons more
strongly drawn towards O.
Answer b:
The EN difference is greater than 1.8, hence ionic.
Answer c:
Identical atoms have zero EN difference, hence nonpolar.
Answer d:
The EN difference is greater than 1.8, hence ionic.
Looking Closer: Linus Pauling

Arguably the most influential chemist of the 20th century, Linus Pauling (1901–94) is the only person to have won two
individual (that is, unshared) Nobel Prizes. In the 1930s, Pauling used new mathematical theories to enunciate some
fundamental principles of the chemical bond. His 1939 book The Nature of the Chemical Bond is one of the most significant
books ever published in chemistry.
By 1935, Pauling’s interest turned to biological molecules, and he was awarded the 1954 Nobel Prize in Chemistry for his
work on protein structure. (He was very close to discovering the double helix structure of DNA when James Watson and James
Crick announced their own discovery of its structure in 1953.) He was later awarded the 1962 Nobel Peace Prize for his efforts
to ban the testing of nuclear weapons.
Linus Pauling was one of the most influential chemists of the 20th century.
In his later years, Pauling became convinced that large doses of vitamin C would prevent disease, including the common cold.
Most clinical research failed to show a connection, but Pauling continued to take large doses daily. He died in 1994, having
spent a lifetime establishing a scientific legacy that few will ever equal.
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Recognize bond characteristics of covalent compounds: bond length and bond polarity.
Use electronegativity values to predict bond polarity.
If there is only one bond in the molecule, the bond polarity determines the molecular polarity. Any diatomic molecule in which the
two atoms are the same element must be a nonpolar molecule. A diatomic molecule that consists of a polar covalent bond, such as
HF, is a polar molecule where one end of the molecule is slightly positive, while the other end is slightly negative. The two
electrically charged regions on either end of the molecule are called poles, similar to a magnet having a north and a south pole.
Hence, a molecule with two poles has a dipole moment.
Figure 4.10.1 : A molecular dipole results from the unequal distribution of electron density throughout a molecule. The H, with less
electron density is partially positive and the F, with more electron density is partially negative. (Figure modified from: Wikipedia
[en.Wikipedia.org])
For molecules with more than two atoms, the molecular geometry must also be taken into account when determining if the
molecule is polar or nonpolar. The figure below shows a comparison between carbon dioxide and water.
Carbon dioxide (CO ) is a linear molecule with carbon in the center and two oxygens at the terminal ends. The oxygen atoms are
2
more electronegative than the carbon atom, so there are two individual dipoles pointing outward from the C atom to each O atom.
However, since the dipoles are of equal strength and pointing in opposite directions, they cancel out and the overall molecular
polarity of CO is zero (no net dipole), therefore CO is a nonpolar molecule.
2 2
Water has a bent molecular structure because it has four electron groups, two bonded groups and two lone electron groups on the
central oxygen atom. The individual O–H bond dipoles point from the slightly positive H atoms toward the more electronegative O
atom. Because of the bent shape, the dipoles, which are equal in strength, both point towards the oxygen atom and will not cancel
each other out, therefore, the water molecule is polar. In the figure below, you can see that the oxygen end of the molecule is
slightly negative and the hydrogen side is slightly positive, there is a separation of charge throughout the whole molecule, a net
dipole (shown in blue) that points upward.
Figure 4.10.2 : The molecular geometry of a molecule affects its polarity. Each CO bond has a dipole moment, but they point in
opposite directions so that the net CO2 molecule is nonpolar. In contrast, water is polar because the OH bond dipole moments do
not cancel out. There is a net separation of charge or overall dipole moment.
Some other molecules are shown in the figure below. Notice that a tetrahedral molecule such as CH is nonpolar. However, if one
4
of the peripheral H atoms is replaced with another atom that has a different electronegativity, the molecule becomes polar. A
trigonal planar molecule (BF ) may be nonpolar if all three peripheral atoms are the same, but a trigonal pyramidal molecule
3
(NH ) is polar.
3
Figure 4.10.3 : Some examples of polar and nonpolar molecules based on molecular geometry.
To summarize, to be polar, a molecule must:
1. Contain at least one polar covalent bond.
2. Have a molecular structure such that the sum of the vectors of each bond dipole moment do not cancel.
 Steps to Identify Polar Molecules

1. Draw the Lewis structure.
2. Figure out the geometry (using VSEPR theory).
3. Visualize or draw the geometry.
4. Find the net dipole moment (you don't have to actually do calculations if you can visualize it).
5. If the net dipole moment is zero, it is non-polar. Otherwise, it is polar.
Properties of Polar Molecules

Polar molecules tend to align when placed in an electric field with the positive end of the molecule oriented toward the negative
plate and the negative end toward the positive plate (Figure 4.10.4). We can use an electrically charged object to attract polar
molecules, but nonpolar molecules are not attracted. Also, polar solvents are better at dissolving polar substances, and nonpolar
solvents are better at dissolving nonpolar substances.
Figure 4.10.4 : (a) Molecules are always randomly distributed in the liquid state in the absence of an electric field. (b) When an
electric field is applied, polar molecules like HF will align to the dipoles with the field direction. (OpenStax CC-BY-SA);
While molecules can be described as "polar covalent" or "ionic", it must be noted that this is often a relative term, with one
molecule simply being more polar or less polar than another. However, the following properties are typical of such molecules.
Polar molecules tend to:
have higher melting points than nonpolar molecules
have higher boiling points than nonpolar molecules
be more soluble in water (dissolve better) than nonpolar molecules
have lower vapor pressures than nonpolar molecules
 Example 4.10.1: Polarity Simulations
Open the molecule polarity simulation (above) and select the “Three Atoms” tab at the top. This should display a molecule
ABC with three electronegativity adjustors. You can display or hide the bond moments, molecular dipoles, and partial charges
at the right. Turning on the Electric Field will show whether the molecule moves when exposed to a field.
Use the electronegativity controls to determine how the molecular dipole will look for the starting bent molecule if:
a. A and C are very electronegative and B is in the middle of the range.
b. A is very electronegative, and B and C are not.
Solution
a. Molecular dipole moment points immediately between A and C.
b. Molecular dipole moment points along the A–B bond, toward A.
 Exercise 4.10.1
Determine the partial charges that will give the largest possible bond dipoles.
Answer
The largest bond moments will occur with the largest partial charges. The two solutions above represent how unevenly the
electrons are shared in the bond. The bond moments will be maximized when the electronegativity difference is greatest.
The controls for A and C should be set to one extreme, and B should be set to the opposite extreme. Although the
magnitude of the bond moment will not change based on whether B is the most electronegative or the least, the direction of
the bond moment will.
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Name binary molecular compounds.
Naming binary (two-element) covalent compounds is very similar to naming simple ionic compounds. The first element in the
formula is simply listed using the name of the element. The second element is named by taking the stem of the element name and
adding the suffix -ide. Unlike for ionic compounds, molecular compounds can be formed using the same elements in different
ratios. Therefore, it is important to indicate the number of each type of atom, using a system of numerical prefixes, listed in Table
4.11.1. Normally, no prefix is added to the first element’s name if there is only one atom of the first element in a molecule. If the
second element is oxygen, the trailing vowel is usually omitted from the end of a polysyllabic prefix but not a monosyllabic one
(that is, we would say “monoxide” rather than “monooxide” and “trioxide” rather than “troxide”).
Table 4.11.1 : Numerical Prefixes for Naming Binary Covalent Compounds
Number of Atoms in Compound Prefix on the Name of the Element
1 mono-*
2 di-
3 tri-
4 tetra-
5 penta-
6 hexa-
7 hepta-
8 octa-
9 nona-
10 deca-
*This prefix is not used for the first element’s name.
Let us practice by naming the compound whose molecular formula is CCl4. The name begins with the name of the first element
carbon. The second element, chlorine, becomes chloride, and we attach the correct numerical prefix (“tetra-”) to indicate that the
molecule contains four chlorine atoms. Putting these pieces together gives the name carbon tetrachloride for this compound.
 Example 4.11.1
Write the molecular formula for each compound.
a. chlorine trifluoride
b. phosphorus pentachloride
c. sulfur dioxide
d. dinitrogen pentoxide
Solution
If there is no numerical prefix on the first element’s name, we can assume that there is only one atom of that element in a
molecule.
a. ClF3
b. PCl5
c. SO2
d. N2O5 (The di- prefix on nitrogen indicates that two nitrogen atoms are present.)
 Exercise 4.11.1
Write the molecular formula for each compound.

a. nitrogen dioxide
b. dioxygen difluoride
c. sulfur hexafluoride
d. selenium monoxide
Answer a:
a. NO2
Answer b:
O2F2
Answer c:
SF6
Answer d:
SeO
Because it is so unreactive, sulfur hexafluoride is used as a spark suppressant in electrical devices such as transformers.
 Example 4.11.2
Write the name for each compound.

a. BrF5
b. S2F2
c. CO
Solution
a. bromine pentafluoride
b. disulfur difluoride
c. carbon monoxide
 Exercise 4.11.2
Write the name for each compound.

a. CF4
b. SeCl2
c. SO3
Answer a:
carbon tetrafluoride
Answer b:
selenium dichloride
Answer c:
sulfur trioxide
For some simple covalent compounds, we use common names rather than systematic names. We have already encountered these
compounds, but we list them here explicitly:
H2O: water
NH3: ammonia
CH4: methane
Methane is the simplest organic compound. Organic compounds are compounds with carbon atoms and are named by a separate
nomenclature system that we will introduce later.
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CHAPTER OVERVIEW
5: Classification and Balancing of Chemical Reactions

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1
Learning Objectives
Define chemical reaction.
Understand the Law of Conservation of Matter
Water (H2O) is composed of hydrogen and oxygen. Suppose we imagine a process in which we take some elemental hydrogen (H2)
and elemental oxygen (O2) and let them react to make water. The statement
"hydrogen and oxygen react to make water"
is one way to represent that process, which is called a chemical reaction. Figure 5.1.1 shows a rather dramatic example of this very
reaction.
Figure 5.1.1 : The Formation of Water. Hydrogen and oxygen combine to form water. Here, the hydrogen gas in the zeppelin SS
Hindenburg reacts with oxygen in the air to make water. Source: Photo courtesy of the US Navy. For a video of this see
www.youtube.com/watch?v=CgWHbpMVQ1U.
To simplify the writing of reactions, we use formulas instead of names when we describe a reaction. We can also use symbols to
represent other words in the reaction. A plus sign connects the initial substances (and final substances, if there is more than one),
and an arrow (→) represents the chemical change:
H +O → H O (5.1.1)
2 2 2
This statement is one example of a chemical equation, an abbreviated way of using symbols to represent a chemical change. The
substances on the left side of the arrow are called reactants, and the substances on the right side of the arrow are called products.
It is not uncommon to include a phase label with each formula—(s) for solid, (ℓ) for liquid, (g) for gas, and (aq) for a substance
dissolved in water, also known as an aqueous solution. If we included phase labels for the reactants and products, under normal
environmental conditions, the reaction would be as follows:
H (g) + O (g) → H O(ℓ) (5.1.2)

2 2 2
This equation is still not complete because it does not satisfy the law of conservation of matter. Count the number of atoms of each
element on each side of the arrow. On the reactant side, there are two H atoms and two O atoms; on the product side, there are two
H atoms and only one oxygen atom. The equation is not balanced because the number of oxygen atoms on each side is not the same
(Figure 5.1.2).
Figure 5.1.2 : Balanced—Yes or No? By counting the atoms of each element, we can see that the reaction is not balanced as written.
To make this chemical equation conform to the law of conservation of matter, we must revise the amounts of the reactants and the
products as necessary to get the same number of atoms of a given element on each side. Because every substance has a
characteristic chemical formula, we cannot change the chemical formulas of the individual substances. For example, we cannot
change the formula for elemental oxygen to O. However, we can assume that different numbers of reactant molecules or product
molecules may be involved. For instance, perhaps two water molecules are produced, not just one:
H (g) + O (g) → 2 H O(ℓ) (5.1.3)

2 2 2
The 2 preceding the formula for water is called a coefficient. It implies that two water molecules are formed. There are now two
oxygen atoms on each side of the equation.
This point is so important that we should repeat it. You cannot change the formula of a chemical substance to balance a
chemical reaction! You must use the proper chemical formula of the substance.
Unfortunately, by inserting the coefficient 2 in front of the formula for water, we have also changed the number of hydrogen atoms
on the product side as well. As a result, we no longer have the same number of hydrogen atoms on each side. This can be easily
fixed, however, by putting a coefficient of 2 in front of the diatomic hydrogen reactant:
2 H (g) + O (g) → 2 H O(ℓ) (5.1.4)

2 2 2
Now we have four hydrogen atoms and two oxygen atoms on each side of the equation. The law of conservation of matter is
satisfied because we now have the same number of atoms of each element in the reactants and in the products. We say that the
reaction is now balanced (Figure 5.1.3). Note: The diatomic oxygen has a coefficient of 1, which typically is not written but
assumed in balanced chemical equations.
Figure 5.1.3 : Balanced—Yes or No? By counting the atoms of each element, we can see that the reaction is now balanced.
Proper chemical equations should be balanced. Writing balanced reactions is a chemist’s way of acknowledging the law of
conservation of matter.
Example
Is each chemical equation balanced?

a. 2Na(s) + O2(g) → 2Na2O(s)
b. CH4(g) + 2O2(g) → CO2(g) + 2H2O(ℓ)
c. AgNO3(aq) + 2KCl(aq) → AgCl(s) + KNO3(aq)
Solution
a. By counting, we find two sodium atoms and two oxygen atoms in the reactants and four sodium atoms and two oxygen
atoms in the products. This equation is not balanced.
b. The reactants have one carbon atom, four hydrogen atoms, and four oxygen atoms. The products have one carbon atom,
four hydrogen atoms, and four oxygen atoms. This equation is balanced.
c. The reactants have one silver atom, one nitrogen atom, three oxygen atoms, two potassium atoms, and two chlorine atoms.
The products have one silver atom, one chlorine atom, one potassium atom, one nitrogen atom, and three oxygen atoms.
Because there are different numbers of chlorine and potassium atoms, this equation is not balanced.
Exercise
Is each chemical equation balanced?

a. 2H g + O
(ℓ) → Hg O
2(g) 2 2(s)
b. C H
2 + 2O
4(g)
→ 2C O + 2H O
2(g) 2(g) 2 (ℓ)
c. M g(N O ) + 2Li
3 → Mg
2(s) + 2LiN O
(s) (s) 3(s) .
Answer a:
balanced
Answer b:
O is not balanced; the 4 atoms of oxygen on the left does not balance with the 6 oxygen atoms on the right
Answer c:
balanced
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Balance chemical equations.
How does one balance a chemical equation, starting with the correct formulas of the reactants and products? Basically, a back-and-
forth (or trial-and-error) approach is adopted, counting the number of atoms of one element on one side, checking the number of
atoms of that element on the other side, and changing a coefficient if necessary. Then check another element, going back and forth
from one side of the equation to another, until each element has the same number of atoms on both sides of the arrow. In many
cases, it does not matter which element is balanced first and which is balanced last, as long as all elements have the same number
of atoms on each side of the equation.
Below are guidelines for writing and balancing chemical equations.
1. Determine the correct chemical formulas for each reactant and product. Write the skeleton equation.
2. Count the number of atoms of each element that appears as a reactant and as a product. If a polyatomic ion is unchanged on
both sides of the equation, count it as a unit.
3. Balance each element one at a time by placing coefficients in front of the formulas. No coefficient is written for a 1. It is best to
begin by balancing elements that only appear in one chemical formula on each side of the equation. NEVER change the
subscripts in a chemical formula - you can only balance equations by using coefficients.
4. Check each atom or polyatomic ion to be sure that they are equal on both sides of the equation.
5. Make sure that all coefficients are in the lowest possible ratio. If necessary, reduce to the lowest ratio.
For example, to balance the equation
Step 1: Write the skeleton equation with the correct formulas.
CH + Cl → CCl + HCl (5.2.1)

4 2 4
Step 2: Count the number of each atom or polyatomic ion on both sides of the equation.
Reactants Products
1 C atom 1 C atom
(5.2.2)
4 H ions 1 H ions
2 Cl atom 5 Cl atoms
Step 3: We find that both sides are already balanced with one carbon atom. So we proceed to balance the hydrogen atoms. We find
that the reactant side has four hydrogen atoms, so the product side must also have four hydrogen atoms. This is balanced by putting
a 4 in front of the HCl:
CH + Cl → CCl + 4 HCl (5.2.3)

4 2 4
Reactants Products
1 C atom 1 C atom
(5.2.4)
4 H ions 4 H ions
Now each side has four hydrogen atoms. The product side has a total of eight chlorine atoms (four from the C C l and four from
4
the four molecules of HCl), so we need eight chlorine atoms as reactants. Because elemental chlorine is a diatomic molecule, we
need four chlorine molecules to get a total of eight chlorine atoms. We add another 4 in front of the Cl2 reactant:
CH + 4 Cl → CCl + 4 HCl (5.2.5)
4 2 4
Reactants Products
1 C atom 1 C atom
(5.2.6)
4 H ions 4 H ions
Step 3: Now we check: each side has one carbon atom, four hydrogen atoms, and eight chlorine atoms. The chemical equation is
balanced. And, the coefficients are in the lowest possible ratio.
 Example 5.2.2
Aqueous solutions of lead (II) nitrate and sodium chloride are mixed. The products of the reaction are an aqueous solution of
sodium nitrate and a solid precipitate of lead (II) chloride. Write the balanced chemical equation for this reaction.
Solution
Step 1: Write the skeleton equation with the correct formulas.
Pb(NO ) (aq) + NaCl (aq) → NaNO (aq) + PbCl (s) (5.2.7)
3 2 3 2
Step 2: Count the number of each atom or polyatomic ion on both sides of the equation.
Reactants Products
1 Pb atom 1 Pb atom
− −
2 NO3 ions 1 NO3 ions (5.2.8)
1 Na atom 1 Na atom
Step 3: Solve. The nitrate ions and the chlorine atoms are unbalanced. Start by placing a 2 in front of the NaCl. This increases
the reactant counts to 2 Na atoms and 2 Cl atoms. Then place a 2 in front of the NaNO . The result is:
3
Pb(NO ) (aq) + 2NaCl (aq) → 2 NaNO (aq) + PbCl (s) (5.2.9)

3 2 3 2
Step 4: The new count for each atom and polyatomic ion becomes:
Reactants Products
1 Pb atom 1 Pb atom
− −
2 NO3 ions 2 NO3 ions (5.2.10)
2 Na atom 2 Na atom
Step 5: Think about the result.

The equation is now balanced since there are equal numbers of atoms of each element on both sides of the equation. And, the
coefficients are in the lowest possible ratio.
 Exercise 5.2.2
Fermentation is a biochemical process that enables yeast cells to live in the absence of oxygen. Humans have exploited it for
centuries to produce wine and beer and make bread rise. In fermentation, sugars such as glucose (C6H12O6) are converted to
ethanol (C2H5OH) and carbon dioxide CO2. Write a balanced chemical reaction for the fermentation of glucose.
Commercial use of fermentation. (a) Microbrewery vats are used to prepare beer. (b) The fermentation of glucose by yeast
cells is the reaction that makes beer production possible.
Answer
C6H12O6(s) → 2C2H5OH(l) + 2CO2(g)
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Use solubility rules to predict whether a precipitate will form.
Write and balance chemical equations for precipitation reactions.
There are many types of chemical reactions that you will learn about in chemistry. In this chapter, we will focus on some reactions
of ionic compounds: precipitation reactions (a type of double-replacement reaction), acid-base neutralization reactions, and
oxidation-reduction reactions.
The practice of barter (trading one thing for another) has been in existence since the beginning of time. In the past, for example,
items like chickens were bartered for newspapers. Person A had something that person B wanted, and vice versa. So, when person
A and person B traded items, they each had something new. Some chemical reactions are like that—compounds swap parts, and the
products are new materials.
A double-replacement reaction is a reaction in which the positive and negative ions of two ionic compounds exchange places to
form two new compounds. The general form of a double-replacement (also called double-displacement) reaction is:
AB + CD → AD + CB (5.3.1)
In this reaction, A and C are positively-charged cations, while B and D are negatively-charged anions. Double-replacement
reactions generally occur between substances in aqueous solution. In order for a reaction to occur, one of the products is usually a
solid precipitate, a gas, or a molecular compound such as water.
Formation of a Precipitate
A precipitate forms in a double-replacement reaction when the cations from one of the reactants combine with the anions from the
other reactant to form an insoluble ionic compound. When aqueous solutions of potassium iodide and lead (II) nitrate are mixed,
the following reaction occurs:
2KI (aq) + Pb(NO ) (aq) → 2 KNO (aq) + PbI (s) (5.3.2)

3 2 3 2
There are very strong attractive forces that occur between Pb and I ions and the result is a brilliant yellow precipitate (see
2 + −
Figure 5.3.1 below). The other product of the reaction, potassium nitrate, remains soluble.
Figure 5.3.1 : Formation of lead iodide precipitate. (CC BY-NC; CK-12)

To judge whether double-replacement reactions will occur, we need to know what kinds of ionic compounds form precipitates. For
this, we use solubility rules, which are general statements that predict which ionic compounds dissolve (are soluble) and which do
not (are not soluble, or insoluble). Table 5.3.1 lists some general solubility rules. We need to consider each ionic compound (both
the reactants and the possible products) in light of the solubility rules. If a compound is soluble, we use the (aq) label with it,
indicating that it dissolves. If a compound is not soluble, we use the (s) label with it and assume that it will precipitate out of
solution. If everything is soluble, then no reaction will be expected.
Table 5.3.1 : Solubility Rules: Soluble Compounds and Their Exceptions
These compounds generally dissolve in water (are soluble): Exceptions:
All compounds of Li+, Na+, K+, Rb+, Cs+, and NH4+ None
All compounds of NO3− and C2H3O2− None
Compounds of Cl−, Br−, I− Ag+, Hg22+, Pb2+
Compounds of SO42 Hg22+, Pb2+, Sr2+, Ba2+
Table 5.3.2 : Solubility Rules: Insoluble Compounds and Their Exceptions

These compounds generally do not dissolve in water (are insoluble): Exceptions:
Compounds of CO32− and PO43− Compounds of Li+, Na+, K+, Rb+, Cs+, and NH4+
Compounds of OH− Compounds of Li+, Na+, K+, Rb+, Cs+, NH4+, Sr2+, and Ba2+
For example, consider the possible double-replacement reaction between Na2SO4 and SrCl2. The solubility rules say that all ionic
sodium compounds are soluble and all ionic chloride compounds are soluble, except for Ag+, Hg22+, and Pb2+, which are not
being considered here. Therefore, Na2SO4 and SrCl2 are both soluble. The possible double-replacement reaction products are
NaCl and SrSO4. Are these soluble? NaCl is (by the same rule we just quoted), but what about SrSO4? Compounds of the sulfate
ion are generally soluble, but Sr2+ is an exception: we expect it to be insoluble—a precipitate. Therefore, we expect a reaction to
occur, and the balanced chemical equation would be:
Na SO (aq) + SrCl (aq) → 2 NaCl(aq) + SrSO (s)

2 4 2 4
You would expect to see a visual change corresponding to SrSO4 precipitating out of solution (Figure 5.3.2).
Figure 5.3.2 : Double-Replacement Reactions. Some double-replacement reactions are obvious because you can see a solid
precipitate coming out of solution. Source: Photo courtesy of Choij, Wikimedia(opens in new window) [commons.wikimedia.org].
A blue solution is shown in a glass beaker. White precipitate can be seen forming at the bottom of the beaker.
 Example 5.3.4:
Will a precipitation reaction occur? If so, identify the products.
1. Ca(NO3)2 + KBr → ?
2. NaOH + FeCl2 → ?
Solution
1. According to the solubility rules, both Ca(NO3)2 and KBr are soluble. Now we consider what the double-replacement
products would be by switching the cations (or the anions)—namely, CaBr2 and KNO3. However, the solubility rules
predict that these two substances would also be soluble, so no precipitate would form. Thus, we predict no reaction in this
case.
2. According to the solubility rules, both NaOH and FeCl2 are expected to be soluble. If we assume that a double-replacement
reaction may occur, we need to consider the possible products, which would be NaCl and Fe(OH)2. NaCl is soluble, but,
according to the solubility rules, Fe(OH)2 is not. Therefore, a reaction would occur, and Fe(OH)2(s) would precipitate out
of solution. The balanced chemical equation is
2 NaOH(aq) + FeCl (aq) → 2 NaCl(aq) + Fe(OH) (s)

2 2
 Exercise 5.3.4
Sr(NO ) + KCl →
3 2
Answer
No reaction; all possible products are soluble.
Key Takeaways
A single-replacement reaction replaces one element for another in a compound.
The periodic table or an activity series can help predict whether single-replacement reactions occur.
A double-replacement reaction exchanges the cations (or the anions) of two ionic compounds.
A precipitation reaction is a double-replacement reaction in which one product is a solid precipitate.
Solubility rules are used to predict whether some double-replacement reactions will occur.
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Identify an acid-base neutralization reaction and predict its products.
Previously, you learned that an acid is any compound that produces hydrogen ions (H+) in an aqueous solution, and the chemical
opposite of an acid is a base, which is a compound that produces hydroxide ions (OH−) in an aqueous solution. These original
definitions were proposed by Arrhenius (the same person who proposed ion dissociation) in 1884, so they are referred to as the
Arrhenius definition of an acid and a base, respectively.
You may recognize that, based on the description of a hydrogen atom, an H+ ion is a hydrogen atom that has lost its lone electron;
that is, H+ is simply a proton. Do we really have bare protons moving about in aqueous solution? No. What is more likely is that
the H+ ion has attached itself to one (or more) water molecule(s). To represent this chemically, we define the hydronium ion as
H3O+, which represents an additional proton attached to a water molecule. We use the hydronium ion as the more logical way that
a hydrogen ion appears in an aqueous solution, although in many chemical reactions H+ and H3O+ are treated equivalently.
The reaction of an acid and a base is called a neutralization reaction. Although acids and bases have their own unique
chemistries, the acid and base "cancel" each other's chemistry to produce a rather innocuous substance, water. In fact, the general
reaction between an acid and a base is:
acid + base → water + salt
where the term salt is generally used to define any ionic compound (soluble or insoluble) that is formed from a reaction between an
acid and a base. (In chemistry, the word salt refers to more than just table salt.) For example, the balanced chemical equation for
the reaction between HCl(aq) and KOH(aq) is
HCl(aq) + KOH(aq) → H O(ℓ) + KCl(aq)

2
where the salt is KCl. By counting the number of atoms of each element, we find that only one water molecule is formed as a
product. However, in the reaction between HCl(aq) and Mg(OH)2(aq), additional molecules of HCl and H2O are required to
balance the chemical equation:
2 HCl(aq) + Mg (OH) (aq) → 2 H O(ℓ) + MgCl (aq)

2 2 2
Here, the salt is MgCl2. (This is one of several reactions that take place when a type of antacid, a base, is used to treat stomach
acid.)
 Example 5.4.1:
Write the neutralization reactions between each acid and base.
a. HNO3(aq) and Ba(OH)2(aq)
b. H3PO4(aq) and Ca(OH)2(aq)
Solution
First, we will write the chemical equation with the formulas of the reactants and the expected products; then we will balance
the equation.
a. The expected products are water and barium nitrate, so the initial chemical reaction is
HNO (aq) + Ba (OH) (aq) → H O(ℓ) + Ba (NO ) (aq)

3 2 2 3 2
To balance the equation, we need to realize that there will be two H2O molecules, so two HNO3 molecules are required:
2 HNO (aq) + Ba (OH) (aq) → 2 H O(ℓ) + Ba (NO ) (aq)

3 2 2 3 2
This chemical equation is now balanced.
b. The expected products are water and calcium phosphate, so the initial chemical equation is
H PO (aq) + Ca (OH) (aq) → H O(ℓ) + Ca (PO ) (s)

3 4 2 2 3 4 2
According to the solubility rules, Ca3(PO4)2 is insoluble, so it has an (s) phase label. To balance this equation, we need two
phosphate ions and three calcium ions. We end up with six water molecules to balance the equation:
2 H PO (aq) + 3 Ca (OH) (aq) → 6 H O(ℓ) + Ca (PO ) (s)

3 4 2 2 3 4 2
This chemical equation is now balanced.
 Exercise 5.4.1
Write the neutralization reaction between H2SO4(aq) and Sr(OH)2(aq).
Answer
H SO (aq) + Sr(OH) (aq) → 2 H O(ℓ) + SrSO (aq)
2 4 2 2 4
Neutralization reactions are one type of chemical reaction that proceeds even if one reactant is not in the aqueous phase. For
example, the chemical reaction between HCl(aq) and Fe(OH)3(s) still proceeds according to the equation:
3 HCl(aq) + Fe(OH) (s) → 3 H O(ℓ) + FeCl (aq)

3 2 3
even though Fe(OH)3 is not soluble. When one realizes that Fe(OH)3(s) is a component of rust, this explains why some cleaning
solutions for rust stains contain acids; the neutralization reaction produces products that are soluble and wash away. (Washing with
acids like HCl is one way to remove rust and rust stains, but HCl must be used with caution!)
Key Takeaways
The Arrhenius definition of an acid is a substance that increases the amount of H+ in an aqueous solution.
The Arrhenius definition of a base is a substance that increases the amount of OH− in an aqueous solution.
Neutralization is the reaction of an acid and a base, which forms water and a salt.
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To identify a chemical reaction as an oxidation-reduction reaction.
When zinc metal is submerged into a quantity of aqueous HCl, the following reaction occurs (Figure 5.5.1):
Zn(s) + 2 HCl(aq) → H (g) + ZnCl (aq) (5.5.1)
2 2
This is one example of what is sometimes called a single replacement reaction because Zn replaces H in combination with Cl.
Figure 5.5.1 : Zinc Metal plus Hydrochloric Acid. It is fairly obvious that zinc metal reacts with aqueous hydrochloric acid! The
bubbles are hydrogen gas (right side of Equation 5.5.1 ).
Because some of the substances in this reaction are aqueous, we can separate them into ions:
+ − 2 + −
Zn(s) + 2 H (aq) + 2 Cl (aq) → H (g) + Zn (aq) + 2 Cl (aq)
2
Viewed this way, the net reaction seems to be a charge transfer between zinc and hydrogen atoms. (There is no net change
experienced by the chloride ion.) In fact, electrons are being transferred from the zinc atoms to the hydrogen atoms (which
ultimately make a molecule of diatomic hydrogen), changing the charges on both elements.
To understand electron-transfer reactions like the one between zinc metal and hydrogen ions, chemists separate them into two parts:
one part focuses on the loss of electrons, and one part focuses on the gain of electrons. The loss of electrons is called oxidation. The
gain of electrons is called reduction. Because any loss of electrons by one substance must be accompanied by a gain in electrons by
something else, oxidation and reduction always occur together. As such, electron-transfer reactions are also called oxidation-
reduction reactions, or simply redox reactions. The atom that loses electrons is oxidized, and the atom that gains electrons is
reduced. Also, because we can think of the species being oxidized as causing the reduction, the species being oxidized is called the
reducing agent, and the species being reduced is called the oxidizing agent.
Because batteries are used as sources of electricity (that is, of electrons), all batteries are
based on redox reactions.
Although the two reactions occur together, it can be helpful to write the oxidation and reduction reactions separately as half
reactions. In half reactions, we include only the reactant being oxidized or reduced, the corresponding product species, any other
species needed to balance the half reaction, and the electrons being transferred. Electrons that are lost are written as products;
electrons that are gained are written as reactants. For example, in our earlier equation, now written without the chloride ions,
+ 2 +
Zn(s) + 2 H (aq) → Zn (aq) + H (g)
2
2+
zinc atoms are oxidized to Zn . The half reaction for the oxidation reaction, omitting phase labels, is as follows:
2 + −
Zn → Zn +2 e
This half reaction is balanced in terms of the number of zinc atoms, and it also shows the two electrons that are needed as products
to account for the zinc atom losing two negative charges to become a 2+ ion. With half reactions, there is one more item to balance:
the overall charge on each side of the reaction. If you check each side of this reaction, you will note that both sides have a zero net
charge.
Hydrogen is reduced in the reaction. The balanced reduction half reaction is as follows:
+ −
2H +2 e → H
2
There are two hydrogen atoms on each side, and the two electrons written as reactants serve to neutralize the 2+ charge on the
reactant hydrogen ions. Again, the overall charge on both sides is zero.
The overall reaction is simply the combination of the two half reactions and is shown by adding them together.
Because we have two electrons on each side of the equation, they can be canceled. This is the key criterion for a balanced redox
reaction: the electrons have to cancel exactly. If we check the charge on both sides of the equation, we see they are the same—2+.
(In reality, this positive charge is balanced by the negative charges of the chloride ions, which are not included in this reaction
because chlorine does not participate in the charge transfer.)
Redox reactions are often balanced by balancing each individual half reaction and then combining the two balanced half reactions.
Sometimes a half reaction must have all of its coefficients multiplied by some integer for all the electrons to cancel. The following
example demonstrates this process.
 Example 5.5.1: Reducing Silver Ions
Write and balance the redox reaction that has silver ions and aluminum metal as reactants and silver metal and aluminum ions
as products. Identify the substance oxidized, substance reduced, reducing agent and reducing agent.
Solution
We start by using symbols of the elements and ions to represent the reaction:
+ 3 +
Ag + Al → Ag + Al
The equation looks balanced as it is written. However, when we compare the overall charges on each side of the equation, we
find a charge of +1 on the left but a charge of +3 on the right. This equation is not properly balanced. To balance it, let us write
the two half reactions. Silver ions are reduced, and it takes one electron to change Ag+ to Ag:
Reduction half-reaction:
+ −
Ag +e → Ag
Aluminum is oxidized, losing three electrons to change from Al to Al3+:

Oxidation half-reaction:
3 + −
Al → Al +3 e
To combine these two half reactions and cancel out all the electrons, we need to multiply the silver reduction reaction by 3:
Now the equation is balanced, not only in terms of elements but also in terms of charge.
The substance oxidized is the reactant that had undergone oxidation: Al
The substance reduced is the reactant that had undergone reduction: Ag+
The reducing agent is the same as the substance oxidized: Al
The oxidizing agent is the same as the substance reduced: Ag+
 Exercise 5.5.1
Write and balance the redox reaction that has calcium ions and potassium metal as reactants and calcium metal and potassium
ions as products. Identify the substance oxidized, substance reduced, reducing agent and reducing agent.
Answer
Reduction: Ca2+ + 2e− → Ca
Oxidation: 2 (K → K+ + e−)
Combined: Ca2+ + 2K → Ca + 2K+
The substance oxidized is the reactant that had undergone oxidation: K
The substance reduced is the reactant that had undergone reduction: Ca2+
The reducing agent is the same as the substance oxidized: K
The oxidizing agent is the same as the substance reduced: Ca2+
Potassium has been used as a reducing agent to obtain various metals in their elemental form.
 To Your Health: Redox Reactions and Pacemaker Batteries
All batteries use redox reactions to supply electricity because electricity is basically a stream of electrons being transferred
from one substance to another. Pacemakers—surgically implanted devices for regulating a person’s heartbeat—are powered by
tiny batteries, so the proper operation of a pacemaker depends on a redox reaction.
Pacemakers used to be powered by NiCad batteries, in which nickel and cadmium (hence the name of the battery) react with
water according to this redox reaction:
Cd(s) + 2 NiOOH(s) + 2 H O(ℓ) → Cd(OH) (s) + 2 Ni(OH)2 (s)

2 2
The cadmium is oxidized, while the nickel atoms in NiOOH are reduced. Except for the water, all the substances in this
reaction are solids, allowing NiCad batteries to be recharged hundreds of times before they stop operating. Unfortunately,
NiCad batteries are fairly heavy batteries to be carrying around in a pacemaker. Today, the lighter lithium/iodine battery is used
instead. The iodine is dissolved in a solid polymer support, and the overall redox reaction is as follows:
2 Li(s) + I (s) → 2 LiI(s)

2
Lithium is oxidized, and iodine is reduced. Although the lithium/iodine battery cannot be recharged, one of its advantages is
that it lasts up to 10 years. Thus, a person with a pacemaker does not have to worry about periodic recharging; about once per
decade a person requires minor surgery to replace the pacemaker/battery unit. Lithium/iodine batteries are also used to power
calculators and watches.
Figure 5.5.1 : A small button battery like this is used to power a watch, pacemaker, or calculator. (CC BY-SA; Gerhard H
Wrodnigg via Wikipedia)
Oxidation and reduction can also be defined in terms of changes in composition. The original meaning of oxidation was “adding
oxygen,” so when oxygen is added to a molecule, the molecule is being oxidized. The reverse is true for reduction: if a molecule
loses oxygen atoms, the molecule is being reduced. For example, the acetaldehyde (CH CHO) molecule takes on an oxygen atom
3
to become acetic acid (CH COOH ).

3
2 CH CHO + O → 2 CH COOH
3 2 3
Thus, acetaldehyde is being oxidized.
Similarly, reduction and oxidation can be defined in terms of the gain or loss of hydrogen atoms. If a molecule adds hydrogen
atoms, it is being reduced. If a molecule loses hydrogen atoms, the molecule is being oxidized. For example, in the conversion of
acetaldehyde into ethanol (CH CH OH ), hydrogen atoms are added to acetaldehyde, so the acetaldehyde is being reduced:
3 2
CH CHO + H → CH CH OH
3 2 3 2
Table 5.5.1 : Oxidation-Reduction Reactions and the Changes in Oxygen and Hydrogen.
Process Change in oxygen (some reactions) Change in hydrogen (some reactions)
Oxidation gain lose
Reduction lose gain
 Example 5.5.2
In each conversion, indicate whether oxidation or reduction is occurring.

a. N2 → NH3
b. CH3CH2OHCH3 → CH3COCH3
c. HCHO → HCOOH
Solution
a. Hydrogen is being added to the original reactant molecule, so reduction is occurring.
b. Hydrogen is being removed from the original reactant molecule, so oxidation is occurring.
c. Oxygen is being added to the original reactant molecule, so oxidation is occurring.
 Exercise 5.5.2
In each conversion, indicate whether oxidation or reduction is occurring.

a. CH4 → CO2 + H2O
b. NO2 → N2
c. CH2=CH2 → CH3CH3
Answer a:
Oxygen is being added. Oxidation is occurring.
Answer b:
Oxygen is being removed. Reduction is occurring.
Answer a:
Hydrogen is being added. Reduction is occurring.
Key Takeaway
Chemical reactions in which electrons are transferred are called oxidation-reduction, or redox, reactions. Oxidation is the loss of
electrons. Reduction is the gain of electrons. Oxidation and reduction always occur together, even though they can be written as
separate chemical equations.
5.5: Redox Reactions is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
5.5: Oxidation-Reduction (Redox) Reactions by Anonymous is licensed CC BY-NC-SA 4.0. Original source:
Assign oxidation numbers to atoms in simple compounds.
Recognize a reaction as an oxidation-reduction reaction.
Redox reactions require that we keep track of the electrons assigned to each atom in a chemical reaction. How do we do that? We
use oxidation numbers to keep track of electrons in atoms. Oxidation numbers are assigned to atoms based on four rules.
Oxidation numbers are not necessarily equal to the charge on the atom (although sometimes they can be); we must keep the
concepts of charge and oxidation numbers separate.
 Assigning Oxidation Numbers
The rules for assigning oxidation numbers to atoms are as follows:

1. Atoms in their elemental state are assigned an oxidation number of 0.
2. Atoms in monatomic (i.e., one-atom) ions are assigned an oxidation number equal to their charge. Oxidation numbers are
usually written with the sign first, then the magnitude, to differentiate them from charges.
3. In compounds, fluorine is assigned a −1 oxidation number; oxygen is usually assigned a −2 oxidation number (except in
peroxide compounds [where it is −1] and in binary compounds with fluorine [where it is positive]); and hydrogen is usually
assigned a +1 oxidation number (except when it exists as the hydride ion [H−], in which case rule 2 prevails).
4. In compounds, all other atoms are assigned an oxidation number so that the sum of the oxidation numbers on all the atoms
in the species equals the charge on the species (which is zero if the species is neutral).
Here are some examples for practice. In H2, both H atoms have an oxidation number of 0 by rule 1. In MgCl2, magnesium has an
oxidation number of +2, while chlorine has an oxidation number of −1 by rule 2. In H2O, the H atoms each have an oxidation
number of +1, while the O atom has an oxidation number of −2, even though hydrogen and oxygen do not exist as ions in this
compound (rule 3). By contrast, by rule 3, each H atom in hydrogen peroxide (H2O2) has an oxidation number of +1, while each O
atom has an oxidation number of −1. We can use rule 4 to determine oxidation numbers for the atoms in SO2. Each O atom has an
oxidation number of −2; for the sum of the oxidation numbers to equal the charge on the species (which is zero), the S atom is
assigned an oxidation number of +4. Does this mean that the sulfur atom has a 4+ charge on it? No, it means only that the S atom is
assigned a +4 oxidation number by our rules of apportioning electrons among the atoms in a compound.
 Example 5.6.1
Assign oxidation numbers to the atoms in each substance.
1. Cl2
2. GeO2
3. Ca(NO3)2
Solution
1. Cl2 is the elemental form of chlorine. Rule 1 states each atom has an oxidation number of 0.
2. By rule 3, oxygen is normally assigned an oxidation number of −2. For the sum of the oxidation numbers to equal the
charge on the species (zero), the Ge atom is assigned an oxidation number of +4.
3. Ca(NO3)2 can be separated into two parts: the Ca2+ ion and the NO3− ion. Considering these separately, the Ca2+ ion has
an oxidation number of +2 by rule 2. Now consider the NO3− ion. Oxygen is assigned an oxidation number of −2, and
there are three of them. According to rule 4, the sum of the oxidation numbers on all atoms must equal the charge on the
species, so we have the simple algebraic equation x + 3(−2) = −1
where x is the oxidation number of the N atom and the −1 represents the charge on the species. Evaluating for x,
x + (−6) = −1x = +5
Thus the oxidation number on the N atom in the NO3− ion is +5.
 Exercise 5.6.1: Phosphoric Acid

Assign oxidation numbers to the atoms in H3PO4.
Answer
H: +1; O: −2; P: +5
All redox reactions occur with a simultaneous change in the oxidation numbers of some atoms. At least two elements must change
their oxidation numbers. When an oxidation number of an atom is increased in the course of a redox reaction, that atom is being
oxidized. When an oxidation number of an atom is decreased in the course of a redox reaction, that atom is being reduced.
Oxidation and reduction can also be defined in terms of increasing or decreasing oxidation numbers, respectively.
 Example 5.6.2:
Identify what is being oxidized and reduced in this redox reaction.

2 Na + Br → 2 NaBr
2
Solution
Both reactants are the elemental forms of their atoms, so the Na and Br atoms have oxidation numbers of 0. In the ionic
product, the Na+ ions have an oxidation number of +1, while the Br− ions have an oxidation number of −1.
2 N a + Br2 → 2 N aBr
0 0 +1−1
Sodium is increasing its oxidation number from 0 to +1, so it is being oxidized; bromine is decreasing its oxidation number
from 0 to −1, so it is being reduced:
Because oxidation numbers are changing, this is a redox reaction. The total number of electrons being lost by sodium (two, one
lost from each Na atom) is gained by bromine (two, one gained for each Br atom).
 Exercise 5.6.2
Identify what is being oxidized and reduced in this redox reaction.
C +O → CO
2 2
Answer
C is being oxidized from 0 to +4; O is being reduced from 0 to −2.
Oxidation reactions can become quite complex, as attested by the following redox reaction:
+ − 2+
6H (aq) + 2 M nO (aq) + 5 H2 O2 (l) → 2 M n (aq) + 5 O2 (g) + 8 H2 O(l)
4
−1 +2 0
+7
To demonstrate that this is a redox reaction, the oxidation numbers of the species being oxidized and reduced are listed; can you
determine what is being oxidized and what is being reduced?
 Food and Drink Application: Fortifying Food with Iron
Iron is an essential mineral in our diet; iron-containing compounds like the heme protein in hemoglobin could not function
without it. Most biological iron has the form of the Fe2+ ion; iron with other oxidation numbers is almost inconsequential in
human biology (although the body does contain an enzyme to reduce Fe3+ to Fe2+, so Fe3+ must have some biological
significance, albeit minor). To ensure that we ingest enough iron, many foods are enriched with iron. Although Fe2+
compounds are the most logical substances to use, some foods use "reduced iron" as an ingredient (bread and breakfast cereals
are the most well-known examples). Reduced iron is simply iron metal; iron is added as a fine metallic powder. The metallic
iron is oxidized to Fe2+ in the digestive system and then absorbed by the body, but the question remains: Why are we ingesting
metallic iron? Why not just use Fe2+ salts as an additive?
Figure 5.6.1 Ingredients. Many prepared foods list reduced iron in their ingredients list.
The ingredients list contains Flour (Contains: wheat flour, malted barley flour, niacin, reduced iron, thiamine mononitrate,
riboflavin, folic acid), water, sourdough (6.4%) (contains: water, flour [wheat flour, malted barley flour, niacin, reduced iron,
thiamine mononitrate, riboflavin, folic acid], yeast), salt, wheat germ, semolina (contains: durum wheat semolina, niacin,
ferrous sulphate, thiamine mononitrate, riboflavin, folic acid).
Although it is difficult to establish conclusive reasons, a search of scientific and medical literature suggests a few reasons. One
reason is that fine iron filings do not affect the taste of the product. The size of the iron powder (several dozen micrometers) is
not noticeable when chewing iron-supplemented foods, and the tongue does not detect any changes in flavor that can be
detected when using Fe2+ salts. Fe2+ compounds can affect other properties of foodstuffs during preparation and cooking, like
dough pliability, yeast growth, and color. Finally, of the common iron substances that might be used, metallic iron is the least
expensive. These factors appear to be among the reasons why metallic iron is the supplement of choice in some foods.
Key Takeaways
Oxidation numbers are used to keep track of electrons in atoms.
There are rules for assigning oxidation numbers to atoms.
Oxidation is an increase in oxidation number (loss of electrons); reduction is a decrease in oxidation number (gain of electrons).
5.6: Recognizing Redox Reactions is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
14.2: Oxidation-Reduction Reactions by Anonymous is licensed CC BY-NC-SA 3.0. Original source:
Write ionic and net ionic equations for chemical reactions involving ions.
At sports events around the world, a small number of athletes fiercely compete on fields and in stadiums. They get tired, dirty, and
sometimes hurt as they try to win the game. Surrounding them are thousands of spectators watching and cheering. Would the game
be different without the spectators? Definitely! Spectators provide encouragement to the team and generate enthusiasm. Although
the spectators are not playing the game, they are certainly a part of the process.
Net Ionic Equations

We can write a molecular equation for the formation of silver chloride precipitate:
NaCl + AgNO → NaNO + AgCl
3 3
The corresponding ionic equation is written to show the ions that are dissolved in solution:
+ − + − + −
Na (aq) + Cl (aq) + Ag (aq) + NO3 (aq) → Na (aq) + NO3 (aq) + AgCl (s)
If you look carefully at the ionic equation, you will notice that the sodium ion and the nitrate ion appear unchanged on both sides of
the equation. When the two solutions are mixed, neither the Na nor the NO ions participate in the reaction. They can be
+ −
3
eliminated from the reaction.

+ − + − + −
Na (aq) + Cl (aq) + Ag (aq) + NO (aq) → Na (aq) + NO (aq) + AgCl (s)
3 3
A spectator ion is an ion that does not take part in the chemical reaction and is found in solution both before and after the reaction.
In the above reaction, the sodium ion and the nitrate ion are both spectator ions. The equation can now be written without the
spectator ions:
+ −
Ag (aq) + Cl (aq) → AgCl (s)
The net ionic equation is the chemical equation that shows only those elements, compounds, and ions that are directly involved in
the chemical reaction. Notice that in writing the net ionic equation, the positively-charged silver cation was written first on the
reactant side, followed by the negatively-charged chloride anion. This is somewhat customary because that is the order in which the
ions must be written in the silver chloride product. However, it is not absolutely necessary to order the reactants in this way.
Net ionic equations must be balanced by both mass and charge. Balancing by mass means ensuring that there are equal masses of
each element on the product and reactant sides. Balancing by charge means making sure that the overall charge is the same on both
sides of the equation. In the above equation, the overall charge is zero, or neutral, on both sides of the equation. As a general rule, if
you balance the molecular equation properly, the net ionic equation will end up being balanced by both mass and charge.
Example
5.7.1
When aqueous solutions of copper (II) chloride and potassium phosphate are mixed, a precipitate of copper (II) phosphate is
formed. Write a balanced net ionic equation for this reaction.
Solution
Step 1: Plan the problem.

Write and balance the molecular equation first, making sure that all formulas are correct. Then write the ionic equation,
showing all aqueous substances as ions. Carry through any coefficients. Finally, eliminate spectator ions and write the net ionic
equation.
Step 2: Solve.
Molecular equation:
3 CuCl (aq) + 2 K PO (aq) → 6KCl (aq) + Cu (PO ) (s)

2 3 4 3 4 2
Ionic equation:
2 + − + 3 − + −
3 Cu (aq) + 6 Cl (aq) + 6 K (aq) + 2 PO4 (aq) → 6 K (aq) + 6 Cl (aq) + Cu (PO ) (s)
3 4 2
Notice that the balance of the equation is carried through when writing the dissociated ions. For example, there are six chloride
ions on the reactant side because the coefficient of 3 is multiplied by the subscript of 2 on the copper (II) chloride formula. The
spectator ions, K and Cl , can be eliminated.
+ −
Net ionic equation:

2 + 3 −
3 Cu (aq) + 2 PO4 (aq) → Cu (PO ) (s)
3 4 2

For a precipitation reaction, the net ionic equation always shows the two ions that come together to form the precipitate. The
equation is balanced by mass and charge.
Summary
A spectator ion is an ion that does not take part in the chemical reaction and is found in solution both before and after the
reaction.
The net ionic equation is the chemical equation that shows only those elements, compounds, and ions that are directly involved
in the chemical reaction.
An example of writing a net ionic equation is outlined.
5.7: Net Ionic Equations is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
16.18: Net Ionic Equations by CK-12 Foundation is licensed CK-12. Original source: https://flexbooks.ck12.org/cbook/ck-12-chemistry-
flexbook-2.0/.
CHAPTER OVERVIEW
6: Chemical Reactions - Mole and Mass Relationships

6: Chemical Reactions - Mole and Mass Relationships is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by
LibreTexts.
1
Calculate formula masses for covalent and ionic compounds.
Define the amount unit mole and the related quantity Avogadro’s number.
Calculate molar mass of a compound from the molecular formula.
We can argue that modern chemical science began when scientists started exploring the quantitative as well as the qualitative
aspects of chemistry. For example, Dalton’s atomic theory was an attempt to explain the results of measurements that allowed him
to calculate the relative masses of elements combined in various compounds. Understanding the relationship between the masses of
atoms and the chemical formulas of compounds allows us to quantitatively describe the composition of substances.
Formula Mass
In an earlier chapter, we described the development of the atomic mass unit, the concept of average atomic masses, and the use of
chemical formulas to represent the elemental makeup of substances. These ideas can be extended to calculate the formula mass of
a substance, which is equal to the sum of the atomic masses for all the atoms represented in the substance’s formula.
Formula Mass for Covalent Substances

For covalent substances, the formula represents the numbers and types of atoms composing a single molecule of the substance;
therefore, the formula mass may be correctly referred to as a molecular mass. Consider chloroform (CHCl3), a covalent compound
once used as a surgical anesthetic and now primarily used in the production of tetrafluoroethylene, the building block for the “anti-
stick” polymer, Teflon. The molecular formula of chloroform indicates that a single molecule contains one carbon atom, one
hydrogen atom, and three chlorine atoms. The average molecular mass of a chloroform molecule is therefore equal to the sum of
the average atomic masses of these atoms. Figure 6.1.1 outlines the calculations used to derive the molecular mass of chloroform,
which is 119.37 amu.
Figure 6.1.1 : The average mass of a chloroform molecule, CHCl3, is 119.37 amu, which is the sum of the average atomic masses of
each of its constituent atoms. The model shows the molecular structure of chloroform.
A table and diagram are shown. The table is made up of six columns and five rows. The header row reads: “Element,” “Quantity,”
a blank space, “Average atomic mass (a m u),” a blank space, and “Subtotal (a m u).” The first column contains the symbols “C,”
“H,” “C l” and a blank, merged cell that runs the width of the first five columns. The second column contains the numbers “1,” “1,”
and “3” as well as the merged cell. The third column contains the multiplication symbol in each cell except for the last, merged
cell. The fourth column contains the numbers “12.01,” “1.008,” and “35.45” as well as the merged cell. The fifth column contains
the symbol “=” in each cell except for the last, merged cell. The sixth column contains the values “12.01,” “1.008,” “106.35,” and
“119.37.” There is a thick black line below the number 106.35. The merged cell under the first five columns reads “Molecular
mass.” To the left of the table is a diagram of a molecule. Three green spheres are attached to a slightly smaller black sphere, which
is also attached to a smaller white sphere. The green spheres lie beneath and to the sides of the black sphere while the white sphere
is located straight up from the black sphere.
Likewise, the molecular mass of an aspirin molecule, C9H8O4, is the sum of the atomic masses of nine carbon atoms, eight
hydrogen atoms, and four oxygen atoms, which amounts to 180.15 amu (Figure 6.1.2).
Figure 6.1.2 : The average mass of an aspirin molecule is 180.15 amu. The model shows the molecular structure of aspirin,
C9H8O4.
A table and diagram are shown. The table is made up of six columns and five rows. The header row reads: “Element,” “Quantity,”
a blank space, “Average atomic mass (a m u),” a blank space, and “Subtotal (a m u).” The first column contains the symbols “C,”
“H,” “O,” and a merged cell. The merged cell runs the length of the first five columns. The second column contains the numbers
“9,” “8,” and “4” as well as the merged, cell. The third column contains the multiplication symbol in each cell except for the last,
merged cell. The fourth column contains the numbers “12.01,” “1.008,” and “16.00” as well as the merged cell. The fifth column
contains the symbol “=” in each cell except for the last, merged cell. The sixth column contains the values: “108.09,” “8.064,”
“64.00,” and “180.15.” There is a thick black line below the number 64.00. The merged cell under the first five columns reads
“Molecular mass.” To the left of the table is a diagram of a molecule. Six black spheres are located in a six-sided ring and
connected by alternating double and single black bonds. Attached to each of the four black spheres is one smaller white sphere.
Attached to the farthest right black sphere is a red sphere, connected to two more black spheres, all in a row. Attached to the last
black sphere of that row are two more white spheres. Attached to the first black sphere of that row is another red sphere. A black
sphere, attached to two red spheres and a white sphere is attached to the black sphere on the top right of the six-sided ring.
 Example 6.1.1: Computing Molecular Mass for a Covalent Compound
Ibuprofen, C13H18O2, is a covalent compound and the active ingredient in several popular nonprescription pain medications,
such as Advil and Motrin. What is the molecular mass (amu) for this compound?
Solution
Molecules of this compound are comprised of 13 carbon atoms, 18 hydrogen atoms, and 2 oxygen atoms. Following the
approach described above, the average molecular mass for this compound is therefore:
 Exercise 6.1.1
Acetaminophen, C8H9NO2, is a covalent compound and the active ingredient in several popular nonprescription pain
medications, such as Tylenol. What is the molecular mass (amu) for this compound?
Answer
151.16 amu
Formula Mass for Ionic Compounds

Ionic compounds are composed of discrete cations and anions combined in ratios to yield electrically neutral bulk matter. The
formula mass for an ionic compound is calculated in the same way as the formula mass for covalent compounds: by summing the
average atomic masses of all the atoms in the compound’s formula. Keep in mind, however, that the formula for an ionic compound
does not represent the composition of a discrete molecule, so it may not correctly be referred to as the “molecular mass.”
As an example, consider sodium chloride, NaCl, the chemical name for common table salt. Sodium chloride is an ionic compound
composed of sodium cations, Na+, and chloride anions, Cl−, combined in a 1:1 ratio. The formula mass for this compound is
computed as 58.44 amu (Figure 6.1.3).
Figure 6.1.3 : Table salt, NaCl, contains an array of sodium and chloride ions combined in a 1:1 ratio. Its formula mass is 58.44
amu.
A table and diagram are shown. The table is made up of six columns and four rows. The header row reads: “Element,” “Quantity,”
a blank space, “Average atomic mass (a m u),” a blank space and “Subtotal (a m u).” The first column contains the symbols “N a”,
“C l,” and a merged cell. The merged cell runs the length of the first five columns. The second column contains the numbers “1”
and “1” as well as the merged cell. The third column contains the multiplication symbol in each cell except for the last, merged
cell. The fourth column contains the numbers “22.99” and “35.45” as well as the merged cell. The fifth column contains the symbol
“=” in each cell except for the last, merged cell. The sixth column contains the values “22.99,” “35.45,” and “58.44.” There is a
thick black line below the number “35.45.” The merged cell under the first five columns reads “Formula mass.” To the left of the
table is a diagram of a chemical structure. The diagram shows green and purple spheres placed in an alternating pattern, making up
the corners of eight stacked cubes to form one larger cube. The green spheres are slightly smaller than the purple spheres.
Note that the average masses of neutral sodium and chlorine atoms were used in this computation, rather than the masses for
sodium cations and chlorine anions. This approach is perfectly acceptable when computing the formula mass of an ionic
compound. Even though a sodium cation has a slightly smaller mass than a sodium atom (since it is missing an electron), this
difference will be offset by the fact that a chloride anion is slightly more massive than a chloride atom (due to the extra electron).
Moreover, the mass of an electron is negligibly small with respect to the mass of a typical atom. Even when calculating the mass of
an isolated ion, the missing or additional electrons can generally be ignored, since their contribution to the overall mass is
negligible, reflected only in the nonsignificant digits that will be lost when the computed mass is properly rounded. The few
exceptions to this guideline are very light ions derived from elements with precisely known atomic masses.
 Example 6.1.2: Computing Formula Mass for an Ionic Compound
Aluminum sulfate, Al2(SO4)3, is an ionic compound that is used in the manufacture of paper and in various water purification
processes. What is the formula mass (amu) of this compound?
Solution
The formula for this compound indicates it contains Al3+ and SO42− ions combined in a 2:3 ratio. For purposes of computing a
formula mass, it is helpful to rewrite the formula in the simpler format, Al2S3O12. Following the approach outlined above, the
formula mass for this compound is calculated as follows:
 Exercise 6.1.2
Calcium phosphate, Ca (PO ) , is an ionic compound and a common anti-caking agent added to food products. What is the
3 4 2
formula mass (amu) of calcium phosphate?
Answer
310.18 amu
The Mole
So far, we have been talking about chemical substances in terms of individual atoms and molecules. Yet we do not typically deal
with substances one atom or molecule at a time; we work with millions, billions, and trillions of atoms and molecules at a time. We
need a way to deal with macroscopic, rather than microscopic, amounts of matter. We need a unit of amount that relates quantities
of substances on a scale that we can interact with.
Chemistry uses a unit called mole. The mole (mol) is an counting term similar to familiar units like pair, dozen, gross, etc. It
provides a specific measure of the number of atoms or molecules in a bulk sample of matter. A mole is defined as the amount of
substance containing the same number of discrete entities (such as atoms, molecules, and ions) as the number of atoms in a sample
of pure 12C weighing exactly 12 g. One Latin connotation for the word “mole” is “large mass” or “bulk,” which is consistent with
its use as the name for this unit. The mole provides a link between an easily measured macroscopic property, bulk mass, and an
extremely important fundamental property, number of atoms, molecules, and so forth.
The number of entities composing a mole has been experimentally determined to be 6.02214179 × 10 , a fundamental constant
23
named Avogadro’s number (N ) or the Avogadro constant in honor of Italian scientist Amedeo Avogadro. This constant is
A
properly reported with an explicit unit of “per mole,” a conveniently rounded version being 6.022 × 10 /mol. 23
How big is a mole? It is very large. Suppose you had a mole of dollar bills that need to be counted. If everyone on earth (about 6
billion people) counted one bill per second, it would take about 3.2 million years to count all the bills. A mole of sand would fill a
cube about 32 km on a side. A mole of pennies stacked on top of each other would have about the same diameter as our galaxy, the
Milky Way. Atoms and molecules are very tiny, so one mole of carbon atoms would make a cube that is 1.74 cm on a side, small
enough to carry in your pocket. One mole of water molecules is approximately 18 mL or just under 4 teaspoons of water.
 Example 6.1.3
How many molecules are present in 2.76 mol of H2O? How many atoms is this?
Solution
The definition of a mole is an equality that can be used to construct a conversion factor. Also, because we know that there are
three atoms in each molecule of H2O, we can also determine the number of atoms in the sample.
23
6.022 × 10 molecules H2 O 24
2.76 mol H2 O × = 1.66 × 10 molecules H2 O
mol H2 O
To determine the total number of atoms, we have

3 atoms
24 24
1.66 × 10 molecules H2 O × = 4.99 × 10 atoms
1 molecule
 Exercise 6.1.3
How many molecules are present in 4.61 × 10−2 mol of O ? 2
Answer
2.78 × 1022 molecules
Molar Mass
Why is the mole unit so important? It represents the link between the microscopic and the macroscopic, especially in terms of
mass. A mole of a substance has the same mass in grams as one unit (atom or molecules) has in atomic mass units. The mole unit
allows us to express amounts of atoms and molecules in visible amounts that we can understand.
For example, we already know that, by definition, a mole of carbon has a mass of exactly 12 g. This means that exactly 12 g of C
has 6.022 × 1023 atoms:
23
12 g C = 6.022 × 1023 atoms C
We can use this equality as a conversion factor between the number of atoms of carbon and the number of grams of carbon. How
many grams are there, say, in 1.50 × 1025 atoms of carbon? This is a one-step conversion:
12.0000 g C
25
1.50 × 10 atoms C × = 299 g C
23
6.022 × 10 atoms C
But it also goes beyond carbon. Previously we defined atomic and molecular masses as the number of atomic mass units per atom
or molecule. Now we can do so in terms of grams. The atomic mass of an element is the number of grams in 1 mol of atoms of that
element, while the molecular mass of a compound is the number of grams in 1 mol of molecules of that compound. Sometimes
these masses are called molar masses to emphasize the fact that they are the mass for 1 mol of things. (The term molar is the
adjective form of mole and has nothing to do with teeth.)
Consistent with its definition as an amount unit, 1 mole of any element contains the same number of atoms as 1 mole of any other
element. The masses of 1 mole of different elements, however, are different, since the masses of the individual atoms are drastically
different. The molar mass of an element (or compound) is the mass in grams of 1 mole of that substance, a property expressed in
units of grams per mole (g/mol) (Figure 6.1.1).
Figure 6.1.1 : Each sample contains 6.022 × 10 atoms —1.00 mol of atoms. From left to right (top row): 65.4 g zinc, 12.0 g
23
carbon, 24.3 g magnesium, and 63.5 g copper. From left to right (bottom row): 32.1 g sulfur, 28.1 g silicon, 207 g lead, and 118.7 g
tin. (credit: modification of work by Mark Ott).
This figure contains eight different substances displayed on white circles. The amount of each substance is visibly different.
Because the definitions of both the mole and the atomic mass unit are based on the same reference substance, 12C, the molar mass
of any substance is numerically equivalent to its atomic or formula weight in amu. Per the amu definition, a single 12C atom weighs
12 amu (its atomic mass is 12 amu). According to the definition of the mole, 12 g of 12C contains 1 mole of 12C atoms (its molar
mass is 12 g/mol). This relationship holds for all elements, since their atomic masses are measured relative to that of the amu-
reference substance, 12C.
Table 6.1.1 : Mass of one mole of elements
Element Average Atomic Mass (amu) Molar Mass (g/mol) Atoms/Mole
C 12.01 12.01 6.022 × 10

23
H 1.008 1.008 6.022 × 10

23
O 16.00 16.00 6.022 × 10

23
Na 22.99 22.99 6.022 × 10

23
Cl 33.45 35.45 6.022 × 10

23
While atomic mass and molar mass are numerically equivalent, keep in mind that they are vastly different in terms of scale, as
represented by the vast difference in the magnitudes of their respective units (amu versus g). To appreciate the enormity of the
mole, consider a small drop of water after a rainfall. Although this represents just a tiny fraction of 1 mole of water (~18 g), it
contains more water molecules than can be clearly imagined. If the molecules were distributed equally among the roughly seven
billion people on earth, each person would receive more than 100 billion molecules.
How big is a mole? (Not the animal, the …
Video 6.1.1 : The mole is used in chemistry to represent 6.022 × 10 of something, but it can be difficult to conceptualize such a
23
large number. Watch this video and then complete the “Think” questions that follow. Explore more about the mole by reviewing the
information under “Dig Deeper.”
The relationships between formula mass, the mole, and Avogadro’s number can be applied to compute various quantities that
describe the composition of substances and compounds. For example, if we know the mass and chemical composition of a
substance, we can determine the number of moles and calculate number of atoms or molecules in the sample. Likewise, if we know
the number of moles of a substance, we can derive the number of atoms or molecules and calculate the substance’s mass.
Here are some examples. The mass of 1 hydrogen atom is 1.0079 u; the mass of 1 mol of hydrogen atoms is 1.0079 g. Elemental
hydrogen exists as a diatomic molecule, H2. One molecule has a mass of 1.0079 u + 1.0079 u = 2.0158 u, while 1 mol of H2 has a
mass of 1.0079 g + 1.0079 g = 2.0158 g. One molecule of H2O has a mass of about 18.01 u; 1 mol H2O has a mass of 18.01 g. A
single unit of NaCl has a mass of 58.45 u; NaCl has a molar mass of 58.45 g. In each of these moles of substances, there are 6.022
× 1023 units: 6.022 × 1023 atoms of H, 6.022 × 1023 molecules of H2 and H2O, 6.022 × 1023 units of NaCl ions. These
relationships give us plenty of opportunities to construct conversion factors for simple calculations.
  Example 6.1.4: Sugar

What is the molar mass of sugar (C 6
H
12
O
6
)?
Solution
To determine the molar mass, we simply add the atomic masses of the atoms in the molecular formula; but express the total in
grams per mole, not atomic mass units. The masses of the atoms can be taken from the periodic table.
6 C = 6 × 12.011 = 72.066
12 H = 12 × 1.0079 = 12.0948
6 O = 6 × 15.999 = 95.994
TOTAL = 180.155 g/mol
Per convention, the unit grams per mole is written as a fraction.
 Exercise 6.1.4
What is the molar mass of AgNO ? 3
Answer
169.87 g/mol
Summary
The mole is a key unit in chemistry. The molar mass of a substance, in grams, is numerically equal to one atom's or molecule's
mass in atomic mass units.
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To convert between mass units and mole units.
As we just discussed, molar mass is defined as the mass (in grams) of 1 mole of substance (or Avogadro's number of molecules or
formula units).
The simplest type of manipulation using molar mass as a conversion factor is a mole-gram conversion (or its reverse, a gram-mole
conversion).
We also established that 1 mol of Al has a mass of 26.98 g (Example 6.2.1). Stated mathematically,
1 mol Al = 26.98 g Al
We can divide both sides of this expression by either side to get one of two possible conversion factors:
1 mol Al 26.98 g Al
and
26.98 g Al 1 mol Al
The first conversion factor can be used to convert from mass to moles, and the second converts from moles to mass. Both can be
used to solve problems that would be hard to do “by eye.”
 Example 6.2.1
What is the mass of 3.987 mol of Al?
Solution
The first step in a conversion problem is to decide what conversion factor to use. Because we are starting with mole units, we
want a conversion factor that will cancel the mole unit and introduce the unit for mass in the numerator. Therefore, we should
26.98 g Al
use the conversion factor. We start with the given quantity and multiply by the conversion factor:
1 mol Al
26.98 g Al
3.987 mol Al ×
1 mol Al
Note that the mol units cancel algebraically. (The quantity 3.987 mol is understood to be in the numerator of a fraction that has
1 in the unwritten denominator.) Canceling and solving gives
26.98 g Al
3.987 mol Al × = 107.6 g Al
1 mol Al
Our final answer is expressed to four significant figures.
 Exercise 6.2.1
How many moles are present in 100.0 g of Al? (Hint: you will have to use the other conversion factor we obtained for
aluminum.)
Answer
1 mol Al
100.0 g Al × = 3.706 mol Al
26.98 g Al
Conversions like this are possible for any substance, as long as the proper atomic mass, formula mass, or molar mass is known (or
can be determined) and expressed in grams per mole. Figure 6.2.1 is a chart for determining what conversion factor is needed, and
Figure 6.2.2 is a flow diagram for the steps needed to perform a conversion.
Figure 6.2.1 A Simple Flowchart for Converting between Mass and Moles of a Substance. It takes one mathematical step to
convert from moles to mass or from mass to moles.
Figure 6.2.2 A Flowchart Illustrating the Steps in Performing a Unit Conversion. When performing many unit conversions, the
same logical steps can be taken.
 Example 6.2.2
A biochemist needs 0.00655 mol of bilirubin (C33H36N4O6) for an experiment. How many grams of bilirubin will that be?
Solution
To convert from moles to mass, we need the molar mass of bilirubin, which we can determine from its chemical formula:
33 C molar mass: 33 × 12.01 g = 396.33 g
36 H molar mass: 36 × 1.01 g = 36.36 g
4 N molar mass: 4 × 14.01 g = 56.04 g
6 O molar mass: 6 × 16.00 g = 96.00 g
Total: 584.73 g
The molar mass of bilirubin is 584.73 g. Using the relationship

1 mol bilirubin = 584.73 g bilirubin
we can construct the appropriate conversion factor for determining how many grams there are in 0.00655 mol. Following the
steps from Figure 6.2.2:
584.73 g bilirubin
0.00655 mol bilirubin × = 3.83 g bilirubin
mol bilirubin
The mol bilirubin unit cancels. The biochemist needs 3.83 g of bilirubin.
 Exercise 6.2.2
A chemist needs 457.8 g of KMnO4 to make a solution. How many moles of KMnO4 is that?
Answer
1 mol KMnO4
457.8 g KMnO4 × = 2.897 mol KMnO4
158.04 g KMnO4
 To Your Health: Minerals
For our bodies to function properly, we need to ingest certain substances from our diets. Among our dietary needs are minerals,
the noncarbon elements our body uses for a variety of functions, such developing bone or ensuring proper nerve transmission.
The US Department of Agriculture has established some recommendations for the RDIs of various minerals. The
accompanying table lists the RDIs for minerals, both in mass and moles, assuming a 2,000-calorie daily diet.
Table 6.2.1 : Essential Minerals and their Composition in Humans
Mineral Male (age 19–30 y) Female (age 19–30 y)
Ca 1,000 mg 0.025 mol 1,000 mg 0.025 mol
Cr 35 µg 6.7 × 10−7 mol 25 µg 4.8 × 10−7 mol
Cu 900 µg 1.4 × 10−5 mol 900 µg 1.4 × 10−5 mol
F 4 mg 2.1 × 10−4 mol 3 mg 1.5 × 10−4 mol
I 150 µg 1.2 × 10−6 mol 150 µg 1.2 × 10−6 mol
Fe 8 mg 1.4 × 10−4 mol 18 mg 3.2 × 10−4 mol
K 3,500 mg 9.0 × 10−2 mol 3,500 mg 9.0 × 10−2 mol
Mg 400 mg 1.6 × 10−2 mol 310 mg 1.3 × 10−2 mol
Mn 2.3 mg 4.2 × 10−5 mol 1.8 mg 3.3 × 10−5 mol
Mo 45 mg 4.7 × 10−7 mol 45 mg 4.7 × 10−7 mol
Na 2,400 mg 1.0 × 10−1 mol 2,400 mg 1.0 × 10−1 mol
P 700 mg 2.3 × 10−2 mol 700 mg 2.3 × 10−2 mol
Se 55 µg 7.0 × 10−7 mol 55 µg 7.0 × 10−7 mol
Zn 11 mg 1.7 × 10−4 mol 8 mg 1.2 × 10−4 mol
Table 6.2.1 illustrates several things. First, the needs of men and women for some minerals are different. The extreme case is
for iron; women need over twice as much as men do. In all other cases where there is a different RDI, men need more than
women.
Second, the amounts of the various minerals needed on a daily basis vary widely—both on a mass scale and a molar scale. The
average person needs 0.1 mol of Na a day, which is about 2.5 g. On the other hand, a person needs only about 25–35 µg of Cr
per day, which is under one millionth of a mole. As small as this amount is, a deficiency of chromium in the diet can lead to
diabetes-like symptoms or neurological problems, especially in the extremities (hands and feet). For some minerals, the body
does not require much to keep itself operating properly.
Although a properly balanced diet will provide all the necessary minerals, some people take dietary supplements. However, too
much of a good thing, even minerals, is not good. Exposure to too much chromium, for example, causes a skin irritation, and
certain forms of chromium are known to cause cancer (as presented in the movie Erin Brockovich).
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To use a balanced chemical reaction to determine molar relationships between the substances.
Previously, you learned to balance chemical equations by comparing the numbers of each type of atom in the reactants and
products. The coefficients in front of the chemical formulas represent the numbers of molecules or formula units (depending on the
type of substance). Here, we will extend the meaning of the coefficients in a chemical equation.
Consider the simple chemical equation
2H +O → 2H O
2 2 2
The convention for writing balanced chemical equations is to use the lowest whole-number ratio for the coefficients. However, the
equation is balanced as long as the coefficients are in a 2:1:2 ratio. For example, this equation is also balanced if we write it as
4H +2 O → 4H O
2 2 2
The ratio of the coefficients is 4:2:4, which reduces to 2:1:2. The equation is also balanced if we were to write it as
22 H + 11 O → 22 H O
2 2 2
because 22:11:22 also reduces to 2:1:2.

Suppose we want to use larger numbers. Consider the following coefficients:
23 23 23
12.044 × 10 H2 + 6.022 × 10 O2 → 12.044 × 10 H2 O
These coefficients also have the ratio 2:1:2 (check it and see), so this equation is balanced. But 6.022 × 1023 is 1 mol, while 12.044
× 1023 is 2 mol (and the number is written that way to make this more obvious), so we can simplify this version of the equation by
writing it as
2 mol H + 1 mol O → 2 mol H O

2 2 2
We can leave out the word mol and not write the 1 coefficient (as is our habit), so the final form of the equation, still balanced, is
2H +O → 2H O
2 2 2
Now we interpret the coefficients as referring to molar amounts, not individual molecules. The lesson? Balanced chemical
equations are balanced not only at the molecular level but also in terms of molar amounts of reactants and products. Thus, we can
read this reaction as “two moles of hydrogen react with one mole of oxygen to produce two moles of water.”
2 molecules H2 1 molecule O2 2 molecules H2O

2 moles H2 1 mole O2 2 moles H2O
2 x 2.02 g=4.04 g H2 32.0 g O2 2 x 18.02 g=36.04 g H2O
Figure 6.3.1: This representation of the production of water from oxygen and hydrogen show several ways to interpret the
quantitative information of a chemical reaction.
By the same token, the ratios we constructed to describe molecules reaction can also be constructed in terms of moles rather than
molecules. For the reaction in which hydrogen and oxygen combine to make water, for example, we can construct the following
ratios:
2 mol H2 1 mol O2
or
1 mol O2 2 mol H2
2 mol H2 O 1 mol O2
or
1 mol O2 2 mol H2 O
2 mol H2 2 mol H2 O
or
2 mol H2 O 2 mol H2
We can use these ratios to determine what amount of a substance, in moles, will react with or produce a given number of moles of a
different substance. The study of the numerical relationships between the reactants and the products in balanced chemical reactions
is called stoichiometry. The ratio of coefficients in a balanced chemical equation, used in computations relating amounts of
reactants and products is called the stoichiometric factor.
 Example 6.3.1
How many moles of oxygen react with hydrogen to produce 27.6 mol of H2O? The balanced equation is as follows:
2H +O ⟶ 2H O
2 2 2
Solution
Because we are dealing with quantities of H2O and O2, we will use the stoichiometric ratio that relates those two substances.
Because we are given an amount of H2O and want to determine an amount of O2, we will use the ratio that has H2O in the
denominator (so it cancels) and O2 in the numerator (so it is introduced in the answer). Thus,
1 mol O2
27.6 mol H2 O × = 13.8 mol O2
2 mol H2 O
To produce 27.6 mol of H2O, 13.8 mol of O2 react.
 Exercise 6.3.1
Using 2H2 + O2 → 2H2O, how many moles of hydrogen react with 3.07 mol of oxygen to produce H2O?
Answer
2 mol H2
3.07 mol O2 × = 6.14 mol H2
1 mol O2
Key Takeaway
The balanced chemical reaction can be used to determine molar relationships between substances.
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To convert from mass or moles of one substance to mass or moles of another substance in a chemical reaction.
We have established that a balanced chemical equation is balanced in terms of moles as well as atoms or molecules. We have used
balanced equations to set up ratios, now in terms of moles of materials, that we can use as conversion factors to answer stoichiometric
questions, such as how many moles of substance A react with so many moles of reactant B. We can extend this technique even further.
Recall that we can relate a molar amount to a mass amount using molar mass. We can use that ability to answer stoichiometry
questions in terms of the masses of a particular substance, in addition to moles. We do this using the following sequence:
Collectively, these conversions are called mole-mass calculations.

As an example, consider the balanced chemical equation
Fe O + 3 SO → Fe (SO )
2 3 3 2 4 3
If we have 3.59 mol of Fe2O3, how many grams of SO3 can react with it? Using the mole-mass calculation sequence, we can determine
the required mass of SO3 in two steps. First, we construct the appropriate molar ratio, determined from the balanced chemical equation,
to calculate the number of moles of SO3 needed. Then using the molar mass of SO3 as a conversion factor, we determine the mass that
this number of moles of SO3 has.
The first step resembles the exercises we did in Section 6.4. As usual, we start with the quantity we were given:
3 mol SO3
3.59 mol F e2 O3 × = 10.77 mol SO3
1 mol Fe2 O3
The mol Fe2O3 units cancel, leaving mol SO3 unit. Now, we take this answer and convert it to grams of SO3, using the molar mass of
SO3 as the conversion factor:
80.07 g SO3
10.77 mol SO3 × = 862.4 g SO3
1 mol SO3
Our final answer is expressed to three significant figures. Thus, in a two-step process, we find that 862 g of SO3 will react with 3.59
mol of Fe2O3. Many problems of this type can be answered in this manner.
The same two-step problem can also be worked out in a single line, rather than as two separate steps, as follows:
We get exactly the same answer when combining all the math steps together as we do when we calculate one step at a time.
 Example 6.4.1
How many grams of CO2 are produced if 2.09 mol of HCl are reacted according to this balanced chemical equation?
CaCO + 2 HCl → CaCl + CO +H O

3 2 2 2
Solution
Our strategy will be to convert from moles of HCl to moles of CO2 and then from moles of CO2 to grams of CO2. We will need the
molar mass of CO2, which is 44.01 g/mol. Performing these two conversions in a single-line gives 46.0 g of CO2:
The molar ratio between CO2 and HCl comes from the balanced chemical equation.
 Exercise
How many grams of glucose (C6H12O6) are produced if 17.3 mol of H2O are reacted according to this balanced chemical
equation?
6 CO +6 H O → C H O +6 O
2 2 6 12 6 2
Answer
1 mol C6 H12 O6 180.18 g C6 H12 O6
17.3 mol H2 O × × = 520 g C6 H12 O6
6 mol H2 O 1 mol C6 H12 O6
It is a small step from mole-mass calculations to mass-mass calculations. If we start with a known mass of one substance in a chemical
reaction (instead of a known number of moles), we can calculate the corresponding masses of other substances in the reaction. The first
step in this case is to convert the known mass into moles, using the substance’s molar mass as the conversion factor. Then—and only
then—we use the balanced chemical equation to construct a conversion factor to convert that quantity to moles of another substance,
which in turn can be converted to a corresponding mass. Sequentially, the process is as follows:
This three-part process can be carried out in three discrete steps or combined into a single calculation that contains three conversion
factors. The following example illustrates both techniques.
 Example 6.4.2: Chlorination of Carbon
Methane can react with elemental chlorine to make carbon tetrachloride (CCl ). The balanced chemical equation is as follows:
4
CH + 4 Cl → CCl + 4 HCl
4 2 4
How many grams of HCl are produced by the reaction of 100.0 g of CH ? 4
Solution
First, let us work the problem in stepwise fashion. We begin by converting the mass of CCl
4
to moles of CCl
4
, using the molar
mass of CCl (16.05 g/mol) as the conversion factor:
4
1 mol CH4
100.0 g C H4 × = 6.231 mol C H4
16.05 g CH4
Note that we inverted the molar mass so that the gram units cancel, giving us an answer in moles. Next, we use the balanced
chemical equation to determine the ratio of moles CCl and moles HCl and convert our first result into moles of HCl:
4
4 mol HCl
6.231 mol C H4 × = 24.92 mol HCl
1 mol CH4
Finally, we use the molar mass of HCl (36.46 g/mol) as a conversion factor to calculate the mass of 24.92 mol of HCl:
36.46 g HCl
24.92 mol HCl × = 908.5 g HCl
1 mol HCl
In each step, we have limited the answer to the proper number of significant figures. If desired, we can do all three conversions on
a single line:
1 mol CH4 4 mol HCl 36.46 g HCl
100.0 g C H4 × × × = 908.7 g HCl
16.05 g CH4 1 mol CH4 1 mol HCl
This final answer is slightly different from our first answer because only the final answer is restricted to the proper number of
significant figures. In the first answer, we limited each intermediate quantity to the proper number of significant figures. As you
can see, both answers are essentially the same.
 Exercise 6.4.2: Oxidation of Propanal
The oxidation of propanal (CH3CH2CHO) to propionic acid (CH3CH2COOH) has the following chemical equation:
CH3CH2CHO + 2K2Cr2O7 → CH3CH2COOH + other products
How many grams of propionic acid are produced by the reaction of 135.8 g of K2Cr2O7?
Answer
1 mol K2 C r2 O7 1 mol C H3 C H2 COOH 74.09 g C H3 C H2 COOH
135.8 g K2 C r2 O7 × × × = 17.10 g C H3 C H2 COOH
294.20 g K2 C r2 O7 2 mol K2 C r2 O7 1 mol C H3 C H2 COOH
 To Your Health: The Synthesis of Taxol
Taxol is a powerful anticancer drug that was originally extracted from the Pacific yew tree (Taxus brevifolia). As you can see from
the accompanying figure, taxol is a very complicated molecule, with a molecular formula of C H NO . Isolating taxol from its
47 51 14
natural source presents certain challenges, mainly that the Pacific yew is a slow-growing tree, and the equivalent of six trees must
be harvested to provide enough taxol to treat a single patient. Although related species of yew trees also produce taxol in small
amounts, there is significant interest in synthesizing this complex molecule in the laboratory.
After a 20-year effort, two research groups announced the complete laboratory synthesis of taxol in 1994. However, each synthesis
required over 30 separate chemical reactions, with an overall efficiency of less than 0.05%. To put this in perspective, to obtain a
single 300 mg dose of taxol, you would have to begin with 600 g of starting material. To treat the 26,000 women who are
diagnosed with ovarian cancer each year with one dose, almost 16,000 kg (over 17 tons) of starting material must be converted to
taxol. Taxol is also used to treat breast cancer, with which 200,000 women in the United States are diagnosed every year. This only
increases the amount of starting material needed.
Clearly, there is intense interest in increasing the overall efficiency of the taxol synthesis. An improved synthesis not only will be
easier but also will produce less waste materials, which will allow more people to take advantage of this potentially life-saving
drug.
Figure 6.4.1 The Structure of the Cancer Drug Taxol. Because of the complexity of the molecule, hydrogen atoms are not shown,
but they are present on every atom to give the atom the correct number of covalent bonds (four bonds for each carbon atom).
Key Takeaway
A balanced chemical equation can be used to relate masses or moles of different substances in a reaction.
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Define and determine theoretical yields, actual yields, and percent yields.
Identify a limiting reagent from a set of reactants.
Calculate how much product will be produced from the limiting reagent.
Calculate how much reactant(s) remains when the reaction is complete.
Yield
In all the previous calculations we have performed involving balanced chemical equations, we made two assumptions:
1. The reaction goes exactly as written.
2. The reaction proceeds completely.
In reality, such things as side reactions occur that make some chemical reactions rather messy. For example, in the actual
combustion of some carbon-containing compounds, such as methane, some CO is produced as well as CO2. However, we will
continue to ignore side reactions, unless otherwise noted. The second assumption, that the reaction proceeds completely, is more
troublesome. Many chemical reactions do not proceed to completion as written, for a variety of reasons. When we calculate an
amount of product assuming that all the reactant reacts, we calculate the theoretical yield, an amount that is theoretically produced
as calculated using the balanced chemical reaction.
In many cases, however, this is not what really happens. In many cases, less—sometimes, much less—of a product is made during
the course of a chemical reaction. The amount that is actually produced in a reaction is called the actual yield. By definition, the
actual yield is less than or equal to the theoretical yield. If it is not, then an error has been made.
Both theoretical yields and actual yields are expressed in units of moles or grams. It is also common to see something called a
percent yield. The percent yield is a comparison between the actual yield and the theoretical yield and is defined as
actual yield
percent yield = × 100% (6.5.1)
theoretical yield
It does not matter whether the actual and theoretical yields are expressed in moles or grams, as long as they are expressed in the
same units. However, the percent yield always has units of percent. Proper percent yields are between 0% and 100%. In the
laboratory, a student will occasionally obtain a yield that appears to be greater than 100%. This usually happens when the product
is impure or is wet with a solvent such as water. If this is not the case, then the student must have made an error in weighing either
the reactants or the products. The law of conservation of mass applies even to undergraduate chemistry laboratory experiments. A
100% yield means that everything worked perfectly, and the chemist obtained all the product that could have been produced.
Anyone who has tried to do something as simple as fill a salt shaker or add oil to a car’s engine without spilling knows the
unlikelihood of a 100% yield. At the other extreme, a yield of 0% means that no product was obtained. A percent yield of 80%–
90% is usually considered good to excellent; a yield of 50% is only fair. In part because of the problems and costs of waste
disposal, industrial production facilities face considerable pressures to optimize the yields of products and make them as close to
100% as possible.
 Example 6.5.1:
A worker reacts 30.5 g of Zn with nitric acid and evaporates the remaining water to obtain 65.2 g of Zn(NO3)2. What are the
theoretical yield, the actual yield, and the percent yield?
Zn(s) + 2 HNO (aq) → Zn(NO ) (aq) + H (g)

3 3 2 2
Solution
A mass-mass calculation can be performed to determine the theoretical yield. We need the molar masses of Zn (65.39 g/mol)
and Zn(NO3)2 (189.41 g/mol). In three steps, the mass-mass calculation is:
1 mol Zn(N O3 )2
1 mol Zn 189.41 g Zn(N O3 )2
30.5 g Zn × × × = 88.3 g Zn(N O3 )2
65.39 g Zn 1 mol Zn 1 mol Zn(N O3 )2
Thus, the theoretical yield is 88.3 g of Zn(NO3)2. The actual yield is the amount that was actually made, which was 65.2 g of
Zn(NO3)2. To calculate the percent yield, we take the actual yield and divide it by the theoretical yield and multiply by 100
(Equation 6.5.1):
65.2 g Zn(N O3 )2
× 100% = 73.8%
88.3 g Zn(N O3 )2
The worker achieved almost three-fourths of the possible yield.
 Exercise 6.5.1
A synthesis produced 2.05 g of NH3 from 16.5 g of N2. What is the theoretical yield and the percent yield?
N2 (g) + 3 H2 (g) → 2N H3 (g)
*Technically, this is a reversible reaction (with double arrows), but for this exercise consider it irreversible (single arrow).
Answer
theoretical yield = 20.1 g; percent yield = 10.2%
 Chemistry is Everywhere: Actual Yields in Drug Synthesis and Purification
Many drugs are the product of several steps of chemical synthesis. Each step typically occurs with less than 100% yield, so the
overall percent yield might be very small. The general rule is that the overall percent yield is the product of the percent yields
of the individual synthesis steps. For a drug synthesis that has many steps, the overall percent yield can be very tiny, which is
one factor in the huge cost of some drugs. For example, if a 10-step synthesis has a percent yield of 90% for each step, the
overall yield for the entire synthesis is only 35%. Many scientists work every day trying to improve percent yields of the steps
in the synthesis to decrease costs, improve profits, and minimize waste.
Even purifications of complex molecules into drug-quality purity are subject to percent yields. Consider the purification of
impure albuterol. Albuterol (C13H21NO2; accompanying figure) is an inhaled drug used to treat asthma, bronchitis, and other
obstructive pulmonary diseases. It is synthesized from norepinephrine, a naturally occurring hormone and neurotransmitter. Its
initial synthesis makes very impure albuterol that is purified in five chemical steps. The details of the steps do not concern us;
only the percent yields do:
impure albuterol → intermediate A percent yield = 70%
intermediate A → intermediate B percent yield = 100%
intermediate B → intermediate C percent yield = 40%
intermediate C → intermediate D percent yield = 72%
intermediate D → purified albuterol percent yield = 35%
overall percent yield = 70% × 100% × 40% × 72% × 35% = 7.5%
That is, only about one-fourteenth of the original material was turned into the purified drug. This demonstrates one reason why
some drugs are so expensive—a lot of material is lost in making a high-purity pharmaceutical.
Figure 6.5.1 A child using an albuterol inhaler, the container of albuterol medication, and a molecular model of the albuterol
molecule. Source: Photo on far left © Thinkstock. Photo in center courtesy of Intropin,
http://commons.wikimedia.org/wiki/Fi...te_%281%29.JPG.
Limiting Reagent
In all the examples discussed thus far, the reactants were assumed to be present in stoichiometric quantities. Consequently, none of
the reactants was left over at the end of the reaction. This is often desirable, as in the case of a space shuttle, where excess oxygen
or hydrogen was not only extra freight to be hauled into orbit but also an explosion hazard. More often, however, reactants are
present in mole ratios that are not the same as the ratio of the coefficients in the balanced chemical equation. As a result, one or
more of them will not be used up completely but will be left over when the reaction is completed. In this situation, the amount of
product that can be obtained is limited by the amount of only one of the reactants. The reactant that restricts the amount of product
obtained is called the limiting reactant. The reactant that remains after a reaction has gone to completion is in excess.
Consider a nonchemical example. Assume you have invited some friends for dinner and want to bake brownies for dessert. You
find two boxes of brownie mix in your pantry and see that each package requires two eggs. The balanced equation for brownie
preparation is thus
1 box mix + 2 eggs → 1 batch brownies (6.5.2)
If you have a dozen eggs, which ingredient will determine the number of batches of brownies that you can prepare? Because each
box of brownie mix requires two eggs and you have two boxes, you need four eggs. Twelve eggs is eight more eggs than you need.
Although the ratio of eggs to boxes in is 2:1, the ratio in your possession is 6:1. Hence the eggs are the ingredient (reactant) present
in excess, and the brownie mix is the limiting reactant. Even if you had a refrigerator full of eggs, you could make only two batches
of brownies.
Figure 6.5.1 : The Concept of a Limiting Reactant in the Preparation of Brownies

A similar situation exists for many chemical reactions: you usually run out of one reactant before all of the other reactant has
reacted. The reactant you run out of is called the limiting reagent; the other reactant or reactants are considered to be in excess. A
crucial skill in evaluating the conditions of a chemical process is to determine which reactant is the limiting reagent and which is in
excess.
The key to recognizing which reactant is the limiting reagent is based on a mole-mass or mass-mass calculation: whichever reactant
gives the lesser amount of product is the limiting reagent. What we need to do is determine an amount of one product (either moles
or mass), assuming all of each reactant reacts. Whichever reactant gives the least amount of that particular product is the limiting
reagent. It does not matter which product we use, as long as we use the same one each time. It does not matter whether we
determine the number of moles or grams of that product; however, we will see shortly that knowing the final mass of product can
be useful.
For example, consider this reaction:
4As(s) + 3 O2 (g) → 2As2 O3 (s)
Suppose we start a reaction with 50.0 g of As and 50.0 g of O2. Which one is the limiting reagent? We need to perform two mole-
mass calculations, each assuming that each reactant reacts completely. Then we compare the amount of the product produced by
each and determine which is less.
The calculations are as follows:
1 mol As 2 mol As2 O3

50.0 g As × × = 0.334 mol As2 O3
74.92 g As 4 mol As
1 mol O2 2 mol As2 O3

50.0 g O2 × × = 1.04 mol As2 O3
32.00 g O2 3 mol O2
Comparing these two answers, it is clear that 0.334 mol of As2O3 is less than 1.04 mol of As2O3, so arsenic is the limiting
reagent. If this reaction is performed under these initial conditions, the arsenic will run out before the oxygen runs out. We say that
the oxygen is "in excess."
Identifying the limiting reagent, then, is straightforward. However, there are usually two associated questions: (1) what mass of
product (or products) is then actually formed? and (2) what mass of what reactant is left over? The first question is straightforward
to answer: simply perform a conversion from the number of moles of product formed to its mass, using its molar mass. For As2O3,
the molar mass is 197.84 g/mol; knowing that we will form 0.334 mol of As2O3 under the given conditions, we will get
197.84 g As2
0.334 mol As2 O3 × = 66.1 g As2 O3
1 mol As2 O3
The second question is somewhat more convoluted to answer. First, we must do a mass-mass calculation relating the limiting
reagent (here, As) to the other reagent (O2). Once we determine the mass of O2 that reacted, we subtract that from the original
amount to determine the amount left over. According to the mass-mass calculation,
1 mol As 3 mol O2 32.00 g O2

50.0 g As × × × = 16.0 g O2 reacted
74.92 g As 4 mol As 1 mol O2
Because we reacted 16.0 g of our original O2, we subtract that from the original amount, 50.0 g, to get the mass of O2 remaining:
50.0 g O2 − 16.0 g O2 reacted = 34.0 g O2 left over
You must remember to perform this final subtraction to determine the amount remaining; a common error is to report the 16.0 g as
the amount remaining.
 Example 6.5.1:
A 5.00 g quantity of Rb is combined with 3.44 g of MgCl2 according to this chemical reaction:
2Rb(s) + M gC l2 (s) → M g(s) + 2RbC l(s)
What mass of Mg is formed, and what mass of what reactant is left over?
Solution
Because the question asks what mass of magnesium is formed, we can perform two mass-mass calculations and determine
which amount is less.
1 mol Rb 1 mol M g
24.31 g M g
5.00 g Rb × × × = 0.711 g M g
85.47 g Rb 2 mol Rb 1 mol M g
1 mol M gC l2 1 mol M g 24.31 g M g
3.44 g M gC l2 × × × = 0.878 g M g
95.21 g M gC l2 1 mol M gC l2 1 mol M g
The 0.711 g of Mg is the lesser quantity, so the associated reactant—5.00 g of Rb—is the limiting reagent. To determine how
much of the other reactant is left, we have to do one more mass-mass calculation to determine what mass of MgCl2 reacted
with the 5.00 g of Rb, and then subtract the amount reacted from the original amount.
1 mol Rb 1 mol M gC l2
95.21 g M g
5.00 g Rb × × × = 2.78 g M gC l2 reacted
85.47 g Rb 2 mol Rb 1 mol M gC l2
Because we started with 3.44 g of MgCl2, we have

3.44 g MgCl2 − 2.78 g MgCl2 reacted = 0.66 g MgCl2 left
 Exercise 6.5.1
Given the initial amounts listed, what is the limiting reagent, and what is the mass of the leftover reagent?
22.7 g + 17.9 g → M gS(s) + H2 O(l)

 
MgO(s) H2 S
Answer
H2S is the limiting reagent; 1.5 g of MgO are left over.
Summary
Theoretical yield is the calculated yield using the balanced chemical reaction. Actual yield is what is actually obtained in a
chemical reaction. Percent yield is a comparison of the actual yield with the theoretical yield.
The limiting reagent is the reactant that produces the least amount of product. Mass-mass calculations can determine how much
product is produced and how much of the other reactants remain.
6.5: Limiting Reagent and Percent Yield is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
5.7: Limiting Reagents by Anonymous is licensed CC BY-NC-SA 3.0. Original source: https://2012books.lardbucket.org/books/beginning-
chemistry.
5.6: Yields by Anonymous is licensed CC BY-NC-SA 3.0. Original source: https://2012books.lardbucket.org/books/beginning-chemistry.
CHAPTER OVERVIEW
7: Chemical Reactions - Energy, Rates, and Equilibrium

7: Chemical Reactions - Energy, Rates, and Equilibrium is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated
by LibreTexts.
1
Define energy and distinguish the different types of energy, potential and kinetic.
Chemical changes and their accompanying changes in energy are important parts of our everyday world (Figure 7.1.1). The
macronutrients in food (proteins, fats, and carbohydrates) undergo metabolic reactions that provide the energy to keep our bodies
functioning. We burn a variety of fuels (gasoline, natural gas, coal) to produce energy for transportation, heating, and the
generation of electricity. Industrial chemical reactions use enormous amounts of energy to produce raw materials (such as iron and
aluminum). Energy is then used to manufacture those raw materials into useful products, such as cars, skyscrapers, and bridges.
Figure 7.1.1 : The energy involved in chemical changes is important to our daily lives: (a) A cheeseburger for lunch provides the
energy you need to get through the rest of the day; (b) the combustion of gasoline provides the energy that moves your car (and
you) between home, work, and school; and (c) coke, a processed form of coal, provides the energy needed to convert iron ore into
iron, which is essential for making many of the products we use daily. (credit a: modification of work by “Pink Sherbet
Photography”/Flickr; credit b: modification of work by Jeffery Turner).
Over 90% of the energy we use comes originally from the sun. Every day, the sun provides the earth with almost 10,000 times the
amount of energy necessary to meet all of the world’s energy needs for that day. Our challenge is to find ways to convert and store
incoming solar energy so that it can be used in reactions or chemical processes that are both convenient and nonpolluting. Plants
and many bacteria capture solar energy through photosynthesis. We release the energy stored in plants when we burn wood or plant
products such as ethanol. We also use this energy to fuel our bodies by eating food that comes directly from plants or from animals
that got their energy by eating plants. Burning coal and petroleum also releases stored solar energy: These fuels are fossilized plant
and animal matter.
Energy
Energy can be defined as the capacity to supply heat or do work. One type of work (w) is the process of causing matter to move
against an opposing force. For example, we do work when we inflate a bicycle tire—we move matter (the air in the pump) against
the opposing force of the air surrounding the tire.
Like matter, energy comes in different types. One scheme classifies energy into two types: potential energy, the energy an object
has because of its relative position, composition, or condition, often referred to as stored energy, and kinetic energy, the energy
that an object possesses because of its motion. Water at the top of a waterfall or dam has potential energy because of its position;
when it flows downward through generators, it has kinetic energy that can be used to do work and produce electricity in a
hydroelectric plant (Figure 7.1.2). A battery has potential energy because the chemicals within it can produce electricity that can do
work.
Figure 7.1.2 : (a) Water that is higher in elevation, for example, at the top of Victoria Falls, has a higher potential energy than water
at a lower elevation. As the water falls, some of its potential energy is converted into kinetic energy. (b) If the water flows through
generators at the bottom of a dam, such as the Hoover Dam shown here, its kinetic energy is converted into electrical energy.
(credit a: modification of work by Steve Jurvetson; credit b: modification of work by “curimedia”/Wikimedia commons).
Energy can be converted from one form into another, but all of the energy present before a change occurs always exists in some
form after the change is completed. This observation is expressed in the law of conservation of energy: during a chemical or
physical change, energy can be neither created nor destroyed, although it can be changed in form. (This is also one version of the
first law of thermodynamics, as you will learn later.)
When one substance is converted into another, there is always an associated conversion of one form of energy into another. Heat is
usually released or absorbed, but sometimes the conversion involves light, electrical energy, or some other form of energy. For
example, chemical energy (a type of potential energy) is stored in the molecules that compose gasoline. When gasoline is
combusted within the cylinders of a car’s engine, the rapidly expanding gaseous products of this chemical reaction generate
mechanical energy (a type of kinetic energy) when they move the cylinders’ pistons.
According to the law of conservation of matter (seen in an earlier chapter), there is no detectable change in the total amount of
matter during a chemical change. When chemical reactions occur, the energy changes are relatively modest and the mass changes
are too small to measure, so the laws of conservation of matter and energy hold well. However, in nuclear reactions, the energy
changes are much larger (by factors of a million or so), the mass changes are measurable, and matter-energy conversions are
significant. This will be examined in more detail in a later chapter on nuclear chemistry. To encompass both chemical and nuclear
changes, we combine these laws into one statement: The total quantity of matter and energy in the universe is fixed.
7.1: Energy and Chemical Bonds is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
5.1: Energy Basics by OpenStax is licensed CC BY 4.0. Original source: https://openstax.org/details/books/chemistry-2e.
Define bond dissociation energy.
Determine if a chemical process is exothermic or endothermic.
A general statement, based on countless observations over centuries of study, is that all objects tend to move spontaneously to a
position of minimum energy unless acted on by some other force or object.
Bond Dissociation Energy

Atoms bond together to form compounds because in doing so they attain lower energies than they possess as individual atoms. A
quantity of energy, equal to the difference between the energies of the bonded atoms and the energies of the separated atoms, is
released, usually as heat. That is, the bonded atoms have a lower energy than the individual atoms do. When atoms combine to
make a compound, energy is always given off, and the compound has a lower overall energy. In making compounds, atoms act like
a basketball on a playground slide; they move in the direction of decreasing energy.
We can reverse the process by putting energy into a molecule, which causes its bonds to break, separating the molecule into
individual atoms. Bonds between certain specific elements usually have a characteristic energy, called the bond dissociation
energy, that is needed to break the bond. The same amount of energy was liberated when the atoms made the chemical bond in the
first place. The term bond dissociation energy is usually used to describe the strength of interactions between atoms that make
covalent bonds. A C–C bond has an approximate bond energy of 80 kcal/mol, while a C=C has a bond energy of about 145
kcal/mol. The C=C bond is stronger than C-C (as discussed in relation to bond length in Section 4.4). For atoms in ionic
compounds attracted by opposite charges, the term lattice energy is used. For now, we will deal with covalent bonds in molecules.
Although each molecule has its own characteristic bond dissociation energy, some generalizations are possible. For example,
although the exact value of a C–H bond energy depends on the particular molecule, all C–H bonds have a bond energy of roughly
the same value because they are all C–H bonds. It takes roughly 100 kcal of energy to break 1 mol of C–H bonds, so we speak of
the bond dissociation energy of a C–H bond as being about 100 kcal/mol. Table 7.2.1 lists the approximate bond dissociation
energies of various covalent bonds.
Table 7.2.1 : Approximate Bond Dissociation Energies
Bond Bond Dissociation Energy (kcal/mol)
C–H 100
C–O 86
C=O 190
C–N 70
C–C 85
C=C 145
C≡C 200
N–H 93
H–H 105
Br-Br 46
Cl–Cl 58
O–H 110
O=O 119
H–Br 87
H–Cl 103
When a chemical reaction occurs, the atoms in the reactants rearrange their chemical bonds to make products. The new
arrangement of bonds does not have the same total energy as the bonds in the reactants. Therefore, when chemical reactions occur,
there will always be an accompanying energy change. The energy change, for a given reaction can be calculated using the bond
dissociation energy values from Table 7.2.1.
Enthalpy Change or Heat of Reaction, ΔH

During a chemical reaction, bonds are broken and new bonds are formed. Breaking chemical bonds is endothermic, a process that
requires an input of energy or absorption of heat. The reverse process of bond breaking is bond formation, which is exothermic,
meaning it releases energy or gives off heat. The bond dissociation energy values listed in the above table give the amount of
energy required to break a specific bond. When that same bond is reformed, an identical amount of energy is released. The
numerical value of energy is the same for breaking and forming a bond, but the sign, or direction of the process is different. The
overall energy change of a specific bond breaking and reforming would be zero, in other words energy is neither created or
destroyed, following the law of conservation of energy.
In a chemical reaction, the bonds breaking are often different than the bonds reforming, sometimes there is more heat absorbed
(more bonds are broken) and sometimes more heat is released (more bonds are formed). The measured difference between the total
heat absorbed and the total heat released during a chemical reaction (performed at constant pressure) is called the heat of reaction
or enthalpy change, and is represented by the symbol ΔH (where the Δ stands for change and the H represents enthalpy).
enthalpy change ≈ Σ (bond dissociation energies ) − Σ (bond dissociation energies ) (7.2.1)
reactants products
The ≈ sign is used because we are adding together average bond dissociation energies; hence this approach does not give exact
values for the enthalpy change, ΔH.
Let’s consider the reaction of 2 mols of hydrogen gas (H2) with 1 mol of oxygen gas (O2) to give 2 mol water:
2 H2 (g) + O2 (g) → 2 H2 O(g) (7.2.2)
H–H = 105 kcal/mol O=O = 119 kcal/mol O–H = 110 kcal/mol

In this reaction, 2 H–H bonds and 1 O=O bonds from the reactant side are broken, while 4 O–H bonds (two for each H2O) are
formed on the product side. The energy changes can be tabulated and calculated as follows:
Reactant Bond Dissociation Energy (kcal/mol) Product Bond Dissociation Energy (kcal/mol)
2 H–H 2 mol x 105 kcal/mol = 210 kcal 4 O–H 4 mols x 110 kcal/mol = 440 kcal
1 O=O 1 mol x 119 kcal/mol = 119 kcal
Total = 329 kcal Total = 440 kcal
ΔH ≈ Σ (bond dissociation energies reactants ) − Σ (bond dissociation energies products ) (7.2.3)
ΔH ≈ 329 kcal − 440 kcal (7.2.4)
ΔH ≈ −111 kcal (7.2.5)
The enthalpy change (ΔH) of the reaction is approximately −111 kcal/mol. This means that bonds in the products (440 kcal) are
stronger than the bonds in the reactants (329 kcal) by about 111 kcal/mol. Because the bonds in the products are stronger than those
in the reactants, the reaction releases more energy than it absorbs. This excess energy is released as heat, so the reaction is
exothermic. Hence, we can re-write the reaction with the heat released (111 kcal) on the product side of the equation, as follows:
We can also re-write the reaction equation with the ΔH information (see below). Note that an exothermic reaction has a negative
ΔH value.
2 H2 (g) + O2 (g) → 2 H2 O(g) ΔH = −111 kcal (7.2.6)
 Example 7.2.1
What is the enthalpy change for this reaction? Is the reaction exothermic or endothermic?
H2 (g) + Br2 (g) → 2H Br(g) (7.2.7)
Solution
Step 1- First look at the equation and identify which bonds exist on in the reactants (bonds broken).
one H-H bond and
one Br-Br bond
Step 2- Do the same for the products (bonds formed)
two H-Br bonds
Step 3- Identify the bond dissociation energies of these bonds from Table 7.2.1:
H-H bonds: 105 kcal/mol
Br-Br bonds: 46 kcal/mol
Step 4- Set up the table (see below) and apply the formula for enthalpy change.
Reactant Bond Dissociation Energy (kcal/mol) Product Bond Dissociation Energy (kcal/mol)
1 H–H 1 mol x 105 kcal/mol = 105 kcal 2 H–Br 2 mols x 87 kcal/mol = 174 kcal
1 Br–Br 1 mol x 46 kcal/mol = 46 kcal
Total = 151 kcal Total = 174 kcal
ΔH ≈ 151 kcal − 174 kcal (7.2.8)
ΔH ≈ −23 kcal (7.2.9)
Step 5- Since ΔH is negative (−23 kcal), the reaction is exothermic.
 Exercise 7.2.1
Using the bond dissociation energies given in the chart above, find the enthalpy change for the thermal decomposition of
water:
H2 (g) + C l2 (g) → 2H C l(g) (7.2.10)
Is the reaction written above exothermic or endothermic? Explain.
Answer
ΔH = −43 kcal
Since ΔH is negative (−43 kcal), the reaction is exothermic.
7.2: Heat Changes during Chemical Reactions is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by
LibreTexts.
Use bond dissociation energies to calculate enthalpy change or heat of reaction.
Determine if a chemical process is exothermic or endothermic.
Endothermic and Exothermic Reactions

Endothermic and exothermic reactions can be thought of as having energy as either a reactant of the reaction or a product.
Endothermic reactions require energy, so energy is a reactant. Heat flows from the surroundings to the system (reaction mixture)
and the enthalpy of the system increases (ΔH is positive). As discussed in the previous section, heat is released (considered a
product) in an exothermic reaction, and the enthalpy of the system decreases (ΔH is negative).
In the course of an endothermic process, the system gains heat from the surroundings and so the temperature of the surroundings
decreases (gets cold). A chemical reaction is exothermic if heat is released by the system into the surroundings. Because the
surroundings is gaining heat from the system, the temperature of the surroundings increases. See Figure 7.3.1.
Figure 7.3.1 : (A) Endothermic reaction. (B) Exothermic reaction.

Endothermic Reaction: When 1 mol of calcium carbonate decomposes into 1 mol of calcium oxide and 1 mol of carbon dioxide,
177.8 kJ of heat is absorbed. Because the heat is absorbed by the system, the 177.8 kJ is written as a reactant. The ΔH is positive
for an endothermic reaction.
CaCO (s) → CaO (s) + CO (g) ΔH = +177.8 kJ (7.3.1)

3 2
Exothermic Reaction: When methane gas is combusted, heat is released, making the reaction exothermic. Specifically, the
combustion of 1 mol of methane releases 890.4 kilojoules of heat energy. This information can be shown as part of the balanced
equation in two ways. First, the amount of heat released can be written in the product side of the reaction. Another way is to write
the ΔH information with a negative sign, −890.4 kJ.
CH (g) + 2 O (g) → CO (g) + 2 H O (l) ΔH = −890.4 kJ (7.3.2)

4 2 2 2
 Example 7.3.1
Is each chemical reaction exothermic or endothermic?
a. CH4(g) + 2O2(g) → CO2(g) + 2H2O(ℓ) + 213 kcal
b. N2(g) + O2(g) + 45 kcal → 2NO(g)
Solution
a. Because energy (213 kcal) is a product, energy is given off by the reaction. Therefore, this reaction is exothermic.
b. Because energy (45 kcal) is a reactant, energy is absorbed by the reaction. Therefore, this reaction is endothermic.
 Exercise 7.3.1
Is each chemical reaction exothermic or endothermic?
a. H2(g) + F2(g) → 2HF (g) + 130 kcal
b. 2C(s) + H2(g) + 5.3 kcal → C2H2(g)
Answer
a. The energy (130 kcal) is produced, hence the reaction is exothermic
b. The energy (5.3 kcal) is supplied or absorbed to react, hence, the reaction is
endothermic
Energy Diagrams
Endothermic and exothermic reactions can be visually represented by energy-level diagrams like the ones in Figure 7.3.2. In
endothermic reactions, the reactants have higher bond energy (stronger bonds) than the products. Strong bonds have lower
potential energy than weak bonds. Hence, the energy of the reactants is lower than that of the products. This type of reaction is
represented by an "uphill" energy-level diagram shown in Figure 7.3.2A. For an endothermic chemical reaction to proceed, the
reactants must absorb energy from their environment to be converted to products.
In an exothermic reaction, the bonds in the product have higher bond energy (stronger bonds) than the reactants. In other words, the
energy of the products is lower than the energy of the reactants, hence is energetically downhill, shown in Figure 7.3.2B. Energy is
given off as reactants are converted to products. The energy given off is usually in the form of heat (although a few reactions give
off energy as light). In the course of an exothermic reaction, heat flows from the system to its surroundings, and thus, gets warm.
Figure 7.3.2A: Endothermic Reactions Figure 7.3.2B : Exothermic Reactions

Table 7.3.1 : Endothermic and Exothermic Reactions
Endothermic Reactions Exothermic Reactions
Heat is absorbed by reactants to form products. Heat is released.
Heat is absorbed from the surroundings; as a result, the surroundings

Heat is released by the reaction to surroundings; surroundings feel hot.
get cold.
Endothermic Reactions Exothermic Reactions
ΔHrxn is positive ΔHrxn is negative
The bonds broken in the reactants are stronger than the bonds formed in The bonds formed in the products are stronger than the bonds broken in
the products. the reactants.
The reactants are lower in energy than the products. The products are lower in energy than the reactants.
Represented by an "uphill" energy diagram. Represented by an "downhill" energy diagram

1. What is the connection between energy and chemical bonds?
2. Why does energy change during the course of a chemical reaction?
3. Two different reactions are performed in two identical test tubes. In reaction A, the test tube becomes very warm as the reaction
occurs. In reaction B, the test tube becomes cold. Which reaction is endothermic and which is exothermic? Explain.
4. Classify "burning paper" as endothermic or exothermic processes.
Answers
1. Chemical bonds have a certain energy that is dependent on the elements in the bond and the number of bonds between the
atoms.
2. Energy changes because bonds rearrange to make new bonds with different energies.
3. Reaction A is exothermic because heat is leaving the system making the test tube feel hot. Reaction B is endothermic because
heat is being absorbed by the system making the test tube feel cold.
4. "Burning paper" is exothermic because burning (also known as combustion) releases heat
Key Takeaways
Atoms are held together by a certain amount of energy called bond energy.
Energy is required to break bonds. Energy is released when chemical bonds are formed because atoms become more stable.
Chemical processes are labeled as exothermic or endothermic based on whether they give off or absorb energy, respectively.
7.3: Exothermic and Endothermic Reactions is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by
LibreTexts.
 Learning Outcomes
Describe the meaning of a spontaneous reaction in terms of enthalpy and entropy changes.
Define free energy.
Determine the spontaneity of a reaction based on the value of its change in free energy at high and low temperatures.
Spontaneous Reactions
A spontaneous reaction is a reaction that favors the formation of products at the conditions under which the reaction is occurring.
A roaring bonfire (see Figure 7.4.1 below) is an example of a spontaneous reaction. A fire is exothermic, which means a decrease
in the energy of the system as energy is released to the surroundings as heat. The products of a fire are composed mostly of gases
such as carbon dioxide and water vapor, so the entropy of the system increases during most combustion reactions. This
combination of a decrease in energy and an increase in entropy means that combustion reactions occur spontaneously.
Figure 7.4.1 : Combustion reactions, such as this fire, are spontaneous reactions. Once the reaction begins, it continues on its own
until one of the reactants (fuel or oxygen) is gone.
A nonspontaneous reaction is a reaction that does not favor the formation of products at the given set of conditions. In order for a
reaction to be nonspontaneous, one or both of the driving forces must favor the reactants over the products. In other words, the
reaction is endothermic, is accompanied by a decrease in entropy, or both. Out atmosphere is composed primarily of a mixture of
nitrogen and oxygen gases. One could write an equation showing these gases undergoing a chemical reaction to form nitrogen
monoxide.
N (g) + O (g) → 2NO (g) (7.4.1)
2 2
Fortunately, this reaction is nonspontaneous at normal temperatures and pressures, it is a highly endothermic reaction. However,
nitrogen monoxide is capable of being produced at very high temperatures, and this reaction has been observed to occur as a result
of lightning strikes.
One must be careful not to confuse the term spontaneous with the notion that a reaction occurs rapidly. A spontaneous reaction is
one in which product formation is favored, even if the reaction is extremely slow. You do not have to worry about a piece of paper
on your desk suddenly bursting into flames, although its combustion is a spontaneous reaction. What is missing is the required
activation energy to get the reaction started. If the paper were to be heated to a high enough temperature, it would begin to burn, at
which point the reaction would proceed spontaneously until completion.
Entropy as a Driving Force

An example of a very simple spontaneous process is that of a melting ice cube. Energy is transferred from the room to the ice cube,
causing it to change from the solid to the liquid state.
H O (s) + 6.01 kJ → H O (l) (7.4.2)
2 2
The solid state of water, ice, is highly ordered because its molecules are fixed in place. The melting process frees the water
molecules from their hydrogen-bonded network and allows them a greater degree of movement. Water is more disordered than ice.
The change from the solid to the liquid state of any substance corresponds to an increase in the disorder of the system.
The tendency in nature for systems to proceed toward a state of greater disorder or randomness is called entropy, which is
symbolized by S, and expressed in units of Joules per mole-kelvin, J/(mol ⋅ K). Larger values of S indicate that the particles in a
substance have more disorder or randomness. In the example above, the particles in the ice cube (solid water) have lower freedom
of motion, they are less random. As the ice melts to liquid water, the particles become more disordered and entropy increases. If the
liquid water was heated further, the particles would even gain more freedom of motion, become more disordered, and eventually
change to a gas, which has even higher entropy.
Chemical reactions also tend to proceed in such a way as to increase the total entropy of the system, measured by the entropy
change (ΔS ) between reactants and products. How can you tell if a certain reaction shows an increase or a decrease in entropy?
The states of the reactants and produces provide certain clues. The general cases below illustrate entropy at the molecular level.
1. For a given substance, the entropy of the liquid state is greater than the entropy of the solid state. Likewise, the entropy of the
gas is greater than the entropy of the liquid. Therefore, entropy increases in processes in which solid or liquid reactants form
gaseous products. Entropy also increases when solid reactants form liquid products.
2. Entropy increases when a substance is broken up into multiple parts. The process of dissolving increases entropy because the
solute particles become separated from one another when a solution is formed.
3. Entropy increases as temperature increases. An increase in temperature means that the particles of the substance have greater
kinetic energy. The faster moving particles have more disorder than particles that are moving more slowly at a lower
temperature.
4. Entropy generally increases in reactions in which the total number of product molecules is greater than the total number of
reactant molecules. An exception to this rule is when nongaseous products are formed from gaseous reactants.
The examples below will serve to illustrate how the entropy change in a reaction can be predicted.
Cl (g) → Cl (l) (7.4.3)

2 2
The entropy is decreasing because a gas is becoming a liquid.

CaCO (s) → CaO (s) + CO (g) (7.4.4)
3 2
The entropy is increasing because a gas is being produced, and the number of molecules is increasing.
N (g) + 3 H (g) → 2 NH (g) (7.4.5)
2 2 3
The entropy is decreasing because four total reactant molecules are forming two total product molecules. All are gases.
AgNO (aq) + NaCl (aq) → NaNO (aq) + AgCl (s) (7.4.6)
3 3
The entropy is decreasing because a solid is formed from aqueous reactants.

H (g) + Cl (g) → 2HCl (g) (7.4.7)
2 2
The entropy change is unknown (but likely not zero) because there are equal numbers of molecules on both sides of the equation,
and all are gases.
Gibbs Free Energy

Many chemical reactions and physical processes release energy that can be used to do other things. When the fuel in a car is
burned, some of the released energy is used to power the vehicle. Free energy is energy that is available to do work. Spontaneous
reactions release free energy as they proceed. The determining factors for spontaneity of a reaction depend on both the enthalpy
and entropy changes that occur for the system. The free energy change (ΔG ) of a reaction is a mathematical combination of the
enthalpy change and the entropy change.
o o o
ΔG = ΔH − T ΔS (7.4.8)
The symbol for free energy is G, in honor of American scientist Josiah Gibbs (1839 - 1903), who made many contributions to
thermodynamics. The change in Gibbs free energy is equal to the change in enthalpy minus the mathematical product of the change
in entropy multiplied by the Kelvin temperature. Each thermodynamic quantity in the equation is for substances in their standard
states, as indicated by the superscripts.
o
A spontaneous reaction is one that releases free energy, and so the sign of ΔG must be negative. Since both ΔH and ΔS can be
either positive or negative, depending on the characteristics of the particular reaction, there are four different possible
combinations. The outcomes for ΔG based on the signs of ΔH and ΔS are outlined in the table below. Recall that −ΔH indicates
that the reaction is exothermic and a +ΔH means the reaction is endothermic. For entropy, +ΔS means the entropy is increasing
and the system is becoming more disordered. A −ΔS means that entropy is decreasing and the system is becoming less disordered
(more ordered).
A process that releases free energy, (−ΔG), is said to be exergonic. Processes that require free energy (+ΔG), are
endergonic. These terms are used when considering chemical reactions that occur in living systems.
Table 7.4.1 : Enthalpy, Entropy, and Free Energy Changes.

ΔH ΔS ΔG
negative positive always negative
negative at higher temperatures, positive at

positive positive
lower temperatures
negative at lower temperatures, positive at
negative negative
higher temperatures
positive negative always positive
Keep in mind that the temperature in the Gibbs free energy equation is the Kelvin temperature, so it can only have a positive value.
When ΔH is negative and ΔS is positive, the sign of ΔG will always be negative, and the reaction will be spontaneous at all
temperatures. This corresponds to both driving forces being in favor of product formation. When ΔH is positive and ΔS is
negative, the sign of ΔG will always be positive, and the reaction can never be spontaneous. This corresponds to both driving
forces working against product formation.
When one driving force favors the reaction, but the other does not, it is the temperature that determines the sign of ΔG. Consider
first an endothermic reaction (positive ΔH ) that also displays an increase in entropy (positive ΔS ). It is the entropy term that
favors the reaction. Therefore, as the temperature increases, the T ΔS term in the Gibbs free energy equation will begin to
predominate and ΔG will become negative. A common example of a process which falls into this category is the melting of ice
(see figure below). At a relatively low temperature (below 273 K), the melting is not spontaneous because the positive ΔH term
"outweighs" the T ΔS term. When the temperature rises above 273 K, the process becomes spontaneous because the larger T value
has tipped the sign of ΔG over to being negative.
Figure 7.4.2 : Ice melts spontaneously only when the temperature is above o
0 C . The increase in entropy is then able to drive the
unfavorable endothermic process.
When the reaction is exothermic (negative ΔH ) but undergoes a decrease in entropy (negative ΔS ), it is the enthalpy term which
favors the reaction. In this case, a spontaneous reaction is dependent upon the T ΔS term being small relative to the ΔH term, so
that ΔG is negative. The freezing of water is an example of this type of process. It is spontaneous only at a relatively low
temperature. Above 273. K, the larger T ΔS value causes the sign of ΔG to be positive, and freezing does not occur.
7.4: Why Do Chemical Reactions Occur? Free Energy is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by
LibreTexts.
Define reaction rate.
Explain the concept of activation energy.
Label a diagram with reactants, products, enthalpy of forward and reverse reactions, activation energy of forward and
reverse reactions, and activated complex.
Chemical kinetics is the study of the rates of chemical reactions. In this lesson, you will learn how to express the rate of a chemical
reaction and about various factors that influence reaction rates.
Expressing Reaction Rate

Chemical reactions vary widely in the speeds with which they occur. Some reactions occur very quickly. It a lighted match is
brought into contact with lighter fluid or another flammable liquid, it erupts into flame instantly and burns fast. Other reactions
occur very slowly. A container of milk in the refrigerator will be good to drink for weeks before it begins to turn sour. Millions of
years were required for dead plants under Earth's surface to accumulate and eventually turn into fossil fuels such as coal and oil.
Chemists need to be concerned with the rates at which chemical reactions occur. Rate is another word for speed. If a sprinter takes
11.0 seconds (s) to run a 100 meter (\left( m \right)\) dash, his rate or speed is given by the distance traveled divided by the time
(see figure below).
distance 100 m
speed = = = 9.09 m/s (7.5.1)
time 11.0 s
The sprinter's average running rate for the race is 9.09 m/s. We say that it is his average rate because he did not run at that speed
for the entire race. At the very beginning of the race, while coming from a standstill, his rate must be slower until he is able to get
up to his top speed. His top speed must the be greater than 9.09 m/s so that taken over the entire race, the average ends up at
9.09 m/s.
Figure 7.5.1 : Usain Bolt set the world record for the 100 meter dash in 2009 with a time of 9.58 seconds. His average running rate
over the course of this race was 10.4 m/s , or 23.4 mph.
Chemical reactions can't be measured in units of meters per second, as that would not make any sense. A reaction rate is the
change in concentration of a reactant or product with time. Suppose that a simple reaction were to take place in which a 1.00 molar
(M) aqueous solution of substance A was converted to substance B .
A (aq) → B (aq) (7.5.2)
Suppose that after 20.0 seconds, the concentration of A had dropped from 1.00 M to 0.72 M as it was being converted to substance
B . We can express the rate of this reaction as the change in concentration of A divided by the time.
Δ [A] [A]final − [A]initial

rate = − =− (7.5.3)
Δt Δt
A bracket around a symbol or formula means the concentration in molarity of that substance. The change in concentration of A is
its final concentration minus its initial concentration. Because the concentration of A is decreasing over time, the negative sign is
used. Thus, the rate for the reaction is positive, and the units are molarity per second or M/s.
0.72 M − 1.00 M −0.28 M
rate = − =− = 0.041 M/s (7.5.4)
20.0 s 20.0 s
Over the first 20.0 seconds of this reaction, the molarity of A decreases by an average rate of 0.041 M every second. In summary,
the rate of a chemical reaction is measured by the change in concentration over time for a reactant or product. The unit of
measurement for a reaction rate is molarity per second (M/s).
Collision Theory
The behavior of the reactant atoms, molecules, or ions is responsible for the rates of a given chemical reaction. Collision theory is
a set of principles based around the idea that reactant particles form products when they collide with one another, but only when
those collisions have enough kinetic energy and the correct orientation to cause a reaction. Particles that lack the necessary kinetic
energy may collide, but the particles will simply bounce off one another unchanged. The figure below illustrates the difference. In
the first collision, the particles bounce off one another, and no rearrangement of atoms has occurred. The second collision occurs
with greater kinetic energy, and so the bond between the two red atoms breaks. One red atom bonds with the other molecule as one
product, while the single red atom is the other produce. The first collision is called an ineffective collision, while the second
collision is called an effective collision.
Figure 7.5.2 : (A) An ineffective collision is one that does not result in product formation. (B) An effective collision is one in which
chemical bonds are broken, and a product is formed.
Supplying reactant particles with energy causes the bonds between the atoms to vibrate with a greater frequency. This increase in
vibrational energy makes a chemical bond more likely to break and a chemical reaction more likely to occur when those particles
collide with other particles. Additionally, more energetic particles have more forceful collisions, which also increases the likelihood
that a rearrangement of atoms will take place. The activation energy for a reaction is the minimum energy that colliding particles
must have in order to undergo a reaction. Some reactions occur readily at room temperature because most of the reacting particles
already have the requisite activation energy at that temperature. Other reactions only occur when heated because the particles do
not have enough energy to react unless more is provided by an external source of heat.
Potential Energy Diagrams

Then energy changes that occur during a chemical reaction can be shown in a diagram called a potential energy diagram,
sometimes called a reaction progress curve. A potential energy diagram shows the change in the potential energy of a system as
reactants are converted into products. The figure below shows basic potential energy diagrams for an endothermic (left) and an
exothermic (right) reaction. Recall that the enthalpy change (ΔH ) is positive for an endothermic reaction and negative for an
exothermic reaction. This can be seen in the potential energy diagrams. The total potential energy of the system increases for the
endothermic reaction as the system absorbs energy from the surroundings. The total potential energy of the system decreases for
the exothermic reaction as the system releases energy to the surroundings.
Figure 7.5.3 : A potential energy diagram shows the total potential energy of a reacting system as the reaction proceeds. (Left) In an
endothermic reaction, the energy of the products is greater than the energy of the reactants, and ΔH is positive. (Right) In an
exothermic reaction, the energy of the products is lower than the energy of the reactants, and ΔH is negative.
The activation energy for a reaction is illustrated in the potential energy diagram by the height of the hill between the reactants and
the products. For this reason, the activation energy of a reaction is sometimes referred to as the activation energy barrier. Reacting
particles must have enough energy so that when they collide, they can overcome this barrier (see figure below).
Figure 7.5.4 : The activation energy (E ) of a reaction is the barrier that must be overcome in order for the reactants to become
a
products. (A) The activation energy is low, meaning that the reaction is likely to be fast. (B) The activation energy is high, meaning
that the reaction is likely to be slow.
As discussed earlier, reactant particles sometimes collide with one another and yet remain unchanged by the collision. Other times,
the collision leads to the formation of products. The state of the particles that is in between the reactants and products is called the
activated complex. An activated complex is an unstable arrangement of atoms that exists momentarily at the peak of the
activation energy barrier. Because of its high energy, the activated complex exists only for an extremely short period of time (about
s). The activated complex is equally likely to either reform the original reactants or go on to form the products. The figure
−13
10
below shows the formation of a possible activated complex between colliding hydrogen and oxygen molecules. Because of their
unstable nature and brief existence, very little is known about the exact structures of most activated complexes.
Figure 7.5.5 : An activated complex is a short-lived state in which the colliding particles are at the peak of the potential energy
curve.
7.5: How Do Chemical Reactions Occur? Reaction Rates is shared under a CK-12 license and was authored, remixed, and/or curated by
LibreTexts.
Describe how temperatures, concentration of reactant, and a catalyst affect the reaction rate.
By their nature, some reactions occur very quickly, while others are very slow. However, certain changes in the reaction conditions
can have an effect on the rate of a given chemical reaction. Collision theory can be utilized to explain these rate effects.
Concentration
Increasing the concentration of one or more of the reacting substances generally increases the reaction rate. When more particles
are present in a given amount of space, a greater number of collisions will naturally occur between those particles. Since the rate of
a reaction is dependent on the frequency of collisions between the reactants, the rate increases as the concentration increases.
Temperature
Raising the temperature of a chemical reaction results in a higher reaction rate. When the reactant particles are heated, they move
faster and faster, resulting in a greater frequency of collisions. An even more important effect of the temperature increase is that the
collisions occur with a greater force, which means the reactants are more likely to surmount the activation energy barrier and go on
to form products. Increasing the temperature of a reaction increases not only the frequency of collisions, but also the percentage of
those collisions that are effective, resulting in an increased reaction rate.
Paper is certainly a highly combustible material, but paper does not burn at room temperature because the activation energy for the
reaction is too high. The vast majority of collisions between oxygen molecules and the paper are ineffective. However, when the
paper is heated by the flame from a match, it reaches a point where the molecules now have enough energy to react. The reaction is
very exothermic, so the heat released by the initial reaction will provide enough energy to allow the reaction to continue, even if the
match is removed. The paper continues to burn rapidly until it is gone.
Catalysts
The rates of some chemical reactions can be increased dramatically by introducing certain other substances into the reaction
mixture. Hydrogen peroxide is used as a disinfectant for scrapes and cuts, and it can be found in many medicine cabinets as a 3%
aqueous solution. Hydrogen peroxide naturally decomposes to produce water and oxygen gas, but the reaction is very slow. A
bottle of hydrogen peroxide will last for several years before it needs to be replaced. However, the addition of just a small amount
of manganese (IV) oxide to hydrogen peroxide will cause it to decompose completely in just a matter of minutes. A catalyst is a
substance that increases the rate of a chemical reaction without being used up in the reaction. It accomplishes this task by
providing an alternate reaction pathway that has a lower activation energy barrier. After the reaction occurs, a catalyst returns to its
original state, so catalysts can be used over and over again. Because it is neither a reactant nor a product, a catalyst is shown in a
chemical equation by being written above the yield arrow.
MnO
2
2H O (aq) → 2 H O (l) + O (g) (7.6.1)

2 2 2 2
A catalyst works by changing the mechanism of the reaction, which can be though of as the specific set of smaller steps by which
the reactants become products. The important point is that the use of a catalyst lowers the overall activation energy of the reaction
(see figure below). With a lower activation energy barrier, a greater percentage of reactant molecules are able to have effective
collisions, and the reaction rate increases.
Figure 7.6.7 : The addition of a catalyst to a reaction lowers the activation energy, increasing the rate of the reaction. The activation
energy of the uncatalyzed reaction is shown by E , while the catalyzed reaction is shown by E . The heat of reaction (ΔH ) is
a
′
a
unchanged by the presence of the catalyst.

Catalysts are extremely important parts of many chemical reactions. Enzymes in your body act as nature's catalysts, allowing
important biochemical reactions to occur at reasonable rates. Chemical companies constantly search for new and better catalysts to
make reactions go faster and thus make the company more profitable.
7.6: Effects of Temperature, Concentration, and Catalysts on Reaction Rates is shared under a CK-12 license and was authored, remixed, and/or
curated by LibreTexts.
Define chemical equilibrium.
Recognize chemical equilibrium as a dynamic process.
Consider the following reaction occurring in a closed container (so that no material can go in or out):
H2 + I2 → 2HI
This is simply the reaction between elemental hydrogen and elemental iodine to make hydrogen iodide. The way the equation is
written, we are led to believe that the reaction goes to completion, that all the H2 and the I2 react to make HI.
However, this is not the case because it is a reversible reaction, meaning it can go in either direction. As soon as there is enough
product formed, the HI can react and the reverse chemical reaction occurs essentially "undoing" the first reaction:
2HI → H2 + I2
Eventually, the reverse reaction proceeds so quickly that it matches the speed of the forward reaction. When that happens, the
concentration of the reactants and products remains constant, there is no further change; the reaction has reached chemical
equilibrium (sometimes just spoken as equilibrium; plural equilibria), the point at which the forward and reverse processes
balance each other's progress.
Because two opposing processes are occurring at once, it is conventional to represent an equilibrium using a double arrow, like this:
H2 + I2 ⇌ 2H I
The double arrow implies that the reaction is going in both directions. Note that the reaction must still be balanced.
 Example 7.7.1
Write the equilibrium equation that exists between calcium carbonate as a reactant and calcium oxide and carbon dioxide as
products.
Solution
As this is an equilibrium situation, a double arrow is used. The equilibrium equation is written as follows:
C aC O3 + ⇌ C aO + C O2
 Exercise 7.7.1
Write the equilibrium equation between elemental hydrogen and elemental oxygen as reactants and water as the product.
Answer
2 H2 + O2 + ⇌ 2 H2 O
One thing to note about equilibrium is that the reactions do not stop; both the forward reaction and the reverse reaction continue to
occur. They both occur at the same rate, so any overall change by one reaction is canceled by the reverse reaction. We say that
chemical equilibrium is dynamic, rather than static. Also, because both reactions are occurring simultaneously, the equilibrium can
be written backward. For example, representing an equilibrium as
H2 + I2 ⇌ 2H I
is the same thing as representing the same equilibrium as
2H I ⇌ H2 + I2
The reaction must be at equilibrium for this to be the case, however.
Key Takeaways
Chemical reactions eventually reach equilibrium, a point at which forward and reverse reactions balance each other's progress.
Chemical equilibria are dynamic: the chemical reactions are always occurring; they just cancel each other's progress.
7.7: Reversible Reactions and Chemical Equilibrium is shared under a not declared license and was authored, remixed, and/or curated by
LibreTexts.
13.2: Chemical Equilibrium by Anonymous is licensed CC BY-NC-SA 3.0. Original source:
Define the equilibrium constant.
Construct an equilibrium constant expression for a chemical reaction.
In the mid 1860s, Norwegian scientists C. M. Guldberg and P. Waage noted a peculiar relationship between the amounts of
reactants and products in an equilibrium. No matter how many reactants they started with, a certain ratio of reactants and products
was achieved at equilibrium. Today, we call this observation the law of mass action. It relates the amounts of reactants and
products at equilibrium for a chemical reaction. For a general chemical reaction occurring in solution,
aA + bB ⇌ cC + dD
the equilibrium constant, also known as Keq, is defined by the following expression:
c d
[C ] [D]
Keq =
a b
[A] [B]
where [A] is the molar concentration of species A at equilibrium, and so forth. The coefficients a, b, c, and d in the chemical
equation become exponents in the expression for Keq. The Keq is a characteristic numerical value for a given reaction at a given
temperature; that is, each chemical reaction has its own characteristic Keq. The concentration of each reactant and product in a
chemical reaction at equilibrium is related; the concentrations cannot be random values, but they depend on each other. The
numerator of the expression for Keq has the concentrations of every product (however many products there are), while the
denominator of the expression for Keq has the concentrations of every reactant, leading to the common products over reactants
definition for the Keq.
Let us consider a simple example. Suppose we have this equilibrium:
A ⇌ B
There is one reactant, one product, and the coefficients on each are just 1 (assumed, not written). The Keq expression for this
equilibrium is
[B]
Keq =
[A]
(Exponents of 1 on each concentration are understood.) Suppose the numerical value of Keq for this chemical reaction is 2.0. If [B]
= 4.0 M, then [A] must equal 2.0 M so that the value of the fraction equals 2.0:
[B] 4.0
Keq = = = 2.0
[A] 2.0
By convention, the units are understood to be M and are omitted from the Keq expression. Suppose [B] were 6.0 M. For the Keq
value to remain constant (it is, after all, called the equilibrium constant), then [A] would have to be 3.0 M at equilibrium:
[B] 6.0
Keq = = = 2.0
[A] 3.0
If [A] were not equal to 3.0 M, the reaction would not be at equilibrium, and a net reaction would occur until that ratio was indeed
2.0. At that point, the reaction is at equilibrium, and any net change would cease. (Recall, however, that the forward and reverse
reactions do not stop because chemical equilibrium is dynamic.)
The issue is the same with more complex expressions for the Keq; only the mathematics become more complex. Generally
speaking, given a value for the Keq and all but one concentration at equilibrium, the missing concentration can be calculated.
 Example 7.8.1
Given the following reaction:
H +I −
↽⇀
− 2 HI (7.8.1)
2 2
If the equilibrium [HI] is 0.75 M and the equilibrium [H2] is 0.20 M, what is the equilibrium [I2] if the Keq is 0.40?
Solution
We start by writing the Keq expression. Using the products over reactants approach, the Keq expression is as follows:
2
[H I ]
Keq =
[ H2 ][ I2 ]
Note that [HI] is squared because of the coefficient 2 in the balanced chemical equation. Substituting for the equilibrium [H2]
and [HI] and for the given value of Keq:
2
(0.75)
0.40 =
(0.20)[ I2 ]
To solve for [I2], we have to do some algebraic rearrangement: divide the 0.40 into both sides of the equation and multiply
both sides of the equation by [I2]. This brings [I2] into the numerator of the left side and the 0.40 into the denominator of the
right side:
2
(0.75)
[ I2 ] =
(0.20)(0.40)
Solving,
[I2] = 7.0 M
The concentration unit is assumed to be molarity. This value for [I2] can be easily verified by substituting 0.75, 0.20, and 7.0
into the expression for Keq and evaluating: you should get 0.40, the numerical value of Keq (and you do).
 Exercise 7.8.1
Given the following reaction:
H +I −
↽⇀
− 2 HI (7.8.2)
2 2
If the equilibrium [HI] is 0.060 M and the equilibrium [I2] is 0.90 M, what is the equilibrium [H2] if the Keq is 0.40?
Answer
0.010 M
In some types of equilibrium problems, square roots, cube roots, or even higher roots need to be analyzed to determine a final
answer. Make sure you know how to perform such operations on your calculator; if you do not know, ask your instructor for
assistance.
 Example 7.8.2
The following reaction is at equilibrium:
N +3 H −
↽⇀
− 2 NH (7.8.3)
2 2 3
The Keq at a particular temperature is 13.7. If the equilibrium [N2] is 1.88 M and the equilibrium [NH3] is 6.62 M, what is the
equilibrium [H2]?
Solution
We start by writing the Keq expression from the balanced chemical equation:
2
[N H3 ]
Keq =
3
[ N2 ][ H2 ]
Substituting for the known equilibrium concentrations and the Keq, this becomes
2
(6.62)
13.7 =
(1.88)[H2 ]3
Rearranging algebraically and then evaluating the numerical expression, we get

2
(6.62)
3
[ H2 ] = = 1.7015219754
(1.88)(13.7)
To solve for [H2], we need to take the cube root of the equation. Performing this operation, we get
[H2] = 1.19 M
You should verify that this is correct using your own calculator to confirm that you know how to do a cube root correctly.
 Exercise 7.8.2
The following reaction is at equilibrium:
N +3 H −
↽⇀
− 2 NH (7.8.4)
2 2 3
The Keq at a particular temperature is 13.7. If the equilibrium [N2] is 0.055 M and the equilibrium [H2] is 1.62 M, what is the
equilibrium [NH3]?
Answer
1.79 M
The Keq was defined earlier in terms of concentrations. For gas-phase reactions, the Keq can also be defined in terms of the partial
pressures of the reactants and products, Pi. For the gas-phase reaction
aA(g) + bB(g) ⇌ cC (g) + dD(g)
the pressure-based equilibrium constant, KP, is defined as follows:

c d
P P
C D
KP =
a b
P P
A B
where PA is the partial pressure of substance A at equilibrium in atmospheres, and so forth. As with the concentration-based
equilibrium constant, the units are omitted when substituting into the expression for KP.
 Example 7.8.3
What is the KP for this reaction, given the equilibrium partial pressures of 0.664 atm for NO2 and 1.09 for N2O4?
2 NO (g) −
↽⇀
− N O (g) (7.8.5)
2 2 4
Solution
Write the KP expression for this reaction:
PN2 O4
KP =
2
P
N O2
Then substitute the equilibrium partial pressures into the expression and evaluate:
(1.09)
KP = = 2.47
2
(0.664)
 Exercise 7.8.3
What is the KP for this reaction, given the equilibrium partial pressures of 0.44 atm for H2, 0.22 atm for Cl2, and 2.98 atm for
HCl?
H + Cl −
↽⇀
− 2 HCl (7.8.6)
2 2
Answer
91.7
There is a simple relationship between Keq (based on concentration units) and KP (based on pressure units):
Δn
KP = Keq ⋅ (RT )
where R is the ideal gas law constant (in units of L·atm/mol·K), T is the absolute temperature, and Δn is the change in the number
of moles of gas in the balanced chemical equation, defined as ngas,prods − ngas,rcts. Note that this equation implies that if the
number of moles of gas are the same in reactants and products, Keq = KP.
 Example 7.8.4
What is the KP at 25°C for this reaction if the Keq is 4.2 × 10−2?
N +3 H −
↽⇀
− 2 NH (7.8.7)
2 2 3
Solution
Before we use the relevant equation, we need to do two things: convert the temperature to kelvins and determine Δn.
Converting the temperature is easy:
T = 25 + 273 = 298 K
To determine the change in the number of moles of gas, take the number of moles of gaseous products and subtract the number
of moles of gaseous reactants. There are 2 mol of gas as product and 4 mol of gas of reactant:
Δn = 2 − 4 = −2 mol
Note that Δn is negative. Now we can substitute into our equation, using R = 0.08205 L·atm/mol·K. The units are omitted for
clarity:
KP = (4.2 × 10−2)(0.08205)(298)−2
Solving,
KP = 7.0 × 10−5
.
 Exercise 7.8.4
What is the KP at 25°C for this reaction if the Keq is 98.3?,-
I (g) −
↽⇀
− 2 I(g) (7.8.8)
2
Answer
2.40 × 103
Finally, we recognize that many chemical reactions involve substances in the solid or liquid phases. For example, a particular
chemical reaction is represented as follows:
2 NaHCO (s) −
↽⇀
− Na CO (s) + CO (g) + H O(l) (7.8.9)
3 2 3 2 2
This chemical equation includes all three phases of matter. This kind of equilibrium is called a heterogeneous equilibrium
because there is more than one phase present.
The rule for heterogeneous equilibria is as follows: Do not include the concentrations of pure solids and pure liquids in Keq
expressions. Only partial pressures for gas-phase substances or concentrations in solutions are included in the expressions of
equilibrium constants. As such, the equilibrium constant expression for this reaction would simply be
KP = PC O
2
because the two solids and one liquid would not appear in the expression.
Key Takeaways
Every chemical equilibrium can be characterized by an equilibrium constant, known as Keq.
The Keq and KP expressions are formulated as amounts of products divided by amounts of reactants; each amount (either a
concentration or a pressure) is raised to the power of its coefficient in the balanced chemical equation.
Solids and liquids do not appear in the expression for the equilibrium constant.
7.8: Equilibrium Equations and Equilibrium Constants is shared under a not declared license and was authored, remixed, and/or curated by
LibreTexts.
13.3: The Equilibrium Constant by Anonymous is licensed CC BY-NC-SA 3.0. Original source:
Define Le Chatelier's principle.
Predict the direction of shift for an equilibrium under stress.
Once equilibrium is established, the reaction is over, right? Not exactly. An experimenter has some ability to affect the equilibrium.
Chemical equilibria can be shifted by changing the conditions that the system experiences. We say that we "stress" the equilibrium.
When we stress the equilibrium, the chemical reaction is no longer at equilibrium, and the reaction starts to move back toward
equilibrium in such a way as to decrease the stress. The formal statement is called Le Chatelier's principle: If an equilibrium is
stressed, then the reaction shifts to reduce the stress.
Effect of Changes in Concentration
There are several ways to stress an equilibrium. One way is to add or remove a product or a reactant in a chemical reaction at
equilibrium. When additional reactant is added, the equilibrium shifts to reduce this stress: it makes more product. When additional
product is added, the equilibrium shifts to reactants to reduce the stress. If reactant or product is removed, the equilibrium shifts to
make more reactant or product, respectively, to make up for the loss.
 Example 7.9.1
Given this reaction at equilibrium:

N2 + 3 H2 ⇌ 2N H3
In which direction—toward reactants or toward products-—does the reaction shift if the equilibrium is stressed by each
change?
1. H2 is added.
2. NH3 is added.
3. NH3 is removed.
Solution
1. If H2 is added, there is now more reactant, so the reaction will shift toward products to reduce the added H2.
2. If NH3 is added, there is now more product, so the reaction will shift toward reactants to reduce the added NH3.
3. If NH3 is removed, there is now less product, so the reaction will shift toward products to replace the product removed.
 Exercise 7.9.1
Given this reaction at equilibrium:
C O(g) + Br2 (g) ⇌ C OBr2 (g)
In which direction—toward reactants or toward products—does the reaction shift if the equilibrium is stressed by each change?
1. Br2 is removed.
2. COBr2 is added.
Answers
1. toward reactants
2. toward reactants
It is worth noting that when reactants or products are added or removed, the value of the Keq does not change. The chemical
reaction simply shifts, in a predictable fashion, to reestablish concentrations so that the Keq expression reverts to the correct value.
Effect of Changes in Pressure and Temperature
How does an equilibrium react to a change in pressure? Pressure changes do not markedly affect the solid or liquid phases.
However, pressure strongly impacts the gas phase. Le Chatelier's principle implies that a pressure increase shifts an equilibrium to
the side of the reaction with the fewer number of moles of gas, while a pressure decrease shifts an equilibrium to the side of the
reaction with the greater number of moles of gas. If the number of moles of gas is the same on both sides of the reaction, pressure
has no effect.
 Example 7.9.2
What is the effect on this equilibrium if pressure is increased?
N2 (g) + 3 H2 (g) ⇌ 2N H3 (g)
Solution
According to Le Chatelier's principle, if pressure is increased, then the equilibrium shifts to the side with the fewer number of
moles of gas. This particular reaction shows a total of 4 mol of gas as reactants and 2 mol of gas as products, so the reaction
shifts toward the products side.
 Exercise 7.9.2
What is the effect on this equilibrium if pressure is decreased?
3 O2 (g) ⇌ 2 O3 (g)
Answer
Reaction shifts toward reactants.
What is the effect of temperature changes on an equilibrium? It depends on whether the reaction is endothermic or exothermic.
Recall that endothermic means that energy is absorbed by a chemical reaction, while exothermic means that energy is given off by
the reaction. As such, energy can be thought of as a reactant or a product, respectively, of a reaction:
endothermic reaction: energy + reactants → products
exothermic reaction: reactants → products + energy
Because temperature is a measure of the energy of the system, increasing temperature can be thought of as adding energy. The
reaction will react as if a reactant or a product is being added and will act accordingly by shifting to the other side. For example, if
the temperature is increased for an endothermic reaction, essentially a reactant is being added, so the equilibrium shifts toward
products. Decreasing the temperature is equivalent to decreasing a reactant (for endothermic reactions) or a product (for exothermic
reactions), and the equilibrium shifts accordingly.
 Example 7.9.3
Predict the effect of increasing the temperature on this equilibrium.
P C l3 + C l2 ⇌ P C l5 + 60kJ
Solution
Because energy is listed as a product, it is being produced, so the reaction is exothermic. If the temperature is increasing, a
product is being added to the equilibrium, so the equilibrium shifts to minimize the addition of extra product: it shifts back
toward reactants.
 Exercise 7.9.3
Predict the effect of decreasing the temperature on this equilibrium.
N2 O4 + 57kJ ⇌ 2N O2
Answer
Equilibrium shifts toward reactants.
In the case of temperature, the value of the equilibrium has changed because the Keq is dependent on temperature. That is why
equilibria shift with changes in temperature.
A catalyst is a substance that increases the speed of a reaction. Overall, a catalyst is not a reactant and is not used up, but it still
affects how fast a reaction proceeds. However, a catalyst does not affect the extent or position of a reaction at equilibrium. It helps
a reaction achieve equilibrium faster.
 Chemistry is Everywhere: Equilibria in the Garden
Hydrangeas are common flowering plants around the world. Although many hydrangeas are white, there is one common
species (Hydrangea macrophylla) whose flowers can be either red or blue, as shown in the accompanying figure. How is it that
a plant can have different colored flowers like this?
Figure 7.9.1 Garden Equilibria © Thinkstock. This species of hydrangea has flowers that can be either red or blue. Why the
color difference?
Interestingly, the color of the flowers is due to the acidity of the soil that the hydrangea is planted in. An astute gardener can
adjust the pH of the soil and actually change the color of the flowers. However, it is not the H+ or OH− ions that affect the
color of the flowers. Rather, it is the presence of aluminum that causes the color change.
The solubility of aluminum in soil, and the ability of plants to absorb it, is dependent upon the acidity of the soil. If the soil is
relatively acidic, the aluminum is more soluble, and plants can absorb it more easily. Under these conditions, hydrangea
flowers are blue, as Al ions interact with anthocyanin pigments in the plant. In more basic soils, aluminum is less soluble, and
under these conditions the hydrangea flowers are red. Gardeners who change the pH of their soils to change the color of their
hydrangea flowers are therefore employing Le Chatelier's principle: the amount of acid in the soil changes the equilibrium of
aluminum solubility, which in turn affects the color of the flowers.
Key Takeaways
Le Chatelier's principle addresses how an equilibrium shifts when the conditions of an equilibrium are changed.
The direction of shift can be predicted for changes in concentrations, temperature, or pressure.
Catalysts do not affect the position of an equilibrium; they help reactions achieve equilibrium faster.
 Exercise 7.9.1
1. Define Le Chatelier's principle.
2. What is meant by a stress? What are some of the ways an equilibrium can be stressed?
3. Given this equilibrium, predict the direction of shift for each stress.
H2 (g) + I2 (s) + 53kJ ⇌ 2H I (g)
a. decreased temperature
b. increased pressure
c. removal of HI
H2 (g) + F2 (g) ⇌ 2H F (g) + 546kJ
a. increased temperature
b. addition of H2
c. decreased pressure
2S O2 (g) + O2 (g) ⇌ 2S O3 (g) + 196kJ
a. removal of SO3
b. addition of O2
c. decreased temperature
C O2 (g) + C (s) + 171kJ ⇌ 2C O(g)
a. addition of CO
b. increased pressure
c. addition of a catalyst
7. The synthesis of NH3 uses this chemical reaction.
N2 (g) + 3 H2 (g) ⇌ 2N H3 (g) + 92kJ
Identify three stresses that can be imposed on the equilibrium to maximize the amount of NH3.
8. The synthesis of CaCO3 uses this chemical reaction.
C aO(s) + C O2 (g) ⇌ C aC O3 (s) + 180kJ
Identify three stresses that can be imposed on the equilibrium to maximize the amount of CaCO3.
Answers
1. When an equilibrium is stressed, the equilibrium shifts to minimize that stress.
2.
3. a. toward reactants
toward reactants
toward products
a. toward products
b. toward products
c. toward products
increased pressure, decreased temperature, removal of NH3
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CHAPTER OVERVIEW
8: Gases, Liquids, and Solids

8.4: Pressure
8.12: Liquids
8.13: Solids
8: Gases, Liquids, and Solids is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
1
Review the states of matter and their properties
Describe how change in temperature will affect the state of matter.
Previously, you were introduced to the three states, also called phases, of matter; solid, liquid, and gas. A phase is a certain form of
matter that includes a specific set of physical properties. That is, the atoms, the molecules, or the ions that make up the phase do so
in a consistent manner throughout the phase. Science recognizes three stable phases: the solid phase, in which individual particles
can be thought of as in contact and held in place; the liquid phase, in which individual particles are in contact but moving with
respect to each other; and the gas phase, in which individual particles are separated from each other by relatively large distances
(see Figure 8.1.1).
The state of a substance depends on the balance between the kinetic energy of the individual particles (molecules or atoms) and the
attractive forces between molecules, called intermolecular forces. The kinetic energy keeps the molecules apart and moving
around, and is a function of the temperature of the substance. The intermolecular forces draw the particles together. A discussed
previously, gasses are very sensitive to temperatures and pressure. However, these also affect liquids and solids too. Heating and
cooling can change the kinetic energy of the particles in a substance, and so, we can change the physical state of a substance by
heating or cooling it. Increasing the pressure on a substance forces the molecules closer together, which increases the strength of
intermolecular forces.
(a) in the gaseous state (b) as a liquid (c) in solid form
Figure 8.1.1 : Molecular level picture of gases, liquids and solids.

We take advantage of changes between the gas, liquid, and solid states to cool a drink with ice cubes (solid to liquid), cool our
bodies by perspiration (liquid to gas), and cool food inside a refrigerator (gas to liquid and vice versa). We use dry ice, which is
solid CO2, as a refrigerant (solid to gas), and we make artificial snow for skiing and snowboarding by transforming a liquid to a
solid. In this section, we examine what happens when any of the three forms of matter is converted to either of the other two. These
changes of state are often called phase changes. The six most common phase changes are shown in Figure 8.1.2.
Figure 8.1.2 : Enthalpy changes that accompany phase transitions are indicated by purple and green arrows. (CC BY-SA-NC;
anoymous)
Energy Changes That Accompany Phase Changes

Phase changes are always accompanied by a change in the enthalpy, ΔH , of a system. For example, converting a liquid, in which
the molecules are close together, to a gas, in which the molecules are, on average, far apart, requires an input of energy (heat) to
give the molecules enough kinetic energy to allow them to overcome the intermolecular attractive forces. The stronger the
attractive forces, the more energy is needed to overcome them. Solids, which are highly ordered, have the strongest intermolecular
interactions, whereas gases, which are very disordered, have the weakest. Thus any transition from a more ordered to a less ordered
state (solid to liquid, liquid to gas, or solid to gas) requires an input of energy; the ΔH is positive (endothermic). Conversely, any
transition from a less ordered to a more ordered state (liquid to solid, gas to liquid, or gas to solid) releases energy; the ΔH is
negative (exothermic). The energy change associated with each common phase change is shown in Figure 8.1.2.
ΔH is positive for any transition from a more ordered to a less ordered state and
negative for a transition from a less ordered to a more ordered state.
Previously, we defined the enthalpy changes associated with various chemical and physical processes. The molar enthalpy of
fusion (ΔH ), is the energy required to convert a solid to a liquid, a process known as fusion (or melting). As noted above, the
f us
process of melting requires energy and therefore, the (ΔH ) is positive. The reverse process of freezing would release energy
f us
making the (ΔH ) negative. The molar enthalpy of vaporization (ΔH ), is the energy required to convert a liquid to a gas,
f us vap
known as vaporization. Melting points, enthalpies of fusion, boiling points, and enthalpies of vaporization for selected compounds
are listed in Table 8.1.1.
Table 8.1.1 : Melting and Boiling Points and Enthalpies of Fusion and Vaporization for Selected Substances. Values given under 1 atm. of
external pressure.
Substance Melting Point (°C) ΔHfus (kJ/mol) Boiling Point (°C) ΔHvap (kJ/mol)
N2 −210.0 0.71 −195.8 5.6
HCl −114.2 2.00 −85.1 16.2
Br2 −7.2 10.6 58.8 30.0
CCl4 −22.6 2.56 76.8 29.8
CH3CH2OH (ethanol) −114.1 4.93 78.3 38.6
CH3(CH2)4CH3 (n-
−95.4 13.1 68.7 28.9
hexane)
Substance Melting Point (°C) ΔHfus (kJ/mol) Boiling Point (°C) ΔHvap (kJ/mol)
H2O 0 6.01 100 40.7
Na 97.8 2.6 883 97.4
NaF 996 33.4 1704 176.1
The substances with the highest melting points usually have the highest enthalpies of fusion; they tend to be ionic compounds that
are held together by very strong electrostatic interactions. Substances with high boiling points are those with strong intermolecular
interactions that must be overcome to convert a liquid to a gas, resulting in high enthalpies of vaporization. The enthalpy of
vaporization of a given substance is much greater than its enthalpy of fusion because it takes more energy to completely separate
molecules (conversion from a liquid to a gas) than to enable them only to move past one another freely (conversion from a solid to
a liquid).
8.1: States of Matter and Their Changes is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
11.1: A Molecular Comparison of Gases, Liquids, and Solids is licensed CC BY-NC-SA 3.0.
11.4: Phase Changes is licensed CC BY-NC-SA 3.0.
Identify the different types of intermolecular forces.
Relate the physical properties of a substance to the strength of attractive forces.
Why does a substance exist as a solid, liquid, or a gas at specific temperatures? Why do some substances evaporate quickly or melt
more easily? These questions can be answered by considering the balance between the energy of the particles and intermolecular
forces (or intermolecular interactions) between the particles. If the forces between particles are strong enough, the substance is a
liquid or, if stronger, a solid. If the forces between particles are weak and sufficient energy is present, the particles separate from
each other, so the gas phase is the preferred phase. The energy of the particles is mostly determined by temperature, so temperature
is the main variable that determines what phase is stable at any given point.
There are three types of intermolecular forces: London Dispersion, dipole-dipole, and hydrogen bonding, collectively termed van
der Waals forces, that will be introduced below.
London Dispersion Forces

There are forces between all molecules that are caused by electrons being in different places in a molecule at any one time, which
sets up a temporary separation of charge (a temporary dipole moment) that disappears almost as soon as it appears. These very
weak intermolecular interactions are called dispersion forces (or London dispersion forces, named for the physicist Fritz London,
who first described this force in the early 1900s).
Dispersion forces that develop between atoms in different molecules can attract the two molecules to each other. The forces are
relatively weak, however, and become significant only when the molecules are very close. Larger and heavier atoms and
molecules exhibit stronger dispersion forces than do smaller and lighter atoms and molecules. F2 and Cl2 are gases at room
temperature (reflecting weaker attractive forces); Br2 is a liquid, and I2 is a solid (reflecting stronger attractive forces). Trends in
observed melting and boiling points for the halogens clearly demonstrate this effect, as seen in Table 8.2.1.
Table 8.2.1 : Melting and Boiling Points of the Halogens
Halogen Molar Mass Atomic Radius Melting Point Boiling Point
fluorine, F2 38 g/mol 72 pm 53 K 85 K
chlorine, Cl2 71 g/mol 99 pm 172 K 238 K
bromine, Br2 160 g/mol 114 pm 266 K 332 K
iodine, I2 254 g/mol 133 pm 387 K 457 K
astatine, At2 420 g/mol 150 pm 575 K 610 K
The increase in melting and boiling points with increasing atomic/molecular size may be rationalized by considering how the
strength of dispersion forces is affected by the electronic structure of the atoms or molecules in the substance. In a larger atom, the
valence electrons are, on average, farther from the nuclei than in a smaller atom. Thus, they are less tightly held and can more
easily form the temporary dipoles that produce the attraction. The measure of how easy or difficult it is for another electrostatic
charge (for example, a nearby ion or polar molecule) to distort a molecule’s charge distribution (its electron cloud) is known as
polarizability. A molecule that has a charge cloud that is easily distorted is said to be very polarizable and will have large
dispersion forces; one with a charge cloud that is difficult to distort is not very polarizable and will have small dispersion forces.
 Example 8.2.1
Order the following compounds of a group 14 element and hydrogen from lowest to highest boiling point: CH4, SiH4, GeH4,
and SnH4. Explain your reasoning.
Solution
Applying the skills acquired in the chapter on chemical bonding and molecular geometry, all of these compounds are predicted
to be nonpolar, so they may experience only dispersion forces: the smaller the molecule, the less polarizable and the weaker the
dispersion forces; the larger the molecule, the larger the dispersion forces. The molar masses of CH4, SiH4, GeH4, and SnH4
are approximately 16 g/mol, 32 g/mol, 77 g/mol, and 123 g/mol, respectively. Therefore, CH4 is expected to have the lowest
boiling point and SnH4 the highest boiling point. The ordering from lowest to highest boiling point is expected to be
CH4 < SiH4 < GeH4 < SnH4
A graph of the actual boiling points of these compounds versus the period of the group 14 elements shows this prediction to be
correct:
 Exercise 8.2.1
Order the following hydrocarbons from lowest to highest boiling point: C2H6, C3H8, and C4H10.
Answer
All of these compounds are nonpolar and only have London dispersion forces: the larger the molecule, the larger the
dispersion forces and the higher the boiling point. The ordering from lowest to highest boiling point is therefore
C2H6 < C3H8 < C4H10.
Dipole-Dipole Intermolecular Forces

Recall that a polar molecule will have a net unequal distribution of electrons in its covalent bonds resulting in a partial positive
charge on one side of the molecule and a partial negative charge on the other side of the molecule—a separation of charge called a
dipole. The electrostatic attraction between oppositely charged ends of polar molecules are called dipole-dipole interactions, (as
illustrated in Figure 8.2.1). Dipole-dipole attractions are between permanent dipoles and are therefore generally stronger than
dispersion forces, which are between temporary dipoles. Thus, a polar molecule such as CH2Cl2 has a significantly higher boiling
point (313 K, or 40°C) than a nonpolar molecule like CF4 (145 K, or −128°C), even though it has a lower molar mass (85 g/mol vs.
88 g/mol).
Figure 8.2.1 : This image illustrates a dipole-dipole interaction, two arrangements of polar molecules that allow an attraction
between the partial negative end of one molecule and the partial positive end of another.
 Example 8.2.2
Predict which will have the higher boiling point: N2 or CO. Explain your reasoning.
Solution
CO and N2 are both diatomic molecules with masses of about 28 amu, so they experience similar London dispersion forces.
Because CO is a polar molecule, it experiences dipole-dipole attractions. Because N2 is nonpolar, its molecules cannot exhibit
dipole-dipole attractions. The dipole-dipole attractions between CO molecules are comparably stronger than the dispersion
forces between nonpolar N2 molecules, so CO is expected to have the higher boiling point.
 Exercise 8.2.2
Predict which will have the higher boiling point: ICl or Br . Explain your reasoning.
2
Answer
ICl. ICl and Br2 have similar masses (~160 amu) and therefore experience similar London dispersion forces. ICl is polar
and thus also exhibits dipole-dipole attractions; Br2 is nonpolar and does not. The relatively stronger dipole-dipole
attractions require more energy to overcome, so ICl will have the higher boiling point.
Hydrogen Bonds
An unusually strong form of dipole-dipole interaction is called hydrogen bonding. Hydrogen bonding is found in molecules with
an H atom bonded to an N atom, an O atom, or an F atom. Such covalent bonds are very polar, and the dipole-dipole interaction
between these bonds in two or more molecules is strong enough to create a new category of intermolecular force. Hydrogen
bonding is the reason water has unusual properties. For such a small molecule (its molar mass is only 18 g/mol), H2O has relatively
high melting and boiling points. Its boiling point is 373 K (100°C), while the boiling point of a similar molecule, H2S, is 233 K
(−60°C). This is because H2O molecules experience hydrogen bonding, while H2S molecules do not. This strong attraction
between H2O molecules requires additional energy to separate the molecules in the condensed phase, so its boiling point is higher
than would be expected. Hydrogen bonding is also responsible for water's ability as a solvent, its high heat capacity, and its ability
to expand when freezing; the molecules line up in such a way that there is extra space between the molecules, increasing its volume
in the solid state (Figure 8.2.2).
Figure 8.2.2 : Hydrogen Bonding. When water solidifies, hydrogen bonding between the molecules forces the molecules to line up
in a way that creates empty space between the molecules, increasing the overall volume of the solid. This is why ice is less dense
than liquid water.
Despite use of the word “bond,” keep in mind that hydrogen bonds are intermolecular attractive forces, not intramolecular
attractive forces (covalent bonds). Hydrogen bonds are much weaker than covalent bonds, but are generally much stronger than
other dipole-dipole attractions and dispersion forces.
Hydrogen Bonding and DNA
Deoxyribonucleic acid (DNA) is found in every living organism and contains the genetic information that determines the
organism’s characteristics, provides the blueprint for making the proteins necessary for life, and serves as a template to pass this
information on to the organism’s offspring. A DNA molecule consists of two (anti-)parallel chains of repeating nucleotides, which
form its well-known double helical structure, as shown in Figure 8.2.3.
Figure 8.2.3 : Two separate DNA molecules form a double-stranded helix in which the molecules are held together via hydrogen
bonding. (credit: modification of work by Jerome Walker, Dennis Myts)
Each nucleotide contains a (deoxyribose) sugar bound to a phosphate group on one side, and one of four nitrogenous bases on the
other. Two of the bases, cytosine (C) and thymine (T), are single-ringed structures known as pyrimidines. The other two, adenine
(A) and guanine (G), are double-ringed structures called purines. These bases form complementary base pairs consisting of one
purine and one pyrimidine, with adenine pairing with thymine, and cytosine with guanine. Each base pair is held together by
hydrogen bonding. A and T share two hydrogen bonds, C and G share three, and both pairings have a similar shape and structure
Figure 8.2.4
Figure 8.2.4 : The geometries of the base molecules result in maximum hydrogen bonding between adenine and thymine (AT) and
between guanine and cytosine (GC), so-called “complementary base pairs.”
The cumulative effect of millions of hydrogen bonds effectively holds the two strands of DNA together. Importantly, the two
strands of DNA can relatively easily “unzip” down the middle since hydrogen bonds are relatively weak compared to the covalent
bonds that hold the atoms of the individual DNA molecules together. This allows both strands to function as a template for
replication.
 Applications: Geckos and Intermolecular Forces
Geckos have an amazing ability to adhere to most surfaces. They can quickly run up smooth walls and across ceilings that have
no toe-holds, and they do this without having suction cups or a sticky substance on their toes. And while a gecko can lift its
feet easily as it walks along a surface, if you attempt to pick it up, it sticks to the surface. How are geckos (as well as spiders
and some other insects) able to do this? Although this phenomenon has been investigated for hundreds of years, scientists only
recently uncovered the details of the process that allows geckos’ feet to behave this way.
Figure 8.2.12 : Geckos’ toes contain large numbers of tiny hairs (setae), which branch into many triangular tips (spatulae).
Geckos adhere to surfaces because of van der Waals attractions between the surface and a gecko’s millions of spatulae. By
changing how the spatulae contact the surface, geckos can turn their stickiness “on” and “off.” (credit photo: modification of
work by “JC*+A!”/Flickr)
Geckos’ toes are covered with hundreds of thousands of tiny hairs known as setae, with each seta, in turn, branching into
hundreds of tiny, flat, triangular tips called spatulae. The huge numbers of spatulae on its setae provide a gecko, shown in
Figure 8.1.12, with a large total surface area for sticking to a surface. In 2000, Kellar Autumn, who leads a multi-institutional
gecko research team, found that geckos adhered equally well to both polar silicon dioxide and nonpolar gallium arsenide. This
proved that geckos stick to surfaces because of dispersion forces—weak intermolecular attractions arising from temporary,
synchronized charge distributions between adjacent molecules. Although dispersion forces are very weak, the total attraction
over millions of spatulae is large enough to support many times the gecko’s weight.
In 2014, two scientists developed a model to explain how geckos can rapidly transition from “sticky” to “non-sticky.” Alex
Greaney and Congcong Hu at Oregon State University described how geckos can achieve this by changing the angle between
their spatulae and the surface. Geckos’ feet, which are normally nonsticky, become sticky when a small shear force is applied.
By curling and uncurling their toes, geckos can alternate between sticking and unsticking from a surface, and thus easily move
across it. Further investigations may eventually lead to the development of better adhesives and other applications.
Boiling Points and Bonding Types

In order for a substance to enter the gas phase, its particles must completely overcome the intermolecular forces holding them
together. Therefore, a comparison of boiling points is essentially equivalent to comparing the strengths of the attractive
intermolecular forces exhibited by the individual molecules. For small molecular compounds, London dispersion forces are the
weakest intermolecular forces. Dipole-dipole forces are somewhat stronger, and hydrogen bonding is a particularly strong form of
dipole-dipole interaction. However, when the mass of a nonpolar molecule is sufficiently large, its dispersion forces can be stronger
than the dipole-dipole forces in a lighter polar molecule. Thus, nonpolar Cl2 has a higher boiling point than polar HCl.
Table 8.2.3 : Intermolecular Forces and Boiling Points
Substance Strongest Intermolecular Force Boiling Point (
o
C)
H
2
dispersion -253
Ne dispersion -246
O
2
dispersion -183
Cl
2
dispersion -34
HCl dipole-dipole -85
HBr dipole-dipole -66
H S
2
dipole-dipole -61
NH
3
hydrogen bonding -33
Substance Strongest Intermolecular Force Boiling Point (
o
C)
HF hydrogen bonding 20
H O
2
hydrogen bonding 100
 Example 8.2.3
Consider the compounds dimethylether (CH3OCH3), ethanol (CH3CH2OH), and propane (CH3CH2CH3). Their boiling points,
not necessarily in order, are −42.1 °C, −24.8 °C, and 78.4 °C. Match each compound with its boiling point. Explain your
reasoning.
Solution
The shapes of CH3OCH3, CH3CH2OH, and CH3CH2CH3 are similar, as are their molar masses (46 g/mol, 46 g/mol, and 44
g/mol, respectively), so they will exhibit similar dispersion forces. Since CH3CH2CH3 is nonpolar, it may exhibit only
dispersion forces. Because CH3OCH3 is polar, it will also experience dipole-dipole attractions. Finally, CH3CH2OH has an
−OH group, and so it will experience the uniquely strong dipole-dipole attraction known as hydrogen bonding. So the ordering
in terms of strength of IMFs, and thus boiling points, is CH3CH2CH3 < CH3OCH3 < CH3CH2OH. The boiling point of propane
is −42.1 °C, the boiling point of dimethylether is −24.8 °C, and the boiling point of ethanol is 78.5 °C.
 Exercise 8.2.3
Ethane (CH3CH3) has a melting point of −183 °C and a boiling point of −89 °C. Predict the melting and boiling points for
methylamine (CH3NH2). Explain your reasoning.
Answer
The melting point and boiling point for methylamine are predicted to be significantly greater than those of ethane. CH3CH3
and CH3NH2 are similar in size and mass, but methylamine possesses an −NH group and therefore may exhibit hydrogen
bonding. This greatly increases its IMFs, and therefore its melting and boiling points. It is difficult to predict values, but the
known values are a melting point of −93 °C and a boiling point of −6 °C.
 Example 8.2.4: Intermolecular Forces

What intermolecular forces besides dispersion forces, if any, exist in each substance? Are any of these substances solids at
room temperature?
a. potassium chloride (KCl)
b. ethanol (C2H5OH)
c. bromine (Br2)
Solution
a. Potassium chloride is composed of ions, so the intermolecular interaction in potassium chloride is ionic forces. Because
ionic interactions are strong, it might be expected that potassium chloride is a solid at room temperature.
b. Ethanol has a hydrogen atom attached to an oxygen atom, so it would experience hydrogen bonding. If the hydrogen
bonding is strong enough, ethanol might be a solid at room temperature, but it is difficult to know for certain. (Ethanol is
actually a liquid at room temperature.)
c. Elemental bromine has two bromine atoms covalently bonded to each other. Because the atoms on either side of the
covalent bond are the same, the electrons in the covalent bond are shared equally, and the bond is a nonpolar covalent bond.
Thus, diatomic bromine does not have any intermolecular forces other than dispersion forces. It is unlikely to be a solid at
room temperature unless the dispersion forces are strong enough. Bromine is a liquid at room temperature.
 Exercise 8.2.4
What intermolecular forces besides dispersion forces, if any, exist in each substance? Are any of these substances solids at
room temperature?
a. methylamine (CH3NH2)
b. calcium sulfate (CaSO4)
c. carbon monoxide (CO)
Answer
a. dipole-dipole, hydrogen bonding
b. ionic forces (solid at room temperature)
c. dipole-dipole
Concept Review Exercise

1. What types of intermolecular interactions can exist in compounds?
2. What is the difference between covalent network and covalent molecular compounds?
Answer
1. ionic bonding, network covalent, dispersion forces, dipole-dipole interactions, and hydrogen bonding.
2. Covalent network compounds contain atoms that are covalently bonded to other individual atoms in a giant 3-dimensional
network. Covalent molecular compounds contain individual molecules that are attracted to one another through dispersion, dipole-
dipole or hydrogen bonding.
Key Takeaways
A phase is a form of matter that has the same physical properties throughout.
Molecules interact with each other through various forces: dipole-dipole interactions, hydrogen bonding, and dispersion forces.
Dipole-dipole attractions result from the electrostatic attraction of the partial negative end of one dipolar molecule for the
partial positive end of another.
Hydrogen bonds are a special type of dipole-dipole attraction that results when hydrogen is bonded to one of the three most
electronegative elements: F, O, or N.
The temporary dipole that results from the motion of the electrons in an atom can induce a dipole in an adjacent atom and give
rise to the London dispersion force. London forces increase with increasing molecular size.
Exercises
1. List the three common phases in the order you are likely to find them—from lowest temperature to highest temperature.
2. List the three common phases in the order they exist from lowest energy to highest energy.
3. List these intermolecular interactions from weakest to strongest: London forces, hydrogen bonding, and ionic interactions.
4. List these intermolecular interactions from weakest to strongest: covalent network bonding, dipole-dipole interactions, and
dispersion forces.
5. What type of intermolecular interaction is predominate in each substance?
a. water (H2O)
b. sodium sulfate (Na2SO4)
c. decane (C10H22)
6. What type of intermolecular interaction is predominate in each substance?
a. diamond (C, crystal)
b. helium (He)
c. ammonia (NH3)
7. Explain how a molecule like carbon dioxide (CO2) can have polar covalent bonds but be nonpolar overall.
8. Sulfur dioxide (SO2) has a formula similar to that of carbon dioxide (see Exercise 7) but is a polar molecule overall. What can
you conclude about the shape of the SO2 molecule?
9. What are some of the physical properties of substances that experience covalent network bonding?
10. What are some of the physical properties of substances that experience only dispersion forces?
Answers
1. solid, liquid, and gas
2. solid, liquid, and gas

3. London forces, hydrogen bonding, and ionic interactions
4. dispersion, dipole-dipole, network covalent
5. a. hydrogen bonding
b. ionic interactions
c. dispersion forces
6. a. network covalent
b. dispersion
c. hydrogen bonding
7. The two covalent bonds are oriented in such a way that their dipoles cancel out.
8. SO2 is not a linear molecule. It has a bent or V-shape.
9. very hard, high melting point
10. very soft, very low melting point
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State the major concepts behind the kinetic theory of gases.
Relate the general properties of gases to the kinetic theory.
Gases were among the first substances studied in terms of the modern scientific method, which was developed in the 1600s. It did
not take long to recognize that gases all shared certain physical behaviors, suggesting that all gases could be described by one all-
encompassing theory. Today, that theory is the kinetic theory of gases. The kinetic theory of gases is based on the following
statements:
1. Gases consist of tiny particles of matter that are in constant motion.
2. Gas particles are constantly colliding with each other and the walls of a container. These collisions are elastic—that is, there is
no net loss of energy from the collisions.
3. Gas particles are separated by large distances, with the size of a gas particle tiny compared to the distances that separate them.
4. There are no interactive forces (i.e., attraction or repulsion) between the particles of a gas.
5. The average speed of gas particles is dependent on the temperature of the gas.
Figure 8.3.1 shows a representation of how we mentally picture the gas phase.
Figure 8.3.1 : The Kinetic Theory of Gases. The kinetic theory of gases describes this state of matter as composed of tiny particles
in constant motion, with a lot of distance between the particles.
This model of gases explains some of the physical properties of gases. Because most of a gas is empty space, a gas has a low
density and can expand or contract under the appropriate influence. The fact that gas particles are in constant motion means that
two or more gases will always mix, as the particles from the individual gases move and collide with each other.
An ideal gas is a gas that exactly follows the statements of the kinetic theory. Unfortunately, real gases are not ideal. Many gases
deviate slightly from agreeing perfectly with the kinetic theory of gases. However, most gases adhere to the statements, and the
kinetic theory of gases is well accepted by the scientific community.
The physical behavior of gases is explained by the kinetic theory of gases.
An ideal gas adheres exactly to the kinetic theory of gases.
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8.4: Pressure
To describe and measure the pressure of a gas.
At the macroscopic level, a complete physical description of a sample of a gas requires four quantities: temperature (expressed in
kelvins), volume (expressed in liters), amount (expressed in moles), and pressure (in atmospheres). As we explain in this section,
these variables are not independent. If we know the values of any three of these quantities, we can calculate the fourth and thereby
obtain a full physical description of the gas. Temperature, volume, and amount have been discussed in previous chapters. We now
discuss pressure and its units of measurement.
Units of Pressure
Any object, whether it is your computer, a person, or a sample of gas, exerts a force on any surface with which it comes in contact.
The air in a balloon, for example, exerts a force against the interior surface of the balloon, and a liquid injected into a mold exerts a
force against the interior surface of the mold, just as a chair exerts a force against the floor because of its mass and the effects of
gravity. If the air in a balloon is heated, the increased kinetic energy of the gas eventually causes the balloon to burst because of the
increased pressure (an increase in the collisions between gas molecules) inside the balloon. Pressure (P) is defined as the amount of
force (F) per unit area (A):
F
P =
A
Pressure is dependent on both the force exerted and the size of the area to which the force is applied. We know from experience
that applying the same force to a smaller area produces a higher pressure. When we use a hose to wash a car, for example, we can
increase the pressure of the water by reducing the size of the opening of the hose with a thumb.
The units of pressure are derived from the units used to measure force and area. The SI unit for pressure, derived from the SI units
for force (newtons) and area (square meters), is the newton per square meter (N /m ), which is called the Pascal (Pa), after the
2
French mathematician Blaise Pascal (1623–1662):

2
1 Pa = 1 N/m (8.4.1)
 Example 8.4.1
Assuming a paperback book has a mass of 2.00 kg, a length of 27.0 cm, a width of 21.0 cm, and a thickness of 4.5 cm, what
pressure does it exert on a surface if it is
a. lying flat?
b. standing on edge in a bookcase?
Given: mass and dimensions of object
Asked for: pressure
Strategy:
A. Calculate the force exerted by the book and then compute the area that is in contact with a surface.
B. Substitute these two values into Equation ??? to find the pressure exerted on the surface in each orientation.
Solution:
The force exerted by the book does not depend on its orientation. Recall that the force exerted by an object is F = ma, where m
is its mass and a is its acceleration. In Earth’s gravitational field, the acceleration is due to gravity (9.8067 m/s2 at Earth’s
surface). In SI units, the force exerted by the book is therefore
m kg ⋅ m
F = ma = 2.00 kg × 9.8067 = 19.6 = 19.6 N
2 2
s s
A We calculated the force as 19.6 N. When the book is lying flat, the area is
2
A = 0.270 m × 0.210 m = 0.0567 m .
B The pressure exerted by the text lying flat is thus

F 19.6 N 2
P = = = 3.46 × 10 Pa
2
A 0.0567 m
A If the book is standing on its end, the force remains the same, but the area decreases:
−3 2
A = 21.0 cm × 4.5 cm = 0.210 m × 0.045 m = 9.5 × 10 m
B The pressure exerted by the text lying flat is thus

19.6 N 3
P = = 2.06 × 10 Pa
−3 2
9.5 × 10 m
 Exercise 8.4.1
What pressure does a 60.0 kg student exert on the floor

a. when standing flat-footed in the laboratory in a pair of tennis shoes (the surface area of the soles is approximately 180
cm2)?
b. as she steps heel-first onto a dance floor wearing high-heeled shoes (the area of the heel = 1.0 cm2)?
Answer a
3.27 × 104 Pa
Answer b
5.9 × 106 Pa
Atmospheric Pressure
Just as we exert pressure on a surface because of gravity, so does our atmosphere. We live at the bottom of an ocean of gases that
becomes progressively less dense with increasing altitude. Approximately 99% of the mass of the atmosphere lies within 30 km of
Earth’s surface, and half of it is within the first 5.5 km (Figure 8.4.1). Every point on Earth’s surface experiences a net pressure
called atmospheric pressure. The pressure exerted by the atmosphere is considerable: a 1.0 m2 column, measured from sea level to
the top of the atmosphere, has a mass of about 10,000 kg, which gives a pressure of about 100 kPa.
Figure 8.4.1 : Atmospheric Pressure. Each square meter of Earth’s surface supports a column of air that is more than 200
km high and weighs about 10,000 kg at Earth’s surface, resulting in a pressure at the surface of 1.01 × 105 N/m2. This corresponds
to a pressure of 101 kPa = 760 mmHg = 1 atm.
Atmospheric pressure can be measured using a barometer, a device invented in 1643 by one of Galileo’s students, Evangelista
Torricelli (1608–1647). A barometer may be constructed from a long glass tube that is closed at one end. It is filled with mercury
and placed upside down in a dish of mercury without allowing any air to enter the tube. Some of the mercury will run out of the
tube, but a relatively tall column remains inside (Figure 8.4.2). Why doesn’t all the mercury run out? Gravity is certainly exerting a
downward force on the mercury in the tube, but it is opposed by the pressure of the atmosphere pushing down on the surface of the
mercury in the dish, which has the net effect of pushing the mercury up into the tube. Because there is no air above the mercury
inside the tube in a properly filled barometer (it contains a vacuum), there is no pressure pushing down on the column. Thus the
mercury runs out of the tube until the pressure exerted by the mercury column itself exactly balances the pressure of the
atmosphere.
Under normal weather conditions at sea level, the two forces are balanced when the top of the mercury column is approximately
760 mm above the level of the mercury in the dish, as shown in Figure 8.4.2. This value varies with meteorological conditions and
altitude. In Denver, Colorado, for example, at an elevation of about 1 mile, or 1609 m (5280 ft), the height of the mercury column
is 630 mm rather than 760 mm.
Figure 8.4.2 : A Mercury Barometer. The pressure exerted by the atmosphere on the surface of the pool of mercury supports a
column of mercury in the tube that is about 760 mm tall. Because the boiling point of mercury is quite high (356.73°C), there is
very little mercury vapor in the space above the mercury column.
Mercury barometers have been used to measure barometric pressure for so long that they have their own unit for pressure: the
millimeter of mercury (mmHg), often called the torr, after Torricelli. Standard barometric pressure is the barometric pressure
required to support a column of mercury exactly 760 mm tall; this pressure is also referred to as 1 atmosphere (atm). These units
are also related to the pascal:
1 atm = 760 mmH g (8.4.2)
= 760 torr (8.4.3)
5
= 1.01325 × 10 Pa (8.4.4)
= 101.325 kP a (8.4.5)
Thus a pressure of 1 atm equals 760 mmHg exactly.

We are so accustomed to living under this pressure that we never notice it. Instead, what we notice are changes in the pressure,
such as when our ears pop in fast elevators in skyscrapers or in airplanes during rapid changes in altitude. We make use of
barometric pressure in many ways. We can use a drinking straw because sucking on it removes air and thereby reduces the pressure
inside the straw. The barometric pressure pushing down on the liquid in the glass then forces the liquid up the straw.
 Example 8.4.2: Barometric Pressure
One of the authors visited Rocky Mountain National Park several years ago. After departing from an airport at sea level in the
eastern United States, he arrived in Denver (altitude 5280 ft), rented a car, and drove to the top of the highway outside Estes
Park (elevation 14,000 ft). He noticed that even slight exertion was very difficult at this altitude, where the barometric pressure
is only 454 mmHg. Convert this pressure to
a. atmospheres (atm).
b. bar.
Given: pressure in millimeters of mercury
Asked for: pressure in atmospheres and bar
Strategy:
Use the conversion factors in Equation 8.4.5 to convert from millimeters of mercury to atmospheres and kilopascals.
Solution:
From Equation 8.4.5, we have 1 atm = 760 mmHg = 101.325 kPa. The pressure at 14,000 ft in atm is thus
1 atm
P = 454 mmHg × (8.4.6)
760 mmHg
= 0.597 atm
The pressure in bar is given by

1.01325 bar
P = 0.597 atm × (8.4.7)
1 atm
= 0.605 bar
 Exercise 8.4.2: Barometric Pressure
Mt. Everest, at 29,028 ft above sea level, is the world’s tallest mountain. The normal barometric pressure at this altitude is
about 0.308 atm. Convert this pressure to
a. millimeters of mercury.
b. bar.
Answer a
234 mmHg;
Answer b
0.312 bar
Barometers measure atmospheric pressure, but manometers measure the pressures of samples of gases contained in an apparatus.
The key feature of a manometer is a U-shaped tube containing mercury (or occasionally another nonvolatile liquid). A closed-end
manometer is shown schematically in part (a) in Figure 8.4.3. When the bulb contains no gas (i.e., when its interior is a near
vacuum), the heights of the two columns of mercury are the same because the space above the mercury on the left is a near vacuum
(it contains only traces of mercury vapor). If a gas is released into the bulb on the right, it will exert a pressure on the mercury in
the right column, and the two columns of mercury will no longer be the same height. The difference between the heights of the two
columns is equal to the pressure of the gas.
Figure 8.4.3 : The Two Types of Manometer. (a) In a closed-end manometer, the space above the mercury column on the left (the
reference arm) is essentially a vacuum (P ≈ 0), and the difference in the heights of the two columns gives the pressure of the gas
contained in the bulb directly. (b) In an open-end manometer, the left (reference) arm is open to the atmosphere (P ≈ 1 atm), and the
difference in the heights of the two columns gives the difference between barometric pressure and the pressure of the gas in the
bulb.
If the tube is open to the atmosphere instead of closed, as in the open-end manometer shown in part (b) in Figure 8.4.3, then the
two columns of mercury have the same height only if the gas in the bulb has a pressure equal to the barometric pressure. If the gas
in the bulb has a higher pressure, the mercury in the open tube will be forced up by the gas pushing down on the mercury in the
other arm of the U-shaped tube. The pressure of the gas in the bulb is therefore the sum of the barometric pressure (measured with
a barometer) and the difference in the heights of the two columns. If the gas in the bulb has a pressure less than that of the
atmosphere, then the height of the mercury will be greater in the arm attached to the bulb. In this case, the pressure of the gas in the
bulb is the barometric pressure minus the difference in the heights of the two columns.
Summary
Pressure is defined as the force exerted per unit area; it can be measured using a barometer or manometer. Four quantities must be
known for a complete physical description of a sample of a gas: temperature, volume, amount, and pressure. Pressure is force per
unit area of surface; the SI unit for pressure is the pascal (Pa), defined as 1 newton per square meter (N/m2). The pressure exerted
by an object is proportional to the force it exerts and inversely proportional to the area on which the force is exerted. The pressure
exerted by Earth’s atmosphere, called barometric pressure, is about 101 kPa or 14.7 lb/in.2 at sea level. barometric pressure can be
measured with a barometer, a closed, inverted tube filled with mercury. The height of the mercury column is proportional to
barometric pressure, which is often reported in units of millimeters of mercury (mmHg), also called torr. Standard barometric
pressure, the pressure required to support a column of mercury 760 mm tall, is yet another unit of pressure: 1 atmosphere (atm).
A manometer is an apparatus used to measure the pressure of a sample of a gas.
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Define the relationship between gas volume and pressure, Boyle's Law.
Use Boyle's Law to calculate changes in pressure or volume of a gas.
When seventeenth-century scientists began studying the physical properties of gases, they noticed some simple relationships
between some of the measurable properties of the gas. Take pressure (P) and volume (V), for example. Scientists noted that for a
given amount of a gas (usually expressed in units of moles [n]), if the temperature (T) of the gas was kept constant, pressure and
volume were related: As one increases, the other decreases. As one decreases, the other increases. We say that pressure and volume
are inversely related.
There is more to it, however: pressure and volume of a given amount of gas at constant temperature are numerically related. If you
take the pressure value and multiply it by the volume value, the product is a constant (k) for a given amount of gas at a constant
temperature:
P × V = k (at constant n and T )
If either volume or pressure changes while amount and temperature stay the same, then the other property must change so that the
product of the two properties still equals that same constant. That is, if the original conditions are labeled P1 and V1 and the new
conditions are labeled P2 and V2, we have
P1 V1 = k = P2 V2
where the properties are assumed to be multiplied together. Leaving out the middle part, we have simply
P1 V1 = P2 V2 (at constant n and T )
This equation is an example of a gas law. A gas law is a simple mathematical formula that allows you to model, or predict, the
behavior of a gas. This particular gas law is called Boyle's law, after the English scientist Robert Boyle, who first announced it in
1662. Figure 8.5.1 shows two representations of how Boyle's law works.
Figure 8.5.1 : Boyle's Law. A piston having a certain pressure and volume (left piston) will have half the volume when its pressure
is twice as much (right piston). One can also plot P versus V for a given amount of gas at a certain temperature; such a plot will
look like the graph on the right.
Boyle's law is an example of a second type of mathematical problem we see in chemistry—one based on a mathematical formula.
Tactics for working with mathematical formulas are different from tactics for working with conversion factors. First, most of the
questions you will have to answer using formulas are word-type questions, so the first step is to identify what quantities are known
and assign them to variables. Second, in most formulas, some mathematical rearrangements (i.e., algebra) must be performed to
solve for an unknown variable. The rule is that to find the value of the unknown variable, you must mathematically isolate the
unknown variable by itself and in the numerator of one side of the equation. Finally, units must be consistent. For example, in
Boyle's law there are two pressure variables; they must have the same unit. There are also two volume variables; they also must
have the same unit. In most cases, it won't matter what the unit is, but the unit must be the same on both sides of the equation.
 Example 8.5.1
A sample of gas has an initial pressure of 2.44 atm and an initial volume of 4.01 L. Its pressure changes to 1.93 atm. What is
the new volume if temperature and amount are kept constant?
Solution
First, determine what quantities we are given. We are given an initial pressure and an initial volume, so let these values be P1
and V1:
P1 = 2.44 atm and V1 = 4.01 L
We are given another quantity, final pressure of 1.93 atm, but not a final volume. This final volume is the variable we will
solve for.
P2 = 1.93 atm and V2 = ? L
Substituting these values into Boyle's law, we get
(2.44 atm)(4.01 L) = (1.93 atm)V2
To solve for the unknown variable, we isolate it by dividing both sides of the equation by 1.93 atm—both the number and the
unit:
(2.44 atm)(4.01 L) (1.93 atm) V2
=
1.93 atm 1.93 atm
Note that, on the left side of the equation, the unit atm is in the numerator and the denominator of the fraction. They cancel
algebraically, just as a number would. On the right side, the unit atm and the number 1.93 are in the numerator and the
denominator, so the entire quantity cancels:
(2.44 atm )(4.01 L) (1.93 atm ) V2

=
1.93 atm 1.93 atm
What we have left is

(2.44)(4.01 L)
= V2
1.93
Now we simply multiply and divide the numbers together and combine the answer with the L unit, which is a unit of volume.
Doing so, we get V = 5.07 L
2
Does this answer make sense? We know that pressure and volume are inversely related; as one decreases, the other increases.
Pressure is decreasing (from 2.44 atm to 1.93 atm), so volume should be increasing to compensate, and it is (from 4.01 L to
5.07 L). So the answer makes sense based on Boyle's law.
 Exercise 8.5.1
If P1 = 334 torr, V1 = 37.8 mL, and P2 = 102 torr, what is V2?
Answer
124 mL
As mentioned, you can use any units for pressure or volume, but both pressures must be expressed in the same units, and both
volumes must be expressed in the same units.
 Example 8.5.2
A sample of gas has an initial pressure of 722 torr and an initial volume of 88.8 mL. Its volume changes to 0.663 L. What is the
new pressure?
Solution
We can still use Boyle's law to answer this, but now the two volume quantities have different units. It does not matter which
unit we change, as long as we perform the conversion correctly. Let us change the 0.663 L to milliliters:
1000 ml
0.663 L × = 663 ml
1L
Now that both volume quantities have the same units, we can substitute into Boyle's law:
(722 torr)(88.8 ml) = P2 (663 ml)
(722 torr)(88.8) ml
= P2
(663 ml)
The mL units cancel, and we multiply and divide the numbers to get P2 = 96.7 torr
The volume is increasing, and the pressure is decreasing, which is as expected for Boyle's law.
 Exercise 8.5.2
If V1 = 456 mL, P1 = 308 torr, and P2 = 1.55 atm, what is V2?
Answer
119 mL
 To Your Health: Breathing and Boyle’s Law
What do you do about 20 times per minute for your whole life, without break, and often without even being aware of it? The
answer, of course, is respiration, or breathing. How does it work? It turns out that the gas laws apply here. Your lungs take in
gas that your body needs (oxygen) and get rid of waste gas (carbon dioxide). Lungs are made of spongy, stretchy tissue that
expands and contracts while you breathe. When you inhale, your diaphragm and intercostal muscles (the muscles between your
ribs) contract, expanding your chest cavity and making your lung volume larger. The increase in volume leads to a decrease in
pressure (Boyle’s law). This causes air to flow into the lungs (from high pressure to low pressure). When you exhale, the
process reverses: Your diaphragm and rib muscles relax, your chest cavity contracts, and your lung volume decreases, causing
the pressure to increase (Boyle’s law again), and air flows out of the lungs (from high pressure to low pressure). You then
breathe in and out again, and again, repeating this Boyle’s law cycle for the rest of your life (Figure 8.5.2).
Figure 8.5.2 : Breathing occurs because expanding and contracting lung volume creates small pressure differences between
your lungs and your surroundings, causing air to be drawn into and forced out of your lungs.
This figure contains two diagrams of a cross section of the human head and torso. The first diagram on the left is labeled
“Inspiration.” It shows curved arrows in gray proceeding through the nasal passages and mouth to the lungs. An arrow points
downward from the diaphragm, which is relatively flat, just beneath the lungs. This arrow is labeled “Diaphragm contracts.” At
the entrance to the mouth and nasal passages, a label of P subscript lungs equals 1 dash 3 torr lower” is provided. The second,
similar diagram, which is labeled “Expiration,” reverses the direction of both arrows. Arrows extend from the lungs out
through the nasal passages and mouth. Similarly, an arrow points up to the diaphragm, showing a curved diaphragm and lungs
reduced in size from the previous image. This arrow is labeled “Diaphragm relaxes.” At the entrance to the mouth and nasal
passages, a label of P subscript lungs equals 1 dash 3 torr higher” is provided.
Summary
The behavior of gases can be modeled with gas laws.
Boyle's law relates a gas's pressure and volume at constant temperature and amount.
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Define the relationship between gas temperature and volume, Charles's Law.
Use Charles's Law to calculate changes in temperature or volume of a gas.
In addition to pressure and volume, another measurable characteristics of a gas is temperature (T). Perhaps one can vary the
temperature of a gas sample and note what effect it has on the other properties of the gas. Early scientists did just this, discovering
that if the amount of a gas and its pressure are kept constant, then changing the temperature changes the volume (V). As
temperature increases, volume increases; as temperature decreases, volume decreases. We say that these two characteristics are
directly related.
Kelvin Temperature Scale

A mathematical relationship between V and T should be possible except for one thought: what temperature scale should we use?
We know from previous chapters that scientists uses several possible temperature scales. Experiments show that the volume of a
gas is related to its absolute temperature in Kelvin, not its temperature in degrees Celsius. If the temperature of a gas is expressed
in Kelvins, then experiments show that the ratio of volume to temperature is a constant (k):
V
=k
T
Charles's Law
We can modify this equation as we modified Boyle's law: the initial conditions V1 and T1 have a certain value, and the value must
be the same when the conditions of the gas are changed to some new conditions V2 and T2, as long as pressure and the amount of
the gas remain constant. Thus, we have another gas law:
V1 V2
= (at constant P and n)
T1 T2
This gas law is commonly referred to as Charles's law, after the French scientist Jacques Charles, who performed experiments on
gases in the 1780s. The tactics for using this mathematical formula are similar to those for Boyle's law. To determine an unknown
quantity, use algebra to isolate the unknown variable by itself and in the numerator; the units of similar variables must be the same.
But we add one more tactic: all temperatures must be expressed in the absolute temperature scale (Kelvin). As a reminder, we
review the conversion between the absolute temperature scale and the Celsius temperature scale:
K = °C + 273
where K represents the temperature in kelvins, and °C represents the temperature in degrees Celsius.
Figure 8.6.1 : Charles's Law. A piston having a certain volume and temperature (left piston) will have twice the volume when its
temperature is twice as much (right piston). One can also plot V versus T for a given amount of gas at a certain pressure; such a
plot will look like the graph on the right.
 Example 8.6.1
A sample of gas has an initial volume of 34.8 mL and an initial temperature of 315 K. What is the new volume if the
temperature is increased to 559 K? Assume constant pressure and amount for the gas.
Solution
First, we assign the given values to their variables. The initial volume is V1, so V1 = 34.8 mL, and the initial temperature is T1,
so T1 = 315 K. The temperature is increased to 559 K, so the final temperature T2 = 559 K. We note that the temperatures are
already given in kelvins, so we do not need to convert the temperatures. Substituting into the expression for Charles's law
yields
34.8 ml V2
=
315 K 559 K
We solve for V2 by algebraically isolating the V2 variable on one side of the equation. We do this by multiplying both sides of
the equation by 559 K (number and unit). When we do this, the temperature unit cancels on the left side, while the entire 559 K
cancels on the right side:
(559 K )(34.8 ml) V2 ( 559 K )

=
315 K 559 K
The expression simplifies to

(559)(34.8 ml)
= V2
315
By multiplying and dividing the numbers, we see that the only remaining unit is mL, so our final answer is
V2 = 61.8 mL
Does this answer make sense? We know that as temperature increases, volume increases. Here, the temperature is increasing
from 315 K to 559 K, so the volume should also increase, which it does.
 Exercise 8.6.1
If V1 = 3.77 L and T1 = 255 K, what is V2 if T2 = 123 K?
Answer
1.82 L
It is more mathematically complicated if a final temperature must be calculated because the T variable is in the denominator of
Charles's law. There are several mathematical ways to work this, but perhaps the simplest way is to take the reciprocal of Charles's
law. That is, rather than write it as
V1 V2
=
T1 T2
write the equation as

T1 T2
=
V1 V2
It is still an equality and a correct form of Charles's law, but now the temperature variable is in the numerator, and the algebra
required to predict a final temperature is simpler.
 Example 8.6.2
A sample of a gas has an initial volume of 34.8 L and an initial temperature of −67°C. What must the temperature of the gas be
for its volume to be 25.0 L?
Solution
Here, we are looking for a final temperature, so we will use the reciprocal form of Charles's law. However, the initial
temperature is given in degrees Celsius, not kelvins. We must convert the initial temperature to kelvins:
−67°C + 273 = 206 K
In using the gas law, we must use T1 = 206 K as the temperature. Substituting into the reciprocal form of Charles's law, we get
206 K T2
=
34.8 L 25.0 L
Bringing the 25.0 L quantity over to the other side of the equation, we get
(25.0 L )(206 K)
= T2
34.8 L
The L units cancel, so our final answer is T2 = 148 K

This is also equal to −125°C. As temperature decreases, volume decreases, which it does in this example.
 Exercise 8.6.2
If V1 = 623 mL, T1 = 255°C, and V2 = 277 mL, what is T2?
Answer
235 K, or −38°C
Summary
Charles's law relates a gas's volume and temperature at constant pressure and amount.
In gas laws, temperatures must always be expressed in kelvins.
This page titled 8.6: Charles’s Law- The Relation between Volume and Temperature is shared under a CC BY-NC-SA 3.0 license and was
authored, remixed, and/or curated by Anonymous.
Define the relationship between gas pressure and temperature, Gay-Lussac's Law.
A third gas law may be derived as a corollary to Boyle's and Charles's laws. Suppose we double the thermodynamic temperature of
a sample of gas. According to Charles’s law, the volume should double. Now, how much pressure would be required at the higher
temperature to return the gas to its original volume? According to Boyle’s law, we would have to double the pressure to halve the
volume. Thus, if the volume of gas is to remain the same, doubling the temperature will require doubling the pressure. This law
was first stated by the Frenchman Joseph Gay-Lussac (1778 to 1850). According to Gay-Lussac’s law, for a given amount of gas
held at constant volume, the pressure is proportional to the absolute temperature. Mathematically,
P
P ∝ T or P = k × T or =k
T
where ∝ means “is proportional to,” and k is a proportionality constant that depends on the identity, amount, and volume of the gas.
P1 P2
In terms of two sets of data: = . This equation is useful for pressure-temperature calculations for a confined gas at constant
T1 T2
volume. Note that temperatures must be on the kelvin scale for any gas law calculations (0 on the kelvin scale and the lowest
possible temperature is called absolute zero). (Also note that there are at least three ways we can describe how the pressure of a gas
changes as its temperature changes: We can use a table of values, a graph, or a mathematical equation.)
Gay-Lussac’s law tells us that it may be dangerous to heat a gas in a closed container. The increased pressure might cause the
container to explode, as you can see in the video below. The video shows very, very cold nitrogen gas in a bottle being warmed by
the air. Since the bottle's volume is relatively constant, as the temperature of the nitrogen gas (formed when the liquid nitrogen
boils) increases, so does the pressure inside the bottle until, finally, BOOM!
Don't Put Liquid Nitrogen into Plastic Bo…

Bo…
 Example 8.7.1: Temperature
A container is designed to hold a pressure of 2.5 atm. The volume of the container is 20.0 cm3, and it is filled with air at room
temperature (20°C) and normal atmospheric pressure. Would it be safe to throw the container into a fire where temperatures of
600°C would be reached?
Solution
Using the common-sense method, we realize that the pressure will increase at the higher temperature, and so:
(273.15 + 600) K
P2 = 1.0 atm × = 3.0 atm
(273.15 + 20) K
This would exceed the safe strength of the container. Note that the volume of the container was not needed to solve the
problem.
This concept works in reverse, as well. For instance, if we subject a gas to lower temperatures than their initial state, the
external atmosphere can actually force the container to shrink. The following video demonstrates how a sample of hot gas,
when cooled will collapse a container. A syringe barrel is filled with hot steam (vaporized water) and a plunger placed to cap
off the end. The syringe is then placed in a beaker of ice water to cool the internal gas. When the temperature of the water
vapor decreases, the pressure exerted by the vapor decreases as well. This leads to a difference in pressure between the vapor
inside the barrel and the atmosphere. Atmospheric pressure then pushes the plunger into the barrel.
Summary
Gay-Lussac's law relates a gas's temperature and pressure at constant volume and amount.
In gas laws, temperatures must always be expressed in kelvins.
This page titled 8.7: Gay-Lussac's Law- The Relationship Between Pressure and Temperature is shared under a CC BY-NC-SA 3.0 license and
was authored, remixed, and/or curated by Ed Vitz, John W. Moore, Justin Shorb, Xavier Prat-Resina, Tim Wendorff, & Adam Hahn.
9.9: Gay-Lussac's Law by Ed Vitz, John W. Moore, Justin Shorb, Xavier Prat-Resina, Tim Wendorff, & Adam Hahn is licensed CC BY-NC-
SA 4.0.
Use the combined gas law to determine the relationships between pressure, volume, and temperature of a gas.
One thing we notice about all gas laws, collectively, is that volume and pressure are always in the numerator, and temperature is
always in the denominator. This suggests that we can propose a gas law that combines pressure, volume, and temperature. This gas
law is known as the combined gas law, and its mathematical form is:
P1 V1 P2 V2
= at constant n
T1 T2
This allows us to follow changes in all three major properties of a gas. Again, the usual warnings apply about how to solve for an
unknown algebraically (isolate it on one side of the equation in the numerator), units (they must be the same for the two similar
variables of each type), and units of temperature must be in kelvins.
Notice that each of the previous gas laws introduced, can be derived from the combined gas law:
P1 V1 P2 V2
At constant T, = gives Boyle's Law: P1 V1 = P2 V2
T1 T2
P1 V1 P2 V2 V1 V2
At constant P, = gives Charles's Law: =
T1 T2 T1 T2
P1 V1 P2 V2 P1 P2
At constant V, = gives Gay-Lussac's Law: =
T1 T2 T1 T2
In other words, if you know the equation for the combined gas law, you can calculate relationships between pressure, volume, or
temperature of a fixed amount of gas.
 Example 8.8.2
A sample of gas at an initial volume of 8.33 L, an initial pressure of 1.82 atm, and an initial temperature of 286 K
simultaneously changes its temperature to 355 K and its volume to 5.72 L. What is the final pressure of the gas?
Solution
We can use the combined gas law directly; all the units are consistent with each other, and the temperatures are given in
Kelvin. Substituting,
(1.82 atm)(8.33 L) P2 (5.72 L)
=
286 K 355 K
We rearrange this to isolate the P2 variable all by itself. When we do so, certain units cancel:
(1.82 atm)(8.33 L )(355 K )

= P2
(286 K )(5.72 L )
Multiplying and dividing all the numbers, we get
P2 = 3.29 atm
Ultimately, the pressure increased, which would have been difficult to predict because two properties of the gas were changing.
 Exercise 8.8.2
If P1 = 662 torr, V1 = 46.7 mL, T1 = 266 K, P2 = 409 torr, and T2 = 371 K, what is V2?
Answer
105 mL
Summary
There are gas laws that relate any two physical properties of a gas.
The combined gas law relates pressure, volume, and temperature of a gas.
Contributors
This page titled 8.8: The Combined Gas Law is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by
Anonymous.
6.5: Other Gas Laws by Anonymous is licensed CC BY-NC-SA 3.0. Original source: https://2012books.lardbucket.org/books/beginning-
chemistry.
Describe the relationship between the amount and volume of a gas, Avogadro's Law.
Define the conditions of standard temperature and pressure.
The Relationship between Amount and Volume: Avogadro's Law

We can demonstrate the relationship between the volume and the amount of a gas by filling a balloon; as we add more gas, the
balloon gets larger. The specific quantitative relationship was discovered by the Italian chemist Amedeo Avogadro, who recognized
the importance of Gay-Lussac’s work on combining volumes of gases. In 1811, Avogadro postulated that, at the same temperature
and pressure, equal volumes of gases contain the same number of gaseous particles (Figure 8.9.1). This is the historic “Avogadro’s
hypothesis.”
Figure 8.9.1 : Avogadro’s Hypothesis. Equal volumes of four different gases at the same temperature and pressure contain the same
number of gaseous particles. Because the molar mass of each gas is different, the mass of each gas sample is different even though
all contain 1 mol of gas (CC BY-SA-NC; anonymous).
Because the number of particles is related to the number of moles (1 mol = 6.022 × 1023 particles), Avogadro's law essentially
states that equal volumes of different gases, at the same temperature and pressure, contain the same amount (moles, particles) of
gas. At constant temperature and pressure, the volume (V) of a sample of gas is directly proportional to the number of moles (n) of
gas in the sample. Stated mathematically,
V
V ∝ n or V = k × n or =k
n
where ∝ means “is proportional to,” and k is a proportionality constant that is the same for all gases.
V1 V2
In terms of two sets of data: = .
n1 n2
This relationship is valid for most gases at relatively low pressures, but deviations from strict linearity are observed at elevated
pressures. Mathematical relationships can also be determined for the other variable pairs, such as P versus n, and n versus T.
Visit this interactive PhET simulation to investigate the relationships between pressure,
volume, temperature, and amount of gas. Use the simulation to examine the effect of
changing one parameter on another while holding the other parameters constant (as
described in the preceding sections on the various gas laws).
Standard Temperature and Pressure

It should be obvious by now that some physical properties of gases depend strongly on the conditions. What we need is a set of
standard conditions so that properties of gases can be properly compared to each other. Standard Temperature and Pressure
(STP) is defined as exactly 100 kPa of pressure (0.986 atm) and 273 K (0°C). For simplicity, we will use 1 atm as standard
pressure. Defining STP allows us to more directly compare the properties of gases that differ from one another.
One property shared among gases is a molar volume. The molar volume is the volume of 1 mol of a gas. At STP, the molar
volume of a gas can be easily determined by using the ideal gas law:
L. atm
(1 atm)V = (1 mol) (0.08205 ) (273 K)
mol. K
All the units cancel except for L, the unit of volume. So V = 22.4 L
Note that we have not specified the identity of the gas; we have specified only that the pressure is 1 atm and the temperature is 273
K. This makes for a very useful approximation: any gas at STP has a volume of 22.4 L per mole of gas; that is, the molar volume at
STP is 22.4 L/mol (Figure 8.9.1). This molar volume makes a useful conversion factor in stoichiometry problems if the conditions
are at STP. If the conditions are not at STP, a molar volume of 22.4 L/mol is not applicable. However, if the conditions are at STP,
the combined gas law can be used to calculate what the volume of the gas would be if at STP; then the 22.4 L/mol molar volume
can be used.
Figure 8.9.1 : Molar Volume. A mole of gas at STP occupies 22.4 L, the volume of a cube that is 28.2 cm on a side.
 Example 8.9.4
How many moles of Ar are present in 38.7 L at STP?
Solution
We can use the molar volume, 22.4 L/mol, as a conversion factor, but we need to reverse the fraction so that the L units cancel
and mol units are introduced. It is a one-step conversion:
1 mol
38.7 L × = 1.73 mol
22.4 L
 Exercise 8.9.4
What volume does 4.87 mol of Kr have at STP?
Answer
109 L
 Example 8.9.5
What volume of H is produced at STP when 55.8 g of Zn metal react with excess HCl?
2
Zn(s) + 2 HCl(aq) → ZnCl (aq) + H (g)

2 2
Solution
This is a stoichiometry problem with a twist: we need to use the molar volume of a gas at STP to determine the final answer.
The first part of the calculation is the same as in a previous example:
1 mol Zn 1 mol H2
55.8 g Zn × × = 0.853 H2
65.41 g Zn 1 mol Zn
Now we can use the molar volume, 22.4 L/mol, because the gas is at STP:
22.4 L
0.853 mol H2 × = 19.1 L H2
1 mol H2
Alternatively, we could have applied the molar volume as a third conversion factor in the original stoichiometry calculation.
 Exercise 8.9.5
What volume of HCl is generated if 3.44 g of Cl are reacted at STP?

2
H (g) + Cl (g) → 2 HCl(g)

2 2
Answer
2.17 L
Summary
Avogadro's law states that the volume of gas is directly proportional to the number of moles of gas.
Standard temperature and pressure (STP) are a useful set of benchmark conditions to compare other properties of gases.
At STP, gases have a volume of 22.4 L per mole.
8.9: Avogadro’s Law - The Relation between Volume and Molar Amount is shared under a CC BY-NC-SA 3.0 license and was authored, remixed,
10.3: The Gas Laws is licensed CC BY-NC-SA 3.0.
6.6: The Ideal Gas Law and Some Applications by Anonymous is licensed CC BY-NC-SA 3.0. Original source:
Describe the ideal gas law.
Use the ideal gas law to calculate pressure, volume, temperature, or moles of an ideal gas.
So far, the gas laws we have considered have all required that the gas change its conditions; then we can predict a resulting change
in one of its properties. Are there any gas laws that relate the physical properties of a gas at any given time? Consider a further
extension of the combined gas law to include n. By analogy to Avogadro's law, n is positioned in the denominator of the fraction,
opposite the volume. So,
PV
= constant
nT
Because pressure, volume, temperature, and amount are the only four independent physical properties of a gas, the constant in the
above equation is truly a constant. Indeed, because we do not need to specify the identity of a gas to apply the gas laws, this
constant is the same for all gases. We define this constant with the symbol R, so the previous equation is written as
PV
=R
nT
which is usually rearranged as
P V = nRT
This equation is called the ideal gas law. It relates the four independent properties of a gas at any time. The constant \(R\) is called
the ideal gas law constant. Its value depends on the units used to express pressure and volume.
Table 8.10.1 : Values of the Ideal Gas Law Constant lists the numerical values of R .
Numerical Value Units
L ⋅ atm
0.08205
mol ⋅ K
L ⋅ torr L ⋅ mmHg
62.36 =
mol ⋅ K mol ⋅ K
J
8.314
mol ⋅ K
The ideal gas law is used like any other gas law, with attention paid to the unit and expression of the temperature in kelvin.
However, the ideal gas law does not require a change in the conditions of a gas sample. The ideal gas law implies that if you know
any three of the physical properties of a gas, you can calculate the fourth property.
 Example 8.10.1
A 4.22 mol sample of Ar has a pressure of 1.21 atm and a temperature of 34°C. What is its volume?
Solution
The first step is to convert temperature to kelvins:
34 + 273 = 307 K
Now we can substitute the conditions into the ideal gas law:
L. atm
(1.21atm)(V ) = (4.22 mol) (0.08205 ) (307 K)
mol. K
The atm unit is in the numerator of both sides, so it cancels. On the right side of the equation, the mol and K units appear in the
numerator and the denominator, so they cancel as well. The only unit remaining is L, which is the unit of volume that we are
looking for. We isolate the volume variable by dividing both sides of the equation by 1.21:
(4.22)(0.08205)(307)
V = L
1.21
Then solving for volume, we get V = 87.9 L
 Exercise 8.10.1
A 0.0997 mol sample of O has a pressure of 0.692 atm and a temperature of 333 K. What is its volume?
2
Answer
3.94 L
 Example 8.10.2
At a given temperature, 0.00332 g of Hg in the gas phase has a pressure of 0.00120 mmHg and a volume of 435 L. What is its
temperature?
Solution
We are not given the number of moles of Hg directly, but we are given a mass. We can use the molar mass of Hg to convert to
the number of moles.
1 mol H g −5
0.00332 g H g × = 0.0000165 mol = 1.65 × 10 mol
200.59 g H g
Pressure is given in units of millimeters of mercury. We can either convert this to atmospheres or use the value of the ideal gas
constant that includes the mmHg unit. We will take the second option. Substituting into the ideal gas law,
L. mmH g
−5
(0.00332 mm H g)(435 L) = (1.65 × 10 mol)(62.36 )T
mol. K
The mmHg, L, and mol units cancel, leaving the K unit, the unit of temperature. Isolating T on one side, we get
(0.00332)(435)
T = K
−5
(1.65 × 10 )(62.36)
Then solving for K, we get T = 1,404 K.
 Exercise 8.10.2
For a 0.00554 mol sample of H2, P = 23.44 torr and T = 557 K. What is its volume?
Answer
8.21 L
The ideal gas law can also be used in stoichiometry problems.
 Example 8.10.3
What volume of H is produced at 299 K and 1.07 atm when 55.8 g of Zn metal react with excess HCl?
2
Zn(s) + 2 HCl(aq) ⟶ ZnCl (aq) + H (g)

2 2
Solution
Here we have a stoichiometry problem where we need to find the number of moles of H2 produced. Then we can use the ideal
gas law, with the given temperature and pressure, to determine the volume of gas produced. First, the number of moles of H2 is
calculated:
1 mol Zn 1 mol H2
55.8 g Zn × × = 0.853 H2
65.41 g Zn 1 mol Zn
Now that we know the number of moles of gas, we can use the ideal gas law to determine the volume, given the other
conditions:
L. atm
(1.07atm)V = (0.853 mol) (0.08205 ) (299 K)
mol. K
All the units cancel except for L, for volume, which means V = 19.6 L
 Exercise 8.10.3
What pressure of HCl is generated if 3.44 g of Cl are reacted in 4.55 L at 455 K?

2
H (g) + Cl (g) → 2 HCl(g)

2 2
Answer
0.796 atm
Summary
The ideal gas law relates the four independent physical properties of a gas at any time.
The ideal gas law can be used in stoichiometry problems with chemical reactions that involve gases.
This page titled 8.10: The Ideal Gas Law is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by Anonymous.
6.6: The Ideal Gas Law and Some Applications by Anonymous is licensed CC BY-NC-SA 3.0. Original source:
Define Dalton's law of partial pressures.
Use Dalton's law to calculate partial pressure of a gas in a mixture.
One of the properties of gases is that they mix with each other. When they do so, they become a solution—a homogeneous mixture.
Some of the properties of gas mixtures are easy to determine if we know the composition of the gases in the mix.
In gas mixtures, each component in the gas phase can be treated separately because, according to the kinetic theory of gases, there
are little to no attractive or repulsive forces between particles. Each component of a gas mixture shares the same temperature and
volume, (remember that gases expand to fill the volume of their container; gases in a mixture continue to do that as well). However,
each individual gas will have its own pressure within a mixture. This is called the partial pressure of a gas, P . Partial pressures
i
are expressed in torr, millimeters of mercury, or atmospheres like any other gas pressure; however, we use the term pressure when
talking about pure gases and the term partial pressure when we are talking about the individual gas components in a mixture.
Dalton's law of partial pressures states that the total pressure of a gas mixture, P , is equal to the sum of the partial pressures of
tot
the components, P :i
which is expressed algebraically as
Ptotal = P1 + P2 + P3 . . . = ∑ Pi
or, equivalently
RT
Ptotal = ∑ ni
V
i
where i counts over all gases in mixture.

Although this law may seem trivial, it reinforces the idea that gases behave independently of each other.
 Example 8.11.1
A mixture of H2 at 2.33 atm and N2 at 0.77 atm is in a container. What is the total pressure in the container?
Solution
Dalton's law of partial pressures states that the total pressure is equal to the sum of the partial pressures. We simply add the two
pressures together:
Ptot = 2.33 atm + 0.77 atm = 3.10 atm
 Exercise 8.11.1
N2 and O2. In 760 torr of air, the partial pressure of N2 is 608 torr. What is the partial pressure of O2?
Answer
152 torr
 Example 8.11.2
A 2.00 L container with 2.50 atm of H2 is connected to a 5.00 L container with 1.90 atm of O2 inside. The containers are
opened, and the gases mix. What is the final pressure inside the containers?
Solution
Because gases act independently of each other, we can determine the resulting final pressures using Boyle's law and then add
the two resulting pressures together to get the final pressure. The total final volume is 2.00 L + 5.00 L = 7.00 L. First, we use
Boyle's law to determine the final pressure of H2:
(2.50 atm)(2.00 L) = P2(7.00 L)
Solving for P2, we get P2 = 0.714 atm = partial pressure of H2.
Now we do that same thing for the O2:
(1.90 atm)(5.00 L) = P2(7.00 L)P2 = 1.36 atm = partial pressure of O2
The total pressure is the sum of the two resulting partial pressures:
Ptot = 0.714 atm + 1.36 atm = 2.07 atm
 Exercise 8.11.2
If 0.75 atm of He in a 2.00 L container is connected to a 3.00 L container with 0.35 atm of Ne and the containers are opened,
what is the resulting total pressure?
Answer
0.51 atm
Dalton’s law states that in a gas mixture (P ) each gas will exert a pressure independent of the other gases (P ) and each gas
total n
will behave as if it alone occupies the total volume. By extension, the partial pressure of each gas can be calculated by multiplying
the total pressure (P ) by the gas percentage (%).
total
PT otal = P1 + P2 + P3 + P4 +. . . +Pn
or
% of individual gasn
Pn =
PT otal
Table 8.11.1 : Partial Pressures for the gases in air on a typical day
Gas Partial Pressure (mm Hg) Percentage (%)
Nitrogen, (N_2\) PN
2
= 594 78
Oxygen, O 2 PO
2
= 160 21
Carbon Dioxide, CO 2 PC O
2
= 0.25 0.033
Water Vapor, H 2O PH
2
O = 5.7 0.75
Other trace gases POther = 0.05 0.22
Total air PT otal = 760 1
Application of Dalton's Law: Collecting Gases over Water

A common laboratory method of collecting the gaseous product of a chemical reaction is to conduct it into an inverted tube or
bottle filled with water, the opening of which is immersed in a larger container of water. This arrangement is called a pneumatic
trough, and was widely used in the early days of chemistry. As the gas enters the bottle it displaces the water and becomes trapped
in the upper part.
Figure 8.11.1 :An Apparatus for Collecting Gases by the Displacement of Water
The volume of the gas can be observed by means of a calibrated scale on the bottle, but what about its pressure? The total pressure
confining the gas is just that of the atmosphere transmitting its force through the water. (An exact calculation would also have to
take into account the height of the water column in the inverted tube.) But liquid water itself is always in equilibrium with its vapor,
so the space in the top of the tube is a mixture of two gases: the gas being collected, and gaseous H2O. The partial pressure of H2O
is known as the vapor pressure of water and it depends on the temperature. In order to determine the quantity of gas we have
collected, we must use Dalton's Law to find the partial pressure of that gas.
 Example 8.11.3
Oxygen gas was collected over water as shown above. The atmospheric pressure was 754 torr, the temperature was 22°C, and
the volume of the gas was 155 mL. The vapor pressure of water at 22°C is 19.8 torr. Use this information to estimate the
number of moles of O produced.
2
Solution
From Dalton's law,
PO2 = Ptotal – PH2 O = 754– 19.8 = 734 torr = 0.966 atm
Now use the Ideal Gas Law to convert to moles

PV (0.966 atm)(0.155 L)
n = = = 0.00619 mol
−1 −1
RT (0.082 Latmmol K )(295 K)
 Exercise 8.11.3
CO
2
, generated by the decomposition of CaCO , is collected in a 3.50 L container over water. If the temperature is 50°C and
3
the total pressure inside the container is 833 torr, how many moles of CO were generated?
2
Answer
0.129 mol
 Food and Drink Application: Carbonated Beverages
Carbonated beverages—sodas, beer, sparkling wines—have one thing in common: they have CO gas dissolved in them in
2
such sufficient quantities that it affects the drinking experience. Most people find the drinking experience pleasant—indeed, in
the United States alone, over 1.5 × 109 gal of soda are consumed each year, which is almost 50 gal per person! This figure does
not include other types of carbonated beverages, so the total consumption is probably significantly higher.
All carbonated beverages are made in one of two ways. First, the flat beverage is subjected to a high pressure of CO gas, 2
which forces the gas into solution. The carbonated beverage is then packaged in a tightly-sealed package (usually a bottle or a
can) and sold. When the container is opened, the CO pressure is released, resulting in the well-known hiss of an opening
2
container, and CO bubbles come out of solution. This must be done with care: if the CO comes out too violently, a mess can
2 2
occur!
Figure 8.11.1 : Carbonated beverage. If you are not careful opening a container of a carbonated beverage, you can make a
mess, as the CO comes out of solution suddenly. (Unsplash License; Tina Vanhove via Unsplash)
2
The second way a beverage can become carbonated is by the ingestion of sugar by yeast, which then generates CO
2
as a
digestion product. This process is called fermentation. The overall reaction is
C H O (aq) → 2 C H OH(aq) + 2 CO (aq)

6 12 6 2 5 2
When this process occurs in a closed container, the CO produced dissolves in the liquid, only to be released from solution
2
when the container is opened. Most fine sparkling wines and champagnes are turned into carbonated beverages this way. Less-
expensive sparkling wines are made like sodas and beer, with exposure to high pressures of CO gas. 2
Summary
The pressure of a gas in a gas mixture is termed the partial pressure.
Dalton's law of partial pressure says that the total pressure in a gas mixture is the sum of the individual partial pressures.
This page titled 8.11: Partial Pressure and Dalton's Law is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated
by Anonymous via source content that was edited to the style and standards of the LibreTexts platform; a detailed edit history is available upon
request.
6.7: Gas Mixtures by Anonymous is licensed CC BY-NC-SA 3.0. Original source: https://2012books.lardbucket.org/books/beginning-
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chemistry-general-organic-and-biological.
8.12: Liquids
Define the vapor pressure of liquids.
Explain the origin of both surface tension and capillary action.
There are some properties that all liquids, including water, have. All liquids have a certain portion of particles with enough energy
to enter the gas phase, and if these particles are at the surface of the liquid, they do so (Figure 8.12.1). The formation of a gas from
a liquid at temperatures below the boiling point is called evaporation. At these temperatures, the material in the gas phase is called
vapor, rather than gas; the term gas is reserved for when the gas phase is the stable phase.
Figure 8.12.1 : Evaporation. Some particles of a liquid have enough energy to escape the liquid phase to become a vapor.
If the available volume is large enough, eventually all the liquid will become vapor. But if the available volume is not enough,
eventually some of the vapor particles will reenter the liquid phase (Figure 8.12.2 Equilibrium). At some point, the number of
particles entering the vapor phase will equal the number of particles leaving the vapor phase, so there is no net change in the
amount of vapor in the system. We say that the system is at equilibrium. The partial pressure of the vapor at equilibrium is called
the vapor pressure of the liquid.
Figure 8.12.2 : Equilibrium. At some point, the number of particles entering the vapor phase will be balanced by the number of
particles returning to the liquid. This point is called equilibrium.
Understand that the liquid has not stopped evaporating. The reverse process—condensation—is occurring as fast as evaporation, so
there is no net change in the amount of vapor in the system. The term dynamic equilibrium represents a situation in which a process
still occurs, but the opposite process also occurs at the same rate, so that there is no net change in the system.
The vapor pressure for a substance is dependent on the temperature of the substance; as the temperature increases, so does the
vapor pressure. Figure 8.12.3 - Plots of Vapor Pressure versus Temperature for Several Liquids, is a plot of vapor pressure versus
temperature for several liquids. Having defined vapor pressure, we can also redefine the boiling point of a liquid: the temperature at
which the vapor pressure of a liquid equals the surrounding environmental pressure. The normal boiling point, then, is the
temperature at which the vapor pressure is 760 torr, or exactly 1 atm. Thus boiling points vary with surrounding pressure, a fact that
can have large implications on cooking foods at lower- or higher-than-normal elevations. Atmospheric pressure varies significantly
with altitude.
Figure 8.12.3 : Plots of Vapor Pressure versus Temperature for Several Liquids. The vapor pressure of a liquid depends on the
identity of the liquid and the temperature, as this plot shows.
 Example 8.12.1
Use Figure 8.12.3 to estimate the boiling point of water at 500 torr, which is the approximate atmospheric pressure at the top of
Mount Everest.
Solution
See the accompanying figure. Five hundred torr is between 400 and 600, so we extend a line from that point on the y-axis
across to the curve for water and then drop it down to the x-axis to read the associated temperature. It looks like the point on
the water vapor pressure curve corresponds to a temperature of about 90°C, so we conclude that the boiling point of water at
500 torr is 90°C.
By reading the graph properly, you can estimate the boiling point of a liquid at different temperatures.
 Exercise 8.12.1
Use Figure 8.12.3 to estimate the boiling point of ethanol at 400 torr.
Answer
about 65°C
The vapor pressure curve for water is not exactly zero at the melting point 0°C. Even ice has a vapor pressure—that is why it
sublimes over time. However, the vapor pressures of solids are typically much lower than that of liquids. At −1°C, the vapor
pressure of ice is 4.2 torr. At a freezer temperature of 0°F (−17°C), the vapor pressure of ice is only 1.0 torr; so-called deep freezers
can get down to −23°C, where the vapor pressure of ice is only 0.6 torr.
All liquids share some other properties as well. Surface tension is an effect caused by an imbalance of forces on the atoms at the
surface of a liquid, as shown in Figure 8.12.4. The blue particle in the bulk of the liquid experiences intermolecular forces from all
around, as illustrated by the arrows. However, the yellow particle on the surface does not experience any forces above it because
there are no particles above it. This leads to an imbalance of forces, called surface tension.
Figure 8.12.4 Surface Tension. Surface tension comes from the fact that particles at the surface of a liquid do not experience
interactions from all directions, leading to an imbalance of forces on the surface.
Surface tension is responsible for several well-known behaviors of liquids, including water. Liquids with high surface tension tend
to bead up when present in small amounts (Figure 8.12.5).
Figure 8.12.5 Effects of Surface Tension © Thinkstock. Water on the surface of this apple beads up due to the effect of surface
tension.
Surface tension causes liquids to form spheres in free fall or zero gravity. Surface tension is also responsible for the fact that small
insects can "walk" on water. Because of surface tension, it takes energy to break the surface of a liquid, and if an object (such as an
insect) is light enough, there is not enough force due to gravity for the object to break through the surface, so the object stays on top
of the water (Figure 8.12.6). Carefully done, this phenomenon can also be illustrated with a thin razor blade or a paper clip.
Figure 8.12.6 Walking on Water. Small insects can actually walk on top of water because of surface tension effects. (Unsplash
License; Miguel Alcântara via unsplash)
The fact that small droplets of water bead up on surfaces does not mean that water—or any other liquid—does not interact with
other substances. Sometimes the attraction can be very strong. Adhesion is the tendency of a substance to interact with other
substances because of intermolecular forces, while cohesion is the tendency of a substance to interact with itself. If cohesive forces
within a liquid are stronger than adhesive forces between a liquid and another substance, then the liquid tends to keep to itself; it
will bead up. However, if adhesive forces between a liquid and another substance are stronger than cohesive forces, then the liquid
will spread out over the other substance, trying to maximize the interface between the other substance and the liquid. It is said that
the liquid wets the other substance.
Adhesion and cohesion are important for other phenomena as well. In particular, if adhesive forces are strong, then when a liquid is
introduced to a small-diameter tube of another substance, the liquid will move up or down in the tube, as if ignoring gravity.
Because tiny tubes are called capillaries, this phenomenon is called capillary action. For example, one type of capillary action,
capillary rise, is seen when water or water-based liquids rise up in thin glass tubes (like the capillaries sometimes used in blood
tests), forming an upwardly curved surface called a meniscus. Capillary action is also responsible for the "wicking" effect that
towels and sponges use to dry wet objects; the matting of fibers forms tiny capillaries that have good adhesion with water. Cotton is
a good material for this; polyester and other synthetic fabrics do not display similar capillary action, which is why you seldom find
rayon bath towels. A similar effect is observed with liquid fuels or melted wax and their wicks. Capillary action is thought to be at
least partially responsible for transporting water from the roots to the tops of trees, even tall ones.
On the other hand, some liquids have stronger cohesive forces than adhesive forces. In this case, in the presence of a capillary, the
liquid is forced down from its surface; this is an example of a type of capillary action called capillary depression. In this case, the
meniscus curves downward. Mercury has very strong cohesive forces; when a capillary is placed in a pool of mercury, the surface
of the mercury liquid is depressed (Figure 8.12.7).
Figure 8.12.7 : Capillary Action. (a) Capillary rise is seen when adhesion is strong, such as with water in a thin glass tube. (b)
Capillary depression is seen when cohesive forces are stronger than adhesive forces, such as with mercury and thin glass tubes.
 Chemistry is Everywhere: Waxing a Car
Responsible car owners are encouraged to wax their cars regularly. In addition to making the car look nicer, it also helps
protect the surface, especially if the surface is metal. Why?
The answer has to do with cohesion and adhesion (and, to a lesser extent, rust). Water is an important factor in the rusting of
iron, sometimes used extensively in outer car bodies. Keeping water away from the metal is one way to minimize rusting. A
coat of paint helps with this. However, dirty or scratched paint can attract water, and adhesive forces will allow the water to
wet the surface, maximizing its contact with the metal and promoting rust.
Figure 8.12.8 : Waxing a car. Droplets of water on a freshly waxed car do not wet the car well because of low adhesion between
water and the waxed surface. This helps protect the car from rust. (Unsplash License; Yuvraj Singh via Unspash)
Wax is composed of long hydrocarbon molecules that do not interact well with water. (Hydrocarbons are compounds with C
and H atoms; for more information on hydrocarbons, see Chapter 16). That is, a thin layer of wax will not be wetted by water.
A freshly waxed car has low adhesive forces with water, so water beads up on the surface, as a consequence of its cohesion and
surface tension. This minimizes the contact between water and metal, thus minimizing rust.
Summary
All liquids evaporate.
If volume is limited, evaporation eventually reaches a dynamic equilibrium, and a constant vapor pressure is maintained.
All liquids experience surface tension, an imbalance of forces at the surface of the liquid.
All liquids experience capillary action, demonstrating either capillary rise or capillary depression in the presence of other
substances.
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10.4: Properties of Liquids by Anonymous is licensed CC BY-NC-SA 3.0. Original source:
8.13: Solids
Describe the general properties of a solid.
Describe the six different types of solids.
A solid is like a liquid in that particles are in contact with one another. Solids are unlike liquids in that the intermolecular forces are
strong enough to hold the particles in place. At low enough temperatures, all substances are solids (helium is the lone exception),
but the temperature at which the solid state becomes the stable phase varies widely among substances, from 20 K (−253°C) for
hydrogen to over 3,900 K (3,600°C) for carbon.
The solid phase has several characteristics. First, solids maintain their shape. They do not fill their entire containers like gases do,
and they do not adopt the shape of their containers like liquids do. They cannot be easily compressed like gases can, and they have
relatively high densities.
Solids may also demonstrate a variety of properties. For example, many metals can be beaten into thin sheets or drawn into wires,
while compounds such as NaCl will shatter if they are struck. Some metals, such as sodium and potassium, are rather soft, while
others, such as diamond, are very hard and can easily scratch other substances. Appearances differ as well: most metals are shiny
and silvery, but sulfur (a nonmetal) is yellow, and ionic compounds can take on a rainbow of colors. Solid metals conduct
electricity and heat, while ionic solids do not. Many solids are opaque, but some are transparent. Some dissolve in water, but some
do not. Figure 8.13.1, shows two solids that exemplify the similar and dissimilar properties of solids.
Figure 8.13.1 : Properties of Solids. (a) Sodium metal is silvery, soft, opaque, and conducts electricity and heat well. (b) NaCl is
transparent, hard, colorless, and does not conduct electricity or heat well in the solid state. These two substances illustrate the range
of properties that solids can have. Source: Photo on left courtesy of Images of Elements, http://images-of-
elements.com/sodium.php. Photo on right courtesy of Choba Poncho,
commons.wikimedia.org/wiki/File:Sodiumchloride_crystal_01.jpg.
Solids can have a wide variety of physical properties. We will review the different types of solids and the bonding that gives them
their properties.
First, we must distinguish between two general types of solids. An amorphous solid is a solid with no long-term structure or
repetition. Examples include glass and many plastics, both of which are composed of long chains of molecules with no order from
one molecule to the next. A crystalline solid is a solid that has a regular, repeating three-dimensional structure. A crystal of NaCl
(Figure 8.13.1) is one example: at the atomic level, NaCl is composed of a regular three-dimensional array of Na+ ions and Cl−
ions.
There is only one type of amorphous solid. However, there are several different types of crystalline solids, depending on the
identity of the units that compose the crystal.
An ionic solid is a crystalline solid composed of ions (even if the ions are polyatomic). NaCl is an example of an ionic solid
(Figure 8.13.2 - An Ionic Solid). The Na+ ions and Cl− ions alternate in three dimensions, repeating a pattern that goes on
throughout the sample. The ions are held together by the attraction of opposite charges—a very strong force. Hence most ionic
solids have relatively high melting points; for example, the melting point of NaCl is 801°C. Ionic solids are typically very brittle.
To break them, the very strong ionic attractions need to be broken; a displacement of only about 1 × 10−10 m will move ions next
to ions of the same charge, which results in repulsion. Ionic solids do not conduct electricity in their solid state; however, in the
liquid state and when dissolved in some solvent, they do conduct electricity. This fact originally promoted the idea that some
substances exist as ionic particles.
Figure 8.13.2 : An Ionic Solid. NaCl is a solid composed of a three-dimensional array of alternating Na+ ions (green) and Cl− ions
(purple) held together by the attraction of opposite charges.
A molecular solid is a crystalline solid whose components are covalently bonded molecules. Many molecular substances,
especially when carefully solidified from the liquid state, form solids where the molecules line up with a regular fashion similar to
an ionic crystal, but they are composed of molecules instead of ions. Because the intermolecular forces between molecules are
typically less strong than in ionic solids, molecular solids typically melt at lower temperatures and are softer than ionic solids. Ice is
an example of a molecular solid. In the solid state, the molecules line up in a regular pattern (Figure 8.13.3). Some very large
molecules, such as biological molecules, will form crystals only if they are very carefully solidified from the liquid state or, more
often, from a dissolved state; otherwise, they will form amorphous solids.
Figure 8.13.3 : Molecular Solids. Water molecules line up in a regular pattern to form molecular solids. The dotted lines show how
the polar O–H covalent bonds in one molecule engage in hydrogen bonding with other molecules. The O atoms are red, and the H
atoms are white.
Some solids are composed of atoms of one or more elements that are covalently bonded together in a seemingly never-ending
fashion. Such solids are called covalent network solids. Each piece of the substance is essentially one huge molecule, as the
covalent bonding in the crystal extends throughout the entire crystal. The two most commonly known covalent network solids are
carbon in its diamond form and silicon dioxide (SiO2). Figure 8.13.4 - Covalent Network Solids, shows the bonding in a covalent
network solid. Generally, covalent network solids are poor conductors of electricity, although their ability to conduct heat is
variable: diamond is one of the most thermally conductive substances known, while SiO2 is about 100 times less thermally
conductive. Most covalent network solids are very hard, as exemplified by diamond, which is the hardest known substance.
Covalent network solids have high melting points by virtue of their network of covalent bonds, all of which would have to be
broken for them to transform into a liquid. Indeed, covalent network solids are among the highest-melting substances known: the
melting point of diamond is over 3,500°C, while the melting point of SiO2 is around 1,650°C. These characteristics are explained
by the network of covalent bonds throughout the sample.
Figure 8.13.4 : Covalent Network Solids. Diamond is a covalent network solid, with each C atom making four covalent bonds to
four other C atoms. A diamond is essentially one huge molecule.
A metallic solid is a solid with the characteristic properties of a metal: shiny and silvery in color and a good conductor of heat and
electricity. A metallic solid can also be hammered into sheets and pulled into wires. A metallic solid exhibits metallic bonding, a
type of intermolecular interaction caused by the sharing of the s valence electrons by all atoms in the sample. It is the sharing of
these valence electrons that explains the ability of metals to conduct electricity and heat well. It is also relatively easy for metals to
lose these valence electrons, which explains why metallic elements usually form cations when they make compounds.
 Example 8.13.1
Predict the type of crystal exhibited by each solid.

a. MgO
b. Ag
c. CO2
Solution
a. A combination of a metal and a nonmetal makes an ionic compound, so MgO would exist as ionic crystals in the solid state.
b. Silver is a metal, so it would exist as a metallic solid in the solid state.
c. CO2 is a covalently bonded molecular compound. In the solid state, it would form molecular crystals. (You can actually see
the crystals in dry ice with the naked eye.)
 Exercise 8.13.1
Predict the type of crystal exhibited by each solid.

a. I2
b. Ca(NO3)2
Answers
a. molecular crystals
b. ionic crystals
 Food and Drink Application: The Rocks We Eat
The foods and beverages we eat and drink all have different phases: solid, liquid, and gas. (How do we ingest gases?
Carbonated beverages have gas, which sometimes cause a person to belch.) However, among the solids we eat, three in
particular are, or are produced from, rocks. Yes, rocks!
The first one is NaCl, or common salt. Salt is the only solid that we ingest that is actually mined as a rock (hence the term rock
salt; it really is a rock). Salt provides both Na+ ions and Cl− ions, both of which are necessary for good health. Salt preserves
food, a function that was much more important before the days of modern food preparation and storage. The fact that saltiness
is one of the major tastes the tongue can detect suggests a strong evolutionary link between ingesting salt and survival. There is
some concern today that there is too much salt in the diet; it is estimated that the average person consumes at least three times
as much salt daily as is necessary for proper bodily function.
The other two rocks we eat are related: sodium bicarbonate (NaHCO3) and sodium carbonate (Na2CO3). However, we do not
mine these substances directly from the ground; we mine trona, whose chemical formula is Na3H(CO3)2. This substance is
dissolved in water and treated with CO2 gas to make either Na2CO3 or NaHCO3. Another process, called the Solvay process,
is also used to make Na2CO3. In the Solvay process, NH3 and CO2 are added to solutions of NaCl to make NaHCO3 and
NH4Cl; the NaHCO3 precipitates and is heated to produce Na2CO3. Either way, we get these two products from the ground
(i.e., rocks).
NaHCO3 is also known as baking soda, which is used in many baked goods. Na2CO3 is used in foods to regulate the acid
balance. It is also used in laundry (where it is called washing soda) to interact with other ions in water that tend to reduce
detergent efficiency.
Figure 8.13.5 : Salt Mining © Thinkstock. Salt mining can be at the surface or below ground. Here salt is mined from surface
deposits. Part of the processing facility can be seen in the background.
Summary
Solids can be divided into amorphous solids and crystalline solids.
Crystalline solids can be ionic, molecular, covalent network, or metallic.
8.13: Solids is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
10.5: Solids by Anonymous is licensed CC BY-NC-SA 3.0. Original source: https://2012books.lardbucket.org/books/beginning-chemistry.
Define enthalpy of fusion and enthalpy of vaporization.
Calculate the energy changes that accompany phase changes.
Interpret heating and cooling curves.
Everyday we take advantage of changes between the gas, liquid, and solid states to cool a drink with ice cubes (solid to liquid),
cool our bodies by perspiration (liquid to gas), and cool food inside a refrigerator (gas to liquid and vice versa). We use dry ice,
which is solid CO2, as a refrigerant (solid to gas), and we make artificial snow for skiing and snowboarding by transforming a
liquid to a solid. In this section, we examine the changes in energy that occur during these changes in state or phase changes.
As introduced in an earlier section, changes of state involve changes in enthalpy ΔH , or changes in energy. Melting (changing a
solid to liquid) and evaporating (changing a liquid to a gas) are both endothermic processes, requiring the addition of heat to break
the intermolecular interactions between molecules. The reverse processes, condensation (changing a gas to a liquid) and freezing
(changing a liquid to a solid), are both exothermic, meaning heat is given off or released when intermolecular interactions are
reformed. The specific amount of energy absorbed or released when one gram of substance changes between a solid and a liquid (at
the melting point) is called the enthalpy of fusion or heat of fusion, (ΔH ). At the boiling point, when one gram of substance
f us
changes between a liquid and a gas, the energy change is called the enthalpy of vaporization or heat of vaporization, (ΔH ). vap
Heating Curves
It is important to understand the difference between the energy associated with changes in temperature and changes in state where
the temperature remains constant. This difference is most clearly depicted in a heating curve, which is a plot of the temperature
versus heating time (or heat added). The heating curve in figure 8.14.1 is the temperature change for a 75 g sample of water as heat
is added over time. The sample is initially solid (ice) at 1 atm and −23°C; as heat is added, the temperature of the ice increases
linearly with time. The slope of the line depends on both the mass of the ice and the specific heat (Cs) of ice, which is the amount
of energy (in Joules or calories) required to raise the temperature of 1 g of ice by 1°C. As the temperature increases, the water
molecules in the ice crystal absorb more and more energy and vibrate more vigorously. At the melting point, they have enough
kinetic energy to overcome attractive forces and move with respect to one another. As more heat is added, the temperature of the
system does not increase further but remains constant at 0°C until all the ice has melted. Once all the ice has been converted to
liquid water, the temperature of the water again begins to increase. Now, however, the temperature increases more slowly than
before because the specific heat capacity of liquid water is greater than that of solid water. When the temperature of the water
reaches 100°C, the water begins to boil. Here, too, the temperature remains constant at 100°C until all the water has been converted
to steam. At this point, the temperature again begins to rise, but at a faster rate than seen in the other phases because the heat
capacity of steam is less than that of ice or water.
Figure 8.14.1 : A Heating Curve for Water. This plot of temperature shows what happens to a 75 g sample of ice initially at 1 atm
and −23°C as heat is added at a constant rate: A–B: heating solid ice; B–C: melting ice; C–D: heating liquid water; D–E:
vaporizing water; E–F: heating steam.
It is worth noting again that the temperature of a system does not change during a phase change. In this example, as long as even a
tiny amount of ice is present, the temperature of the system remains at 0°C during the melting process, and as long as even a small
amount of liquid water is present, the temperature of the system remains at 100°C during the boiling process. The rate at which
heat is added does not affect the temperature of the ice/water or water/steam mixture because the added heat is being used
exclusively to overcome the attractive forces that hold the more condensed phase together. Many cooks think that food will cook
faster if the heat is turned up higher so that the water boils more rapidly. Instead, the pot of water will boil to dryness sooner, but
the temperature of the water does not depend on how vigorously it boils.
The temperature of a sample does not change during a phase change.

If heat is added at a constant rate, as in Figure 8.14.1, then the length of the horizontal lines, which represents the time during
which the temperature does not change, is directly proportional to the magnitude of the enthalpies associated with the phase
changes. In Figure 8.14.1, the horizontal line at 100°C is much longer than the line at 0°C because the enthalpy of vaporization of
water is several times greater than the enthalpy of fusion.
A superheated liquid is a sample of a liquid at the temperature and pressure at which it should be a gas. Superheated liquids are not
stable; the liquid will eventually boil, sometimes violently. The phenomenon of superheating causes “bumping” when a liquid is
heated in the laboratory. When a test tube containing water is heated over a Bunsen burner, for example, one portion of the liquid
can easily become too hot. When the superheated liquid converts to a gas, it can push or “bump” the rest of the liquid out of the test
tube. Placing a stirring rod or a small piece of ceramic (a “boiling chip”) in the test tube allows bubbles of vapor to form on the
surface of the object so the liquid boils instead of becoming superheated. Superheating is the reason a liquid heated in a smooth cup
in a microwave oven may not boil until the cup is moved, when the motion of the cup allows bubbles to form.
Cooling Curves
The cooling curve, in Figure 8.14.2 plots temperature versus time as a 75 g sample of steam, initially at 1 atm and 200°C, is cooled
(heat is released). Although we might expect the cooling curve to be the mirror image of the heating curve in Figure 8.14.1, the
cooling curve is not an identical mirror image. As heat is removed from the steam, the temperature falls until it reaches 100°C. At
this temperature, the steam begins to condense to liquid water. No further temperature change occurs until all the steam is
converted to the liquid; then the temperature again decreases as the water is cooled. We might expect to reach another plateau at
0°C, where the water is converted to ice; in reality, however, this does not always occur. Instead, the temperature often drops below
the freezing point for some time, as shown by the little dip in the cooling curve below 0°C. This region corresponds to an unstable
form of the liquid, a supercooled liquid. If the liquid is allowed to stand, if cooling is continued, or if a small crystal of the solid
phase is added (a seed crystal), the supercooled liquid will convert to a solid, sometimes quite suddenly. As the water freezes, the
temperature increases slightly due to the heat evolved during the freezing process and then holds constant at the melting point as
the rest of the water freezes. Subsequently, the temperature of the ice decreases again as more heat is removed from the system.
Figure 8.14.2 : A Cooling Curve for Water. This plot of temperature shows what happens to a 75 g sample of steam initially at 1
atm and 200°C as heat is removed at a constant rate: A–B: cooling steam; B–C: condensing steam; C–D: cooling liquid water to
give a supercooled liquid; D–E: warming the liquid as it begins to freeze; E–F: freezing liquid water; F–G: cooling ice.
Supercooling effects have a huge impact on Earth’s climate. For example, supercooling of water droplets in clouds can prevent the
clouds from releasing precipitation over regions that are persistently arid as a result. Clouds consist of tiny droplets of water, which
in principle should be dense enough to fall as rain. In fact, however, the droplets must aggregate to reach a certain size before they
can fall to the ground. Usually a small particle (a nucleus) is required for the droplets to aggregate; the nucleus can be a dust
particle, an ice crystal, or a particle of silver iodide dispersed in a cloud during seeding (a method of inducing rain). Unfortunately,
the small droplets of water generally remain as a supercooled liquid down to about −10°C, rather than freezing into ice crystals that
are more suitable nuclei for raindrop formation. One approach to producing rainfall from an existing cloud is to cool the water
droplets so that they crystallize to provide nuclei around which raindrops can grow. This is best done by dispersing small granules
of solid CO2 (dry ice) into the cloud from an airplane. Solid CO2 sublimes directly to the gas at pressures of 1 atm or lower, and the
enthalpy of sublimation is substantial (25.3 kJ/mol). As the CO2 sublimes, it absorbs heat from the cloud, often with the desired
results.
The Thermodynamics of Phase Changes
A Video Discussing the Thermodynamics of Phase Changes. Video Source: The Thermodynamics of Phase Changes,
YouTube(opens in new window) [youtu.be]
 Example 8.14.1: Cooling Tea
If a 50.0 g ice cube at 0.0°C is added to 500 mL of tea at 20.0°C, what is the temperature of the tea when the ice cube has just
melted? Assume that no heat is transferred to or from the surroundings. The density of water (and iced tea) is 1.00 g/mL over
the range 0°C–20°C, the specific heats of liquid water and ice are 4.184 J/(g•°C) and 2.062 J/(g•°C), respectively, and the
enthalpy of fusion of ice is 6.01 kJ/mol.
Given: mass, volume, initial temperature, density, specific heats, and ΔH f us
Asked for: final temperature
Strategy
Substitute the given values into the general equation relating heat gained (by the ice) to heat lost (by the tea) to obtain the final
temperature of the mixture.
Solution
When two substances or objects at different temperatures are brought into contact, heat will flow from the warmer one to the
cooler. The amount of heat that flows is given by
q = m Cs ΔT
where q is heat, m is mass, C is the specific heat, and ΔT is the temperature change. Eventually, the temperatures of the two
s
substances will become equal at a value somewhere between their initial temperatures. Calculating the temperature of iced tea
after adding an ice cube is slightly more complicated. The general equation relating heat gained and heat lost is still valid, but
in this case we also have to take into account the amount of heat required to melt the ice cube from ice at 0.0°C to liquid water
at 0.0°C.
The amount of heat gained by the ice cube as it melts is determined by its enthalpy of fusion in kJ/mol:
q = nΔHf us
For our 50.0 g ice cube:

1 mol
qice = 50.0g ⋅ ⋅ 6.01 kJ/mol
18.02 g
= 16.7 kJ
Thus, when the ice cube has just melted, it has absorbed 16.7 kJ of heat from the tea. We can then substitute this value into the
first equation to determine the change in temperature of the tea:
1.00 g
qtea = −16, 700J = 500mL ⋅ ⋅ 4.184J/(g ∙ °C )ΔT
1 mL
ΔT = −7.98°C = Tf − Ti
Tf = 12.02°C
This would be the temperature of the tea when the ice cube has just finished melting; however, this leaves the melted ice still at
0.0°C. We might more practically want to know what the final temperature of the mixture of tea will be once the melted ice has
come to thermal equilibrium with the tea. To determine this, we can add one more step to the calculation by plugging in to the
general equation relating heat gained and heat lost again:
qice = −qtea
qice = mice Cs ΔT = 50.0g ⋅ 4.184J/(g ∙ °C ) ⋅ (Tf − 0.0°C )
= 209.2J/°C ⋅ Tf
qtea = mtea Cs ΔT = 500g ⋅ 4.184J/(g ∙ °C ) ⋅ (Tf − 12.02°C ) = 2092J/°C ⋅ Tf − 25, 150J
209.2J/°C ⋅ Tf = −2092J/°C ⋅ Tf + 25, 150J
2301.2J/°C ⋅ Tf = 25, 150J
Tf = 10.9°C
The final temperature is in between the initial temperatures of the tea (12.02 °C) and the melted ice (0.0 °C), so this answer
makes sense. In this example, the tea loses much more heat in melting the ice than in mixing with the cold water, showing the
importance of accounting for the heat of phase changes!
 Exercise 8.14.1: Death by Freezing
Suppose you are overtaken by a blizzard while ski touring and you take refuge in a tent. You are thirsty, but you forgot to bring
liquid water. You have a choice of eating a few handfuls of snow (say 400 g) at −5.0°C immediately to quench your thirst or
setting up your propane stove, melting the snow, and heating the water to body temperature before drinking it. You recall that
the survival guide you leafed through at the hotel said something about not eating snow, but you cannot remember why—after
all, it’s just frozen water. To understand the guide’s recommendation, calculate the amount of heat that your body will have to
supply to bring 400 g of snow at −5.0°C to your body’s internal temperature of 37°C. Use the data in Example 8.14.1
Answer
200 kJ (4.1 kJ to bring the ice from −5.0°C to 0.0°C, 133.6 kJ to melt the ice at 0.0°C, and 61.9 kJ to bring the water from
0.0°C to 37°C), which is energy that would not have been expended had you first melted the snow.
 Sublimation
There is also a phase change where a solid goes directly to a gas:
solid→ gas (8.14.1)
This phase change is called sublimation. Each substance has a characteristic heat of sublimation associated with this process.
For example, the heat of sublimation (ΔHsub) of H2O is 620 cal/g.
We encounter sublimation in several ways. You may already be familiar with dry ice, which is simply solid carbon dioxide
(CO2). At −78.5°C (−109°F), solid carbon dioxide sublimes, changing directly from the solid phase to the gas phase:
∘
−78.5 C
C O2 (s) −−−−−→ C O2 (g) (8.14.2)
Solid carbon dioxide is called dry ice because it does not pass through the liquid phase. Instead, it does directly to the gas
phase. (Carbon dioxide can exist as liquid but only under high pressure.) Dry ice has many practical uses, including the long-
term preservation of medical samples.
Even at temperatures below 0°C, solid H2O will slowly sublime. For example, a thin layer of snow or frost on the ground may
slowly disappear as the solid H2O sublimes, even though the outside temperature may be below the freezing point of water.
Similarly, ice cubes in a freezer may get smaller over time. Although frozen, the solid water slowly sublimes, redepositing on
the colder cooling elements of the freezer, which necessitates periodic defrosting (frost-free freezers minimize this
redeposition). Lowering the temperature in a freezer will reduce the need to defrost as often.
Under similar circumstances, water will also sublime from frozen foods (e.g., meats or vegetables), giving them an
unattractive, mottled appearance called freezer burn. It is not really a “burn,” and the food has not necessarily gone bad,
although it looks unappetizing. Freezer burn can be minimized by lowering a freezer’s temperature and by wrapping foods
tightly so water does not have any space to sublime into.
Summary
Phase changes are associated with energy changes.
The enthalpy of fusion, ΔH , is the energy absorbed or released when a substance changes between a solid and a liquid.
f us
The enthalpy of vaporization, ΔH , is the energy absorbed or released when a substance changes between a liquid and a gas.
vap
Heating and cooling curves are useful tools to show how temperature, energy, and phases are related.
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CHAPTER OVERVIEW
9: Solutions
9.3: Solubility
9.7: Dilution
9.11: Dialysis
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1
Describe the difference between homogenous and heterogenous mixtures.
Distinguish a homogenous mixture as a solution or colloid.
As introduced previously, mixtures are combinations of two or more substances that each retain their individual physical properties.
A mixture can be classified as either heterogenous or homogenous. In a heterogeneous mixture, the composition is not uniform
throughout the sample, and sometimes the individual substances that make up the mixture can be differentiated by eye. Trail mix,
salad, and blood (which is also called a suspension) are examples of heterogenous mixtures. Homogenous mixtures are uniform and
have the same composition throughout. Air, simple syrup, and seawater are examples of homogenous mixtures.
Homogenous mixtures can be further classified, based on the size of their particles, as solutions or colloids. Solutions are
composed of particles the size of an ion or small molecule, ~0.1-2.0 nm. The examples provided above are all considered solutions;
air is a solution of small gas molecules, simple syrup is a solution of sucrose in water, and seawater is a solution of ions and water.
Homogenous mixtures with larger particles, ~2.0-500 nm, are classified as colloids. Milk, fog, and butter are all considered
colloids. Mixtures with particles larger than 500 nm are called suspensions and are considered to be heterogenous mixtures in
which the particles will settle upon standing. Many medications are classified as suspensions that need to be re-mixed before taking
in order to redistribute the particles throughout the mixture. Some examples and distinguishing characteristics of solutions,
colloids, and suspensions are listed in Table 9.1.1 below.
Table 9.1.1 : Properties of Liquid Solutions, Colloids, and Suspensions
Approximate Size of Particles
Type of Mixture Characteristic Properties Examples
(nm)
not filterable; does not separate on

air, white wine, gasoline, salt
solution <2 standing; does not scatter visible
water
light
scatters visible light; translucent

smoke, fog, ink, milk, butter,
colloid 2–500 or opaque; not filterable; does not
cheese
separate on standing
cloudy or opaque; filterable; muddy water, hot cocoa, blood,

suspension 500–1000
separates on standing paint
The major component of a solution, called the solvent, is typically the same phase as the solution itself. Each minor component of
a solution (and there may be more than one) is called the solute. In most of the solutions we will describe in this textbook, there
will be no ambiguity about whether a component is the solvent or the solute. For example, in a solution of salt in water, the solute
is salt, and solvent is water.
Solutions come in all phases, and the solvent and the solute do not have to be in the same phase to form a solution (such as salt and
water). For example, air is a gaseous solution of about 80% nitrogen and about 20% oxygen, with some other gases present in
much smaller amounts. An alloy is a solid solution consisting of a metal (like iron) with some other metals or nonmetals dissolved
in it. Steel, an alloy of iron and carbon and small amounts of other metals, is an example of a solid solution. Table 9.1.2 lists some
common types of solutions, with examples of each.
Table 9.1.2 : Types of Solutions
Solvent Phase Solute Phase Example
gas gas air
liquid gas carbonated beverages
ethanol (C2H5OH) in H2O (alcoholic

liquid liquid
beverages)
liquid solid saltwater
solid gas H2 gas absorbed by Pd metal
Solvent Phase Solute Phase Example
solid liquid Hg(ℓ) in dental fillings
solid solid steel alloys
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Predict solubility based on interactions between solute and solvent.
What occurs at the molecular level to cause a solute to dissolve in a solvent? The answer depends in part on the strength of
attractions between solute and solvent particles. A good rule of thumb is to use is like dissolves like, which means that substances
must have similar intermolecular attractions to form solutions.
A substance can dissolve in a solvent, and form a solution, if the solute and solvent are attracted to each other. For example, water
molecules that are held together by hydrogen bonding will dissolve solutes that can also hydrogen bond, like ethanol
(CH3CH2OH). The new hydrogen bonds between the water and the ethanol molecules (solvent-solute attractions) are nearly as
strong as the hydrogen bonds in water (solvent-solvent) and ethanol (solute-solute) alone, making the process of solution formation
(also called dissolution or dissolving) favorable.
In the case of a solid or liquid solute, the interactions between the solute particles and the solvent particles are so strong that the
individual solute particles separate from each other and, are surrounded by solvent molecules. (Gaseous solutes already have their
constituent particles separated, but the concept of being surrounded by solvent particles still applies.) This process is called
solvation and is illustrated in Figure 9.2.1. When the solvent is water, the word hydration, rather than solvation, is used.
Figure 9.2.1 : Solvation. When a solute dissolves, the individual particles of solute become surrounded by solvent particles.
Eventually the particle detaches from the remaining solute, surrounded by solvent molecules in solution. Source: Photo ©
Thinkstock
When a solute and solvent that do not have similar intermolecular interactions are mixed, a solution is not formed because the
solute-solute or solvent-solvent attractions are stronger than any favorable interactions between solute and solvent. For example
when water and oil are mixed, stay in separate layers, i.e., they will not mix to yield solutions and the water molecules remain
hydrogen bonded to water molecules while the oil molecules stay together (Figure 9.2.2). Hydrogen bonding is the dominant
intermolecular attractive force present in liquid water; the nonpolar hydrocarbon molecules of cooking oils are not capable of
hydrogen bonding, instead being held together by dispersion forces. Forming an oil-water solution would require overcoming the
very strong hydrogen bonding in water, as well as the significantly strong dispersion forces between the relatively large oil
molecules. And, since the polar water molecules and nonpolar oil molecules would not experience very strong intermolecular
attraction, very little energy would be released by solvation.
Figure 9.2.2 : A mixture of nonpolar cooking oil and polar water does not yield a solution. (credit: Gautam Dogra).
Ionic Compounds and Covalent Compounds as Solutes

In the case of molecular solutes like glucose, the solute particles are individual molecules. However, if the solute is ionic, the
individual ions separate from each other and become surrounded by solvent particles. The positively charged cations are attracted
to the neg and anions of an ionic solute separate when the solute dissolves. This process is referred to as dissociation (Figure
9.2.1).
The dissociation of soluble ionic compounds gives solutions of these compounds an interesting property: they conduct electricity.
Because of this property, soluble ionic compounds are referred to as electrolytes. Many ionic compounds dissociate completely and
are therefore called strong electrolytes. Sodium chloride is an example of a strong electrolyte. Some compounds dissolve but
dissociate only partially, and solutions of such solutes may conduct electricity only weakly. These solutes are called weak
electrolytes. Acetic acid (CH3COOH), the compound in vinegar, is a weak electrolyte. Solutes that dissolve into individual neutral
molecules without dissociation do not impart additional electrical conductivity to their solutions and are called nonelectrolytes.
Table sugar (C12H22O11) is an example of a nonelectrolyte.
The term electrolyte is used in medicine to mean any of the important ions that are
dissolved in aqueous solution in the body. Important physiological electrolytes include
Na+, K+, Ca2+, Mg2+, and Cl−.
 Example 9.2.1
The following substances all dissolve to some extent in water. Classify each as an electrolyte or a nonelectrolyte.
1. potassium chloride (KCl)
2. fructose (C6H12O6)
3. isopropyl alcohol [CH3CH(OH)CH3]
4. magnesium hydroxide [Mg(OH)2]
Solution
Each substance can be classified as an ionic solute or a nonionic solute. Ionic solutes are electrolytes, and nonionic solutes are
nonelectrolytes.
1. Potassium chloride is an ionic compound; therefore, when it dissolves, its ions separate, making it an electrolyte.
2. Fructose is a sugar similar to glucose. (In fact, it has the same molecular formula as glucose.) Because it is a molecular
compound, we expect it to be a nonelectrolyte.
3. Isopropyl alcohol is an organic molecule containing the alcohol functional group. The bonding in the compound is all
covalent, so when isopropyl alcohol dissolves, it separates into individual molecules but not ions. Thus, it is a
nonelectrolyte
4. Magnesium hydroxide is an ionic compound, so when it dissolves it dissociates. Thus, magnesium hydroxide is an
electrolyte.
 Exercise 9.2.1
The following substances all dissolve to some extent in water. Classify each as an electrolyte or a nonelectrolyte.
a. acetone (CH3COCH3)
b. iron(III) nitrate [Fe(NO3)3]
c. elemental bromine (Br2)
d. sodium hydroxide (NaOH)
Answer
a. nonelectrolyte
b. electrolyte
c. nonelectrolyte
d. electrolyte
 Electrolytes in Body Fluids
Our body fluids are solutions of electrolytes and many other things. The combination of blood and the circulatory system is the
river of life, because it coordinates all the life functions. When the heart stops pumping in a heart attack, the life ends quickly.
Getting the heart restarted as soon as one can is crucial in order to maintain life.
The primary electrolytes required in the body fluid are cations (of calcium, potassium, sodium, and magnesium) and anions (of
chloride, carbonates, aminoacetates, phosphates, and iodide). These are nutritionally called macrominerals.
Electrolyte balance is crucial to many body functions. Here's some extreme examples of what can happen with an imbalance of
electrolytes: elevated potassium levels may result in cardiac arrhythmias; decreased extracellular potassium produces paralysis;
excessive extracellular sodium causes fluid retention; and decreased plasma calcium and magnesium can produce muscle
spasms of the extremities.
When a patient is dehydrated, a carefully prepared (commercially available) electrolyte solution is required to maintain health
and well being. In terms of child health, oral electrolyte is given when a child is dehydrated due to diarrhea. The use of oral
electrolyte maintenance solutions, which is responsible for saving millions of lives worldwide over the last 25 years, is one of
the most important medical advances in protecting the health of children in the century, explains Juilus G.K. Goepp, MD,
assistant director of the Pediatric Emergency Department of the Children's Center at Johns Hopkins Hospital. If a parent
provides an oral electrolyte maintenance solution at the very start of the illness, dehydration can be prevented. The
functionality of electrolyte solutions is related to their properties, and interest in electrolyte solutions goes far beyond
chemistry.
Sports drinks are designed to rehydrate the body after excessive fluid depletion. Electrolytes in particular promote normal
rehydration to prevent fatigue during physical exertion. Are they a good choice for achieving the recommended fluid intake?
Are they performance and endurance enhancers like they claim? Who should drink them?
Typically, eight ounces of a sports drink provides between fifty and eighty calories and 14 to 17 grams of carbohydrate, mostly
in the form of simple sugars. Sodium and potassium are the most commonly included electrolytes in sports drinks, with the
levels of these in sports drinks being highly variable. The American College of Sports Medicine says a sports drink should
contain 125 milligrams of sodium per 8 ounces as it is helpful in replenishing some of the sodium lost in sweat and promotes
fluid uptake in the small intestine, improving hydration.
 Gatorade
In the summer of 1965, the assistant football coach of the University of Florida Gators requested scientists affiliated with the
university study why the withering heat of Florida caused so many heat-related illnesses in football players and provide a
solution to increase athletic performance and recovery post-training or game. The discovery was that inadequate replenishment
of fluids, carbohydrates, and electrolytes was the reason for the “wilting” of their football players. Based on their research, the
scientists concocted a drink for the football players containing water, carbohydrates, and
electrolytes and called it “Gatorade.” In the next football season the Gators were nine and
two and won the Orange Bowl. The Gators’ success launched the sports-drink industry,
which is now a multibillion-dollar industry that is still dominated by Gatorade.
University of Florida football player Chip Hinton testing Gatorade in 1965, pictured next to
the leader of its team of inventors, Robert Cade.
Concept Review Exercise

1. Explain how the solvation process describes the dissolution of a solute in a solvent.
Answer
1. Each particle of the solute is surrounded by particles of the solvent, carrying the solute from its original phase.
Key Takeaway
When a solute dissolves, its individual particles are surrounded by solvent molecules and are separated from each other.
Exercises
1. Describe what happens when an ionic solute like Na2SO4 dissolves in a polar solvent.
2. Describe what happens when a molecular solute like sucrose (C12H22O11) dissolves in a polar solvent.
3. Classify each substance as an electrolyte or a nonelectrolyte. Each substance dissolves in H2O to some extent.
a. NH4NO3
b. CO2
c. NH2CONH2
d. HCl
4. Classify each substance as an electrolyte or a nonelectrolyte. Each substance dissolves in H2O to some extent.
a. CH3CH2CH2OH
b. Ca(CH3CO2)2
c. I2
d. KOH
5. Will solutions of each solute conduct electricity when dissolved?
a. AgNO3
b. CHCl3
c. BaCl2
d. Li2O
6. Will solutions of each solute conduct electricity when dissolved?
a. CH3COCH3
b. N(CH3)3
c. CH3CO2C2H5
d. FeCl2
Answers
1. Each ion of the ionic solute is surrounded by particles of solvent, carrying the ion from its associated crystal.
2. Each sucrose molecule is surrounded by solvent molecules (attracted to each

other via intermolecular forces of attraction).
3. a. electrolyte
b. nonelectrolyte
c. nonelectrolyte
d. electrolyte
4.
a. nonelectrolyte
b. electrolyte
c. nonelectrolyte
d. electrolyte
5.
a. yes
b. no
c. yes
d. yes
6.
a. no
b. no
c. no
d. yes
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9.3: Solubility
Describe solutions as saturated or unsaturated by understanding solubility.
To define a solution precisely, we need to state its concentration: how much solute is dissolved in a certain amount of solvent.
Words such as dilute or concentrated are used to describe solutions that have a little or a lot of dissolved solute, respectively, but
these are relative terms whose meanings depend on various factors.
Solubility
There is usually a limit to how much solute will dissolve in a given amount of solvent. This limit is called the solubility of the
solute. Some solutes have a very small solubility, while other solutes are soluble in all proportions. Table 9.3.1 lists the solubilities
of various solutes in water. Solubilities vary with temperature, so Table 9.3.1 includes the temperature at which the solubility was
determined.
Table 9.3.1 : Solubilities of Various Solutes in Water at 25°C (Except as Noted)
Substance Solubility (g in 100 mL of H2O)
AgCl(s) 0.019
C6H6(ℓ) (benzene) 0.178
CH4(g) 0.0023
CO2(g) 0.150
CaCO3(s) 0.058
CaF2(s) 0.0016
Ca(NO3)2(s) 143.9
C6H12O6 (glucose) 120.3 (at 30°C)
KBr(s) 67.8
MgCO3(s) 2.20
NaCl(s) 36.0
NaHCO3(s) 8.41
C12H22O11 (sucrose) 204.0 (at 20°C)
If a solution contains so much solute that its solubility limit is reached, the solution is said to be saturated, and its concentration is
known from information contained in Table 9.3.1. If a solution contains less solute than the solubility limit, it is unsaturated.
Under special circumstances, more solute can be dissolved even after the normal solubility limit is reached; such solutions are
called supersaturated and are not stable. If the solute is solid, excess solute can easily recrystallize. If the solute is a gas, it can
bubble out of solution uncontrollably, like what happens when you shake a soda can and then immediately open it.
Most solutions we encounter are unsaturated, so knowing the solubility of the solute does not accurately express the amount of
solute in these solutions. There are several common ways of specifying the concentration of a solution that will be discussed in
later sections.
Solution Equilibrium
When a solute dissolves, its individual atoms, molecules, or ions interact with the solvent, become solvated, and are able to diffuse
independently throughout the solution (Figure 9.3.1a). This is not, however, a unidirectional process. If the molecule or ion
happens to collide with the surface of a particle of the undissolved solute, it may adhere to the particle in a process called
crystallization. The equilibrium between dissolution and crystallization continue as long as excess solid is present, resulting in a
dynamic equilibrium analogous to the equilibrium that maintains the vapor pressure of a liquid. We can represent these opposing
processes as follows:
dissolution
solute + solvent −
↽⇀
− solution
crystallization
Figure 9.3.1 : Dissolution and Precipitation. (a) When a solid is added to a solvent in which it is soluble, solute particles leave the
surface of the solid and become solvated by the solvent, initially forming an unsaturated solution. (b) When the maximum possible
amount of solute has dissolved, the solution becomes saturated. If excess solute is present, the rate at which solute particles leave
the surface of the solid equals the rate at which they return to the surface of the solid. (c) A supersaturated solution can usually be
formed from a saturated solution by filtering off the excess solute and lowering the temperature. (d) When a seed crystal of the
solute is added to a supersaturated solution, solute particles leave the solution and form a crystalline precipitate.
Starting on the left the solution starts are unsaturated, then saturated, then supersaturated, when seed crystal is added a precipitate
forms.
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Describe how temperature affects solubility of different types of solute.
The solubility of the majority of solid substances increases as the temperature increases. However, the effect is difficult to predict
and varies widely from one solute to another. The temperature dependence of solubility can be visualized with the help of a
solubility curve, a graph of the solubility vs. temperature (Figure 9.4.1 below).
Figure 9.4.1 : A solubility curve is a graph of the solubility of a substance as a function of temperature.
Notice how the temperature dependence of NaCl is fairly flat, meaning that an increase in temperature has relatively little effect on
the solubility of NaCl. The curve for KNO , on the other hand, is very steep, and so an increase in temperature dramatically
3
increases the solubility of KNO . 3
Several substances—HCl, NH , and SO —have solubility that decreases as temperature increases. They are all gases at standard
3 2
pressure. When a solvent with a gas dissolved in it is heated, the kinetic energy of both the solvent and solute increase. As the
kinetic energy of the gaseous solute increases, its molecules have a greater tendency to escape the attraction of the solvent
molecules and return to the gas phase. Therefore, the solubility of a gas decreases as the temperature increases.
Solubility curves can be used to determine if a given solution is saturated or unsaturated. Suppose that 80 g of KNO is added to 3
100 g of water at 30°C. According to the solubility curve in Figure 9.4.1, approximately 48 g of KNO will dissolve at 30°C.
3
This means that the solution will be saturated since 48 g is less than 80 g. We can also determine that there will be 80 − 48 = 32 g
of undissolved KNO remaining at the bottom of the container. In a second scenario, suppose that this saturated solution is heated
3
to 60°C. According to the curve, the solubility of KNO at 60°C is about 107 g. The solution, in this case, is unsaturated since it
3
contains only the original 80 g of dissolved solute. Suppose in a third case, that the solution is cooled all the way down to 0°C. The
solubility at 0°C is about 14 g, meaning that 80 − 14 = 66 g of the KNO will recrystallize.
3
Supersaturated Solutions
Some solutes, such as sodium acetate, do not recrystallize easily. Suppose an exactly saturated solution of sodium acetate is
prepared at 50°C. As it cools back to room temperature, no crystals appear in the solution, even though the solubility of sodium
acetate is lower at room temperature. A supersaturated solution is a solution that contains more than the maximum amount of
solute that is capable of being dissolved at a given temperature. The recrystallization of the excess dissolved solute in a
supersaturated solution can be initiated by the addition of a tiny crystal of solute, called a seed crystal. The seed crystal provides a
nucleation site on which the excess dissolved crystals can begin to grow. Recrystallization from a supersaturated solution is
typically very fast.
crystallization of sodium acetate (v2)
 Chemistry in Everyday Life: Handwarmers
Recrystallization of excess solute from a supersaturated solution usually gives off energy as heat. Commercial heat packs, such
as the one in Figure 9.4.2, containing supersaturated sodium acetate (NaC2H3O2) take advantage of this phenomenon. You can
probably find them at your local drugstore.
Figure 9.4.2: This hand warmer produces heat when the sodium acetate in a supersaturated solution precipitates. Precipitation
of the solute is initiated by a mechanical shockwave generated when the flexible metal disk within the solution is “clicked.”
(credit: modification of work by “Velela”/Wikimedia Commons)
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Describe how pressure affects concentration of a solute in a solution.
Pressure has very little effect on the solubility of solids or liquids, but has a significant effect on the solubility of gases. Gas
solubility increases as the partial pressure of a gas above the liquid increases. Suppose a certain volume of water is in a closed
container with the space above it occupied by carbon dioxide gas at standard pressure. Some of the CO molecules come into 2
contact with the surface of the water and dissolve into the liquid. Now suppose that more CO is added to the space above the
2
container, causing a pressure increase. In this case, more CO molecules are in contact with the water and so more of them
2
dissolve. Thus, the solubility increases as the pressure increases. As with a solid, the CO that is undissolved reaches an
2
equilibrium with the dissolved CO , represented by the equation:

2
CO (g) ⇌ CO (aq)
2 2
At equilibrium, the rate of gaseous CO dissolution is equal to the rate of dissolved CO coming out of the solution.
2 2
When carbonated beverages are packaged, they are done so under high CO pressure so that a large amount of carbon dioxide
2
dissolves in the liquid. When the bottle is open, the equilibrium is disrupted because the CO pressure above the liquid decreases.
2
Immediately, bubbles of CO rapidly exit the solution and escape out of the top of the open bottle, see Figure 9.5.1. The amount of
2
dissolved CO decreases. If the bottle is left open for an extended period of time, the beverage becomes "flat" as more and more
2
CO comes out of the liquid.

2
Figure 9.5.1 : Opening the bottle of carbonated beverage reduces the pressure of the gaseous carbon dioxide above the beverage.
The solubility of CO2 is thus lowered, and some dissolved carbon dioxide may be seen leaving the solution as small gas bubbles.
(credit: modification of work by Derrick Coetzee)
The relationship of gas solubility to pressure is described by Henry's law, named after English chemist William Henry (1774-1836).
Henry's Law states that the solubility of a gas in a liquid is directly proportional to the partial pressure of the gas above the liquid.
Henry's law can be written as follows:
C1 C2
= =k
P1 P2
C1 and P are the concentration and the pressure at an initial set of conditions; C and P are the concentration and pressure at
1 2 2
another changed set of conditions; k is a constant at a constant temperature. The solubility of a gas is typically reported in g/L.
 Example 9.5.1
The solubility of a certain gas in water is 0.745 g/L at standard pressure. What is its solubility when the pressure above the
solution is raised to 4.50 atm? The temperature is constant at 20 C. o
Solution
Known
C1 = 0.745 g/L
P1 = 1.00 atm
P2 = 4.50 atm
Unknown
Substitute into Henry's law and solve for C . 2
Step 2: Solve.
C1 × P2 0.745 g/L × 4.50 atm
C2 = = = 3.35 g/L
P1 1.00 atm

The solubility is increased to 4.5 times its original value, according to the direct relationship.
 Exercise 9.5.1
Exposing a 100.0 mL sample of water at 0 °C to an atmosphere containing a gaseous solute at 20.26 kPa (152 torr) resulted in
the dissolution of 1.45 × 10−3 g of the solute. Use Henry’s law to determine the solubility of this gaseous solute when its
pressure is 101.3 kPa (760 torr).
Answer
7.25 × 10−3 g in 100.0 mL or 0.0725 g/L
 Case Study: Decompression Sickness (“The Bends”)
Decompression sickness (DCS), or “the bends,” is an effect of the increased pressure of the air inhaled by scuba divers when
swimming underwater at considerable depths. In addition to the pressure exerted by the atmosphere, divers are subjected to
additional pressure due to the water above them, experiencing an increase of approximately 1 atm for each 10 m of depth.
Therefore, the air inhaled by a diver while submerged contains gases at the corresponding higher ambient pressure, and the
concentrations of the gases dissolved in the diver’s blood are proportionally higher per Henry’s law.
Figure 9.5.4 : (a) US Navy divers undergo training in a recompression chamber. (b) Divers receive hyperbaric oxygen therapy.
Two photos are shown. The first shows two people seated in a steel chamber on benches that run length of the chamber on each
side. The chamber has a couple of small circular windows and an open hatch-type door. One of the two people is giving a
thumbs up gesture. The second image provides a view through a small, circular window. Inside the two people can be seen
with masks over their mouths and noses. The people appear to be reading.
As the diver ascends to the surface of the water, the ambient pressure decreases and the dissolved gases becomes less soluble.
If the ascent is too rapid, the gases escaping from the diver’s blood may form bubbles that can cause a variety of symptoms
ranging from rashes and joint pain to paralysis and death. To avoid DCS, divers must ascend from depths at relatively slow
speeds (10 or 20 m/min) or otherwise make several decompression stops, pausing for several minutes at given depths during
the ascent. When these preventive measures are unsuccessful, divers with DCS are often provided hyperbaric oxygen therapy
in pressurized vessels called decompression (or recompression) chambers (Figure 9.5.4).
9.5: The Effect of Pressure on Solubility - Henry’s Law is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated
by LibreTexts.
16.6: Henry's Law by CK-12 Foundation is licensed CK-12. Original source: https://flexbooks.ck12.org/cbook/ck-12-chemistry-flexbook-
2.0/.
11.3: Solubility by OpenStax is licensed CC BY 4.0. Original source: https://openstax.org/details/books/chemistry-2e.
Calculate concentration of a solution using different units.
Use concentration units to calculate the amount of solute in a solution.
Use molarity to determine quantities in chemical reactions.
Percent Concentrations
There are several ways of expressing the concentration of a solution by using a percentage. The mass/mass percent (% m/m) is
defined as the mass of a solute divided by the mass of a solution times 100:
mass of solute
% m/m = × 100%
mass of solution
If you can measure the masses of the solute and the solution, determining the mass/mass percent is easy. Each mass must be
expressed in the same units to determine the proper concentration.
 Example 9.6.1
A saline solution with a mass of 355 g has 36.5 g of NaCl dissolved in it. What is the mass/mass percent concentration of the
solution?
Solution
We can substitute the quantities given in the equation for mass/mass percent:
36.5 g
% m/m = × 100% = 10.3%
355 g
 Exercise 9.6.1
A dextrose (also called D-glucose, C6H12O6) solution with a mass of 2.00 × 102 g has 15.8 g of dextrose dissolved in it. What
is the mass/mass percent concentration of the solution?
Answer
7.90%
For gases and liquids, volumes are relatively easy to measure, so the concentration of a liquid or a gas solution can be expressed as
a volume/volume percent (% v/v): the volume of a solute divided by the volume of a solution times 100:
volume of solute
% v/v = × 100%
volume of solution
Again, the units of the solute and the solution must be the same. A hybrid concentration unit, mass/volume percent (% m/v), is
commonly used for intravenous (IV) fluids (Figure 9.6.1). It is defined as the mass in grams of a solute, divided by volume in
milliliters of solution times 100:
mass of solute (g)
% m/v = × 100%
volume of solution (mL)
Figure 9.6.1 : Mass/Volume Percent.The 0.9% NaCl concentration on this IV bag is mass/volume percent (left). Such solution is
used for other purposes and available in bottles (right). Figures used with permission from Wikipedia
Using Percent Concentration in Calculations

The percent concentration can be used to produce a conversion factor between the amount of solute and the amount of solution. As
such, concentrations can be useful in a variety of stoichiometry problems as discussed in Chapter 6. In many cases, it is best to use
the original definition of the concentration unit; it is that definition that provides the conversion factor.
As an example, if the given concentration is 5% v/v alcohol, this means that there are 5 mL of alcohol dissolved in every 100 mL
solution.
5 mL alcohol = 100 mL solution
The two possible conversion factors are written as follows:
5 mL alcohol 100 mL solution
or
100 mL solution 5 mL alcohol
Use the first conversion factor to convert from a given amount of solution to amount of solute. The second conversion factor is
used to convert from a given amount of solute to amount of solution. Given any two quantities in any percent composition, the
third quantity can be calculated, as the following example illustrates.
 Example 9.6.2
A sample of 45.0% v/v solution of ethanol (C2H5OH) in water has a volume of 115 mL. What volume of ethanol solute does
the sample contain?
Solution
A percentage concentration is simply the number of parts of solute per 100 parts of solution. Thus, the percent concentration of
45.0% v/v implies the following:
45 mL C2 H5 OH
45.0% v/v →
100 mL solution
That is, there are 45 mL of C2H5OH for every 100 mL of solution. We can use this fraction as a conversion factor to determine
the amount of C2H5OH in 115 mL of solution:
45 mL C2 H5 OH
115 mL solution × = 51.8 mL C2 H5 OH
100 mL solution
 Exercise 9.6.2
What volume of a 12.75% m/v solution of glucose (C6H12O6) in water is needed to obtain 50.0 g of C6H12O6?
Answer
100 mL solution
50.0 g C6 H1 2 O6 × = 392 mL solution
12.75 g C6 H1 2 O6
 Example 9.6.3
A normal saline IV solution contains 9.0 g of NaCl in every liter of solution. What is the mass/volume percent of normal
saline?
Solution
We can use the definition of mass/volume percent, but first we have to express the volume in milliliter units:
1 L = 1,000 mL
Because this is an exact relationship, it does not affect the significant figures of our result.
9.0 g NaCl
% m/v = × 100% = 0.90% m/v
1, 000 mL solution
 Exercise 9.6.3
The chlorine bleach that you might find in your laundry room is typically composed of 27.0 g of sodium hypochlorite (NaOCl),
dissolved to make 500.0 mL of solution. What is the mass/volume percent of the bleach?
Answer
27.0 g NaOCl
% m/v = × 100% = 5.40% m/v
500.0 mL solution
Parts per Million (ppm) and Parts per Billion (ppb)

In addition to percentage units, the units for expressing the concentration of extremely dilute solutions are parts per million (ppm)
and parts per billion (ppb). Both of these units are mass based and are defined as follows:
mass of solute
ppm = × 1, 000, 000
mass of solution
mass of solute
ppb = × 1, 000, 000, 000
mass of solution
Similar to parts per million and parts per billion, related units include parts per thousand
(ppth) and parts per trillion (ppt).
Concentrations of trace elements in the body—elements that are present in extremely low concentrations but are nonetheless
necessary for life—are commonly expressed in parts per million or parts per billion. Concentrations of poisons and pollutants are
also described in these units. For example, cobalt is present in the body at a concentration of 21 ppb, while the State of Oregon’s
Department of Agriculture limits the concentration of arsenic in fertilizers to 9 ppm.
In aqueous solutions, 1 ppm is essentially equal to 1 mg/L, and 1 ppb is equivalent to 1

µg/L.
 Example 9.6.4
If the concentration of cobalt in a human body is 21 ppb, what mass in grams of Co is present in a body having a mass of 70.0
kg?
Solution
A concentration of 21 ppb means “21 g of solute per 1,000,000,000 g of solution.” Written as a conversion factor, this
concentration of Co is as follows:
21 g Co
21 ppb Co →
1, 000, 000, 000 g solution
We can use this as a conversion factor, but first we must convert 70.0 kg to gram units:
1, 000 g
4
70.0 kg × = 7.00 × 10 g
1 kg
Now we determine the amount of Co:

21 g Co
4
7.00 × 10 g solution × = 0.0015 g Co
1, 000, 000, 000 g solution
This is only 1.5 mg.
 Exercise 9.6.4
An 85 kg body contains 0.012 g of Ni. What is the concentration of Ni in parts per million?
Answer
0.14 ppm
Mole/Volume Concentration: Molarity

Another way of expressing concentration is to give the number of moles of solute per unit volume of solution. Such concentration
units are useful for discussing chemical reactions in which a solute is a product or a reactant. Molar mass can then be used as a
conversion factor to convert amounts in moles to amounts in grams.
Molarity(M) is defined as the number of moles of a solute dissolved per liter of solution:
number of moles of solute
molarity =
number of liters of solution
Molarity is abbreviated M (often referred to as “molar”), and the units are often abbreviated as mol/L. It is important to remember
that “mol” in this expression refers to moles of solute and that “L” refers to liters of solution. For example, if you have 1.5 mol of
NaCl dissolved in 0.500 L of solution, its molarity is therefore
1.5 mol NaCl
= 3.0 M NaCl
0.500 L solution
which is read as “three point oh molar sodium chloride.” Sometimes (aq) is added when the solvent is water, as in “3.0 M
NaCl(aq).”
Before a molarity concentration can be calculated, the amount of the solute must be expressed in moles, and the volume of the
solution must be expressed in liters.
If the quantity of the solute is given in mass units, you must convert mass units to mole units before using the definition of molarity
to calculate concentration. For example, what is the molar concentration of a solution of 22.4 g of HCl dissolved in 1.56 L?
Step 1: convert the mass of solute to moles using the molar mass of HCl (36.46 g/mol):
1 mol H C l
22.4 gH C l × = 0.614 mol H C l
36.46 gH C l
Step 2: use the definition of molarity to determine the concentration:

0.614 mol H C l
M = = 0.394 M H C l
1.56L solution
 Example 9.6.5
What is the molarity of an aqueous solution of 25.0 g of NaOH in 750 mL?
Solution
Before we substitute these quantities into the definition of molarity, we must convert them to the proper units. The mass of
NaOH must be converted to moles of NaOH. The molar mass of NaOH is 40.00 g/mol:
1 mol NaOH
25.0 g NaOH × = 0.625 mol NaOH
40.00 g NaOH
Next, we convert the volume units from milliliters to liters:

1 L
750 mL × = 0.750 L
1, 000 mL
Now that the quantities are expressed in the proper units, we can substitute them into the definition of molarity:
0.625 mol NaOH
M = = 0.833 M NaOH
0.750 L
 Exercise 9.6.5
If a 350 mL cup of coffee contains 0.150 g of caffeine (C8H10N4O2), what is the molarity of this caffeine solution?
Answer
0.00221 M
Using Molarity in Calculations

The definition of molarity can also be used to calculate a needed volume of solution, given its concentration and the number of
moles desired, or the number of moles of solute (and subsequently, the mass of the solute), given its concentration and volume. As
in the percent concentration, molarity can also be expressed as a conversion factor.
Molarity is defined as moles solute per liter solution. There is an understood 1 in the denominator of the conversion factor. For
example, a 3.0 M solution of sucrose means that there are three moles of sucrose dissolved in every liter of solution.
Mathematically, this is stated as follows:
3.0 moles sucrose = 1 L solution
Dividing both sides of this expression by either side, we generate two possible conversion factors:
3.0 mol sucrose 1 L solution
or
1 L solution 3.0 mol sucrose
The first conversion factor can be used to convert from volume (L) of solution to moles solute, and the second converts from moles
of solute to volume (L) of solution.
For example, suppose we are asked how many moles of sucrose are present in 0.108 L of a 3.0 M sucrose solution. The given
volume (0.108 L) is multiplied by the first conversion factor to cancel the L units, and find that 0.32 moles of sucrose are present.
3.0 mol sucrose
0.108 L solution × = 0.32 mol sucrose
1L solution
How many liters of 3.0 M sucrose solution are needed to obtain 4.88 mol of sucrose? In such a conversion, we multiply the given
(4.88 moles sucrose) with the second conversion factor. This cancels the moles units and converts it to liters of solution.
1 L solution
4.88 mol sucrose × = 1.63 L solution
3.0 mol sucrose
 Example 9.6.6
1. What volume of a 0.0753 M solution of dimethylamine [(CH3)2NH] is needed to obtain 0.450 mol of the compound?
2. Ethylene glycol (C2H6O2) is mixed with water to make auto engine coolants. How many grams of C2H6O2 are in 5.00 L of
a 6.00 M aqueous solution?
Solution
1. To solve for the volume, multiply the "given" (0.450 mol of dimethylamine) with the molarity conversion factor (0.0753 M).
Use the proper conversion factor to cancel the unit "mol" and get the unit volume (L) of solution:
1 L solution
0.450 mol dimethylamine × = 5.98 L solution
0.0753 mol dimethylamine
2. The strategy in solving this problem is to convert the given volume (5.00 L) using the 6.00 M (conversion factor) to solve
for moles of ethylene glycol, which can then be converted to grams.
Step 1: Convert the given volume (5.00 L) to moles ethylene glycol.
6.00 mol C2 H6 O2
5.00 L solution × = 30.0 mol C2 H6 O2
1 L solution
Step 2: Convert 30.0 mols C2H6O2 to grams C2H6O2. Molar mass of C2H6O2= 62.08 g/mol
62.08 g C2 H6 O2
30.0 mol C2 H6 O2 × = 1, 860 g C2 H6 O2
1 mol C2 H6 O2
The same two-step problem can also be worked out in a single line, rather than as two separate steps, as follows:
6.00 mol C2 H6 O2 62.08 g C2 H6 O2
5.00 L solution × × = 1, 860 g C2 H6 O2
1 L solution 1 mol C2 H6 O2
The final answer is rounded off to 3 significant figures. Thus, there are 1,860 g of C2H6O2 in the specified amount of
engine coolant.
Note: Dimethylamine has a “fishy” odor. In fact, organic compounds called amines cause the odor of decaying fish.
 Exercise 9.6.6
a. What volume of a 0.0902 M solution of formic acid (HCOOH) is needed to obtain 0.888 mol of HCOOH?
b. Acetic acid (HC2H3O2) is the acid in vinegar. How many grams of HC2H3O2 are in 0.565 L of a 0.955 M solution?
Answer
a. 9.84 L
b. 32.4 g
Solution Stoichiometry
Of all the ways of expressing concentration, molarity is the one most commonly used in stoichiometry problems because it is
directly related to the mole unit. Consider the following chemical equation:
HCl(aq) + NaOH(s) → H2O(ℓ) + NaCl(aq)
Suppose we want to know how many liters of aqueous HCl solution will react with a given mass of NaOH. A typical approach to
answering this question is as follows:
Figure 9.6.2 : Typical approach to solving Molarity problems
In itself, each step is a straightforward conversion. It is the combination of the steps that is a powerful quantitative tool for problem
solving.
 Example 9.6.7
How many milliliters of a 2.75 M HCl solution are needed to react with 185 g of NaOH? The balanced chemical equation for
this reaction is as follows:
HCl(aq) + NaOH(s) → H2O(ℓ) + NaCl(aq)
Solution
We will follow the flowchart to answer this question. First, we convert the mass of NaOH to moles of NaOH using its molar
mass, 40.00 g/mol:
1 mol NaOH
185 g NaOH × = 4.63 mol NaOH
40.00 g NaOH
Using the balanced chemical equation, we see that there is a one-to-one ratio of moles of HCl to moles of NaOH. We use this
to determine the number of moles of HCl needed to react with the given amount of NaOH:
1 mol HCl
4.63 mol NaOH × = 4.63 mol HCl
1 mol NaOH
Finally, we use the definition of molarity to determine the volume of 2.75 M HCl needed:
4.63 mol HCl
2.75 M HCl =
volume of HCl solution
4.63 mol HCl 1, 000 mL

volume of HCl = = 1.68 L × = 1, 680 mL
2.75 M HCl 1 L
We need 1,680 mL of 2.75 M HCl to react with the NaOH.

The same multi-step problem can also be worked out in a single line, rather than as separate steps, as follows:
1 mol NaOH 1 mol HCl 1 L HCl solution 1000 mL HCl solution

185 g NaOH × × × × = 1, 680 mL HCl
40.00 g NaOH 1 mol NaOH 2.75 mol HCl 1 L HCl solution
solution
Our final answer (rounded off to three significant figures) is 1,680 mL HCl solution.
 Exercise 9.6.7
How many milliliters of a 1.04 M H2SO4 solution are needed to react with 98.5 g of Ca(OH)2? The balanced chemical equation
for the reaction is as follows:
H2 S O4(aq) + C a(OH )2(s) → 2 H2 O(ℓ) + C aS O4(aq)
Answer
1,280 mL
The generic steps for performing stoichiometry problems such as this are shown in Figure 9.6.3. You may want to consult this
figure when working with solutions in chemical reactions. The double arrows in Figure 9.6.3 indicate that you can start at either
end of the chart and, after a series of simple conversions, determine the quantity at the other end.
Figure 9.6.3 : Diagram of Steps for Using Molarity in Stoichiometry Calculations. When using molarity in stoichiometry
calculations, a specific sequence of steps usually leads you to the correct answer.
 Solutions in Our Body
Many of the fluids found in our bodies are solutions. The solutes range from simple ionic compounds to complex proteins.
Table 9.6.1 lists the typical concentrations of some of these solutes.
Table 9.6.1 : Approximate Concentrations of Various Solutes in Some Solutions in the Body*
Solution Solute Concentration (M)
Na+ 0.138
K+ 0.005
Ca2+ 0.004
blood plasma
Mg2+ 0.003
Cl− 0.110
HCO3− 0.030
stomach acid HCl 0.10
NaCl 0.15
urine PO43− 0.05
NH2CONH2 (urea) 0.30
*Note: Concentrations are approximate and can vary widely.
 Looking Closer: The Dose Makes the Poison
Why is it that we can drink 1 qt of water when we are thirsty and not be harmed, but if we ingest 0.5 g of arsenic, we might
die? There is an old saying: the dose makes the poison. This means that what may be dangerous in some amounts may not be
dangerous in other amounts.
Take arsenic, for example. Some studies show that arsenic deprivation limits the growth of animals such as chickens, goats,
and pigs, suggesting that arsenic is actually an essential trace element in the diet. Humans are constantly exposed to tiny
amounts of arsenic from the environment, so studies of completely arsenic-free humans are not available; if arsenic is an
essential trace mineral in human diets, it is probably required on the order of 50 ppb or less. A toxic dose of arsenic
corresponds to about 7,000 ppb and higher, which is over 140 times the trace amount that may be required by the body. Thus,
arsenic is not poisonous in and of itself. Rather, it is the amount that is dangerous: the dose makes the poison.
Similarly, as much as water is needed to keep us alive, too much of it is also risky to our health. Drinking too much water too
fast can lead to a condition called water intoxication, which may be fatal. The danger in water intoxication is not that water
itself becomes toxic. It is that the ingestion of too much water too fast dilutes sodium ions, potassium ions, and other salts in
the bloodstream to concentrations that are not high enough to support brain, muscle, and heart functions. Military personnel,
endurance athletes, and even desert hikers are susceptible to water intoxication if they drink water but do not replenish the salts
lost in sweat. As this example shows, even the right substances in the wrong amounts can be dangerous!
9.6: Units of Concentration is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
9.7: Dilution
Learning Objective
Calculate the concentration of solutions prepared by dilution.
Often, a worker will need to change the concentration of a solution by changing the amount of solvent. Dilution is the addition of
solvent, which decreases the concentration of the solute in the solution. Concentration is the removal of solvent, which increases
the concentration of the solute in the solution. (Do not confuse the two uses of the word concentration here!)
In both dilution and concentration, the amount of solute stays the same. This gives us a way to calculate what the new solution
volume must be for the desired concentration of solute. From the definition of molarity,
moles of solute
molarity =
liters of solution
we can solve for the number of moles of solute:

moles of solute = Molarity (mol/L) x Volume of solution (L)
A simpler way of writing this is to use M to represent molarity and V to represent volume. So the equation becomes
moles of solute = M x V
Because this quantity does not change before and after the change in concentration, the product MV must be the same before and
after the concentration change. Using numbers to represent the initial and final conditions, we have
M1 V1 = M2 V2
as the dilution equation. The volumes must be expressed in the same units. Note that this equation gives only the initial and final
conditions, not the amount of the change. The amount of change in volume is determined by subtraction.
Example
If 25.0 mL of a 2.19 M solution are diluted to 72.8 mL, what is the final concentration?
Solution
It does not matter which set of conditions is labeled 1 or 2, as long as the conditions are paired together properly. Using the
dilution equation, we have
(2.19 M)(25.0 mL) = M2(72.8 mL)
Solving for the second concentration (noting that the milliliter units cancel),
M2 = 0.752 M
The concentration of the solution has decreased. In going from 25.0 mL to 72.8 mL, 72.8 − 25.0 = 47.8 mL of solvent must be
added.
Exercise
A 0.885 M solution of KBr whose initial volume is 76.5 mL has more water added until its concentration is 0.500 M. What is
the new volume of the solution?
Answer
135.4 mL
Concentrating solutions involves removing solvent. Usually this is done by evaporating or boiling, assuming that the heat of
boiling does not affect the solute. The dilution equation is used in these circumstances as well.
Chemistry is Everywhere: Preparing IV Solutions
In a hospital emergency room, a physician orders an intravenous (IV) delivery of 100 mL of 0.5% KCl for a patient suffering
from hypokalemia (low potassium levels). Does an aide run to a supply cabinet and take out an IV bag containing this
concentration of KCl?
Not likely. It is more probable that the aide must make the proper solution from an IV bag of sterile solution and a more
concentrated, sterile solution, called a stock solution, of KCl. The aide is expected to use a syringe to draw up some stock
solution and inject it into the waiting IV bag and dilute it to the proper concentration. Thus the aide must perform a dilution
calculation.
Figure 9.7.1 Preparing IV Solution © Thinkstock. Medical personnel commonly must perform dilutions for IV solutions.
If the stock solution is 10.0% KCl and the final volume and concentration need to be 100 mL and 0.50%, respectively, then it is
easy to calculate how much stock solution to use:
(10%)V1 = (0.50%)(100 mL)V1 = 5 mL
Of course, the addition of the stock solution affects the total volume of the diluted solution, but the final concentration is likely
close enough even for medical purposes.
Medical and pharmaceutical personnel are constantly dealing with dosages that require concentration measurements and
dilutions. It is an important responsibility: calculating the wrong dose can be useless, harmful, or even fatal!
9.7: Dilution is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
11.4: Dilutions and Concentrations by Anonymous is licensed CC BY-NC-SA 3.0. Original source:
Define solutes as strong electrolytes, weak electrolytes, or nonelectrolytes.
Calculate equivalents for an ionic solute.
When some substances are dissolved in water, they undergo either a physical or a chemical change that yields ions in solution.
These substances constitute an important class of compounds called electrolytes. Substances that do not yield ions when dissolved
are called nonelectrolytes. If the physical or chemical process that generates the ions is essentially 100% efficient (all of the
dissolved compound yields ions), then the substance is known as a strong electrolyte. If only a relatively small fraction of the
dissolved substance undergoes the ion-producing process, it is called a weak electrolyte.
Substances may be identified as strong, weak, or nonelectrolytes by measuring the electrical conductance of an aqueous solution
containing the substance. To conduct electricity, a substance must contain freely mobile, charged species. Most familiar is the
conduction of electricity through metallic wires, in which case the mobile, charged entities are electrons. Solutions may also
conduct electricity if they contain dissolved ions, with conductivity increasing as ion concentration increases. Applying a voltage to
electrodes immersed in a solution permits assessment of the relative concentration of dissolved ions, either quantitatively, by
measuring the electrical current flow, or qualitatively, by observing the brightness of a light bulb included in the circuit (Figure
9.8.1).
Figure 9.8.1 : Solutions of nonelectrolytes such as ethanol do not contain dissolved ions and cannot conduct electricity. Solutions of
electrolytes contain ions that permit the passage of electricity. The conductivity of an electrolyte solution is related to the strength
of the electrolyte.
Ionic Electrolytes
Water and other polar molecules are attracted to ions, as shown in Figure 9.8.2. The electrostatic attraction between an ion and a
molecule with a dipole is called an ion-dipole attraction. These attractions play an important role in the dissolution of ionic
compounds in water.
Figure 9.8.2 : As potassium chloride (KCl) dissolves in water, the ions are hydrated. The polar water molecules are attracted by the
charges on the K+ and Cl− ions. Water molecules in front of and behind the ions are not shown.
When ionic compounds dissolve in water, the ions in the solid separate and disperse uniformly throughout the solution because
water molecules surround and solvate the ions, reducing the strong electrostatic forces between them. This process represents a
physical change known as dissociation. Under most conditions, ionic compounds will dissociate nearly completely when dissolved,
and so they are classified as strong electrolytes.
Let us consider what happens at the microscopic level when we add solid KCl to water. Ion-dipole forces attract the positive
(hydrogen) end of the polar water molecules to the negative chloride ions at the surface of the solid, and they attract the negative
(oxygen) ends to the positive potassium ions. The water molecules penetrate between individual K+ and Cl− ions and surround
them, reducing the strong interionic forces that bind the ions together and letting them move off into solution as solvated ions, as
Figure shows. The reduction of the electrostatic attraction permits the independent motion of each hydrated ion in a dilute solution,
resulting in an increase in the disorder of the system as the ions change from their fixed and ordered positions in the crystal to
mobile and much more disordered states in solution. This increased disorder is responsible for the dissolution of many ionic
compounds, including KCl, which dissolve with absorption of heat.
In other cases, the electrostatic attractions between the ions in a crystal are so large, or the ion-dipole attractive forces between the
ions and water molecules are so weak, that the increase in disorder cannot compensate for the energy required to separate the ions,
and the crystal is insoluble. Such is the case for compounds such as calcium carbonate (limestone), calcium phosphate (the
inorganic component of bone), and iron oxide (rust).
Covalent Electrolytes
Pure water is an extremely poor conductor of electricity because it is only very slightly ionized—only about two out of every 1
billion molecules ionize at 25 °C. Water ionizes when one molecule of water gives up a proton to another molecule of water,
yielding hydronium and hydroxide ions.
+ + −
H O(l) H O(l) ⇌ H O (aq) + OH (aq) (9.8.1)
2 2 3
In some cases, we find that solutions prepared from covalent compounds conduct electricity because the solute molecules react
chemically with the solvent to produce ions. For example, pure hydrogen chloride is a gas consisting of covalent HCl molecules.
This gas contains no ions. However, when we dissolve hydrogen chloride in water, we find that the solution is a very good
conductor. The water molecules play an essential part in forming ions: Solutions of hydrogen chloride in many other solvents, such
as benzene, do not conduct electricity and do not contain ions.
Hydrogen chloride is an acid, and so its molecules react with water, transferring H+ ions to form hydronium ions (H 3O
+
) and
chloride ions (Cl−):
This reaction is essentially 100% complete for HCl (i.e., it is a strong acid and, consequently, a strong electrolyte). Likewise, weak
acids and bases that only react partially generate relatively low concentrations of ions when dissolved in water and are classified as
weak electrolytes. Acids and bases will be explored further in a later chapter.
Equivalents
Concentrations of ionic solutes are occasionally expressed in units called equivalents (Eq). One equivalent equals 1 mol of positive
or negative charge. Thus, 1 mol/L of Na+(aq) is also 1 Eq/L because sodium has a 1+ charge. A 1 mol/L solution of Ca2+(aq) ions
has a concentration of 2 Eq/L because calcium has a 2+ charge. Dilute solutions may be expressed in milliequivalents (mEq)—for
example, human blood plasma has a total concentration of about 150 mEq/L.
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To describe how the properties of solutions differ from those of pure solvents.
Solutions are likely to have properties similar to those of their major component—usually the solvent. However, some solution
properties differ significantly from those of the solvent. Here, we will focus on liquid solutions that have a solid solute, but many of
the effects we will discuss in this section are applicable to all solutions.
Colligative Properties
Solutes affect some properties of solutions that depend only on the concentration of the dissolved particles. These properties are
called colligative properties. Four important colligative properties that we will examine are vapor pressure depression, boiling
point elevation, freezing point depression, and osmotic pressure.
Molecular compounds separate into individual molecules when they are dissolved, so for every 1 mol of molecules dissolved, we
get 1 mol of particles. In contrast, ionic compounds separate into their constituent ions when they dissolve, so 1 mol of an ionic
compound will produce more than 1 mol of dissolved particles. For example, every mole of NaCl that dissolves yields 1 mol of
Na+ ions and 1 mol of Cl− ions, for a total of 2 mol of particles in solution. Thus, the effect on a solution’s properties by dissolving
NaCl may be twice as large as the effect of dissolving the same amount of moles of glucose (C6H12O6).
Vapor Pressure Depression

All liquids evaporate. In fact, given enough volume, a liquid will turn completely into a vapor. If enough volume is not present, a
liquid will evaporate only to the point where the rate of evaporation equals the rate of vapor condensing back into a liquid. The
pressure of the vapor at this point is called the vapor pressure of the liquid.
The presence of a dissolved solid lowers the characteristic vapor pressure of a liquid so that it evaporates more slowly. (The
exceptions to this statement are if the solute itself is a liquid or a gas, in which case the solute will also contribute something to the
evaporation process. We will not discuss such solutions here.) This property is called vapor pressure depression and is depicted in
Figure 9.9.1.
Figure Vapor Pressure Depression. The presence of solute particles blocks some of the
9.9.1 :
ability for liquid particles to evaporate. Thus, solutions of solid solutes typically have a lower
vapor pressure than the pure solvent.
Boiling Point Elevation
A related property of solutions is that their boiling points are higher than the boiling point of the pure solvent. Because the presence
of solute particles decreases the vapor pressure of the liquid solvent, a higher temperature is needed to reach the boiling point. This
phenomenon is called boiling point elevation. For every mole of particles dissolved in a liter of water, the boiling point of water
increases by about 0.51°C.
ΔTboiling = mol particles × 0.51°C
The addition of one mole of sucrose (molecular compound) in one liter of water will raise the boiling point from 100°C to
100.51°C, but the addition of one mole of NaCl in one liter of water will raise the boiling point by 2 x 0.51°C = 1.02°C.
Furthermore, the addition of one mole of CaCl in one liter of water will raise the boiling point by 3 x 0.51°C = 1.53°C.
2
 Everyday Application: Adding Salt to Pasta Water
When cooking dried pasta, many recipes call for salting the water before cooking the pasta. Some argue—with colligative
properties on their side—that adding salt to the water raises the boiling point, thus cooking the pasta faster. Is there any truth to
this?
Figure 9.9.2 : Cooking dried pasta. Why do so many recipes call for adding salt to water when boiling pasta? Is it to raise the
boiling temperature of the water? (Public Domain; Jan Vašek via pixabay)
In order to increase the boiling temperature of 4 L of water by 1.0°C, with the presumption that dried pasta cooks noticeably
faster at 101°C than at 100°C (although a 1° difference may make only a negligible change in cooking times), over 1 lb of salt
(~1 cup) would be needed. In your experience, do you add almost a cup of salt to a pot of water to make pasta? Certainly not!
A few pinches, perhaps one-fourth of a teaspoon, but not almost a cup! It is obvious that the little amount of salt that most
people add to their pasta water is not going to significantly raise the boiling point of the water.
So why do people add some salt to boiling water? There are several possible reasons, the most obvious of which is taste:
adding salt adds a little bit of salt flavor to the pasta. It cannot be much because most of the salt remains in the water, not in the
cooked pasta. However, it may be enough to detect with our taste buds. The other obvious reason is habit; recipes tell us to add
salt, so we do, even if there is little scientific or culinary reason to do so.
Freezing Point Depression

The presence of solute particles has the opposite effect on the freezing point of a solution. When a solution freezes, only the solvent
particles come together to form a solid phase, and the presence of solute particles interferes with that process. Therefore, for the
liquid solvent to freeze, more energy must be removed from the solution, which lowers the temperature. Thus, solutions have lower
freezing points than pure solvents do. This phenomenon is called freezing point depression. For every mole of particles in a liter of
water, the freezing point decreases by about 1.86°C.
ΔTf reezing = mol particles × −1.86°C
Figure 9.9.3 : Comparison of boiling and freezing points of a pure liquid (right side) with a solution (left side).
Both boiling point elevation and freezing point depression have practical uses. For example, solutions of water and ethylene glycol
(C2H6O2) are used as coolants in automobile engines because the boiling point of such a solution is greater than 100°C, the normal
boiling point of water. In winter, salts like NaCl and CaCl are sprinkled on the ground to melt ice or keep ice from forming on
2
roads and sidewalks (Figure 9.9.4). This is because the solution made by dissolving sodium chloride or calcium chloride in water
has a lower freezing point than pure water, so the formation of ice is inhibited.
Figure 9.9.4 : Effect of Freezing Point Depression. The salt sprinkled on this sidewalk makes the water on the sidewalk have a
lower freezing point than pure water, so it does not freeze as easily. This makes walking on the sidewalk less hazardous in winter.
© Thinkstock
 Example 9.9.1
Which solution’s freezing point deviates more from that of pure water—a 1 M solution of NaCl or a 1 M solution of CaCl ? 2
Solution
Colligative properties depend on the number of dissolved particles, so the solution with the greater number of particles in
solution will show the greatest deviation. When NaCl dissolves, it separates into two ions, Na+ and Cl−. But when CaCl 2
dissolves, it separates into three ions—one Ca2+ ion and two Cl− ions. Thus, mole for mole, CaCl will have 50% more impact
2
on freezing point depression than NaCl.
 Exercise 9.9.1
Which solution’s boiling point deviates more from that of pure water—a 1 M solution of CaCl or a 1 M solution of MgSO4?
2
Answer
CaCl
2
 Example 9.9.2
Estimate the boiling point of 0.2 M CaCl solution.

2
Solution
The boiling point increases 0.51°C for every mole of solute per liter of water. For this estimation, let's assume that 1 liter of
solution is roughly the same volume as 1 liter of water. A 0.2 M CaCl solution contains 0.2 moles of CaCl solution formula
2 2
units per liter of solution. Each CaCl unit separates into three ions.
2
3 mol ions 0.51°C

0.2 mol CaC l2 × × = 0.306°C
1 mol CaCl2 1 mol ion
The normal boiling point of water is 100°C, so the boiling point of the solution is raised to 100.31°C.
 Exercise 9.9.2
Estimate the freezing point of 0.3 M CaCl solution.
2
Answer
–1.7°C
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Describe osmosis and how it relates to osmotic pressure.
Osmotic Pressure
The last colligative property of solutions we will consider is a very important one for biological systems. It involves osmosis, the
process by which solvent molecules can pass through certain membranes but solute particles cannot. When two solutions of
different concentration are present on either side of these membranes (called semipermeable membranes), there is a tendency for
solvent molecules to move from the more dilute solution to the more concentrated solution until the concentrations of the two
solutions are equal. This tendency is called osmotic pressure. External pressure can be exerted on a solution to counter the flow of
solvent; the pressure required to halt the osmosis of a solvent is equal to the osmotic pressure of the solution.
Consider the apparatus illustrated in Figure 9.10.1, in which samples of pure solvent and a solution are separated by a membrane
that only solvent molecules may permeate. Solvent molecules will diffuse across the membrane in both directions. Since the
concentration of solvent is greater in the pure solvent than the solution, these molecules will diffuse from the solvent side of the
membrane to the solution side at a faster rate than they will in the reverse direction. The result is a net transfer of solvent molecules
from the pure solvent to the solution. Diffusion-driven transfer of solvent molecules through a semipermeable membrane is a
process known as osmosis.
Figure 9.10.1 : Osmosis results in the transfer of solvent molecules from a sample of low (or zero) solute concentration to a sample
of higher solute concentration.
When osmosis is carried out in an apparatus like that shown in Figure 9.10.1, the volume of the solution increases as it becomes
diluted by accumulation of solvent. This causes the level of the solution to rise, increasing its hydrostatic pressure (due to the
weight of the column of solution in the tube) and resulting in a faster transfer of solvent molecules back to the pure solvent side.
When the pressure reaches a value that yields a reverse solvent transfer rate equal to the osmosis rate, bulk transfer of solvent
ceases. This pressure is called the osmotic pressure (π) of the solution. The osmotic pressure of a dilute solution can be determined
in a similar way the pressure of an ideal gas is calculated using the ideal gas law:
n
π =( ) RT
V
where n is the number of moles of particles in solution, V is the volume, and R is the universal gas constant.
Osmolarity (osmol) is a way of reporting the total number of particles in a solution to determine osmotic pressure. It is defined as
the molarity of a solute times the number of particles a formula unit of the solute makes when it dissolves (represented by i):
osmol = M × i
If more than one solute is present in a solution, the individual osmolarities are additive to get the total osmolarity of the solution.
Solutions that have the same osmolarity have the same osmotic pressure. If solutions of differing osmolarities are present on
opposite sides of a semipermeable membrane, solvent will transfer from the lower-osmolarity solution to the higher-osmolarity
solution. Counterpressure exerted on the high-osmolarity solution will reduce or halt the solvent transfer. An even higher pressure
can be exerted to force solvent from the high-osmolarity solution to the low-osmolarity solution, a process called reverse osmosis.
Reverse osmosis is used to make potable water from saltwater where sources of fresh water are scarce.
 Example 9.10.1
A 0.50 M NaCl aqueous solution and a 0.30 M Ca(NO3)2 aqueous solution are placed on opposite sides of a semipermeable
membrane. Determine the osmolarity of each solution and predict the direction of solvent flow.
Solution
The solvent will flow into the solution of higher osmolarity. The NaCl solute separates into two ions—Na+ and Cl−—when it
dissolves, so its osmolarity is as follows:
osmol (NaCl) = 0.50 M × 2 = 1.0 osmol
The Ca(NO3)2 solute separates into three ions—one Ca2+ and two NO3−—when it dissolves, so its osmolarity is as follows:
osmol [Ca(NO3)2] = 0.30 M × 3 = 0.90 osmol
The osmolarity of the Ca(NO3)2 solution is lower than that of the NaCl solution, so water will transfer through the membrane
from the Ca(NO3)2 solution to the NaCl solution.
 Exercise 9.10.1
A 1.5 M C6H12O6 aqueous solution and a 0.40 M Al(NO3)3 aqueous solution are placed on opposite sides of a semipermeable
membrane. Determine the osmolarity of each solution and predict the direction of solvent flow.
Answer
osmol C6H12O6 = 1.5; osmol Al(NO3)3 = 1.6
The solvent flows from C6H12O6 solution (lower osmolarity) to Al(NO 3
)
3
solution (higher osmolarity).
Examples of osmosis are evident in many biological systems because cells are surrounded by semipermeable membranes. Carrots
and celery that have become limp because they have lost water can be made crisp again by placing them in water. Water moves into
the carrot or celery cells by osmosis. A cucumber placed in a concentrated salt solution loses water by osmosis and absorbs some
salt to become a pickle. Osmosis can also affect animal cells. Solute concentrations are particularly important when solutions are
injected into the body. Solutes in body cell fluids and blood serum give these solutions an osmotic pressure of approximately 7.7
atm. Solutions injected into the body must have the same osmotic pressure as blood serum; that is, they should be isotonic with
blood serum. If a less concentrated solution, a hypotonic solution, is injected in sufficient quantity to dilute the blood serum, water
from the diluted serum passes into the blood cells by osmosis, causing the cells to expand and rupture (Figure 9.10.2a). This
process is called hemolysis. When a more concentrated solution, a hypertonic solution, is injected, the cells lose water to the more
concentrated solution, shrivel, and possibly die in a process called crenation (Figure 9.10.2c). Only if red blood cells are placed in
isotonic solutions that have the same osmolarity as exists inside the cells are they unaffected by negative effects of osmotic
pressure (Figure 9.10.2b). Glucose solutions of about 0.31 M, or sodium chloride (NaCl) solutions of about 0.16 M, are isotonic
with blood plasma.
Figure 9.10.2 : Red blood cell membranes are water permeable and will (a) swell and possibly rupture in a hypotonic solution; (b)
maintain normal volume and shape in an isotonic solution; and (c) shrivel and possibly die in a hypertonic solution. (credit a/b/c:
modifications of work by “LadyofHats”/Wikimedia commons)
 Note: Isotonic Solutions for Red Blood Cells
The concentration of an red blood cell isotonic solution made with sodium chloride (NaCl) is half that of an isotonic solution
made with glucose (0.16 M and 0.31 M respectively). This is because NaCl produces two ions when a formula unit dissolves,
while molecular glucose produces only one particle when a formula unit dissolves. The osmolarities are therefore the same
even though the concentrations of the two solutions are different.
isotonic NaCl solution: osmol = 0.16 M × 2 = 0.32 osmol/L
isotonic glucose solution: osmol = 0.31 M × 1 = 0.31 osmol/L
Osmotic pressure explains why you should not drink seawater if you are abandoned in a life raft in the middle of the ocean. Its
osmolarity is about three times higher than most bodily fluids. You would actually become thirstier as water from your cells was
drawn out to dilute the salty ocean water you ingested. Our bodies do a better job coping with hypotonic solutions than with
hypertonic ones. The excess water is collected by our kidneys and excreted.
Osmotic pressure effects are used in the food industry to make pickles from cucumbers and other vegetables and in brining meat to
make corned beef. It is also a factor in the mechanism of getting water from the roots to the tops of trees!
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9.11: Dialysis
Understand the difference between dialysis and osmosis.
As introduced in a previous section, osmosis is the process by which solvent particles can pass through a semipermeable
membrane. Dialysis is similar to osmosis with the difference being that the pores in the semipermeable membranes are larger, thus
allowing both solvent and small solute molecules to pass through. Larger solute particles, such as colloids and proteins, that cannot
pass through the pores in the membrane are left behind. The size of the pores in the semipermeable membranes can be varied to
allow for separation (or purification) of specific solute molecules from a solution based on their size. Biochemists and molecular
biologists use dialysis to purify proteins from mixtures or to change the concentration of solute particles for different types of
experiments, as illustrated in Figure 9.11.1.
Figure 9.11.1 : Dialysis separates colloidal particles like protein and starch from water, small molecules, and ions. Source:
Potcherboy at English Wikipedia / CC BY (https://creativecommons.org/licenses/by/3.0)
Role of dialysis in the human body

Kidneys filter the blood by dialysis, which occurs in tubular structures called nephrons (Figure 9.11.2. The nephrons filter the
water, and small molecules, like glucose, amino acids, urea, and ions from the blood. Useful products and most of the water
reabsorb later on, but urea and other waste products are excreted through urine. (You can read more about kidney structure and
function here.)
Close up of a nephron and its place in the kidney. Labels on the kidney cross section show where
unfiltered blood enters, filtered blood leaves, and urine exits. On the nephron, the glomerulus,
tubule, and collecting duct are labeled along with where unfiltered blood enters, filtered blood exits,
and urine exits.
Figure 9.11.2 : Image of a close up nephron and its place in the kidney. Labels on the kidney cross section show where unfiltered
blood enters, filtered blood leaves, and urine exits. On the nephron, the glomerulus, tubule, and collecting duct are labeled along
with where unfiltered blood enters, filtered blood exits, and urine exits. (National Institute of Diabetes and Digestive and Kidney
Diseases, National Institutes of Health. CC0 1.0)
The main function of the kidneys is to filter the blood to remove wastes and extra water, which are then expelled from the body as
urine. Some diseases rob the kidneys of their ability to perform this function, causing a buildup of waste materials in the
bloodstream. If a kidney transplant is not available or desirable, a procedure called dialysis can be used to remove waste materials
and excess water from the blood.
In one form of dialysis, called hemodialysis, (see Figure 9.11.3), a patient’s blood is passed though a length of tubing that travels
through an artificial kidney machine (also called a dialysis machine). In the dialyser, a section of tubing composed of cellophane (a
semipermeable membrane) is immersed in dialysate, a solution of sterile water, glucose, amino acids, and certain electrolytes. The
osmotic pressure of the blood forces waste molecules, such as urea, and excess water through the membrane into the dialysate. Red
and white blood cells are too large to pass through the membrane, so they remain in the blood. After being cleansed in this way, the
blood is returned to the body.
Dialysis is a continuous process, as the osmosis of waste materials and excess water takes time. Typically, 5–10 lb of waste-
containing fluid is removed in each dialysis session, which can last 2–8 hours and must be performed several times a week.
Although some patients have been on dialysis for 30 or more years, dialysis is always a temporary solution because waste materials
are constantly building up in the bloodstream. A more permanent solution is a kidney transplant.
undefined
Figure 9.11.3 : Simplified hemodialysis circuit. (Yassine Mrabet, CC BY 3.0)
 Career Connection: Dialysis Technician
Dialysis is a medical process of removing wastes and excess water from the blood by diffusion and ultrafiltration. When
kidney function fails, dialysis must be done to artificially rid the body of wastes. This is a vital process to keep patients alive.
In some cases, the patients undergo artificial dialysis until they are eligible for a kidney transplant. In others who are not
candidates for kidney transplants, dialysis is a life-long necessity.
Dialysis technicians typically work in hospitals and clinics. While some roles in this field include equipment development and
maintenance, most dialysis technicians work in direct patient care. Their on-the-job duties, which typically occur under the
direct supervision of a registered nurse, focus on providing dialysis treatments. This can include reviewing patient history and
current condition, assessing and responding to patient needs before and during treatment, and monitoring the dialysis process.
Treatment may include taking and reporting a patient’s vital signs and preparing solutions and equipment to ensure accurate
and sterile procedures.
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5.5: Osmosis by Muhammad Arif Malik is licensed Public Domain.
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CHAPTER OVERVIEW
10: Acids and Bases

10.11: Titration
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1
Identify an Arrhenius acid and an Arrhenius base.
Identify a Brønsted-Lowry acid and a Brønsted-Lowry base.
Identify conjugate acid-base pairs in an acid-base reaction.
There are three major classifications of substances known as acids or bases. The theory developed by Svante Arrhenius in 1883, the
Arrhenius definition, states that an acid produces hydrogen ions, H , in solution and a base produces hydroxide ions, OH . Later,
+ −
two more sophisticated and general theories were proposed. These theories are the Brønsted-Lowry and Lewis definitions of acids
and bases. This section will cover the Arrhenius and Brønsted-Lowry theories; Lewis theory is discussed elsewhere.
The Arrhenius Theory of Acids and Bases

In 1884, the Swedish chemist Svante Arrhenius proposed two specific classifications of compounds, termed acids and bases. When
dissolved in an aqueous solution, certain ions were released into the solution. An Arrhenius acid is a compound that increases the
concentration of H ions that are present when added to water. These H ions form the hydronium ion (H O ) when they
+ +
3
+
combine with water molecules. This process is represented in a chemical equation by adding H2O to the reactants side.
+ −
HCl(aq) → H (aq) + Cl (aq) (10.1.1)
In this reaction, hydrochloric acid (H C l) dissociates completely into hydrogen (H ) and chloride (\Cl^{-}\)) ions when dissolved
+
in water, thereby releasing H ions into solution. Formation of the hydronium ion equation:
+
+ −
HCl(aq) + H O(ℓ) → H O (aq) + Cl (aq) (10.1.2)
2 3
An Arrhenius base is a compound that increases the concentration of OH

−
ions that are present when added to water. The
dissociation is represented by the following equation:
+ −
NaOH(aq) → Na (aq) + OH (aq) (10.1.3)
In this reaction, sodium hydroxide (NaOH) disassociates into sodium (N a ) and hydroxide (OH ) ions when dissolved in water,
+ −
thereby releasing OH ions into solution.

−
Arrhenius acids are substances which produce hydrogen ions in solution and Arrhenius
bases are substances which produce hydroxide ions in solution.
 Limitations to the Arrhenius Theory
The Arrhenius theory has many more limitations than the other two theories. The theory does not explain the weak base
ammonia (N H ), which in the presence of water, releases hydroxide ions into solution, but does not contain OH itself. The
3
−
Arrhenius definition of acid and base is also limited to aqueous (i.e., water) solutions.
The Brønsted-Lowry Theory of Acids and Bases

In 1923, Danish chemist Johannes Brønsted and English chemist Thomas Lowry independently proposed new definitions for acids
and bases, ones that focus on proton transfer. A Brønsted-Lowry acid is any species that can donate a proton (H+) to another
molecule. A Brønsted-Lowry base is any species that can accept a proton from another molecule. In short, a Brønsted-Lowry acid
is a proton donor, while a Brønsted-Lowry base is a proton acceptor.
A Brønsted-Lowry acid is a proton donor, while a Brønsted-Lowry base is a proton

acceptor.
Let us use the reaction of ammonia in water to demonstrate the Brønsted-Lowry definitions of an acid and a base. Ammonia and
water molecules are reactants, while the ammonium ion and the hydroxide ion are products:
+ −
NH (aq) + H O(ℓ) −
↽⇀
− NH (aq) + OH (aq) (10.1.4)
3 2 4
What has happened in this reaction is that the original water molecule has donated a hydrogen ion to the original ammonia
molecule, which in turn has accepted the hydrogen ion. We can illustrate this as follows:
Because the water molecule donates a hydrogen ion to the ammonia, it is the Brønsted-Lowry acid, while the ammonia molecule—
which accepts the hydrogen ion—is the Brønsted-Lowry base. Thus, ammonia acts as a base in both the Arrhenius sense and the
Brønsted-Lowry sense.
Is an Arrhenius acid like hydrochloric acid still an acid in the Brønsted-Lowry sense? Yes, but it requires us to understand what
really happens when HCl is dissolved in water. Recall that the hydrogen atom is a single proton surrounded by a single electron. To
make the hydrogen ion, we remove the electron, leaving a bare proton. Do we really have bare protons floating around in aqueous
solution? No, we do not. What really happens is that the H+ ion attaches itself to H2O to make H3O+, which is called the hydronium
ion. For most purposes, H+ and H3O+ represent the same species, but writing H3O+ instead of H+ shows that we understand that
there are no bare protons floating around in solution. Rather, these protons are actually attached to solvent molecules.
With this in mind, how do we define HCl as an acid in the Brønsted-Lowry sense? Consider what happens when HCl is dissolved
in H2O:
+ − +
HCl(g) + H O(ℓ) → H O (aq)Cl (aq) + H O (aq) (10.1.5)
2 3 3
We can depict this process using Lewis electron dot diagrams:
Now we see that a hydrogen ion is transferred from the HCl molecule to the H2O molecule to make chloride ions and hydronium
ions. As the hydrogen ion donor, HCl acts as a Brønsted-Lowry acid; the hydrogen ion acceptor, H2O is a Brønsted-Lowry base. So
HCl is an acid not just in the Arrhenius sense, but also in the Brønsted-Lowry sense. Moreover, by the Brønsted-Lowry definitions,
H2O is a base in the formation of aqueous HCl. So the Brønsted-Lowry definitions of an acid and a base classify the dissolving of
HCl in water as a reaction between an acid and a base—although the Arrhenius definition would not have labeled H2O a base in
this circumstance.
 Note: Acid and Base Definitions

A Brønsted-Lowry acid is a proton (hydrogen ion) donor.
A Brønsted-Lowry base is a proton (hydrogen ion) acceptor.
All Arrhenius acids and bases are Brønsted-Lowry acids and bases as well. However, not all Brønsted-Lowry acids and
bases are Arrhenius acids and bases.
 Example 10.1.1
Aniline (C6H5NH2) is slightly soluble in water. It has a nitrogen atom that can accept a hydrogen ion from a water molecule,
just like the nitrogen atom in ammonia does. Write the chemical equation for this reaction and identify the Brønsted-Lowry
acid and base.
Solution
C6H5NH2 and H2O are the reactants. When C6H5NH2 accepts a proton from H2O, it gains an extra H and a positive charge and
leaves an OH− ion behind. The reaction is as follows:
+ −
C H NH (aq) + H O(ℓ) −
↽⇀
− C H NH (aq) + OH (aq)
6 5 2 2 6 5 3
Because C6H5NH2 accepts a proton, it is the Brønsted-Lowry base. The H2O molecule, because it donates a proton, is the
Brønsted-Lowry acid.
 Exercise 10.1.1
Identify the Brønsted-Lowry acid and the Brønsted-Lowry base in this chemical equation.
− 2 − +
H PO +H O −
↽⇀
− HPO +H O (10.1.6)
2 4 2 4 3
Answer
Brønsted-Lowry acid: H2PO4-; Brønsted-Lowry base: H2O
 Exercise 10.1.2
Which of the following compounds is a Bronsted-Lowry base?

a. HCl
b. HPO42-
c. H3PO4
d. NH4+
e. CH3NH3+
Answer
A Brønsted-Lowry Base is a proton acceptor, which means it will take in an H+. This eliminates HCl, H 3
PO , NH and
4
+
4
CH NH
3
+
3
because they are Bronsted-Lowry acids. They all give away protons. In the case of HPO 2 −
4
, consider the
following equation:
2 − 3 − +
HPO (aq) + H O(l) → PO (aq) + H O (aq)
4 2 4 3
Here, it is clear that HPO42- is the acid since it donates a proton to water to make H3O+ and PO43-. Now consider the
following equation:
2 − − −
HPO (aq) + H O(l) → H PO + OH (aq)
4 2 2 4
In this case, HPO42- is the base since it accepts a proton from water to form H2PO4- and OH-. Thus, HPO42- is an acid and
base together, making it amphoteric.
Since HPO42- is the only compound from the options that can act as a base, the answer is (b) HPO42-.
Conjugate Acid-Base Pair

In reality, all acid-base reactions involve the transfer of protons between acids and bases. For example, consider the acid-base
reaction that takes place when ammonia is dissolved in water. A water molecule (functioning as an acid) transfers a proton to an
ammonia molecule (functioning as a base), yielding the conjugate base of water, OH , and the conjugate acid of ammonia, NH :
− +
4
In the reaction of ammonia with water to give ammonium ions and hydroxide ions, ammonia acts as a base by accepting a proton
from a water molecule, which in this case means that water is acting as an acid. In the reverse reaction, an ammonium ion acts as an
acid by donating a proton to a hydroxide ion, and the hydroxide ion acts as a base. The conjugate acid–base pairs for this reaction
are N H /N H and H O/OH .
+
4 3 2
−
Figure 10.1.1 . The pairing of parent acids and bases with conjugate acids and bases.
Figure 10.1.2 : The Relative Strengths of Some Common Conjugate Acid-Base Pairs. The strongest acids are at the bottom left, and
the strongest bases are at the top right. The conjugate base of a strong acid is a very weak base, and, conversely, the conjugate acid
of a strong base is a very weak acid.
 Example 10.1.2
Identify the conjugate acid-base pairs in this equilibrium.

+ −
CH CO H + H O −
↽⇀
− H O + CH CO
3 2 2 3 3 2
Solution
Similarly, in the reaction of acetic acid with water, acetic acid donates a proton to water, which acts as the base. In the reverse
reaction, H O is the acid that donates a proton to the acetate ion, which acts as the base.
3
+
Once again, we have two conjugate acid-base pairs:
the parent acid and its conjugate base (C H C O H /C H
3 2
−
3 C O2 ) and
the parent base and its conjugate acid (H O /H O).
3
+
2
 Example 10.1.3

+ −
(C H3 )3 N + H2 O ⇌ (C H3 )3 N H + OH
Solution
One pair is H2O and OH−, where H2O has one more H+ and is the conjugate acid, while OH− has one less H+ and is the
conjugate base.
The other pair consists of (CH3)3N and (CH3)3NH+, where (CH3)3NH+ is the conjugate acid (it has an additional proton) and
(CH3)3N is the conjugate base.
 Exercise 10.1.3
− −
NH + H O ⇌ NH + OH
2 2 3
Answer
H2O (acid) and OH− (base); NH2− (base) and NH3 (acid)

10.1: Acids and Bases Definitions is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
Define a strong and a weak acid and base.
Recognize an acid or a base as strong or weak.
Strong and Weak Acids

Except for their names and formulas, so far we have treated all acids as equals, especially in a chemical reaction. However, acids
can be very different in a very important way. Consider HCl(aq). When HCl is dissolved in H O , it completely dissociates
2
(separates) into H+(aq) and Cl−(aq) ions; all the HCl molecules become ions:
100 %
+ −
HCl → H (aq) + Cl (aq) (10.2.1)
Any acid that dissociates 100% into ions is called a strong acid. If it does not dissociate 100%, it is a weak acid. HC2H3O2 is an
example of a weak acid:
∼5%
+ −
H C2 H3 O2 ⟶ H (aq) + C2 H3 O (aq) (10.2.2)
2
Because this reaction does not go 100% to completion, it is more appropriate to write it as a reversible reaction:
+ −
H C2 H3 O2 ⇌ H (aq) + C2 H3 O (aq) (10.2.3)
2
As it turns out, there are very few strong acids, which are given in Table 10.2.1 . If an acid is not listed here, it is a weak acid. It
may be 1% ionized or 99% ionized, but it is still classified as a weak acid.
Any acid that dissociates 100% into ions is called a strong acid. If it does not dissociate
100%, it is a weak acid.
Figure 10.2.1 : Some of the common strong acids and bases are listed here.
Strong Acids Strong Bases
HClO
4
perchloric acid LiOH lithium hydroxide
HCl hydrochloric acid NaOH sodium hydroxide
HBr hydrobromic acid KOH potassium hydroxide
HI hydroiodic acid Ca(OH)

2
calcium hydroxide
HNO
3
nitric acid Sr(OH)
2
strontium hydroxide
H SO
2 4
sulfuric acid Ba(OH)
2
barium hydroxide
Strong and Weak Bases

The issue is similar with bases: a strong base is a base that is 100% ionized in solution. If it is less than 100% ionized in solution,
it is a weak base. There are very few strong bases (Table 10.2.1); any base not listed is a weak base. All strong bases are OH–
compounds. So a base based on some other mechanism, such as NH3 (which does not contain OH− ions as part of its formula), will
be a weak base.
 Example 10.2.1: Identifying Strong and Weak Acids and Bases
Identify each acid or base as strong or weak.

a. HCl
b. Mg(OH)2
c. C5H5N
Solution
a. Because HCl is listed in Table 10.2.1, it is a strong acid.
b. Because Mg(OH)2 is listed in Table 10.2.1, it is a strong base.
c. The nitrogen in C5H5N would act as a proton acceptor and therefore can be considered a base, but because it does not
contain an OH compound, it cannot be considered a strong base; it is a weak base.
 Exercise 10.2.1
Identify each acid or base as strong or weak.

a. RbOH
b. HNO 2
Answer
a. strong base
b. weak acid
 Example 10.2.2: Characterizing Base Ionization
Write the balanced chemical equation for the dissociation of Ca(OH)2 and indicate whether it proceeds 100% to products or
not.
Solution
This is an ionic compound of Ca2+ ions and OH− ions. When an ionic compound dissolves, it separates into its constituent
ions:
2 + −
Ca (OH) → Ca (aq) + 2 OH (aq)
2
Because Ca(OH)2 is listed in Table 10.2.1, this reaction proceeds 100% to products.
 Exercise 10.2.2
Write the balanced chemical equation for the dissociation of hydrazoic acid (HN3) and indicate whether it proceeds 100% to
products or not.
Answer a
The reaction is as follows:
+ −
HN → H (aq) + N (aq)
3 3
It does not proceed 100% to products because hydrazoic acid is not a strong acid.
 Looking Closer: Household Acids and Bases
Many household products are acids or bases. For example, the owner of a swimming pool may use muriatic acid to clean the
pool. Muriatic acid is another name for hydrochloric acid [HCl(aq)]. Vinegar has already been mentioned as a dilute solution
of acetic acid [HC H O (aq)]. In a medicine chest, one may find a bottle of vitamin C tablets; the chemical name of vitamin
2 3 2
C is ascorbic acid (HC H O ).6 7 6
One of the more familiar household bases is ammonia (NH ), which is found in numerous cleaning products. As we mentioned
3
previously, ammonia is a base because it increases the hydroxide ion concentration by reacting with water:
+ −
NH (aq) + H O(ℓ) → NH (aq) + OH (aq) (10.2.4)
3 2 4
Many soaps are also slightly basic because they contain compounds that act as Brønsted-Lowry bases, accepting protons from
water and forming excess hydroxide ions. This is one reason that soap solutions are slippery.
Figure 10.2.1 : (left) Bottles of alkaline drain cleaners containing sodium hydroxide can dissolve greases and hair. (right)
Chemical burns caused by sodium hydroxide solution photographed 44 hours after exposure. Figures used with permission
from Wikipedia.
Perhaps the most dangerous household chemical is the lye-based drain cleaner. Lye is a common name for sodium hydroxide,
although it is also used as a synonym for potassium hydroxide. Lye is an extremely caustic chemical that can react with grease,
hair, food particles, and other substances that may build up and form a clog in a pipe. Unfortunately, lye can also attack tissues
and other substances in our bodies. Thus, when we use lye-based drain cleaners, we must be very careful not to touch any of
the solid drain cleaner or spill the water it was poured into. Safer, nonlye drain cleaners use peroxide compounds to react on
the materials in the clog and clear the drain.
Chemical Equilibrium in Weak Acids and Bases

Ionization of weak acids or bases are reversible reactions, which means the forward and reverse reactions occur and eventually
reach equilbrium. For example, the ionization of the weak acid HC H O (aq) is as follows:
2 3 2
+ −
HC H O (aq) + H O(ℓ) → H O (aq) + C H O (aq) (10.2.5)
2 3 2 2 3 2 3 2
The reverse process also begins to occur:

+ −
H O (aq) + C H O2 (aq) → HC H O (aq) + H O(ℓ) (10.2.6)
3 2 3 2 3 2 2
Eventually, there is a balance between the two opposing processes, and no additional change occurs. The chemical reaction is better
represented at this point with a double arrow:
+ −
HC H O (aq) + H O(ℓ) −
↽⇀
− H O (aq) + C H O (aq) (10.2.7)
2 3 2 2 3 2 3 2
The ⇌ implies that both the forward and reverse reactions are occurring, and their effects cancel each other out. A process at this
point is considered to be at chemical equilibrium (or equilibrium). It is important to note that the processes do not stop. They
balance out each other so that there is no further net change; that is, chemical equilibrium is a dynamic equilibrium.
 Example 10.2.3: Partial Ionization
Write the equilibrium chemical equation for the partial ionization of each weak acid or base.
a. HNO2(aq)
b. C5H5N(aq)
Solution
a. HNO2(aq) + H2O(ℓ) ⇆ NO2−(aq) + H3O+(aq)
b. C5H5N(aq) + H2O(ℓ) ⇆ C5H5NH+(aq) + OH−(aq)
 Exercise 10.2.3
Write the equilibrium chemical equation for the partial ionization of each weak acid or base.
a. H F
(aq)
b. AgOH (aq)
c. CH3NH2(aq)
Answer
a. HF(aq) + H2O(ℓ) ⇆ F−(aq) + H3O+(aq)
b. AgOH(aq) ⇆ Ag+(aq) + OH−(aq)
c. CH3NH2(aq) + H2O(ℓ) ⇆ CH3NH3+(aq) + OH−(aq)
Strengths of Conjugate Acid and Base Pairs

The extent to which an acid, HA, donates protons to water molecules depends on the strength of the conjugate base, A , of the
−
acid. If A is a strong base, any protons that are donated to water molecules are recaptured by A . Thus there is relatively little
− −
A
−
and H O in solution, and the acid, HA, is weak. If A is a weak base, water binds the protons more strongly, and the
3
+ −
solution contains primarily A and H O —the acid is strong. Strong acids form very weak conjugate bases, and weak acids form
−
3
+
stronger conjugate bases (Figure 10.2.2).

The first six acids in Figure 10.2.2 are the most common strong acids. These acids are completely dissociated in aqueous solution.
The conjugate bases of these acids are weaker bases than water. When one of these acids dissolves in water, their protons are
completely transferred to water, the stronger base.
Those acids that lie between the hydronium ion and water in Figure 10.2.2 form conjugate bases that can compete with water for
possession of a proton. Both hydronium ions and non-ionized acid molecules are present in equilibrium in a solution of one of
these acids. Compounds that are weaker acids than water (those found below water in the column of acids) in Figure 10.2.2 exhibit
no observable acidic behavior when dissolved in water. Their conjugate bases are stronger than the hydroxide ion, and if any
conjugate base were formed, it would react with water to re-form the acid.
Figure 10.2.2 : The chart shows the relative strengths of conjugate acid-base pairs.
The extent to which a base forms hydroxide ion in aqueous solution depends on the strength of the base relative to that of the
hydroxide ion, as shown in the last column in Figure 10.2.2. A strong base, such as one of those lying below hydroxide ion, accepts
protons from water to yield 100% of the conjugate acid and hydroxide ion. Those bases lying between water and hydroxide ion
accept protons from water, but a mixture of the hydroxide ion and the base results. Bases that are weaker than water (those that lie
above water in the column of bases) show no observable basic behavior in aqueous solution.
Key Takeaways
Strong acids and bases are 100% ionized in aqueous solution.
Weak acids and bases are less than 100% ionized in aqueous solution.
10.2: Acid and Base Strength is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by Marisa Alviar-Agnew &
Henry Agnew.
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10.4: The Strengths of Acids and Bases by Anonymous is licensed CC BY-NC-SA 4.0. Original source:
Write the acid dissociation constant (K ) expression.
a
Determine the relative strength of an acid using the (K ) value. a
The ionization for a general weak acid, HA, can be written as follows:
+ −
HA (aq) ⇌ H (aq) + A (aq)
Because the acid is weak, an equilibrium expression can be written. An acid ionization constant (K a) is the equilibrium constant
for the ionization of an acid.
+ −
[H ] [A ]
Ka =
[HA]
The acid ionization represents the fraction of the original acid that has been ionized in solution. Therefore, the numerical value of
K is a reflection of the strength of the acid. Weak acids with relatively higher K values are stronger than acids with relatively
a a
lower K values. Because strong acids are essentially 100% ionized, the concentration of the acid in the denominator is nearly zero
a
and the K value approaches infinity. For this reason, K values are generally reported for weak acids only.
a a
The table below is a listing of acid ionization constants for several acids. Note that polyprotic acids have a distinct ionization
constant for each ionization step, with each successive ionization constant being smaller than the previous one.
Table 10.3.1 : Acid Ionization Constants at 25 o
C
Name of Acid Ionization Equation Ka
H SO ⇌ H
+
+ HSO
−
very large
Sulfuric acid 2 4
+ 2 −
4
−2
HSO ⇌ H + SO 1.3 × 10
4 4
Hydrofluoric acid HF ⇌ H
+
+F
−
7.1 × 10
−4
Nitrous acid HNO

2
⇌ H
+
+ NO
−
2
4.5 × 10
−4
Benzoic acid C H COOH ⇌ H

6 5
+
+ C H COO
6 5
−
6.5 × 10
−5
Acetic acid CH COOH ⇌ H

3
+
+ CH COO
3
−
1.8 × 10
−5
+ − −7
H CO ⇌ H + HCO 4.2 × 10
Carbonic acid 2
−
3
+ 2 −
3
−11
HCO ⇌ H + CO 4.8 × 10
3 3
Hydrofluoric acid H F (aq)

reacts directly with glass (very few chemicals react with glass). Hydrofluoric acid is used in glass
etching.
10.3: Acid Dissociation Constants is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
To write chemical equations for water acting as an acid and as a base.
Define and use the ion product constant for water, K , to calculate concentrations of H
w 3
+
O and OH in aqueous
−
solutions.
Water (H2O) is an interesting compound in many respects. Here, we will consider its ability to behave as an acid or a base.
In some circumstances, a water molecule will accept a proton and thus act as a Brønsted-Lowry base. We saw an example in the
dissolving of HCl in H2O:
+ −
H C l + H2 O(ℓ) → H3 O (aq) + C l (aq) (10.4.1)
In other circumstances, a water molecule can donate a proton and thus act as a Brønsted-Lowry acid. For example, in the presence
of the amide ion, a water molecule donates a proton, making ammonia as a product:
− −
H2 O(ℓ) + N H (aq) → OH (aq) + N H3 (aq) (10.4.2)
2
In this case, N H2
−
is a Brønsted-Lowry base (the proton acceptor).
So, depending on the circumstances, H2O can act as either a Brønsted-Lowry acid or a Brønsted-Lowry base. Water is not the only
substance that can react as an acid in some cases or a base in others, but it is certainly the most common example—and the most
important one. A substance that can either donate or accept a proton, depending on the circumstances, is called an amphiprotic
compound.
A water molecule can act as an acid or a base even in a sample of pure water. About 6 in every 100 million (6 in 108) water
molecules undergo the following reaction:
+ −
H2 O(ℓ) + H2 O(ℓ) → H3 O (aq) + OH (aq) (10.4.3)
This process is called the autoionization of water (Figure 10.4.1) and occurs in every sample of water, whether it is pure or part of
a solution. Autoionization occurs to some extent in any amphiprotic liquid. (For comparison, liquid ammonia undergoes
autoionization as well, but only about 1 molecule in a million billion (1 in 1015) reacts with another ammonia molecule.)
Figure 10.4.1 Autoionization. A small fraction of water molecules—approximately 6 in 100 million—ionize spontaneously into
hydronium ions and hydroxide ions. This picture necessarily overrepresents the amount of autoionization that really occurs in pure
water.
 Example 10.4.1
Identify water as either a Brønsted-Lowry acid or a Brønsted-Lowry base.
1. H2O(ℓ) + NO2−(aq) → HNO2(aq) + OH−(aq)
2. HC2H3O2(aq) + H2O(ℓ) → H3O+(aq) + C2H3O2−(aq)
Solution
1. In this reaction, the water molecule donates a proton to the NO2− ion, making OH−(aq). As the proton donor, H2O acts as a
Brønsted-Lowry acid.
2. In this reaction, the water molecule accepts a proton from HC2H3O2, becoming H3O+(aq). As the proton acceptor, H2O is a
Brønsted-Lowry base.
 Exercise 10.4.2
Identify water as either a Brønsted-Lowry acid or a Brønsted-Lowry base.

1. HCOOH(aq) + H2O(ℓ) → H3O+(aq) + HCOO−(aq)
2. H2O(ℓ) + PO43−(aq) → OH−(aq) + HPO42−(aq)
Answer
1. H2O acts as the proton acceptor (Brønsted-Lowry base)
2. H2O acts as the proton donor (Brønsted-Lowry acid)
Dissociation of Water
As we have already seen, H2O can act as an acid or a base. Within any given sample of water, some H 2
O molecules are acting as
acids, and other H O molecules are acting as bases. The chemical equation is as follows:
2
+ −
H O+H O −
↽⇀
− H O + OH (10.4.4)
2 2 3
 
acid base
Figure 10.4.2 : Autoionization of water, giving hydroxide and hydronium ions.

Similar to a weak acid, the autoionization of water is an equilibrium process, and is more properly written as follows:
+ −
H O(ℓ) + H O(ℓ) −
↽⇀
− H O (aq) + OH (aq) (10.4.5)
2 2 3
We often use the simplified form of the reaction:

+
H O(l) −
↽⇀
− H (aq) + OH − (aq)
2
The equilibrium constant for the autoionization of water is referred to as the ion-product for water and is given the symbol K . w
+ −
Kw = [ H ][ OH ]
The ion-product constant for water (K ) is the mathematical product of the concentration of hydrogen ions and hydroxide ions.
w
Note that H2O is not included in the ion-product expression because it is a pure liquid. The value of K is very small, in w
accordance with a reaction that favors the reactants. At 25oC, the experimentally determined value of K in pure water is w
1.0×10−14.
+ − −14
Kw = [ H ][ OH ] = 1.0 × 10
In a sample of pure water, the concentrations of hydrogen and hydroxide ions are equal to one another. Pure water or any other
aqueous solution in which this ratio holds is said to be neutral. To find the molarity of each ion, the square root of K is taken. w
+ − −7
[H ] = [OH ] = 1.0×10
−14
The product of these two concentrations is 1.0×10
+ − −7 −7 −14
[H ]×[ OH ] = (1.0 × 10 )(1.0 × 10 ) = 1.0 × 10
For acids, the concentration of H+ or [H+] is greater than 1.0×10−7 M

For bases, the concentration of OH− or [OH−] is greater than 1.0×10−7 M.
Aqueous HCl is an example of acidic solution. Hydrogen chloride (HCl) ionizes to produce H+ and Cl− ions upon dissolving in
water. This increases the concentration of H+ ions in the solution. According to Le Chatelier's principle, the equilibrium represented
by
+ −
H O(l) −
↽⇀
− H (aq) + OH (aq)
2
+ −
HCl(g) ⟶ H (aq) + Cl (aq)
is forced to the left, towards the reactant. As a result, the concentration of the hydroxide ion decreases.
Now, consider KOH (aq), a basic solution. Solid potassium hydroxide (KOH) dissociates in water to yield potassium ions and
hydroxide ions.
KOH(s) → K+(aq) + OH−(aq)
The increase in concentration of the OH− ions will cause a decrease in the concentration of the H+ ions.
No matter whether the aqueous solution is an acid, a base, or neutral:and the ion-product of [H+][OH−] remains constant.
For acidic solutions, [H+] is greater than [OH−].
For basic solutions, [OH−] is greater than [H+].
For neutral solutions, [H3O+] = [OH−] = 1.0×10−7M
This means that if you know [H ] for a solution, you can calculate what [OH ]) has to be for the product to equal 1.0 × 10 , or
+ − −14
if you know [OH ]), you can calculate [H ]. This also implies that as one concentration goes up, the other must go down to
− +
compensate so that their product always equals the value of K . w
+ − −14
Kw = [ H O ][ OH ] = 1.0 × 10 (10.4.6)
3
 Example 10.4.2
Hydrochloric acid (HCl) is a strong acid, meaning it is 100% ionized in solution. What is the [H+] and the [OH−] in a solution
of 2.0×10−3 M HCl?
Solution
Step 1: List the known values and plan the problem.
Known
[HCl] = 2.0×10−3 M
Kw = 1.0×10−14
Unknown
[H+]=?M
[OH−]=?M
Because HCl is 100% ionized, the concentration of H+ ions in solution will be equal to the original concentration of HCl. Each
HCl molecule that was originally present ionizes into one H+ ion and one Cl− ion. The concentration of OH− can then be
determined from the [H+] and Kw.
Step 2: Solve.
[H+]=2.0×10−3 M
Kw = [H+][OH−] = 1.0×10−14
[OH−] = Kw/[H+] = 1.0×10−14/2.0×10−3 = 5.0×10−12 M
The [H+] is much higher than the [OH−] because the solution is acidic. As with other equilibrium constants, the unit for Kw is
customarily omitted.
 Exercise 10.4.2
Sodium hydroxide (NaOH) is a strong base. What is the [H+] and the [OH−] in a 0.001 M NaOH solution at 25 °C?
Answer
[OH−] = 0.001M or 1 x 10-3M; [H+]=1×10−11M.

1. Explain how water can act as an acid.
2. Explain how water can act as a base.
Answers
1. Under the right conditions, H2O can donate a proton, making it a Brønsted-Lowry acid.
2. Under the right conditions, H2O can accept a proton, making it a Brønsted-Lowry base.
Key Takeaway
Water molecules can act as both an acid and a base, depending on the conditions.
Exercises
1. Is H2O(ℓ) acting as an acid or a base?
H2O(ℓ) + NH4+(aq) → H3O+(aq) + NH3(aq)
2. Is H2O(ℓ) acting as an acid or a base?
CH3−(aq) + H2O(ℓ) → CH4(aq) + OH−(aq)
3. In the aqueous solutions of some salts, one of the ions from the salt can react with water molecules. In some C2H3O2− solutions,
the following reaction can occur:
C2H3O2−(aq) + H2O(ℓ) → HC2H3O2(aq) + OH−(aq)
Is H2O acting as an acid or a base in this reaction?
4. In the aqueous solutions of some salts, one of the ions from the salt can react with water molecules. In some NH4+ solutions, the
following reaction can occur:
NH4+(aq) + H2O → NH3(aq) + H3O+(aq)
Is H2O acting as an acid or a base in this reaction?
5. Why is pure water considered neutral?
Answers
1. base
2. acid
3. acid
4. base
5. When water ionizes, equal amounts of H+ (acid) and OH− (base) are formed, so the solution is neither acidic nor basic: H2O(ℓ)
→ H+(aq) + OH−(aq)
[SIDE NOTE: It is rare to truly have pure water. Water exposed to air will usually be slightly acidic because dissolved carbon
dioxide gas, or carbonic acid, decreases the pH slightly below 7. Alternatively, dissolved minerals, like calcium carbonate
(limestone), can make water slightly basic.]
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Define the pH scale and use it to describe acids and bases.
Calculate the pH of a solution from [H O ] and [OH ].
3
+ −
Knowing the amount of acid and base in solutions is extremely important for a wide variety of applications ranging from brewing
beer or wine to studying the effects of ocean acidification to health and medicine. Scientists are good at calculating and measuring
the concentration of hydronium in a solution, however, there is a more convenient way to make comparisons between solutions –
the pH scale.
The pH Scale
One qualitative measure of the strength of an acid or a base solution is the pH scale, which is based on the concentration of the
hydronium (or hydrogen) ion in aqueous solution.
+
pH = − log[ H ]
or
+
pH = − log[ H3 O ]
Figure 10.5.1 illustrates this relationship, along with some examples of various solutions. Because hydrogen ion concentrations are
generally less than one (for example 1.3 × 10 M ), the log of the number will be a negative number. To make pH even easier to
−3
work with, pH is defined as the negative log of [H O ], which will give a positive value for pH.
3
+
Figure 10.5.1 : The relationaship between [H+] and pH values for several common materials.
A neutral (neither acidic nor basic) solution has a pH of 7. A pH below 7 means that a solution is acidic, with lower values of pH
corresponding to increasingly acidic solutions. A pH greater than 7 indicates a basic solution, with higher values of pH
corresponding to increasingly basic solutions. Thus, given the pH of several solutions, you can state which ones are acidic, which
ones are basic, and which are more acidic or basic than others. These are summarized in Table \(\PageIndex{1}.
Table 10.5.1: Acidic, Basic and Neutral pH Values
Classification Relative Ion Concentrations pH at 25 °C
acidic [H+] > [OH−] pH < 7
neutral [H+] = [OH−] pH = 7
Classification
basic Relative[H
Ion Concentrations
+] < [OH−] pHpH
at >257°C
acidic [H+] > [OH−] pH < 7

 Example 10.5.1
neutral [H+] = [OH−] pH = 7
Find the pH, given basic
the [H +
] of the following: [H+] < [OH−] pH > 7
-3
a. 1 ×10 M
b. 2.5 ×10-11 M
c. 4.7 ×10-9 M
Solution
pH = - log [H3O+]
Substitute the known quantity into the equation and solve. Use a scientific calculator for b and c.
a. pH = - log [1 × 10−3 ] = 3.0 (1 decimal place since 1 has 1 significant figure)
b. pH = - log [2.5 ×10-11] = 10.60 (2 decimal places since 2.5 has 2 significant figures)
c. pH = - log [4.7 ×10-9] = 8.33 (2 decimal places since 4.7 has 2 significant figures)
Note on significant figures:
Because the number(s) before the decimal point in the pH value relate to the power on 10, the number of digits after the
decimal point (underlined) is what determines the number of significant figures in the final answer.
 Exercise 10.5.1
Find the pH, given [H+] of the following:

a. 5.8 ×10-4 M
b. 1.0×10-7 M
Answer
a. 3.24
b. 7.00
Figure 10.5.2 lists the pH of several common solutions. The most acidic among the listed solutions is 1 M HCl with the lowest pH
value (0.0): battery acid is the next most acidic solution with a pH value of 0.3. The most basic is 1M NaOH solution with the
highest pH value of 14.0. Notice that some biological fluids (stomach acid and urine) are nowhere near neutral. You may also
notice that many food products are slightly acidic. They are acidic because they contain solutions of weak acids. If the acid
components of these foods were strong acids, the food would likely be inedible.
Figure 10.5.2 : A Plot of pH versus [H+] for Some Common Aqueous Solutions. Although many substances exist in a range of pH
values (indicated in parentheses), they are plotted using typical values.
 Example 10.5.2
Label each solution as acidic, basic, or neutral based only on the stated pH.
a. milk of magnesia, pH = 10.5
b. pure water, pH = 7
c. wine, pH = 3.0
Solution
a. With a pH greater than 7, milk of magnesia is basic. (Milk of magnesia is largely Mg(OH)2.)
b. Pure water, with a pH of 7, is neutral.
c. With a pH of less than 7, wine is acidic.
 Exercise 10.5.2
Identify each substance as acidic, basic, or neutral based only on the stated pH.
a. human blood with pH = 7.4
b. household ammonia with pH = 11.0
c. cherries with pH = 3.6
Answer
a. slightly basic
b. basic
c. acidic
Measuring pH
Tools have been developed that make the measurement of pH simple and convenient. For example, pH paper (Figure
10.5.3)consists of strips of paper impregnated with one or more acid-base indicators, which are intensely colored organic
molecules whose colors change dramatically depending on the pH of the solution. Placing a drop of a solution on a strip of pH
paper and comparing its color with standards give the solution’s approximate pH. A more accurate tool, the pH meter, uses a glass
electrode, a device whose voltage depends on the H+ ion concentration (Figure 10.5.3).
Figure 10.5.3 : Ways to measure pH. (left) These pH strips can measure pH in a series of ranges by putting sample on a strip and
comparing its color change with colors on the box that correspond to a certain pH. The strip on the left measures pH 0-7 and shows
results of a strong acid sample; the center strip is pH range 5-10 and shows results of a 6.97 buffer solution sample; the strip on the
right measures a broad range (pH 1-14) and shows results of a 10% bleach water solution sample. This image can be enlarged by
clicking on it. (right) These three meters and probes can measure pH (left) and electrical conductivity (center and right). Photos by
Monica Bruckner (courtesy of the Science Education Resource Center (SERC) at Carleton College).
 Acid Rain
Normal rainwater has a pH between 5 and 6 due to the presence of dissolved CO2 which forms carbonic acid:
H O(l) + CO (g) ⟶ H CO (aq) (10.5.1)
2 2 2 3
+ −
H CO (aq) ⇌ H (aq) + HCO (aq) (10.5.2)
2 3 3
Acid rain is rainwater that has a pH of less than 5, due to a variety of nonmetal oxides, including CO2, SO2, SO3, NO, and NO2
being dissolved in the water and reacting with it to form not only carbonic acid, but sulfuric acid and nitric acid. The formation
and subsequent ionization of sulfuric acid are shown here:
H O(l) + SO (g) ⟶ H SO (aq) (10.5.3)
2 3 2 4
+ −
H SO (aq) ⟶ H (aq) + HSO (aq) (10.5.4)
2 4 4
Carbon dioxide is naturally present in the atmosphere because we and most other organisms produce it as a waste product of
metabolism. Carbon dioxide is also formed when fires release carbon stored in vegetation or when we burn wood or fossil
fuels. Sulfur trioxide in the atmosphere is naturally produced by volcanic activity, but it also stems from burning fossil fuels,
which have traces of sulfur, and from the process of “roasting” ores of metal sulfides in metal-refining processes. Oxides of
nitrogen are formed in internal combustion engines where the high temperatures make it possible for the nitrogen and oxygen
in air to chemically combine.
Acid rain is a particular problem in industrial areas where the products of combustion and smelting are released into the air
without being stripped of sulfur and nitrogen oxides. In North America and Europe until the 1980s, it was responsible for the
destruction of forests and freshwater lakes, when the acidity of the rain actually killed trees, damaged soil, and made lakes
uninhabitable for all but the most acid-tolerant species. Acid rain also corrodes statuary and building facades that are made of
marble and limestone (Figure 10.5.4). Regulations limiting the amount of sulfur and nitrogen oxides that can be released into
the atmosphere by industry and automobiles have reduced the severity of acid damage to both natural and manmade
environments in North America and Europe. It is now a growing problem in industrial areas of China and India.
Figure 10.5.4: (a) Acid rain makes trees more susceptible to drought and insect infestation, and depletes nutrients in the soil.
(b) It also is corrodes statues that are carved from marble or limestone. (credit a: modification of work by Chris M Morris;
credit b: modification of work by “Eden, Janine and Jim”/Flickr)
10.5: Measuring Acidity in Aqueous Solutions- The pH Scale is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or
Calculate pH from [H 3O
+
] and [H3O
+
] from pH.
Calculating pH from Hydronium Concentration

The pH of solutions can be determined by using logarithms as illustrated in the next example for stomach acid. Stomach acid is a
solution of H C l with a hydronium ion concentration of 1.2 × 10 M , what is the pH of the solution?
−3
+
pH = − log[ H3 O ]
−3
= − log(1.2 × 10 ) (10.6.1)
= −(−2.92) = 2.92
 Logarithms
To get the log value on your calculator, enter the number (in this case, the hydronium ion concentration) first, then press the
LOG key.
If the number is 1.0 x 10-5 (for [H3O+] = 1.0 x 10-5 M) you should get an answer of "-5".
If you get a different answer, or an error, try pressing the LOG key before you enter the number.
 Example 10.6.2: Converting Ph to Hydronium Concentration
Find the pH, given the [H 3O

+
] of the following:
-3
a. 1 ×10 M
b. 2.5 ×10-11 M
c. 4.7 ×10-9 M
Solution
Steps for Problem Solving
Given:
a. [H3O+] =1 × 10−3 M
Identify the "given" information and what the problem is asking you
b. [H3O+] =2.5 ×10-11 M
to "find."
c. [H3O+] = 4.7 ×10-9 M
Find: ? pH
Need to use the expression for pH (Equation ???).
Plan the problem.
pH = - log [H3O+]
Now substitute the known quantity into the equation and solve.
a. pH = - log [1 × 10−3 ] = 3.0 (1 decimal places since 1 has 1
significant figure)
b. pH = - log [2.5 ×10-11] = 10.60 (2 decimal places since 2.5 has 2
significant figures)
c. pH = - log [4.7 ×10-9] = 8.30 (2 decimal places since 4.7 has 2
significant figures)
Calculate.
The other issue that concerns us here is significant figures. Because
the number(s) before the decimal point in a logarithm relate to the
power on 10, the number of digits after the decimal point is what
determines the number of significant figures in the final answer:
 Exercise 10.6.2
Find the pH, given [H3O+] of the following:

a. 5.8 ×10-4 M
b. 1.0×10-7
Answer a
3.22
Answer b
7.00
Calculating Hydronium Concentration from pH

Sometimes you need to work "backwards"—you know the pH of a solution and need to find [H O ], or even the concentration of
3
+
the acid solution. How do you do that? To convert pH into [H O ] we solve Equation ??? for [H O ]. This involves taking the
3
+
3
+
antilog (or inverse log) of the negative value of pH .

+
[H O ] = antilog(−pH ) (10.6.2)
3
or
+ −pH
[H O ] = 10 (10.6.3)
3
As mentioned above, different calculators work slightly differently—make sure you can do the following calculations using your
calculator.
 Calculator Skills
We have a solution with a pH = 8.3. What is [H3O+] ?
With some calculators you will do things in the following order:
1. Enter 8.3 as a negative number (use the key with both the +/- signs, not the subtraction key).
2. Use your calculator's 2nd or Shift or INV (inverse) key to type in the symbol found above the LOG key. The shifted
function should be 10x.
3. You should get the answer 5.0 × 10-9.
Other calculators require you to enter keys in the order they appear in the equation.
1. Use the Shift or second function to key in the 10x function.
2. Use the +/- key to type in a negative number, then type in 8.3.
3. You should get the answer 5.0 × 10-9.
If neither of these methods work, try rearranging the order in which you type in the keys. Don't give up—you must master your
calculator!
 Example 10.6.3: Calculating Hydronium Concentration from pH
Find the hydronium ion concentration in a solution with a pH of 12.6. Is this solution an acid or a base? How do you know?
Solution
Identify the "given" information and what the problem is asking you Given: pH = 12.6
to "find." Find: [H3O+] = ? M
Need to use the expression for [H3O+] (Equation 10.6.3 ).

Plan the problem.
[H3O+] = antilog (-pH) or [H3O+] = 10-pH
Now substitute the known quantity into the equation and solve.
[H3O+] = antilog (12.60) = 2.5 x 10-13 M (2 significant figures since
4.7 has 12.60 2 decimal places)
or
[H3O+] = 10-12.60 = 2.5 x 10-13 M (2 significant figures since 4.7 has
12.60 2 decimal places)
Calculate. The other issue that concerns us here is significant figures. Because
the number(s) before the decimal point in a logarithm relate to the
power on 10, the number of digits after the decimal point is what
determines the number of significant figures in the final answer:
 Exercise 10.6.3
If moist soil has a pH of 7.84, what is [H3O+] of the soil solution?
Answer
1.5 x 10-8 M
10.6: Working with pH is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
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Identify a salt solution as acidic, basic, or neutral.
A salt is an ionic compound that is formed when an acid and a base neutralize each other. While it may seem that salt solutions are
always neutral, they can frequently be either acidic or basic.
Consider the salt formed when the weak acid hydrofluoric acid is neutralized by the strong base sodium hydroxide. The molecular
and net ionic equations are shown below.
HF (aq) + NaOH (aq) → NaF (aq) + H O (l)

2
− −
HF (aq) + OH (aq) → F (aq) + H O (l)
2
Since sodium fluoride is soluble, the sodium ion is a spectator ion in the neutralization reaction. The fluoride ion is capable of
reacting, to a small extent, with water, accepting a proton.
− −
F (aq) + H O (l) ⇌ HF (aq) + OH (aq)
2
The fluoride ion is acting as a weak Brønsted-Lowry base. The hydroxide ion that is produced as a result of the above reaction
makes the solution slightly basic. Salt hydrolysis is a reaction in which one of the ions from a salt reacts with water, forming either
an acidic or basic solution.
Salts That Form Basic Solutions

When solid sodium fluoride is dissolved into water, it completely dissociates into sodium ions and fluoride ions. The sodium ions
do not have any capability of hydrolyzing, but the fluoride ions hydrolyze to produce a small amount of hydrofluoric acid and
hydroxide ion.
− −
F (aq) + H O (l) ⇌ HF (aq) + OH (aq)
2
Salts that are derived from the neutralization of a weak acid (HF) by a strong base (NaOH) will always produce salt solutions that
are basic.
Salts That Form Acidic Solutions

Ammonium chloride (NH Cl) is a salt that is formed when the strong acid HCl is neutralized by the weak base NH . Ammonium
4 3
chloride is soluble in water. The chloride ion produced is incapable of hydrolyzing because it is the conjugate base of the strong
acid HCl. In other words, the Cl ion cannot accept a proton from water to form HCl and OH , as the fluoride ion did in the
− −
previous section. However, the ammonium ion is capable of reacting slightly with water, donating a proton and so acting as an acid.
+ +
NH (aq) + H O (l) ⇌ H O (aq) + NH (aq)
4 2 3 3
Salts That Form Neutral Solutions

A salt that is derived from the reaction of a strong acid with a strong base forms a solution that has a pH of 7. An example is
sodium chloride, formed from the neutralization of HCl by NaOH. A solution of NaCl in water has no acidic or basic properties,
since neither ion is capable of hydrolyzing. Other salts that form neutral solutions include potassium nitrate (KNO ) and lithium 3
bromide (LiBr). The table below summarizes how to determine the acidity or basicity of a salt solution.
Table 10.9.1
Salt formed from: Salt Solution
Strong acid + Strong base Neutral
Strong acid + Weak base Acidic
Weak acid + Strong base Basic
Salts formed from the reaction of a weak acid and a weak base are more difficult to analyze due to competing hydrolysis reactions
between the cation and the anion. These salts are not considered in this chapter's concept.
Summary
Salt hydrolysis is a reaction in which one of the ions from a salt reacts with water, forming either an acidic or basic solution.
Salts that are derived from the neutralization of a weak acid by a strong base will always produce salt solutions that are basic.
Salts that are derived from the neutralization of a strong acid by a weak base will always produce salt solutions that are acidic.
A salt that is derived from the reaction of a strong acid with a strong base forms a solution that has a pH of 7.
10.9: Acidity and Basicity of Salt Solutions is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by
LibreTexts.
21.21: Hydrolysis of Salts - Equations by CK-12 Foundation is licensed CK-12. Original source: https://flexbooks.ck12.org/cbook/ck-12-
Describe the composition and function of acid–base buffers
Calculate the pH of a buffer before and after the addition of added acid or base
A mixture of a weak acid and its conjugate base (or a mixture of a weak base and its conjugate acid) is called a buffer solution, or a
buffer. Buffer solutions resist a change in pH when small amounts of a strong acid or a strong base are added (Figure 10.10.1). A
solution of acetic acid (CH COOH and sodium acetate CH COONa) is an example of a buffer that consists of a weak acid and
3 3
its salt. An example of a buffer that consists of a weak base and its salt is a solution of ammonia (NH (aq)) and ammonium
3
chloride (NH Cl(aq)).

4
Figure 10.10.1: (a) The unbuffered solution on the left and the buffered solution on the right have the same pH (pH 8); they are
basic, showing the yellow color of the indicator methyl orange at this pH. (b) After the addition of 1 mL of a 0.01-M HCl solution,
the buffered solution has not detectably changed its pH but the unbuffered solution has become acidic, as indicated by the change
in color of the methyl orange, which turns red at a pH of about 4. (credit: modification of work by Mark Ott)
How Buffers Work

A mixture of acetic acid and sodium acetate is acidic because the Ka of acetic acid is greater than the Kb of its conjugate base
acetate. It is a buffer because it contains both the weak acid and its salt. Hence, it acts to keep the hydronium ion concentration (and
the pH) almost constant by the addition of either a small amount of a strong acid or a strong base. If we add a base such as sodium
hydroxide, the hydroxide ions react with the few hydronium ions present. Then more of the acetic acid reacts with water, restoring
the hydronium ion concentration almost to its original value:
+ −
CH CO H(aq) + H O(l) ⟶ H O (aq) + CH CO2 (aq)
3 2 2 3 3
The pH changes very little. If we add an acid such as hydrochloric acid, most of the hydronium ions from the hydrochloric acid
combine with acetate ions, forming acetic acid molecules:
+ −
H O (aq) + CH CO2 (aq) ⟶ CH CO H(aq) + H O(l)
3 3 3 2 2
Thus, there is very little increase in the concentration of the hydronium ion, and the pH remains practically unchanged (Figure
10.10.2).
Figure 10.10.2: This diagram shows the buffer action of these reactions.
A mixture of ammonia and ammonium chloride is basic because the Kb for ammonia is greater than the Ka for the ammonium ion.
It is a buffer because it also contains the salt of the weak base. If we add a base (hydroxide ions), ammonium ions in the buffer
react with the hydroxide ions to form ammonia and water and reduce the hydroxide ion concentration almost to its original value:
+ −
NH (aq) + OH (aq) ⟶ NH (aq) + H O(l)
4 3 2
If we add an acid (hydronium ions), ammonia molecules in the buffer mixture react with the hydronium ions to form ammonium
ions and reduce the hydronium ion concentration almost to its original value:
+ +
H O (aq) + NH (aq) ⟶ NH (aq) + H O(l)
3 3 4 2
The three parts of the following example illustrate the change in pH that accompanies the addition of base to a buffered solution of
a weak acid and to an unbuffered solution of a strong acid.
 Example 10.10.1: pH Changes in Buffered and Unbuffered Solutions
Acetate buffers are used in biochemical studies of enzymes and other chemical components of cells to prevent pH changes that
might change the biochemical activity of these compounds.
a. Calculate the pH of an acetate buffer that is a mixture with 0.10 M acetic acid and 0.10 M sodium acetate.
b. Calculate the pH after 1.0 mL of 0.10 M NaOH is added to 100 mL of this buffer, giving a solution with a volume of 101
mL.
Solution
a. Calculate the pH of an acetate buffer that is a mixture with 0.10 M acetic acid and 0.10 M sodium acetate.
To determine the pH of the buffer solution we use a typical equilibrium calculation (as illustrated in earlier Examples):
1. Determine the direction of change. The equilibrium in a mixture of H3O+, CH 3

−
CO
2
, and CH3CO2H is:
+ −
CH CO H(aq) + H O(l) ⇌ H O (aq) + CH CO (aq)
3 2 2 3 3 2
The equilibrium constant for CH3CO2H is not given, so we look it up in Table E1: Ka = 1.8 × 10−5. With [CH3CO2H] =
+ +
[ CH CO ] = 0.10 M and [H3O ] = ~0 M, the reaction shifts to the right to form H3O .
−
3 2
2. Determine x and equilibrium concentrations. A table of changes and concentrations follows:
Solve for x and the equilibrium concentrations. We find:

−5
x = 1.8 × 10 M
and
+ −5
[H O ] = 0 + x = 1.8 × 10 M
3
Thus:
+ −5
pH = −log[ H3 O ] = −log(1.8 × 10 )
= 4.74
4. Check the work. If we calculate all calculated equilibrium concentrations, we find that the equilibrium value of the
reaction coefficient, Q = Ka.
(b) Calculate the pH after 1.0 mL of 0.10 M NaOH is added to 100 mL of this buffer, giving a solution with a volume of 101
mL.
First, we calculate the concentrations of an intermediate mixture resulting from the complete reaction between the acid in the
buffer and the added base. Then we determine the concentrations of the mixture at the new equilibrium:
1. Determine the moles of NaOH. One milliliter (0.0010 L) of 0.10 M NaOH contains:
0.10 mol NaOH

−4
0.0010 L × ( ) = 1.0 × 10 mol NaOH
1 L
2. Determine the moles of CH2CO2H. Before reaction, 0.100 L of the buffer solution contains:
0.100 mol C H3 C O2 H
−2
0.100 L × ( ) = 1.00 × 10 mol C H3 C O2 H
1 L
3. Solve for the amount of NaCH3CO2 produced. The 1.0 × 10−4 mol of NaOH neutralizes 1.0 × 10−4 mol of CH3CO2H,
leaving:
−2 −2 −2
(1.0 × 10 ) − (0.01 × 10 ) = 0.99 × 10 mol C H3 C O2 H
and producing 1.0 × 10−4 mol of NaCH3CO2. This makes a total of:
[\mathrm{(1.0×10^{−2})+(0.01×10^{−2})=1.01×10^{−2}\:mol\:NaCH_3CO_2} \nonumber \]
4. Find the molarity of the products. After reaction, CH3CO2H and NaCH3CO2 are contained in 101 mL of the intermediate
solution, so:
−3
9.9 × 10 mol
[ CH CO H] = = 0.098 M
3 2
0.101 L
−2
1.01 × 10 mol
[ NaCH CO ] = = 0.100 M
3 2
0.101 L
Now we calculate the pH after the intermediate solution, which is 0.098 M in CH3CO2H and 0.100 M in NaCH3CO2, comes to
equilibrium. The calculation is very similar to that in part (a) of this example:
This series of calculations gives a pH = 4.75. Thus the addition of the base barely changes the pH of the solution.
(c) For comparison, calculate the pH after 1.0 mL of 0.10 M NaOH is added to 100 mL of a solution of an unbuffered solution
with a pH of 4.74 (a 1.8 × 10−5-M solution of HCl). The volume of the final solution is 101 mL.
Solution
This 1.8 × 10−5-M solution of HCl has the same hydronium ion concentration as the 0.10-M solution of acetic acid-sodium
acetate buffer described in part (a) of this example. The solution contains:
−5
1.8 × 10 mol HCl
−6
0.100 L × ( ) = 1.8 × 10 mol HCl
1 L
As shown in part (b), 1 mL of 0.10 M NaOH contains 1.0 × 10−4 mol of NaOH. When the NaOH and HCl solutions are mixed,
the HCl is the limiting reagent in the reaction. All of the HCl reacts, and the amount of NaOH that remains is:
−4 −6 −5
(1.0 × 10 ) − (1.8 × 10 ) = 9.8 × 10 M
The concentration of NaOH is:

−5
9.8 × 10 M NaOH −4
= 9.7 × 10 M
0.101 L
The pOH of this solution is:

− −4
pOH = −log[OH ] = −log(9.7 × 10 ) = 3.01
The pH is:
pH = 14.00 − pOH = 10.99
The pH changes from 4.74 to 10.99 in this unbuffered solution. This compares to the change of 4.74 to 4.75 that occurred when
the same amount of NaOH was added to the buffered solution described in part (b).
 Exercise 10.10.1
Show that adding 1.0 mL of 0.10 M HCl changes the pH of 100 mL of a 1.8 × 10−5 M HCl solution from 4.74 to 3.00.
Answer
Initial pH of 1.8 × 10−5 M HCl; pH = −log[H3O+] = −log[1.8 × 10−5] = 4.74
Moles of H3O+ added by addition of 1.0 mL of 0.10 M HCl: 0.10 moles/L × 0.0010 L = 1.0 × 10−4 moles; final pH after
addition of 1.0 mL of 0.10 M HCl:
⎛ ⎞
+ −4 −6
+
total moles H3 O ⎜ 1.0 × 10 mol + 1.8 × 10 mol ⎟
pH = −log[ H3 O ] = −log ( ) = −log ⎜ ⎟ = 3.00
total volume ⎜ 1 L ⎟
101 mL ( )
⎝ ⎠
1000 mL
Buffer Capacity
Buffer solutions do not have an unlimited capacity to keep the pH relatively constant (Figure 10.10.3). If we add so much base
to a buffer that the weak acid is exhausted, no more buffering action toward the base is possible. On the other hand, if we add an
excess of acid, the weak base would be exhausted, and no more buffering action toward any additional acid would be possible.
In fact, we do not even need to exhaust all of the acid or base in a buffer to overwhelm it; its buffering action will diminish
rapidly as a given component nears depletion.
Figure 10.10.3: The indicator color (methyl orange) shows that a small amount of acid added to a buffered solution of pH 8
(beaker on the left) has little affect on the buffered system (middle beaker). However, a large amount of acid exhausts the
buffering capacity of the solution and the pH changes dramatically (beaker on the right). (credit: modification of work by Mark
Ott)
The buffer capacity is the amount of acid or base that can be added to a given volume of a buffer solution before the pH changes
significantly, usually by one unit. Buffer capacity depends on the amounts of the weak acid and its conjugate base that are in a
buffer mixture. For example, 1 L of a solution that is 1.0 M in acetic acid and 1.0 M in sodium acetate has a greater buffer
capacity than 1 L of a solution that is 0.10 M in acetic acid and 0.10 M in sodium acetate even though both solutions have the
same pH. The first solution has more buffer capacity because it contains more acetic acid and acetate ion.
Selection of Suitable Buffer Mixtures

There are two useful rules of thumb for selecting buffer mixtures:
1. A good buffer mixture should have about equal concentrations of both of its components. A buffer solution has generally
lost its usefulness when one component of the buffer pair is less than about 10% of the other. Figure 10.10.4 shows an acetic
acid-acetate ion buffer as base is added. The initial pH is 4.74. A change of 1 pH unit occurs when the acetic acid
concentration is reduced to 11% of the acetate ion concentration.
Figure 10.10.4: The graph, an illustration of buffering action, shows change of pH as an increasing amount of a 0.10-M
NaOH solution is added to 100 mL of a buffer solution in which, initially, [CH CO H] = 0.10 M and 3 2
[CH CO ] = 0.10 M .
−
3 2
2. Weak acids and their salts are better as buffers for pHs less than 7; weak bases and their salts are better as buffers for pHs
greater than 7.
Blood is an important example of a buffered solution, with the principal acid and ion responsible for the buffering action being
carbonic acid, H2CO3, and the bicarbonate ion, HCO . When an excess of hydrogen ion enters the blood stream, it is removed
−
3
primarily by the reaction:

+ −
H O (aq) + HCO (aq) ⟶ H CO (aq) + H O(l)
3 3 2 3 2
When an excess of the hydroxide ion is present, it is removed by the reaction:

− −
OH (aq) + H CO (aq) ⟶ HCO (aq) + H O(l)
2 3 3 2
The pH of human blood thus remains very near 7.35, that is, slightly basic. Variations are usually less than 0.1 of a pH unit. A
change of 0.4 of a pH unit is likely to be fatal.
The Henderson-Hasselbalch Approximation

The ionization-constant expression for a solution of a weak acid can be written as:
+ −
[H O ][ A ]
3
Ka =
[HA]
Rearranging to solve for [H3O+], we get:
+
[HA]
[H O ] = Ka ×
3 −
[A ]
Taking the negative logarithm of both sides of this equation, we arrive at:
[HA]
+
−log[ H3 O ] = −log Ka − log
−
[A ]
which can be written as

−
[A ]
pH = pKa + log
[HA]
where pKa is the negative of the common logarithm of the ionization constant of the weak acid (pKa = −log Ka). This equation
relates the pH, the ionization constant of a weak acid, and the concentrations of the weak acid and its salt in a buffered solution.
Scientists often use this expression, called the Henderson-Hasselbalch approximation, to calculate the pH of buffer solutions. It
is important to note that the “x is small” assumption must be valid to use this equation.
 Lawrence Joseph Henderson and Karl Albert Hasselbalch
Lawrence Joseph Henderson (1878–1942) was an American physician, biochemist and physiologist, to name only a few of
his many pursuits. He obtained a medical degree from Harvard and then spent 2 years studying in Strasbourg, then a part of
Germany, before returning to take a lecturer position at Harvard. He eventually became a professor at Harvard and worked
there his entire life. He discovered that the acid-base balance in human blood is regulated by a buffer system formed by the
dissolved carbon dioxide in blood. He wrote an equation in 1908 to describe the carbonic acid-carbonate buffer system in
blood. Henderson was broadly knowledgeable; in addition to his important research on the physiology of blood, he also
wrote on the adaptations of organisms and their fit with their environments, on sociology and on university education. He
also founded the Fatigue Laboratory, at the Harvard Business School, which examined human physiology with specific
focus on work in industry, exercise, and nutrition.
In 1916, Karl Albert Hasselbalch (1874–1962), a Danish physician and chemist, shared authorship in a paper with Christian
Bohr in 1904 that described the Bohr effect, which showed that the ability of hemoglobin in the blood to bind with oxygen
was inversely related to the acidity of the blood and the concentration of carbon dioxide. The pH scale was introduced in
1909 by another Dane, Sørensen, and in 1912, Hasselbalch published measurements of the pH of blood. In 1916,
Hasselbalch expressed Henderson’s equation in logarithmic terms, consistent with the logarithmic scale of pH, and thus the
Henderson-Hasselbalch equation was born.
 Medicine: The Buffer System in Blood

The normal pH of human blood is about 7.4. The carbonate buffer system in the blood uses the following equilibrium
reaction:
− +
CO (g) + 2 H O(l) ⇌ H CO (aq) ⇌ HCO (aq) + H O (aq)
2 2 2 3 3 3
The concentration of carbonic acid, H2CO3 is approximately 0.0012 M, and the concentration of the hydrogen carbonate
ion, HCO , is around 0.024 M. Using the Henderson-Hasselbalch equation and the pKa of carbonic acid at body
−
temperature, we can calculate the pH of blood:

[base] 0.024
pH = pKa + log = 6.1 + log = 7.4
[acid] 0.0012
The fact that the H2CO3 concentration is significantly lower than that of the HCO ion may seem unusual, but this
−
imbalance is due to the fact that most of the by-products of our metabolism that enter our bloodstream are acidic.
Therefore, there must be a larger proportion of base than acid, so that the capacity of the buffer will not be exceeded.
Lactic acid is produced in our muscles when we exercise. As the lactic acid enters the bloodstream, it is neutralized by the
HCO
−
3
ion, producing H2CO3. An enzyme then accelerates the breakdown of the excess carbonic acid to carbon dioxide
and water, which can be eliminated by breathing. In fact, in addition to the regulating effects of the carbonate buffering
system on the pH of blood, the body uses breathing to regulate blood pH. If the pH of the blood decreases too far, an
increase in breathing removes CO2 from the blood through the lungs driving the equilibrium reaction such that [H3O+] is
lowered. If the blood is too alkaline, a lower breath rate increases CO2 concentration in the blood, driving the equilibrium
reaction the other way, increasing [H+] and restoring an appropriate pH.
Summary
A solution containing a mixture of an acid and its conjugate base, or of a base and its conjugate acid, is called a buffer solution.
Unlike in the case of an acid, base, or salt solution, the hydronium ion concentration of a buffer solution does not change greatly
when a small amount of acid or base is added to the buffer solution. The base (or acid) in the buffer reacts with the added acid
(or base).
Key Equations
pKa = −log Ka
pKb = −log Kb
−
[A ]
pH = pKa + log
[HA]
Glossary
buffer capacity
amount of an acid or base that can be added to a volume of a buffer solution before its pH changes significantly (usually by
one pH unit)
buffer
mixture of a weak acid or a weak base and the salt of its conjugate; the pH of a buffer resists change when small amounts of
acid or base are added
Henderson-Hasselbalch equation
equation used to calculate the pH of buffer solutions
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14.6: Buffers by OpenStax is licensed CC BY 4.0. Original source: https://openstax.org/details/books/chemistry-2e.
10.11: Titration
Describe a titration experiment.
Explain what an indicator does.
Perform a titration calculation correctly.
The reaction of an acid with a base to make a salt and water is a common reaction in the laboratory, partly because many
compounds can act as acids or bases. Another reason that acid-base reactions are so prevalent is because they are often used to
determine quantitative amounts of one or the other. Performing chemical reactions quantitatively to determine the exact amount of
a reagent is called a titration. A titration can be performed with almost any chemical reaction for which the balanced chemical
equation is known. Here, we will consider titrations that involve acid-base reactions.
In a titration, one reagent has a known concentration or amount, while the other reagent has an unknown concentration or amount.
Typically, the known reagent (the titrant) is added to the unknown quantity and is dissolved in solution. The unknown amount of
substance (the analyte) may or may not be dissolved in solution (but usually is). The titrant is added to the analyte using a
precisely calibrated volumetric delivery tube called a burette (also spelled buret; see Figure 10.11.1). The burette has markings to
determine how much volume of solution has been added to the analyte. When the reaction is complete, it is said to be at the
equivalence point; the number of moles of titrant can be calculated from the concentration and the volume, and the balanced
chemical equation can be used to determine the number of moles (and then concentration or mass) of the unknown reactant.
Figure 10.11.1 Equipment for Titrations. A burette is a type of liquid dispensing system that can accurately indicate the volume of
liquid dispensed.
For example, suppose 25.66 mL (or 0.02566 L) of 0.1078 M HCl was used to titrate an unknown sample of NaOH. What mass of
NaOH was in the sample? We can calculate the number of moles of HCl reacted:
# mol HCl = (0.02566 L)(0.1078 M) = 0.002766 mol HCl
We also have the balanced chemical reaction between HCl and NaOH:
HCl + NaOH → NaCl + H2O
So we can construct a conversion factor to convert to number of moles of NaOH reacted:
1 mol N aOH
0.002766 mol H C l × = 0.002766 mol N aOH
1 mol H C l
Then we convert this amount to mass, using the molar mass of NaOH (40.00 g/mol):
40.00 g N aOH
0.002766 mol H C l × = 0.1106 g N aOH
1 mol H C l
This type of calculation is performed as part of a titration.
 Example 10.11.1
What mass of Ca(OH)2 is present in a sample if it is titrated to its equivalence point with 44.02 mL of 0.0885 M HNO3? The
balanced chemical equation is as follows:
2HNO3 + Ca(OH)2 → Ca(NO3)2 + 2H2O
Solution
In liters, the volume is 0.04402 L. We calculate the number of moles of titrant:
# moles HNO3 = (0.04402 L)(0.0885 M) = 0.00390 mol HNO3
Using the balanced chemical equation, we can determine the number of moles of Ca(OH)2 present in the analyte:
1 mol C a(OH )2
0.00390 mol H N O3 × = 0.00195 mol C a(OH )2
2 mol H N O3
Then we convert this to a mass using the molar mass of Ca(OH)2:

74.1 g C a(OH )2
0.00195 mol C a(OH )2 × = 0.144 g C a(OH )2
mol C a(OH )2
What mass of H2C2O4 is present in a sample if it is titrated to its equivalence point with 18.09 mL of 0.2235 M NaOH? The
balanced chemical reaction is as follows:
H C O + 2 NaOH → Na C O +2 H O
2 2 4 2 2 4 2
Answer
0.182 g
How does one know if a reaction is at its equivalence point? Usually, the person performing the titration adds a small amount of an
indicator, a substance that changes color depending on the acidity or basicity of the solution. Because different indicators change
colors at different levels of acidity, choosing the correct one is important in performing an accurate titration.
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12.4: Acid-Base Titrations by Anonymous is licensed CC BY-NC-SA 3.0. Original source:
CHAPTER OVERVIEW
11: Nuclear Chemistry

Most chemists pay little attention to the nucleus of an atom except to consider the number of protons it contains because that
determines an element’s identity. However, in nuclear chemistry, the composition of the nucleus and the changes that occur there
are very important. Applications of nuclear chemistry may be more widespread than you realize. Many people are aware of nuclear
power plants and nuclear bombs, but nuclear chemistry also has applications ranging from smoke detectors to medicine, from the
sterilization of food to the analysis of ancient artifacts. In this chapter, we will examine some of the basic concepts of nuclear
chemistry and some of the nuclear reactions that are important in our everyday lives.
11.4: Nuclear Decay
11: Nuclear Chemistry is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
1
Describe nuclear structure in terms of protons, neutrons, and electrons
Identify a nuclear reaction
Identify the key characteristics separating nuclear and chemical reactions
Nuclear chemistry is the study of reactions that involve changes in nuclear structure. The chapter on atoms, molecules, and ions
introduced the basic idea of nuclear structure, that the nucleus of an atom is composed of protons and, with the exception of H , 1
1
neutrons. Recall that the number of protons in the nucleus is called the atomic number (Z ) of the element, and the sum of the
number of protons and the number of neutrons is the mass number (A ). Atoms with the same atomic number but different mass
numbers are isotopes of the same element. When referring to a single type of nucleus, we often use the term nuclide and identify it
by the notation:
A
X (11.1.1)
Z
where
X is the symbol for the element,
A is the mass number, and
Z is the atomic number.
Often a nuclide is referenced by the name of the element followed by a hyphen and the mass number. For example, C is called14
6
“carbon-14.” The element in this example, represented by the symbol C, is carbon. Its atomic number, 6, is the lower left subscript
on the symbol and is the number of protons in the atom. The mass number, the superscript to the upper left of the symbol, is the
sum of the number of protons and neutrons in the nucleus of this particular isotope. In this case, the mass number is 14, which
means that the number of neutrons in the atom is 14 − 6 = 8 (that is, the mass number of the atom minus the number of protons in
the nucleus equals the number of neutrons). Occasionally, the atomic number is omitted in this notation because the symbol of the
element itself conveys its characteristic atomic number. The two isotopes of hydrogen, 2H and 3H, are given their own names:
deuterium (D) and tritium (T), respectively. Another way of expressing a particular isotope is to list the mass number after the
element name, like carbon-12 or hydrogen-3.
Nuclear reactions are very different from chemical reactions. In chemical reactions, atoms become more stable by participating in a
transfer of electrons or by sharing electrons with other atoms. In nuclear reactions, it is the nucleus of the atom that gains stability
by undergoing a change of some kind. The energies that are released in nuclear reactions are many orders of magnitude greater than
the energies involved in chemical reactions. Unlike chemical reactions, nuclear reactions are not noticeably affected by changes in
environmental conditions, such as temperature or pressure.
As the following Sections will discuss, there are three main forms of radioactive emissions. The first is called an alpha
particle,which is symbolized by the Greek letter α. An alpha particle is composed of two protons and two neutrons, and so it is the
same as a helium nucleus. (We often use He to represent an alpha particle.) It has a 2+ charge. When a radioactive atom emits an
4
2
alpha particle, the original atom’s atomic number decreases by two (because of the loss of two protons), and its mass number
decreases by four (because of the loss of four nuclear particles). We can represent the emission of an alpha particle with a nuclear
equation—for example, the alpha-particle emission of uranium-235 is as follows:
235 4 231
92
U → He + 90
Th (11.1.2)
2
Chemists often use the names parent isotope and daughter isotope to represent the original atom and the product other than the
alpha particle. In the previous example, U is the parent isotope, and Th is the daughter isotope. When one element changes
235
92
231
90
into another in this manner, it undergoes radioactive decay.
 Major Differences between Nuclear and Chemical Reactions

1. Nuclear reactions involve a change in an atom's nucleus, usually producing a different element. Chemical reactions, on the
other hand, involve only a rearrangement of electrons and do not involve changes in the nuclei.
2. Different isotopes of an element normally behave similarly in chemical reactions. The nuclear chemistry of different
isotopes vary greatly from each other.
3. Rates of chemical reactions are influenced by temperature and catalysts. Rates of nuclear reactions are unaffected by such
factors.
4. Nuclear reactions are independent of the chemical form of the element.
5. Energy changes accompanying nuclear reactions are much larger. This energy comes from destruction of mass.
6. In a nuclear reaction, mass is not strictly conserved. Some of the mass is converted into energy.
11.1: Nuclear Reactions is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
To define and give examples of the major types of radioactivity.
Atomic theory in the 19th century presumed that nuclei had fixed compositions. But in 1896, the French scientist Henri Becquerel
found that a uranium compound placed near a photographic plate made an image on the plate, even if the compound was wrapped
in black cloth. He reasoned that the uranium compound was emitting some kind of radiation that passed through the cloth to expose
the photographic plate. Further investigations showed that the radiation was a combination of particles and electromagnetic rays,
with its ultimate source as the atomic nucleus. These emanations were ultimately called, collectively, radioactivity.
There are three main forms of radioactive emissions. The first is called an alpha particle,which is symbolized by the Greek letter
α . An alpha particle is composed of two protons and two neutrons, and so it is the same as a helium nucleus. (We often use He to
4
2
represent an alpha particle.) It has a 2+ charge. When a radioactive atom emits an alpha particle, the original atom’s atomic number
decreases by two (because of the loss of two protons), and its mass number decreases by four (because of the loss of four nuclear
particles). We can represent the emission of an alpha particle with a nuclear equation—for example, the alpha-particle emission of
uranium-235 is as follows:
235 4 231
U → He + Th (11.2.1)
92 2 90
Ernest Rutherford’s experiments involving the interaction of radiation with a magnetic or electric field (Figure 11.2.1) helped him
determine that one type of radiation consisted of positively charged and relatively massive α particles; a second type was made up
of negatively charged and much less massive β particles; and a third was uncharged electromagnetic waves, γ rays. We now know
that α particles are high-energy helium nuclei, β particles are high-energy electrons, and γ radiation compose high-energy
electromagnetic radiation. We classify different types of radioactive decay by the radiation produced.
Figure 11.2.1 : Alpha particles, which are attracted to the negative plate and deflected by a relatively small amount, must be
positively charged and relatively massive. Beta particles, which are attracted to the positive plate and deflected a relatively large
amount, must be negatively charged and relatively light. Gamma rays, which are unaffected by the electric field, must be
uncharged. (CC BY 4.0; OpenStax)
Alpha, beta, and gamma emissions have different abilities to penetrate matter (Figure 11.2.2). The relatively large alpha particle is
easily stopped by matter (although it may impart a significant amount of energy to the matter it contacts). Beta particles penetrate
slightly into matter, perhaps a few centimeters at most. Gamma rays can penetrate deeply into matter and can impart a large amount
of energy into the surrounding matter. Table 11.2.1 summarizes the properties of the three main types of radioactive emissions.
Figure 11.2.2 : Different emissions exhibit different pentration powers. (CC BY-NC-SA 3.0; anonymous)
Table 11.2.1 : The Three Main Forms of Radioactive Emissions
Characteristic Alpha Particles Beta Particles Gamma Rays
symbols α, 4
2
He β, −1
0
e γ
identity helium nucleus electron electromagnetic radiation
charge 2+ 1− none
mass number 4 0 0
short (will penetrate skin and deep (will penetrate tissues

penetrating power minimal (will not penetrate skin)
some tissues slightly) deeply)
Key Takeaway
The major types of radioactivity include alpha particles, beta particles, and gamma rays.

Paul Flowers (University of North Carolina - Pembroke), Klaus Theopold (University of Delaware) and Richard Langley
(Stephen F. Austin State University) with contributing authors. Textbook content produced by OpenStax College is licensed
under a Creative Commons Attribution License 4.0 license. Download for free at http://cnx.org/contents/85abf193-
2bd...a7ac8df6@9.110).
11.2: The Discovery and Nature of Radioactivity is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by
LibreTexts.
Recognize that radioactivity is a signature of unstable nuclide - radioisotopes.
Describe a radioisotope.
Explain how the stability of isotopes depends on the composition of its nucleus.
Use the "band of stability" to identify stable isotopes.
The discovery of radioactivity and its effects on the nuclei of elements disproved Dalton's assumption that atoms are indivisible. A
nuclide is a term for an atom with a specific number of protons and neutrons in its nucleus. When nuclides of one type emit
radiation, they are changed into different nuclides. Radioactive decay is spontaneous and does not required an input of energy to
occur. The stability of a particular nuclide depends on the composition of its nucleus, including the number of protons, the number
of neutrons, and the proton-to-neutron ratio.
In nuclear reactions, it is the nucleus of the atom that gains stability by undergoing a change of some kind. Some elements have no
stable isotopes, which means that any atom of that element is radioactive. For some other elements, only certain isotopes are
radioactive. A radioisotope is an isotope of an element that is unstable and undergoes radioactive decay. The energies that are
released in nuclear reactions are many orders of magnitude greater than the energies involved in chemical reactions. Unlike
chemical reactions, nuclear reactions are not noticeably affected by changes in environmental conditions, such as temperature or
pressure.
Carbon-12, with six protons and six neutrons, is a stable nucleus, meaning that it does not spontaneously emit radioactivity.
Carbon-14, with six protons and eight neutrons, is unstable and naturally radioactive. Among atoms with lower atomic numbers,
the ideal ratio of neutrons to protons is approximately 1:1. As the atomic number increases, the stable neutron-proton ratio
gradually increases to about 1.5:1 for the heaviest known elements. For example, lead-206 is a stable nucleus that contains 124
neutrons and 82 protons, a ratio of 1.51 to 1.
This observation is shown in Figure 11.3.1. The band of stability is the range of stable nuclei on a graph that plots the number of
neutrons in a nuclide against the number of protons. Known stable nuclides are shown with individual blue dots, while the 1:1 and
1.5:1 ratios are shown with a solid red line and a green line, respectively.
Figure 11.3.1 : A graph of the number of neutrons in a nucleus as a function of the number of protons. Each known stable nucleus is
represented by a blue dot. The ideal neutron to proton ratio changes from 1:1 for light nuclei to 1.5:1 for the heaviest nuclei.
It should be noted that just because a nucleus is "unstable" (able to undergo spontaneous radioactive decay) does not mean that it
will rapidly decompose. For example, uranium-238 is unstable because it spontaneously decays over time, but if a sample of
uranium-238 is allowed to sit for 1000 years, only 0.0000155%of the sample will have decayed. However, other unstable nuclei,
such as berkelium-243, will be almost completely gone (>99.9999%decayed) in less than a day.
This page titled 11.3: Stable and Unstable Isotopes is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by
CK-12 Foundation.
11.4: Nuclear Decay
Write and balance nuclear equations.
Unstable nuclei spontaneously emit radiation in the form of particles and energy. This generally changes the number of protons
and/or neutrons in the nucleus, resulting in a more stable nuclide. One type of a nuclear reaction is radioactive decay, a reaction in
which a nucleus spontaneously disintegrates into a slightly lighter nucleus, accompanied by the emission of particles, energy, or
both. An example is shown below, in which the nucleus of a polonium atom radioactively decays into a lead nucleus.
235 4 231
U → He + Th (11.4.1)
92 2 90
Note that in a balanced nuclear equation, the sum of the atomic numbers (subscripts) and the sum of the mass numbers
(superscripts) must be equal on both sides of the equation. How do we know that a product of the reaction is Th? We use a
231
90
modified type of the law of conservation of matter, which says that we must have the same number of protons and neutrons on
both sides of the chemical equation. If our uranium nucleus loses 2 protons from the alpha particle, then there are 90 protons
remaining, identifying the element as thorium. Moreover, if we lose 4 nuclear particles of the original 235, there are 231 remaining.
Thus, we use subtraction to identify the isotope of the thorium atom—in this case, Th. 231
90
Because the number of protons changes as a result of this nuclear reaction, the identity of the element changes. Transmutation is a
change in the identity of a nucleus as a result of a change in the number of protons. There are several different types of naturally
occurring radioactive decay, and we will examine each separately.
Alpha Emission
An alpha particle (α) is a helium nucleus with two protons and two neutrons. Alpha particles are emitted during some types of
radioactive decay. The net charge of an alpha particle is 2+, and its mass is approximately 4 amu. The symbol for an alpha particle
in a nuclear equation is usually He, though sometimes α is used. Alpha emission typically occurs for very heavy nuclei in which
4
2
the nuclei are unstable due to large numbers of nucleons. For nuclei that undergo alpha decay, their stability is increased by the
subtraction of two protons and two neutrons. For example, uranium-238 decays into thorium-234 by the emission of an alpha
particle (see Figure 11.4.1).
Figure 11.4.1 : The unstable uranium-238 nucleus spontaneously decays into a thorium-234 nucleus by emitting an alpha particle.
 Example 11.4.1: Radon-222

Write the nuclear equation that represents the radioactive decay of radon-222 by alpha particle emission and identify the
daughter isotope.
Solution
Radon has an atomic number of 86, so the parent isotope is represented as Rn. We represent the alpha particle as
222
86
4
2
He and
use subtraction (222 − 4 = 218 and 86 − 2 = 84) to identify the daughter isotope as an isotope of polonium, Po: 218
84
222 4 218
86
Rn → 2
He + 84
Po
 Exercise 11.4.1: Polonium-209
Write the nuclear equation that represents the radioactive decay of polonium-209 by alpha particle emission and identify the
daughter isotope.
Answer
209 4 205
84
Po → 2
He + 82
Pb
Beta Emission
Nuclei above the band of stability are unstable because their neutron to proton ratio is too high. To decrease that ratio, a neutron in
the nucleus is capable of turning into a proton and an electron. The electron is immediately ejected at a high speed from the
nucleus. A beta particle (β) is a high-speed electron emitted from the nucleus of an atom during some kinds of radioactive decay
(see Figure 11.4.2). The symbol for a beta particle in an equation is either β or e. Carbon-14 undergoes beta decay,
0
−1
transmutating into a nitrogen-14 nucleus.

14 14 0
C → N+ e (11.4.2)
6 7 −1
Note that beta decay increases the atomic number by one, but the mass number remains the same.
Figure 11.4.2 : The beta emission of a carbon-14 nuclide involves the conversion of a neutron to a proton and an electron, with the
electron being emitted from the nucleus.
 Example 11.4.2: Boron-12
Write the nuclear equation that represents the radioactive decay of boron-12 by beta particle emission and identify the daughter
isotope. A gamma ray is emitted simultaneously with the beta particle.
Solution
The parent isotope is B while one of the products is an electron, e. So that the mass and atomic numbers have the same
12
5 −1
0
value on both sides, the mass number of the daughter isotope must be 12, and its atomic number must be 6. The element having
an atomic number of 6 is carbon. Thus, the complete nuclear equation is as follows:
12 12 0
5
B → 6
C+ e+γ
−1
The daughter isotope is 12

6
C .
 Exercise 11.4.2: Iodine-131
Write the nuclear equation that represents the radioactive decay of iodine-131 by beta particle emission and identify the
daughter isotope. A gamma ray is emitted simultaneously with the beta particle.
Answer
131 131 0
I → Xe + e+γ
53 54 −1
Gamma Emission
Gamma rays (γ) are very high energy electromagnetic waves emitted from a nucleus. Gamma rays are emitted by a nucleus when
nuclear particles undergo transitions between nuclear energy levels. This is analogous to the electromagnetic radiation emitted
when excited electrons drop from higher to lower energy levels; the only difference is that nuclear transitions release much more
energetic radiation. Gamma ray emission often accompanies the decay of a nuclide by other means.
230 226 4
90
Th → 88
Ra + 2 He + γ (11.4.3)
The emission of gamma radiation has no effect on the atomic number or mass number of the products, but it reduces their energy.
Positron Emission
Nuclei below the band of stability are unstable because their neutron to proton ratio is too low. One way to increase that ratio is for
a proton in the nucleus to turn into a neutron and another particle called a positron. A positron is a particle with the same mass as
an electron, but with a positive charge. Like the beta particle, a positron is immediately ejected from the nucleus upon its
formation. The symbol for a positron in an equation is e. For example, potassium-38 emits a positron, becoming argon-38.
+1
0
38 38 0
K → Ar + e (11.4.4)
19 18 1
Positron emission decreases the atomic number by one, but the mass number remains the same.
Electron Capture
An alternate way for a nuclide to increase its neutron to proton ratio is by a phenomenon called electron capture, sympolized E.C.
In electron capture, an electron from an inner orbital is captured by the nucleus of the atom and combined with a proton to form a
neutron. For example, silver-106 undergoes electron capture to become palladium-106.
106 0 106
47
Ag + e → 46
Pd (11.4.5)
−1
Note that the overall result of electron capture is identical to positron emission. The atomic number decreases by one while the
mass number remains the same.
Summary of Nuclear Radiation

Table 11.4.1 lists the characteristics of the different types of radioactive decay.
Table 11.4.1 Summary of types of radioactive decay.
Change in Atomic Change in Number of
Type Symbol Change in Mass Number
Number Neutrons
Alpha emission 4
2
He or α –2 –4 –2
Beta emission −1
0
e or β +1 0 –1
Gamma emission γ or 0
0
γ 0 0 0
Positron emission 0
1
e or β +
–1 0 +1
electron capture E.C. –1 0 +1
 Example 11.4.3
Write a balanced nuclear equation to describe each reaction.

a. the beta decay of S 35
16
b. the decay of Hg by electron capture

201
80
c. the decay of P by positron emission

30
15
Given: radioactive nuclide and mode of decay

Asked for: balanced nuclear equation
Strategy:
A Identify the reactants and the products from the information given.
B Use the values of A and Z to identify any missing components needed to balance the equation.
Solution
a.
A We know the identities of the reactant and one of the products (a β particle). We can therefore begin by writing an
equation that shows the reactant and one of the products and indicates the unknown product as X: A
Z
35 A 0
S→ X+ β
16 Z −1
B Because both protons and neutrons must be conserved in a nuclear reaction, the unknown product must have a mass
number of A = 35 − 0 = 35 and an atomic number of Z = 16 − (−1) = 17. The element with Z = 17 is chlorine, so the
balanced nuclear equation is as follows:
35 35 0
S→ Cl + β
16 17 −1
b.
A We know the identities of both reactants: 201
80
Hg and an inner electron, 0
−1
. The reaction is as follows:
e
201 0 A
Hg + e → X
80 −1 Z
B Both protons and neutrons are conserved, so the mass number of the product must be A = 201 + 0 = 201, and the
atomic number of the product must be Z = 80 + (−1) = 79, which corresponds to the element gold. The balanced nuclear
equation is thus
201 0 201
Hg + e → Au
80 −1 79
c.
A As in part (a), we are given the identities of the reactant and one of the products—in this case, a positron. The
unbalanced nuclear equation is therefore
30 A 0
P → X+ β
15 Z +1
B The mass number of the second product is A = 30 − 0 = 30, and its atomic number is Z = 15 − 1 = 14, which
corresponds to silicon. The balanced nuclear equation for the reaction is as follows:
30 30 0
P → Si + β
15 14 +1
 Exercise 11.4.3
Write a balanced nuclear equation to describe each reaction.

a. C by positron emission
11
6
b. the beta decay of molybdenum-99

c. the emission of an α particle followed by gamma emission from 185
74
W
Answer a
11 11 0
C → B+ β
6 5 +1
Answer d
99 99m 0
Mo → Tc + β
42 43 −1
Answer c
185 181 4 0
W → Hf + α+ γ
74 72 2 0
 Example 11.4.4
Predict the kind of nuclear change each unstable nuclide undergoes when it decays.
a. 45
22
Ti
b. 242
94
Pu
c. 12
5
B
d. 256
100
Fm
Given: nuclide
Asked for: type of nuclear decay
Strategy:
Based on the neutron-to-proton ratio and the value of Z, predict the type of nuclear decay reaction that will produce a more
stable nuclide.
Solution
a. This nuclide has a neutron-to-proton ratio of only 1.05, which is much less than the requirement for stability for an element
with an atomic number in this range. Nuclei that have low neutron-to-proton ratios decay by converting a proton to a
neutron. The two possibilities are positron emission, which converts a proton to a neutron and a positron, and electron
capture, which converts a proton and a core electron to a neutron. In this case, both are observed, with positron emission
occurring about 86% of the time and electron capture about 14% of the time.
b. Nuclei with Z > 83 are too heavy to be stable and usually undergo alpha decay, which decreases both the mass number and
the atomic number. Thus Pu is expected to decay by alpha emission.
242
94
c. This nuclide has a neutron-to-proton ratio of 1.4, which is very high for a light element. Nuclei with high neutron-to-proton
ratios decay by converting a neutron to a proton and an electron. The electron is emitted as a β particle, and the proton
remains in the nucleus, causing an increase in the atomic number with no change in the mass number. We therefore predict
that B will undergo beta decay.
12
5
d. This is a massive nuclide, with an atomic number of 100 and a mass number much greater than 200. Nuclides with A ≥ 200
tend to decay by alpha emission, and even heavier nuclei tend to undergo spontaneous fission. We therefore predict that
Fm will decay by either or both of these two processes. In fact, it decays by both spontaneous fission and alpha
256
100
emission, in a 97:3 ratio.
 Exercise 11.4.4
Predict the kind of nuclear change each unstable nuclide undergoes when it decays.
a. 32
14
Si
b. 43
21
Sc
c. 231
91
Pa
Answer a
beta decay
Answer d
positron emission or electron capture
Answer c
alpha decay
11.4: Nuclear Decay is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
Learning Objectives
Define half-life.
Determine the amount of radioactive substance remaining after a given number of half-lives.
Describe common radiometric carbon-14 dating technique.
Whether or not a given isotope is radioactive is a characteristic of that particular isotope. Some isotopes are stable indefinitely,
while others are radioactive and decay through a characteristic form of emission. As time passes, less and less of the radioactive
isotope will be present, and the level of radioactivity decreases. An interesting and useful aspect of radioactive decay is half life
(t1/2), which is the amount of time it takes for one-half of a radioactive isotope to decay. The half-life of a specific radioactive
isotope is constant; it is unaffected by conditions and is independent of the initial amount of that isotope.
Each radioactive nuclide has a characteristic, constant half-life (t1/2), the time required for half of the atoms in a sample to decay.
An isotope’s half-life allows us to determine how long a sample of a useful isotope will be available, and how long a sample of an
undesirable or dangerous isotope must be stored before it decays to a low-enough radiation level that is no longer a problem.
For example, cobalt-60 source, since half of the Co nuclei decay every 5.27 years, both the amount of material and the intensity
60
27
of the radiation emitted is cut in half every 5.27 years. (Note that for a given substance, the intensity of radiation that it produces is
directly proportional to the rate of decay of the substance and the amount of the substance.) Thus, a cobalt-60 source that is used
for cancer treatment must be replaced regularly to continue to be effective.
Figure 11.5.1 : For cobalt-60, which has a half-life of 5.27 years, 50% remains after 5.27 years (one half-life), 25% remains after
10.54 years (two half-lives), 12.5% remains after 15.81 years (three half-lives), and so on. (CC BY 4.0; OpenStax)
We can determine the amount of a radioactive isotope remaining after a given number half-lives by using the following expression:
n
1
amount remaining = initial amount × ( ) (11.5.1)
2
where n is the number of half-lives. This expression works even if the number of half-lives is not a whole number.
Example : Fluorine-20
The half-life of fluorine-20 is 11.0 s. If a sample initially contains 5.00 g of fluorine-20, how much remains after 44.0 s?
Solution
If we compare the time that has passed to the isotope's half-life, we note that 44.0 s is exactly 4 half-lives, so using the previous
expression, n = 4. Substituting and solving results in the following:
4
1
amount remaining = 5.00 g × ( )
2
1
= 5.00 g × ( )
16
= 0.313 g
Less than one-third of a gram of fluorine-20 remains.
Exercise : Titanium-44
The half-life of titanium-44 is 60.0 y. A sample of titanium contains 0.600 g of titanium-44. How much remains after 240.0 y?
Answer
0.0375 g
Half-lives of isotopes range from fractions of a microsecond to billions of years. Table 11.5.1 - Half-Lives of Various Isotopes, lists
the half-lives of some isotopes.
Table 11.5.1 Half-Lives of Various Isotopes
Isotope Half-Life
3H 12.3 y
14C 5730 y
40K 1.26 × 109 y
51Cr 27.70 d
90Sr 29.1 y
131I 8.04 d
222Rn 3.823 d
235U 7.04 × 108 y
238U 4.47 × 109 y
241Am 432.7 y
248Bk 23.7 h
260Sg 4 ms
Chemistry Is Everywhere: Radioactive Elements in the Body

You may not think of yourself as radioactive, but you are. A small portion of certain elements in the human body are
radioactive and constantly undergo decay. Most of the radioactivity in the human body comes from potassium-40 and carbon-
14. Potassium and carbon are two elements that we absolutely cannot live without, so unless we can remove all the radioactive
isotopes of these elements, there is no way to escape at least some radioactivity. There is debate about which radioactive
element is more problematic. There is more potassium-40 in the body than carbon-14, and it has a much longer half-life.
Potassium-40 also decays with about 10 times more energy than carbon-14, making each decay potentially more problematic.
However, carbon is the element that makes up the backbone of most living molecules, making carbon-14 more likely to be
present around important molecules, such as proteins and DNA molecules. Most experts agree that while it is foolhardy to
expect absolutely no exposure to radioactivity, we can and should minimize exposure to excess radioactivity.
Radiometric Dating
Several radioisotopes have half-lives and other properties that make them useful for purposes of “dating” the origin of objects such
as archaeological artifacts, formerly living organisms, or geological formations. The radioactivity of carbon-14 provides a method
for dating objects that were a part of a living organism. This method of radiometric dating, which is also called radiocarbon
dating or carbon-14 dating, is accurate for dating carbon-containing substances that are up to about 30,000 years old, and can
provide reasonably accurate dates up to a maximum of about 50,000 years old.
Naturally occurring carbon consists of three isotopes: C, which constitutes about 99% of the carbon on earth; C, about 1% of
12
6
13
6
the total; and trace amounts of C. Carbon-14 forms in the upper atmosphere by the reaction of nitrogen atoms with neutrons from
14
6
cosmic rays in space:

14 1 14 1
7
N+ n ⟶ 6
C + 1H
0
14 12
All isotopes of carbon react with oxygen to produce CO2 molecules. The ratio of CO to CO depends on the ratio of CO to
6 2 6 2
14
6
CO in the atmosphere. The natural abundance of CO in the atmosphere is approximately 1 part per trillion; until recently, this
12 14
6 6
14 12
has generally been constant over time, as seen is gas samples found trapped in ice. The incorporation of C CO and CO 14
6 6 2 6 2
into plants is a regular part of the photosynthesis process, which means that the C : C ratio found in a living plant is the same
14
6
12
6
as the C : C ratio in the atmosphere. But when the plant dies, it no longer traps carbon through photosynthesis. Because C is
14
6
12
6
12
6
a stable isotope and does not undergo radioactive decay, its concentration in the plant does not change. However, carbon-14 decays
by β emission with a half-life of 5730 years:
14 14 0
6
C ⟶ 7
N+ e
−1
Thus, the C : C ratio gradually decreases after the plant dies. The decrease in the ratio with time provides a measure of the time
14
6
12
6
that has elapsed since the death of the plant (or other organism that ate the plant). Figure 11.5.2 visually depicts this process.
Figure 11.5.2 : Along with stable carbon-12, radioactive carbon-14 is taken in by plants and animals, and remains at a constant
level within them while they are alive. After death, the C-14 decays and the C-14:C-12 ratio in the remains decreases. Comparing
this ratio to the C-14:C-12 ratio in living organisms allows us to determine how long ago the organism lived (and died). (CC BY
4.0; OpenStax)
For example, with the half-life of C being 5730 years, if the C : C ratio in a wooden object found in an archaeological dig is
14
6
14
6
12
6
half what it is in a living tree, this indicates that the wooden object is 5730 years old. Highly accurate determinations of C : C 14
6
12
6
ratios can be obtained from very small samples (as little as a milligram) by the use of a mass spectrometer.
Key Takeaways
Natural radioactive processes are characterized by a half-life, the time it takes for half of the material to decay radioactively.
The amount of material left over after a certain number of half-lives can be easily calculated.
11.5: Radioactive Half-Life is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
15.3: Half-Life by Anonymous is licensed CC BY-NC-SA 3.0. Original source: https://2012books.lardbucket.org/books/beginning-chemistry.
21.3: Radioactive Decay by OpenStax is licensed CC BY 4.0. Original source: https://openstax.org/details/books/chemistry-2e.
Learning Objectives
To know the differences between ionizing and nonionizing radiation and their effects on matter.
To identify natural and artificial sources of radiation.
Because nuclear reactions do not typically affect the valence electrons of the atom (although electron capture draws an electron
from an orbital of the lowest energy level), they do not directly cause chemical changes. Nonetheless, the particles and the photons
emitted during nuclear decay are very energetic, and they can indirectly produce chemical changes in the matter surrounding the
nucleus that has decayed. For instance, an α particle can act as a powerful oxidant.
Ionizing versus Nonionizing Radiation

The effects of radiation on matter are determined primarily by the energy of the radiation, which depends on the nuclear decay
reaction that produced it. Nonionizing radiation is relatively low in energy; when it collides with an atom in a molecule or an ion,
most or all of its energy can be absorbed without causing a structural or a chemical change. Instead, the kinetic energy of the
radiation is transferred to the atom or molecule with which it collides, causing it to rotate, vibrate, or move more rapidly. Because
this energy can be transferred to adjacent molecules or ions in the form of heat, many radioactive substances are warm to the touch.
Highly radioactive elements such as polonium, for example, have been used as heat sources in the US space program. As long as
the intensity of the nonionizing radiation is not great enough to cause overheating, it is relatively harmless, and its effects can be
neutralized by cooling.
In contrast, ionizing radiation is higher in energy, and some of its energy can be transferred to one or more atoms with which it
collides as it passes through matter. If enough energy is transferred, electrons can be excited to very high energy levels, resulting in
the formation of positively charged ions:
+ −
atom + ionizing radiation → io n + e (11.6.1)
Molecules that have been ionized in this way are often highly reactive, and they can decompose or undergo other chemical changes
that create a cascade of reactive molecules that can damage biological tissues and other materials (Figure 11.6.1). Because the
energy of ionizing radiation is very high, we often report its energy in units such as megaelectronvolts (MeV) per particle:
1 MeV/particle = 96 billion J/mol. (11.6.2)
Figure 11.6.1 : Radiation Damage. When high-energy particles emitted by radioactive decay interact with matter, they can break
bonds or ionize molecules, resulting in changes in physical properties such as ductility or color. The glass electrical insulator on the
left has not been exposed to radiation, but the insulator on the right has received intense radiation doses over a long period of time.
Radiation damage changed the chemical structure of the glass, causing it to become bright blue.
The Effects of Ionizing Radiation on Matter

The effects of ionizing radiation depend on four factors:
1. The type of radiation, which dictates how far it can penetrate into matter
2. The energy of the individual particles or photons
3. The number of particles or photons that strike a given area per unit time
4. The chemical nature of the substance exposed to the radiation
Because of its high charge and mass, α radiation interacts strongly with matter. Consequently, it does not penetrate deeply into an
object, and it can be stopped by a piece of paper, clothing, or skin. In contrast, γ rays, with no charge and essentially no mass, do
not interact strongly with matter and penetrate deeply into most objects, including the human body. Several inches of lead or more
than 12 inches of special concrete are needed to completely stop γ rays. Because β particles are intermediate in mass and charge
between α particles and γ rays, their interaction with matter is also intermediate. Beta particles readily penetrate paper or skin, but
they can be stopped by a piece of wood or a relatively thin sheet of metal.
Because of their great penetrating ability, γ rays are by far the most dangerous type of radiation when they come from a source
outside the body. Alpha particles, however, are the most damaging if their source is inside the body because internal tissues absorb
all of their energy. Thus danger from radiation depends strongly on the type of radiation emitted and the extent of exposure, which
allows scientists to safely handle many radioactive materials if they take precautions to avoid, for example, inhaling fine particulate
dust that contains alpha emitters. Some properties of ionizing radiation are summarized in Table 11.6.1.
Table 11.6.1 : Some Properties of Ionizing Radiation
Type Energy Range (MeV) Penetration Distance in Water* Penetration Distance in Air*
α particles 3–9 < 0.05 mm < 10 cm
β particles ≤3 < 4 mm 1m
X rays <10−2 < 1 cm <3m
γ rays 10−2 –101 < 20 cm >3m
*Distance at which half of the radiation has been absorbed.
There are many different ways to measure radiation exposure, or the dose. The roentgen (R), which measures the amount of
energy absorbed by dry air, can be used to describe quantitative exposure. Named after the German physicist Wilhelm Röntgen
(1845–1923; Nobel Prize in Physics, 1901), who discovered X rays. The roentgen is actually defined as the amount of radiation
needed to produce an electrical charge of 2.58 × 10−4 C in 1 kg of dry air. Damage to biological tissues, however, is proportional to
the amount of energy absorbed by tissues, not air. The most common unit used to measure the effects of radiation on biological
tissue is the rad (radiation absorbed dose); the SI equivalent is the gray (Gy). The rad is defined as the amount of radiation that
causes 0.01 J of energy to be absorbed by 1 kg of matter, and the gray is defined as the amount of radiation that causes 1 J of
energy to be absorbed per kilogram:
1 rad = 0.010 J/kg 1 Gy = 1 J/kg (11.6.3)
−4
Thus a 70 kg human who receives a dose of 1.0 rad over his or her entire body absorbs 0.010 J/70 kg = 1.4 × 10 J, or 0.14 mJ. To
put this in perspective, 0.14 mJ is the amount of energy transferred to your skin by a 3.8 × 10−5 g droplet of boiling water. Because
the energy of the droplet of water is transferred to a relatively large area of tissue, it is harmless. A radioactive particle, however,
transfers its energy to a single molecule, which makes it the atomic equivalent of a bullet fired from a high-powered rifle.
Because α particles have a much higher mass and charge than β particles or γ rays, the difference in mass between α and β
particles is analogous to being hit by a bowling ball instead of a table tennis ball traveling at the same speed. Thus the amount of
tissue damage caused by 1 rad of α particles is much greater than the damage caused by 1 rad of β particles or γ rays.
Wilhelm Röntgen
Born in the Lower Rhine Province of Germany, Röntgen was the only child of a cloth manufacturer and merchant. His family
moved to the Netherlands where he showed no particular aptitude in school, but where he was fond of roaming the countryside.
Röntgen was expelled from technical school in Utrecht after being unjustly accused of drawing a caricature of one of the
teachers. He began studying mechanical engineering in Zurich, which he could enter without having the credentials of a regular
student, and received a PhD at the University of Zurich in 1869. In 1876 he became professor of physics.
Summary
Nonionizing radiation is relatively low in energy and can be used as a heat source, whereas ionizing radiation, which is higher in
energy, can penetrate biological tissues and is highly reactive. The effects of radiation on matter depend on the energy of the
radiation. Nonionizing radiation is relatively low in energy, and the energy is transferred to matter in the form of heat. Ionizing
radiation is relatively high in energy, and when it collides with an atom, it can completely remove an electron to form a positively
charged ion that can damage biological tissues. Alpha particles do not penetrate very far into matter, whereas γ rays penetrate more
deeply. Common units of radiation exposure, or dose, are the roentgen (R), the amount of energy absorbed by dry air, and the rad
(radiation absorbed dose), the amount of radiation that produces 0.01 J of energy in 1 kg of matter. The rem (roentgen equivalent in
man) measures the actual amount of tissue damage caused by a given amount of radiation.
11.6: Ionizing Radiation is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
21.8: Biological Effects of Radiation by Anonymous is licensed CC BY-NC-SA 3.0.
Learning Objectives
Define units for measuring radiation exposure
Radioactivity is determined by measuring the number of decay processes per unit time. Perhaps the easiest way is simply to
determine the number of counts/minute, with each count measuring a single decay process, such as the emission of an α -particle. A
particular isotope may have an activity of 5,000 counts/minute (cpm) while another isotope might only have 250 cpm. The
amount of activity gives a rough indication of the amount of the radioisotope present - the higher the activity, the more radioactivity
isotope in the sample.
Figure 11.7.1 : Different units are used to measure the rate of emission from a radioactive source, the energy that is absorbed from
the source, and the amount of damage the absorbed radiation does. (CC BY 4.0; OpenStax)
Measurement of exposure to radioactivity is important for anyone who deals with radioactive materials on a regular basis. Perhaps
the simplest device is a personal dosimeter - a film badge that will fog up when exposed to radiation (Figure 11.7.1). The amount
of fogging is proportional to the amount of radiation present. These devices are not very sensitive to low levels of radiation. More
sensitive systems use crystals that respond in some way to radioactivity by registering the number of emissions in a given time.
These systems tend to be more sensitive and more reliable than film badges.
When alpha, beta or gamma particles collides with a target, some of the energy in the particle is transferred to the target, typically
resulting in the promotion of an electron to an “excited state”. In many “targets”, especially gasses, this results in ionization. A
Geiger counter (or Geiger-Müller counter) takes advantage of this to detect these particles (Figure 11.7.2). In a Geiger tube, the
electron produced by ionization of a captive gas travels to the anode and the change in voltage is detected by the attached circuitry.
Figure 11.7.2 : (left) Geiger counter with pancake type probe. Public Domain; TimVickers via Wikipedia). (right) Schematic of a
Geiger-Müller counter using an "end window" tube for low penetration radiation. A loudspeaker is also used for indication. (CC-
BY-SA-3.0 Svjo-2 vai Wikipedia).
Most counters of this type are designed to emit an audible “click” in response to the change in voltage, and to also show it on a
digital or analog meter.
We previously used mass to indicate the amount of radioactive substance present. However, this is only one of several units used to
express amounts of radiation. Some units describe the number of radioactive events occurring per unit time, while others express
the amount of a person's exposure to radiation. A variety of units are used to measure various aspects of radiation (Table 11.7.1).
Table 11.7.1 : Units Used for Measuring Radiation
Measurement Purpose Unit Quantity Measured Description
amount of sample that undergoes 1

becquerel (Bq)
decay/second
activity of source radioactive decays or emissions
amount of sample that undergoes
curie (Ci) 10
3.7 × 10 decays/second
gray (Gy) 1 Gy = 1 J/kg tissue

absorbed dose energy absorbed per kg of tissue
radiation absorbed dose (rad) 1 rad = 0.01 J/kg tissue
sievert (Sv) Sv = RBE × Gy

biologically effective dose roentgen equivalent for humans tissue damage
Rem = RBE × rad
(rem)
The roentgen equivalent for humans (rem) is the unit for radiation damage that is used most frequently in medicine (1 rem = 1 Sv).
Note that the tissue damage units (rem or Sv) includes the energy of the radiation dose (rad or Gy) along with a biological factor
referred to as the RBE (for relative biological effectiveness) that is an approximate measure of the relative damage done by the
radiation. These are related by:
number of rems = RBE × number of rads (11.7.1)
with RBE approximately 10 for α radiation, 2(+) for protons and neutrons, and 1 for β and γ radiation.
The Becquerel Unit

Perhaps the direct way of reporting radioactivity is the number of radioactive decays per second. One decay per second is called
one becquerel (Bq). Even in a small mass of radioactive material, however, there are thousands upon thousands of decays or
disintegrations per second. The becquerel is named after Henri Becquerel, who discovered radioactivity in 1896.
The Curie Unit

The curie (Ci) is one measure of the rate of decay (named after Pierre and Marie Curie). One curie is equivalent to 3.7 × 10 10
disintegrations per second. Since this is obviously a large and unwieldy number, radiation is often expressed in millicuries or
microcuries (still very large numbers). The curie is named after Polish scientist Marie Curie, who performed some of the initial
investigations into radioactive phenomena in the early 1900s. The curie can be used in place of grams to describe quantities of
radioactive material. As an example, the amount of americium in an average smoke detector has an activity of 0.9 µCi.
The Roentgen Unit

There are many different ways to measure radiation exposure, or the dose. The roentgen (R), which measures the amount of
energy absorbed by dry air, can be used to describe quantitative exposure.Named after the German physicist Wilhelm Röntgen
(1845–1923; Nobel Prize in Physics, 1901), who discovered x-rays. The roentgen is actually defined as the amount of radiation
needed to produce an electrical charge of 2.58 × 10−4 C in 1 kg of dry air. Damage to biological tissues, however, is proportional to
the amount of energy absorbed by tissues, not air.
The Rad Unit

The most common unit used to measure the effects of radiation on biological tissue is the rad (radiation absorbed dose); the SI
equivalent is the gray (Gy). The rad is defined as the amount of radiation that causes 0.01 J of energy to be absorbed by 1 kg of
matter, and the gray is defined as the amount of radiation that causes 1 J of energy to be absorbed per kilogram:
1 rad = 0.010 J/kg 1 Gy = 1 J/kg (11.7.2)
Thus a 70 kg human who receives a dose of 1.0 rad over his or her entire body absorbs 0.010 J/70 kg = 1.4 × 10−4 J, or 0.14 mJ. To
put this in perspective, 0.14 mJ is the amount of energy transferred to your skin by a 3.8 × 10−5 g droplet of boiling water. Because
the energy of the droplet of water is transferred to a relatively large area of tissue, it is harmless. A radioactive particle, however,
transfers its energy to a single molecule, which makes it the atomic equivalent of a bullet fired from a high-powered rifle.
The Gray Unit

Another unit of radiation absorption is the gray (Gy):
1 Gy = 100 rad
The rad is more common. To get an idea of the amount of energy this represents, consider that the absorption of 1 rad by 70,000 g
of H2O (approximately the same mass as a 150 lb person) would increase its temperature by only 0.002°C. This may not seem like
a lot, but it is enough energy to break about 1 × 1021 molecular C–C bonds in a person’s body. That amount of damage would not
be desirable.
The Rem Unit

Because α particles have a much higher mass and charge than β particles or γ rays, the difference in mass between α and β particles
is analogous to being hit by a bowling ball instead of a table tennis ball traveling at the same speed. Thus the amount of tissue
damage caused by 1 rad of α particles is much greater than the damage caused by 1 rad of β particles or γ rays. Thus a unit called
the rem (roentgen equivalent in human) was devised to describe the actual amount of tissue damage caused by a given amount of
radiation. The number of rems of radiation is equal to the number of rads multiplied by the RBE (relative biological effectiveness)
factor:
em = rad × RBE (11.7.3)
where RBE is the relative biological effectiveness factor is a number greater than or equal to 1 that takes into account the type of
radioactive emission and sometimes the type of tissue being exposed. For beta particles, RBE factor equals 1. For alpha particles
striking most tissues, the factor is 10, but for eye tissue, the factor is 30. Most radioactive emissions that people are exposed to are
on the order of a few dozen millirems (mrem) or less; a medical X ray is about 20 mrem.
The Sievert Unit

A sievert (Sv) is related to the rem unit and is defined as 100 rem. Because actual radiation doses tend to be very small, most
measurements are reported in millirems (1 mrem = 10−3 rem).
Assessing the Impact of Radiation Exposure

One of the more controversial public policy issues debated today is whether the radiation exposure from artificial sources,
when combined with exposure from natural sources, poses a significant risk to human health. The effects of single radiation
doses of different magnitudes on humans are listed in Table 11.7.2. Because of the many factors involved in radiation exposure
(length of exposure, intensity of the source, and energy and type of particle), it is difficult to quantify the specific dangers of
one radioisotope versus another. Nonetheless, some general conclusions regarding the effects of radiation exposure are
generally accepted as valid.
Table 11.7.2 : The Effects of a Single Radiation Dose on a 70 kg Human
Dose (rem) Symptoms/Effects
<5 no observable effect
5–20 possible chromosomal damage
20–100 temporary reduction in white blood cell count
50–100 temporary sterility in men (up to a year)
mild radiation sickness, vomiting, diarrhea, fatigue; immune system

100–200
suppressed; bone growth in children retarded
> 300 permanent sterility in women
> 500 fatal to 50% within 30 days; destruction of bone marrow and intestine
> 3000 fatal within hours
Radiation doses of 600 rem and higher are invariably fatal, while a dose of 500 rem kills half the exposed subjects within 30
days. Smaller doses (≤ 50 rem) appear to cause only limited health effects, even though they correspond to tens of years of
natural radiation. This does not, however, mean that such doses have no ill effects; they may cause long-term health problems,
such as cancer or genetic changes that affect offspring. The possible detrimental effects of the much smaller doses attributable
to artificial sources (< 100 mrem/yr) are more difficult to assess.
The tissues most affected by large, whole-body exposures are bone marrow, intestinal tissue, hair follicles, and reproductive
organs, all of which contain rapidly dividing cells. The susceptibility of rapidly dividing cells to radiation exposure explains
why cancers are often treated by radiation. Because cancer cells divide faster than normal cells, they are destroyed
preferentially by radiation. Long-term radiation-exposure studies on fruit flies show a linear relationship between the number
of genetic defects and both the magnitude of the dose and the exposure time. In contrast, similar studies on mice show a much
lower number of defects when a given dose of radiation is spread out over a long period of time rather than received all at
once. Which of the two is applicable to humans?
According to one hypothesis, mice have very low risk from low doses because their bodies have ways of dealing with the
damage caused by natural radiation. At much higher doses, however, their natural repair mechanisms are overwhelmed,
leading to irreversible damage. Because mice are biochemically much more similar to humans than are fruit flies, many
scientists believe that this model also applies to humans. In contrast, the linear model assumes that all exposure to radiation is
intrinsically damaging and suggests that stringent regulation of low-level radiation exposure is necessary. Which view is more
accurate? The answer—while yet unknown—has extremely important consequences for regulating radiation exposure.
Summary
The SI unit for rate of radioactive decay is the becquerel (Bq), with 1 Bq = 1 disintegration per second. The curie (Ci) and
millicurie (mCi) are much larger units and are frequently used in medicine (1 curie = 1 Ci = 3.7 × 10 disintegrations per second).
10
The SI unit for measuring radiation dose is the gray (Gy), with 1 Gy = 1 J of energy absorbed per kilogram of tissue. In medical
applications, the radiation absorbed dose (rad) is more often used (1 rad = 0.01 Gy; 1 rad results in the absorption of 0.01 J/kg of
tissue). The SI unit measuring tissue damage caused by radiation is the sievert (Sv). This takes into account both the energy and the
biological effects of the type of radiation involved in the radiation dose.
11.7: Detecting and Measuring Radiation is shared under a collection 3.0 license and was authored, remixed, and/or curated by LibreTexts.
24.3: Detection of Radioactivity by CK-12 Foundation is licensed CK-12. Original source: https://flexbooks.ck12.org/cbook/ck-12-
21.6: Biological Effects of Radiation by OpenStax is licensed CC BY 4.0. Original source: https://openstax.org/details/books/chemistry-2e.
21.8: Biological Effects of Radiation by Anonymous is licensed CC BY-NC-SA 3.0.
Describe transmutation.
Write and balance transmutation equations.
Although the conversion of one element to another is the basis of natural radioactive decay, it is also possible to convert one
element to another artificially. The conversion of one element to another is the process of transmutation. Between 1921 and 1924,
Patrick Blackett conducted experiments in which he converted a stable isotope of nitrogen to a stable isotope of oxygen. By
bombarding N with α particles he created O. Transmutation may also be accomplished by bombardment with neutrons.
14 17
14 4 17 1
7
N + 2 He → 8
O + 1H
The 17
8
O and 1
1
H nuclei that are produced are stable, so no further (nuclear) changes occur.
To reach the kinetic energies necessary to produce transmutation reactions, devices called particle accelerators are used. These
devices use magnetic and electric fields to increase the speeds of nuclear particles. In all accelerators, the particles move in a
vacuum to avoid collisions with gas molecules. When neutrons are required for transmutation reactions, they are usually obtained
from radioactive decay reactions or from various nuclear reactions occurring in nuclear reactors.
 CERN Particle Accelerator

Located near Geneva, the CERN (“Conseil Européen pour la Recherche Nucléaire,” or European Council for Nuclear
Research) Laboratory is the world’s premier center for the investigations of the fundamental particles that make up matter. It
contains the 27-kilometer (17 mile) long, circular Large Hadron Collider (LHC), the largest particle accelerator in the world
(Figure 11.8.1). In the LHC, particles are boosted to high energies and are then made to collide with each other or with
stationary targets at nearly the speed of light. Superconducting electromagnets are used to produce a strong magnetic field that
guides the particles around the ring. Specialized, purpose-built detectors observe and record the results of these collisions,
which are then analyzed by CERN scientists using powerful computers.
Figure 11.8.1: A small section of the LHC is shown with workers traveling along it. (credit: Christophe Delaere)
In 2012, CERN announced that experiments at the LHC showed the first observations of the Higgs boson, an elementary
particle that helps explain the origin of mass in fundamental particles. This long-anticipated discovery made worldwide news
and resulted in the awarding of the 2103 Nobel Prize in Physics to François Englert and Peter Higgs, who had predicted the
existence of this particle almost 50 years previously.
Prior to 1940, the heaviest-known element was uranium, whose atomic number is 92. Now, many artificial elements have been
synthesized and isolated, including several on such a large scale that they have had a profound effect on society. One of these—
element 93, neptunium (Np)—was first made in 1940 by McMillan and Abelson by bombarding uranium-238 with neutrons. The
reaction creates unstable uranium-239, with a half-life of 23.5 minutes, which then decays into neptunium-239. Neptunium-239 is
also radioactive, with a half-life of 2.36 days, and it decays into plutonium-239. The nuclear reactions are:
238 1 239
92
U+ n ⟶ 92
U
0
239 239 0
92
U ⟶ 93
Np + e half-life = 23.5 min
−1
239 239 0
Np ⟶ Pu + e half-life = 2.36 days
93 94 −1
Plutonium is now mostly formed in nuclear reactors as a byproduct during the decay of uranium. Some of the neutrons that are
released during U-235 decay combine with U-238 nuclei to form uranium-239; this undergoes β decay to form neptunium-239,
which in turn undergoes β decay to form plutonium-239 as illustrated in the preceding three equations. It is possible to summarize
these equations as:
− −
β β
238 1 239 239 239
92
U+ n⟶ 92
U−→ 93
Np −→ 94
Pu (11.8.1)
0
Heavier isotopes of plutonium—Pu-240, Pu-241, and Pu-242—are also produced when lighter plutonium nuclei capture neutrons.
Some of this highly radioactive plutonium is used to produce military weapons, and the rest presents a serious storage problem
because they have half-lives from thousands to hundreds of thousands of years.
Although they have not been prepared in the same quantity as plutonium, many other synthetic nuclei have been produced. Nuclear
medicine has developed from the ability to convert atoms of one type into other types of atoms. Radioactive isotopes of several
dozen elements are currently used for medical applications. The radiation produced by their decay is used to image or treat various
organs or portions of the body, among other uses.
The elements beyond element 92 (uranium) are called transuranium elements. As of this writing, 22 transuranium elements have
been produced and officially recognized by IUPAC; several other elements have formation claims that are waiting for approval.
Some of these elements are shown in Table 11.8.1.
Table 11.8.1 : Preparation of Some of the Transuranium Elements
Name Symbol Atomic Number Reaction
239 240
americium Am 95 94
Pu +
1
0
n ⟶
95
Am +
−1
0
e
curium Cm 96 239
94
Pu +
4
2
He ⟶
242
96
Cm +
1
0
n
californium Cf 98 242
96
Cm +
4
2
He ⟶
243
97
Bk + 2
1
0
n
238 253
einsteinium Es 99 92
U + 15
1
0
n ⟶
99
Es + 7
0
−1
e
mendelevium Md 101 253

99
Es +
4
2
He ⟶
256
101
Md +
1
0
n
nobelium No 102 246

96
Cm +
12
6
C ⟶
254
102
No + 4
1
0
n
rutherfordium Rf 104 249

98
Cf +
12
6
C ⟶
257
104
Rf + 4
1
0
n
206 54 257 1
Pb + Cr ⟶ Sg + 3 n
seaborgium Sg 106 82
249
24
18
106
263
0
1
Cf + O ⟶ Sg + 4 n
98 8 106 0
meitnerium Mt 107 209

83
Bi +
58
26
Fe ⟶
266
109
Mt +
1
0
n
 Example 11.8.1
Write the balanced nuclear equation for the production of the following transuranium elements:
a. berkelium-244, made by the reaction of Am-241 and He-4
b. fermium-254, made by the reaction of Pu-239 with a large number of neutrons
c. lawrencium-257, made by the reaction of Cf-250 and B-11
d. dubnium-260, made by the reaction of Cf-249 and N-15
Solution
a
From the given information we can write the nuclear equation
241 4 244
Am + He → Bk
95 2 97
On the left side the total mass number is
241 + 4 = 245
and the total atomic number is
95 + 2 = 97
On the right side the total mass number is 244 and the total atomic number is 97. This shows that one neutron needs to be
added which would increase the total mass number needs to by one while keeping the total atomic number the same. The
balanced nuclear equation would be
241 4 244 1
Am + He → Bk + n
95 2 97 0
b
239 1 254
Pu + x n→ Fm
94 0 100
On the left side we see that the total mass number is the sum of 239 + (1)x . on the right side we see that the total mass number
is 254. since the total mass number of the reactants must equal that of the products we can write
239 + x = 254
showing 15 neutrons need to be added to balance the mass number.

239 1 254
94
Pu + 15 n → 100
Fm
0
To balance the total atomic number of the equation, 6 electrons need to be added to the right side. Therefore the balanced
equation reads:
239 1 254 0
Pu + 15 n→ Fm + 6 e
94 0 100 −1
c
250 11 257
Cf + 5
B → Lr
98 103
250 + 11 = 261
98 + 5 = 103
On the right side the total mass number is 257 and the total atomic number is 103. This means that 4 neutrons need to be added
to the right side to balance the equation. The balanced nuclear equation is
250 11 257 1
Cf + 5
B → Lr + 4 n
98 103 0
d
249 15 260
Cf + 7
N → Db
98 105
249 + 15 = 264
98 + 7 = 105
On the right side the total mass number is 260 and the total atomic number is 105. This means that 4 neutrons need to be added
to the right side t obalance the equation. The balanced nuclear equation is
249 15 260 1
Cf + N → Lr + 4 n
98 7 105 0

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Explain nuclear fission and fusion processes.
Write and balance nuclear fission and fusion equations.
Relate the concepts of critical mass and nuclear chain reactions.
Nuclear fusion and nuclear fission are two different types of energy-releasing reactions in which energy is released from high-
powered atomic bonds between the particles within the nucleus. The main difference between these two processes is that fission is
the splitting of an atom into two or more smaller ones while fusion is the fusing of two or more smaller atoms into a larger one.
Protons and neutrons make up a nucleus, which is the foundation of nuclear science. Fission and fusion involves the dispersal and
combination of elemental nucleus and isotopes, and part of nuclear science is to understand the process behind this phenomenon.
Adding up the individual masses of each of these subatomic particles of any given element will always give you a greater mass
than the mass of the nucleus as a whole. The missing idea in this observation is the concept called nuclear binding energy. Nuclear
binding energy is the energy required to keep the protons and neutrons of a nucleus intact, and the energy that is released during a
nuclear fission or fusion is nuclear power. There are some things to consider however. The mass of an element's nucleus as a whole
is less than the total mass of its individual protons and neutrons.
To calculate the energy released during mass destruction in both nuclear fission and fusion, we use Einstein’s equation that equates
energy and mass:
2
E = mc (11.9.1)
with m is mass (kilograms), c is speed of light (meters/sec) and E is energy (Joules).
Nuclear Fission
Many heavier elements with smaller binding energies per nucleon can decompose into more stable elements that have intermediate
mass numbers and larger binding energies per nucleon—that is, mass numbers and binding energies per nucleon that are closer to
the “peak” of the binding energy graph near 56. Sometimes neutrons are also produced. This decomposition is called fission, the
breaking of a large nucleus into smaller pieces. The breaking is rather random with the formation of a large number of different
products. Fission usually does not occur naturally, but is induced by bombardment with neutrons. The first reported nuclear fission
occurred in 1939 when three German scientists, Lise Meitner, Otto Hahn, and Fritz Strassman, bombarded uranium-235 atoms with
slow-moving neutrons that split the U-238 nuclei into smaller fragments that consisted of several neutrons and elements near the
middle of the periodic table. Since then, fission has been observed in many other isotopes, including most actinide isotopes that
have an odd number of neutrons. A typical nuclear fission reaction is shown in Figure 11.9.1.
Figure 11.9.1 : When a slow neutron hits a fissionable U-235 nucleus, it is absorbed and forms an unstable U-236 nucleus. The U-
236 nucleus then rapidly breaks apart into two smaller nuclei (in this case, Ba-141 and Kr-92) along with several neutrons (usually
two or three), and releases a very large amount of energy.
Among the products of Meitner, Hahn, and Strassman’s fission reaction were barium, krypton, lanthanum, and cerium, all of which
have nuclei that are more stable than uranium-235. Since then, hundreds of different isotopes have been observed among the
products of fissionable substances. A few of the many reactions that occur for U-235, and a graph showing the distribution of its
fission products and their yields, are shown in Figure 11.9.2. Similar fission reactions have been observed with other uranium
isotopes, as well as with a variety of other isotopes such as those of plutonium.
Figure 11.9.2 : (a) Nuclear fission of U-235 produces a range of fission products. (b) The larger fission products of U-235 are
typically one isotope with a mass number around 85–105, and another isotope with a mass number that is about 50% larger, that is,
about 130–150.
A tremendous amount of energy is produced by the fission of heavy elements. For instance, when one mole of U-235 undergoes
fission, the products weigh about 0.2 grams less than the reactants; this “lost” mass is converted into a very large amount of energy,
about 1.8 × 1010 kJ per mole of U-235. Nuclear fission reactions produce incredibly large amounts of energy compared to chemical
reactions. The fission of 1 kilogram of uranium-235, for example, produces about 2.5 million times as much energy as is produced
by burning 1 kilogram of coal.
When undergoing fission U-235 produces two “medium-sized” nuclei, and two or three neutrons. These neutrons may then cause
the fission of other uranium-235 atoms, which in turn provide more neutrons that can cause fission of even more nuclei, and so on.
If this occurs, we have a nuclear chain reaction (Figure 11.9.3). On the other hand, if too many neutrons escape the bulk material
without interacting with a nucleus, then no chain reaction will occur.
Figure 11.9.3 : The fission of a large nucleus, such as U-235, produces two or three neutrons, each of which is capable of causing
fission of another nucleus by the reactions shown. If this process continues, a nuclear chain reaction occurs.
Material that can sustain a nuclear fission chain reaction is said to be fissile or fissionable. (Technically, fissile material can
undergo fission with neutrons of any energy, whereas fissionable material requires high-energy neutrons.) Nuclear fission becomes
self-sustaining when the number of neutrons produced by fission equals or exceeds the number of neutrons absorbed by splitting
nuclei plus the number that escape into the surroundings. The amount of a fissionable material that will support a self-sustaining
chain reaction is a critical mass. An amount of fissionable material that cannot sustain a chain reaction is a subcritical mass. An
amount of material in which there is an increasing rate of fission is known as a supercritical mass.
Nuclear power plants are designed in such a way that they cannot form a supercritical mass of fissionable material and therefore
cannot create a nuclear explosion. But as history has shown, failures of systems and safeguards can cause catastrophic accidents,
including chemical explosions and nuclear meltdowns (damage to the reactor core from overheating). The following Chemistry in
Everyday Life feature explores three infamous meltdown incidents.
 Nuclear Accidents
The importance of cooling and containment are amply illustrated by three major accidents that occurred with the nuclear
reactors at nuclear power generating stations in the United States (Three Mile Island), the former Soviet Union (Chernobyl),
and Japan (Fukushima).
In March 1979, the cooling system of the Unit 2 reactor at Three Mile Island Nuclear Generating Station in Pennsylvania
failed, and the cooling water spilled from the reactor onto the floor of the containment building. After the pumps stopped, the
reactors overheated due to the high radioactive decay heat produced in the first few days after the nuclear reactor shut down.
The temperature of the core climbed to at least 2200 °C, and the upper portion of the core began to melt. In addition, the
zirconium alloy cladding of the fuel rods began to react with steam and produced hydrogen:
Zr(s) + 2 H O(g) ⟶ ZrO (s) + 2 H (g)

2 2 2
The hydrogen accumulated in the confinement building, and it was feared that there was danger of an explosion of the mixture
of hydrogen and air in the building. Consequently, hydrogen gas and radioactive gases (primarily krypton and xenon) were
vented from the building. Within a week, cooling water circulation was restored and the core began to cool. The plant was
closed for nearly 10 years during the cleanup process.
Although zero discharge of radioactive material is desirable, the discharge of radioactive krypton and xenon, such as occurred
at the Three Mile Island plant, is among the most tolerable. These gases readily disperse in the atmosphere and thus do not
produce highly radioactive areas. Moreover, they are noble gases and are not incorporated into plant and animal matter in the
food chain. Effectively none of the heavy elements of the core of the reactor were released into the environment, and no
cleanup of the area outside of the containment building was necessary (Figure 11.9.4).
Figure 11.9.4 : (a) In this 2010 photo of Three Mile Island, the remaining structures from the damaged Unit 2 reactor are seen
on the left, whereas the separate Unit 1 reactor, unaffected by the accident, continues generating power to this day (right). (b)
President Jimmy Carter visited the Unit 2 control room a few days after the accident in 1979.
Another major nuclear accident involving a reactor occurred in April 1986, at the Chernobyl Nuclear Power Plant in Ukraine,
which was still a part of the former Soviet Union. While operating at low power during an unauthorized experiment with some
of its safety devices shut off, one of the reactors at the plant became unstable. Its chain reaction became uncontrollable and
increased to a level far beyond what the reactor was designed for. The steam pressure in the reactor rose to between 100 and
500 times the full power pressure and ruptured the reactor. Because the reactor was not enclosed in a containment building, a
large amount of radioactive material spewed out, and additional fission products were released, as the graphite (carbon)
moderator of the core ignited and burned. The fire was controlled, but over 200 plant workers and firefighters developed acute
radiation sickness and at least 32 soon died from the effects of the radiation. It is predicted that about 4000 more deaths will
occur among emergency workers and former Chernobyl residents from radiation-induced cancer and leukemia. The reactor has
since been encapsulated in steel and concrete, a now-decaying structure known as the sarcophagus. Almost 30 years later,
significant radiation problems still persist in the area, and Chernobyl largely remains a wasteland.
In 2011, the Fukushima Daiichi Nuclear Power Plant in Japan was badly damaged by a 9.0-magnitude earthquake and resulting
tsunami. Three reactors up and running at the time were shut down automatically, and emergency generators came online to
power electronics and coolant systems. However, the tsunami quickly flooded the emergency generators and cut power to the
pumps that circulated coolant water through the reactors. High-temperature steam in the reactors reacted with zirconium alloy
to produce hydrogen gas. The gas escaped into the containment building, and the mixture of hydrogen and air exploded.
Radioactive material was released from the containment vessels as the result of deliberate venting to reduce the hydrogen
pressure, deliberate discharge of coolant water into the sea, and accidental or uncontrolled events.
An evacuation zone around the damaged plant extended over 12.4 miles away, and an estimated 200,000 people were
evacuated from the area. All 48 of Japan’s nuclear power plants were subsequently shut down, remaining shuttered as of
December 2014. Since the disaster, public opinion has shifted from largely favoring to largely opposing increasing the use of
nuclear power plants, and a restart of Japan’s atomic energy program is still stalled (Figure 11.9.5).
Figure 11.9.5 : (a) After the accident, contaminated waste had to be removed, and (b) an evacuation zone was set up around the
plant in areas that received heavy doses of radioactive fallout. (credit a: modification of work by “Live Action Hero”/Flickr)
The energy produced by a reactor fueled with enriched uranium results from the fission of uranium as well as from the fission of
plutonium produced as the reactor operates. As discussed previously, the plutonium forms from the combination of neutrons and
the uranium in the fuel. In any nuclear reactor, only about 0.1% of the mass of the fuel is converted into energy. The other 99.9%
remains in the fuel rods as fission products and unused fuel. All of the fission products absorb neutrons, and after a period of
several months to a few years, depending on the reactor, the fission products must be removed by changing the fuel rods.
Otherwise, the concentration of these fission products would increase and absorb more neutrons until the reactor could no longer
operate.
Spent fuel rods contain a variety of products, consisting of unstable nuclei ranging in atomic number from 25 to 60, some
transuranium elements, including plutonium and americium, and unreacted uranium isotopes. The unstable nuclei and the
transuranium isotopes give the spent fuel a dangerously high level of radioactivity. The long-lived isotopes require thousands of
years to decay to a safe level. The ultimate fate of the nuclear reactor as a significant source of energy in the United States probably
rests on whether or not a politically and scientifically satisfactory technique for processing and storing the components of spent fuel
rods can be developed.
Nuclear Fusion
The process of converting very light nuclei into heavier nuclei is also accompanied by the conversion of mass into large amounts of
energy, a process called fusion. The principal source of energy in the sun is a net fusion reaction in which four hydrogen nuclei fuse
and produce one helium nucleus and two positrons. This is a net reaction of a more complicated series of events:
1 4 0
4 H ⟶ He + 2 (11.9.2)
1 2 +1
A helium nucleus has a mass that is 0.7% less than that of four hydrogen nuclei; this lost mass is converted into energy during the
fusion. This reaction produces about 3.6 × 1011 kJ of energy per mole of He produced. This is somewhat larger than the energy
4
2
produced by the nuclear fission of one mole of U-235 (1.8 × 1010 kJ), and over 3 million times larger than the energy produced by
the (chemical) combustion of one mole of octane (5471 kJ).
It has been determined that the nuclei of the heavy isotopes of hydrogen, a deuteron, and a triton, , undergo fusion at extremely
2
1
3
1
high temperatures (thermonuclear fusion). They form a helium nucleus and a neutron:
2 3 4 1
H+ H ⟶ He + 2 n (11.9.3)
1 1 2 0
This change proceeds with a mass loss of 0.0188 amu, corresponding to the release of 1.69 × 109 kilojoules per mole of He 4
2
formed. The very high temperature is necessary to give the nuclei enough kinetic energy to overcome the very strong repulsive
forces resulting from the positive charges on their nuclei so they can collide.
Figure 11.9.6 : Fusion of deuterium with tritium creating helium-4, freeing a neutron, and releasing 17.59 MeV of energy, as an
appropriate amount of mass changing forms to appear as the kinetic energy of the products, in agreement with kinetic E = Δmc , 2
where Δm is the change in rest mass of particles.[Image use with permission via Wikipedia (Wykis)
The most important fusion process in nature is the one that powers stars. In the 20th century, it was realized that the energy released
from nuclear fusion reactions accounted for the longevity of the Sun and other stars as a source of heat and light. The fusion of
nuclei in a star, starting from its initial hydrogen and helium abundance, provides that energy and synthesizes new nuclei as a
byproduct of that fusion process. The prime energy producer in the Sun is the fusion of hydrogen to form helium, which occurs at a
solar-core temperature of 14 million kelvin. The net result is the fusion of four protons into one alpha particle, with the release of
two positrons, two neutrinos (which changes two of the protons into neutrons), and energy (Figure 11.9.7).
Figure 11.9.7 : (left) The Sun is a main-sequence star, and thus generates its energy by nuclear fusion of hydrogen nuclei into
helium. In its core, the Sun fuses 620 million metric tons of hydrogen each second. (right) The proton-proton chain dominates in
stars the size of the Sun or smaller.
 Example 11.9.1
Calculate the energy released in each of the following hypothetical processes.

a. 3 4
2
He →
12
6
C
b. 6 1
1
H+6
1
0
n →
12
6
C
c. 6 2
1
D →
12
6
C
Solution
a. Q a = 3 × 4.0026 − 12.000) amu × (1.4924 × 10
−10
J/amu) = 1.17 × 10
−12
J
b. Q b = (6 × (1.007825 + 1.008665) − 12.00000) amu × (1.4924 × 10

1−0
J/amu) = 1.476 × 10
−11
J
c. Q c = 6 × 2.014102 − 12.00000 amu × (1.4924 × 10

−10
J/amu) = 1.263 × 10
−11
J
Fusion of He to give C releases the least amount of energy, because the fusion to produce He has released a large amount. The
difference between the second and the third is the binding energy of deuterium. The conservation of mass-and-energy is well
illustrated in these calculations. On the other hand, the calculation is based on the conservation of mass-and-energy.
Nuclear Reactors
Useful fusion reactions require very high temperatures for their initiation—about 15,000,000 K or more. At these temperatures, all
molecules dissociate into atoms, and the atoms ionize, forming plasma. These conditions occur in an extremely large number of
locations throughout the universe—stars are powered by fusion. Humans have already figured out how to create temperatures high
enough to achieve fusion on a large scale in thermonuclear weapons. A thermonuclear weapon such as a hydrogen bomb contains a
nuclear fission bomb that, when exploded, gives off enough energy to produce the extremely high temperatures necessary for
fusion to occur.
Figure 11.9.8 : (a) This model is of the International Thermonuclear Experimental Reactor (ITER) reactor. Currently under
construction in the south of France with an expected completion date of 2027, the ITER will be the world’s largest experimental
Tokamak nuclear fusion reactor with a goal of achieving larg\times 10^{scale sustained energy production. (b) In 2012, the
National Ignition Facility at Lawrence Livermore National Laboratory briefly produced over 500,000,000,000 watts (500 terawatts,
or 500 TW) of peak power and delivered 1,850,000 joules (1.85 MJ) of energy, the largest laser energy ever produced and 1000
times the power usage of the entire United States in any given moment. Although lasting only a few billionths of a second, the 192
lasers attained the conditions needed for nuclear fusion ignition. This image shows the target prior to the laser shot. (credit a:
modification of work by Stephan Mosel)
Another much more beneficial way to create fusion reactions is in a fusion reactor, a nuclear reactor in which fusion reactions of
light nuclei are controlled. Because no solid materials are stable at such high temperatures, mechanical devices cannot contain the
plasma in which fusion reactions occur. Two techniques to contain plasma at the density and temperature necessary for a fusion
reaction are currently the focus of intensive research efforts: containment by a magnetic field and by the use of focused laser beams
(Figure 11.9.8). A number of large projects are working to attain one of the biggest goals in science: getting hydrogen fuel to ignite
and produce more energy than the amount supplied to achieve the extremely high temperatures and pressures that are required for
fusion. At the time of this writing, there are no self-sustaining fusion reactors operating in the world, although small-scale
controlled fusion reactions have been run for very brief periods.

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CHAPTER OVERVIEW
12: Introduction to Organic Chemistry - Alkanes

12.9: Cycloalkanes
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LibreTexts.
1
Describe the basic structural properties of simple organic molecules.
Organic chemistry is the study of the chemistry of carbon-containing compounds. Carbon is singled out because it has a chemical
diversity unrivaled by any other chemical element. Its diversity is based on the following:
Carbon atoms bond reasonably strongly with other carbon atoms.
Carbon atoms bond reasonably strongly with atoms of other elements.
Carbon atoms make a large number of covalent bonds (four).
Curiously, elemental carbon is not particularly abundant. It does not even appear in the list of the most common elements in Earth’s
crust. Nevertheless, all living things consist of organic compounds. Most organic chemicals are covalent compounds, which is why
we introduce organic chemistry here. By convention, compounds containing carbonate ions and bicarbonate ions, as well as carbon
dioxide and carbon monoxide, are not considered part of organic chemistry, even though they contain carbon.
Structural Properties of Carbon Compounds

A carbon atom has four valence electrons, it is tetravalent. Carbon can form four covalent bonds, or share electrons with up to
four atoms in order to gain a complete octet. The simplest carbon compounds contain only carbon and hydrogen and are called
hydrocarbons. Methane, the simplest hydrocarbon, contains a single carbon with four covalently bonded hydrogen atoms.
Recalling what you have learned about molecular structures and VSEPR, we know that methane is tetrahedral (four electron
groups and no lone pairs).
Figure 12.1.1 : The Tetrahedral Methane Molecule

Carbon can also form double bonds by sharing four electrons with a neighboring carbon atom or triple bonds by sharing six
electrons with a neighboring carbon atom. As shown in Figure 12.1.2 below, carbon with three electron groups attached will be
trigonal planar, and carbon with two electron groups attached will be linear.
Figure 12.1.2 : Two carbons can be attached together in single bond, a double bond, or a triple bond. Notice, in each example
carbon makes four total bonds. The number of hydrogen atoms in each molecule decreases as the number of carbon–carbon bonds
increase.
Simple hydrocarbon compounds are nonpolar due to the shape and the small electronegativity difference between carbon and
hydrogen atoms. When carbon is bonded to a halogen or oxygen atom, the resulting bond is polar. It may be useful to review the
section on electronegativity and polarity of bonds and molecules to be able to describe the properties of different organic
compounds, specifically how they react and interact with other molecules.
Comparing Organic and Inorganic Compounds
Organic compounds, like inorganic compounds, obey all the natural laws. Often there is no clear distinction in the chemical or
physical properties among organic and inorganic molecules. Nevertheless, it is useful to compare typical members of each class, as
in Table 12.1.1. Keep in mind, however, that there are exceptions to every category in this table.
Table 12.1.1 : Contrasting Properties and Examples of Organic and Inorganic Compounds
Organic Properties Example: Hexane Inorganic Properties Example: NaCl
low melting points −95°C high melting points 801°C
low boiling points 69°C high boiling points 1,413°C
low solubility in water; high insoluble in water; soluble in greater solubility in water; low soluble in water; insoluble in
solubility in nonpolar solvents gasoline solubility in nonpolar solvents gasoline
flammable highly flammable nonflammable nonflammable
aqueous solutions do not conduct aqueous solutions conduct

nonconductive conductive in aqueous solution
electricity electricity
exhibit covalent bonding covalent bonds exhibit ionic bonding ionic bonds
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by Lisa Sharpe Elles.
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Identify and describe functional groups in organic molecules.
Organic molecules can be classified into families based on structural similarities. Within a family, molecules have similar physical
behavior and often have predictable chemical reactivity. The structural components differentiating different organic families
involve specific arrangements of atoms or bonds, called functional groups. If you understand the behavior of a particular
functional group, you can describe the general properties of that class of compounds.
The simplest organic compounds are in the alkane family and contain only carbon–carbon and carbon–hydrogen single bonds but
do not have any specific functional group. Hydrocarbons containing at least one carbon–carbon double bond, (denoted C=C), are in
the alkene family. Alkynes have at least one carbon–carbon triple bond (C≡C). Both carbon–carbon double bonds and triple bonds
chemically react in specific ways that differ from reactions of alkanes and each other, making these specific functional groups.
In the next few chapters, we will learn more about additional functional groups that are made up of atoms or groups of atoms
attached to hydrocarbons. Being able to recognize different functional groups will help to understand and describe common
medications and biomolecules such as amino acids, carbohydrates, and fats. Table 12.2.1 and Figure 12.2.1 below list several of
the functional groups to become familiar with as you learn about organic chemistry.
Table 12.2.1: Organic Families and Functional Groups

Functional Group Simple Example Simple Example
Family Name Name Suffix
Structure Structure Name
alkane none CH3CH2CH3 propane -ane
alkene H2C=CH2 ethene (ethylene) -ene
alkyne HC≡CH ethyne (acetylene) -yne
aromatic benzene none
alkyl halide (X = F, Cl, CH3CH2Cl chloroethane none

Br, I)
alcohol CH3CH2OH ethanol -ol
CH3CH2–O–
ether diethyl ether none*
CH2CH3
Atoms and bonds in red indicate the functional group. Bonds not specified are attached to R groups
(carbons and hydrogens).
*Ethers do not have a suffix in their common name; all ethers end with the word ether.
Functional Group Simple Example Simple Example
Family Name Name Suffix
Structure Structure Name
amine CH3CH2NH2 ethylamine -amine
aldehyde ethanal -al
propanone
ketone -one
(acetone)
ethanoic acid
carboxylic acid -oic acid
(acetic acid)
anhydride acetic anhydride none
methyl ethanoate
ester -ate
(methyl acetate)
amide acetamide -amide
thiol CH3CH2SH ethanethiol -thiol
disulfide CH3S–SCH3 dimethyl disulfide none
ethyl methyl
sulfide CH3CH2SCH3 none
sulfide
Atoms and bonds in red indicate the functional group. Bonds not specified are attached to R groups
(carbons and hydrogens).
*Ethers do not have a suffix in their common name; all ethers end with the word ether.
Organic-Functional-Groups-2016_24ee.pdf Organic-Functional-Groups-2016.pdf
Figure 12.2.1: Functional groups in organic chemistry. (CC BY-NC-ND, CompoundChem.com).
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To identify simple alkanes as straight-chain or branched-chain.
Describe and recognize structural and functional group isomers.
As you just learned, there is a wide variety of organic compounds containing different functional groups. However, all organic
compounds are hydrocarbons, they contain hydrogen and carbon. The general rule for hydrocarbons is that any carbon must be
bonded to at least one other carbon atom, except in the case of methane which only contains one carbon. The bonded carbons form
the backbone of the molecule to which the hydrogen atoms (or other functional groups) are attached.
Hydrocarbons with only carbon-to-carbon single bonds (C–C) are called alkanes (or saturated hydrocarbons). Saturated, in this
case, means that each carbon atom is bonded to four other atoms (hydrogen or carbon)—the most possible; there are no double or
triple bonds in these molecules.
Saturated fats and oils are organic molecules that do not have carbon-to-carbon double bonds (C=C).
The three simplest alkanes—methane (CH4), ethane (C2H6), and propane (C3H8) shown in Figure 12.3.1, are the beginning of a
series of compounds in which any two members in a sequence differ by one carbon atom and two hydrogen atoms—namely, a CH2
unit (called methylene). Alkanes follow the general formula: CnH2n+2. Using this formula, we can write a molecular formula for
any alkane with a given number of carbon atoms. For example, an alkane with eight carbon atoms has the molecular formula C8H(2
× 8) + 2 = C8H18.
Figure 12.3.1 : The Three Simplest Alkanes
Isomers
Alkanes that contain one continuous chain of linked carbons are called straight-chain alkanes. As the number of carbons in a chain
increases beyond three, the arrangement of atoms can expand to include branched-chain alkanes. In a branched chain, one or more
hydrogen atoms along the chain is replaced by a carbon atom (or a separate chain of carbon atoms). It is important to note that
while the structural arrangement of these chains are different, continuous versus branched, they both still follow the same general
formula for alkanes as introduced above, CnH2n+2. In fact, alkane chains that have the same molecular formula (same number of
carbon and hydrogen), but a different arrangement of atoms, are called isomers. Let's look at an example below:
The structure of butane (C4H10) is written by stringing four carbon atoms in a row, and then adding enough hydrogen atoms to give
each carbon atom four bonds:
Butane is a straight-chain alkane, but there is another way to put 4 carbon atoms and 10 hydrogen atoms together. Place 3 of the
carbon atoms in a row and then branch the fourth carbon off the middle carbon atom:
Now we add enough hydrogen atoms to give each carbon four bonds:
The result is the isomer 2-methylpropane (also called isobutane), which is a branched-chain alkane with the same formula as
butane, (C4H10). However, it is a different molecule with a different name and different chemical properties. A side-by-side
comparison of these two molecules is shown in the below figure.
Figure 12.3.1 : n-butane and 2-methylpropane. The compounds n-butane and 2-methylpropane are structural isomers, meaning they
have the same molecular formula, C4H10, but different spatial arrangements of the atoms in their molecules. We use the term
normal, or the prefix n, to refer to a chain of carbon atoms without branching.
The four-carbon straight chain butane may be drawn with different bends or kinks in the backbone (Figure 12.3.2) because the
groups can rotate freely about the C–C bonds. This rotation or bending of the carbon chain does not change the identity of the
compound; all of the following structures represent the same compound, butane, with different bends in the chain:
Figure 12.3.2 : These three representations of the structure of n-butane are not isomers because they all contain the same
arrangement of atoms and bonds.
When identifying isomers, it is useful to trace the carbon backbone with your finger or a pencil and count carbons until you need to
lift your hand or pencil to get the another carbon. Try this with each of the above arrangements of four carbons, then do the same
with 2-methylpropane. Butane has a continuous chain of four carbons no matter how the bonds are rotated – you can connect the
carbons in a line without lifting your finger from the page. How many continuous carbons are in the 2-methylpropane backbone?
You should be able to count a continuous chain of three carbon atoms only, with the fourth carbon attached as a branch, (compare
the two structures in Figure 12.3.1). In a later chapter, you will learn how to systematically name compounds by counting the
number of carbons in the longest continuous chain and identifying any functional groups present.
Adding one more carbon to the butane chain gives pentane, which has the formula, C5H12. Pentane and its two branched-chain
isomers are shown below. The compound at the far left is pentane because it has all five carbon atoms in a continuous chain. The
compound in the middle is isopentane; like isobutane, it has a one CH3 branch off the second carbon atom of the continuous chain.
The compound at the far right, discovered after the other two, was named neopentane (from the Greek neos, meaning “new”).
Although all three have the same molecular formula, they have different properties, including boiling points: pentane, 36.1°C;
isopentane, 27.7°C; and neopentane, 9.5°C. The names isopentane and neopentane are common names for these molecules. As
mentioned above, we will learn the systematic rules for naming compounds in later chapters.
A continuous (unbranched) chain of carbon atoms is often called a straight chain even though the tetrahedral arrangement
about each carbon gives it a zigzag shape. Straight-chain alkanes are sometimes called normal alkanes, and their names are
given the prefix n-. For example, butane is called n-butane. We will not use that prefix here because it is not a part of the
system established by the International Union of Pure and Applied Chemistry.
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Draw condensed structures and line structures for simple compounds from the given molecular formulas.
Convert between expanded, condensed and line structures.
We use several kinds of formulas to describe organic compounds. A molecular formula shows only the number and type of atoms
in a molecule. For example, the molecular formula C4H10 tells us there are 4 carbon atoms and 10 hydrogen atoms in a molecule,
but it doesn’t distinguish between butane and 2-methylpropane. A structural formula shows all the carbon and hydrogen atoms and
the bonds attaching them (expanded structure). This type of structure allows for easy identification of specific isomers by
showing the order of attachment of the various atoms.
Unfortunately, structural formulas that show the bonds between all atoms are sometimes difficult to type/write and take up a lot of
space, especially when the number of atoms greatly increases. Chemists often use condensed structures, that show hydrogen
atoms right next to the carbon atoms to which they are attached, to alleviate these problems. The ultimate condensed formula is a
line (or line-angle) structure, in which carbon atoms are implied at the corners and ends of lines rather than written out, and each
carbon atom is understood to be attached to the appropriate amount of hydrogen atoms to give each carbon atom four bonds.
Parentheses in condensed structural formulas indicate that the enclosed grouping of atoms is attached to the adjacent carbon atom.
All three of these structure types are illustrated for butane and its isomer, 2-methylpropane in Figure 12.4.1 below.
Figure 12.4.1 : Structural representations for butane and its isomer, 2-methylpropane. (The colors are used to help identify carbons
and do not represent any special properties.)
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To name alkanes by the IUPAC system and write formulas for alkanes given IUPAC names
As noted in previously, the number of isomers increases rapidly as the number of carbon atoms increases: there are 3 pentanes, 5
hexanes, 9 heptanes, and 18 octanes, etc. It would be difficult to assign each compound unique individual names that we could
remember easily. A systematic way of naming hydrocarbons and other organic compounds has been devised by the International
Union of Pure and Applied Chemistry (IUPAC). These rules, used worldwide, are known as the IUPAC System of Nomenclature.
(Some of the names mentioned earlier, such as isobutane, isopentane, and neopentane, do not follow these rules and are called
common names.)
In the IUPAC system, a compound is named according to the number of carbons in the longest continuous chain (LCC) or parent
chain and the family it belongs to. Atoms or groups attached to this carbon chain, called substituents, are then named, with their
positions indicated by a numerical prefix at the beginning of the name:
Prefix (substituent) – Parent (# carbons) – Suffix (family name)
2-methylpropane
(Table 12.6.1) below lists the IUPAC parent names that are used for charbon chains containing 1 to 10 carbons, along with straight-
chain alkane examples for each. Notice that the suffix for each example in this table is -ane, which indicates these are members of
the alkane family.
Table 12.6.1 : Parent name for 1-10 carbons and Example Alkanes
Example Condensed Structural
Number of Carbons Parent Chain (LCC) Name Example Alkane Name
Formula
1 meth- methane CH4
2 eth- ethane CH3CH3
3 prop- propane CH3CH2CH3
4 but- butane CH3CH2CH2CH3
5 pent- pentane CH3CH2CH2CH2CH3
6 hex- hexane CH3CH2CH2CH2CH2CH3
7 hept- heptane CH3CH2CH2CH2CH2CH2CH3
CH3CH2CH2CH2CH2CH2CH2CH
8 oct- octane
3
9 non- nonane
2CH3
10 dec- decane
2CH2CH3
Atoms or groups of atoms that branch off the parent chain are called substituents. When the substituent is a carbon or group of
carbons, such as –CH3 or –CH2CH3, it is called an alkyl group. Alkyl groups are alkanes that have had one hydrogen removed to
allow for binding to a main chain carbon and are named by replacing the -ane suffix of the parent hydrocarbon with -yl. For
example, the –CH3 group derived from methane (CH4) results from subtracting one hydrogen atom and is called a methyl group.
Removing a hydrogen from ethane, CH3CH3, gives –CH2CH3, or the ethyl group. The alkyl groups we will use most frequently
are listed in Table 12.6.2. Alkyl groups are not independent molecules; they are parts of molecules that we consider as a unit to
name compounds systematically.
Table 12.6.2 : Common Alkyl Groups
Condensed Structural
Parent Alkane Alkyl Group
Formula
Condensed Structural
Parent Alkane Alkyl Group
Formula
methane methyl CH3–
ethane ethyl CH3CH2–
propane propyl CH3CH2CH2–
isopropyl (CH3)2CH–
butane butyl CH3CH2CH2CH2–
sec-butyl
isobutyl
tert-butyl (tBu)
Simplified IUPAC rules for naming alkanes are as follows (demonstrated in Example 12.6.1).
Step 1: Name the parent chain. Find the longest continuous chain, (it may not always be the most obvious chain written in one
line), and name according to the number of carbon atoms it contains. Add the suffix -ane to indicate that the molecule is an alkane.
Use Table 12.6.1 as a reference to start, but it is a good idea to commit these to memory.
Step 2: Number the carbon atoms in the parent chain, giving carbons with any substituents attached the lowest number possible.
These numbers are used to locate where substituents are attached to a main chain.
Step 3: Name any substituents (including the location number). If the same alkyl group appears more than once, the numbers of
all the carbon atoms to which it is attached are expressed. If the same group appears more than once on the same carbon atom, the
number of that carbon atom is repeated as many times as the group appears. Moreover, the number of identical groups is indicated
by the Greek prefixes di-, tri-, tetra-, and so on. These prefixes are not considered in determining the alphabetical order of the
substituents. For example, ethyl is listed before dimethyl; the di- is simply ignored. The last alkyl group named is prefixed to the
name of the parent alkane to form one word.
Step 4: Write the name of the compound as a single word placing the substituent groups first (in alphabetical order), then
the parent name, then the family name. Hyphens are used to separate numbers from the names of substituents; commas separate
numbers from each other.
When these rules are followed, every unique compound receives its own exclusive name. The rules enable us to not only name a
compound from a given structure but also draw a structure from a given name. The best way to learn how to use the IUPAC system
is to practice it, not just memorize the rules. It’s easier than it looks.
 Example 12.6.1
Name each compound.
1.
Solution
1. Step 1: The LCC has five carbon atoms, and so the parent compound name is pentane. Step 2: Number the carbons in the LCC
from left to right. Step 3: There is a methyl group attached to carbon #2 of the pentane chain. Step 4: The name is 2-
methylpentane.
2. Step 1: The LCC has six carbon atoms, so the parent compound is hexane. Step 2: Number the carbons in the LCC from left to
right (or right to left, either way will be identical numbering). Step 3: There are two methyl groups attached to the second and
fifth carbon atoms. Step 4: The name is 2,5-dimethylhexane.
3. Step 1: The LCC has eight carbon atoms, so the parent compound is octane. Step 2: Number the carbons in the LCC from left to
right to give the lower number. Step 3: There are methyl and ethyl groups, both attached to the fourth carbon atom. Step 4: The
correct name is thus 4-ethyl-4-methyloctane.
 Exercise 12.6.1
Name each compound.
1.
 Example 12.6.2
Draw the structure for each compound.

a. 2,3-dimethylbutane
b. 4-ethyl-2-methylheptane
Solution
In drawing structures, always start with the parent chain.
a. The parent chain is butane, indicating four carbon atoms in the LCC.
Then add the substituents at their proper positions. You can number the parent chain from either direction as long as you are
consistent; just don’t change directions before the structure is done. The name indicates two methyl (–CH3) groups, one on the
second carbon atom and one on the third.
Finally, fill in all the hydrogen atoms, keeping in mind that each carbon atom must have four bonds total.
Adding the substituents at their proper positions gives
Filling in all the hydrogen atoms gives the following condensed structural formulas (both are correct):
Note that the bonds (dashes) can be shown or not; sometimes they are needed for spacing.
 Exercise 12.6.2
a. 4-ethyloctane
b. 3-ethyl-2-methylpentane
c. 3,3,5-trimethylheptane
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To identify the physical properties of alkanes and describe trends in these properties.
Because alkanes have relatively predictable physical properties and undergo relatively few chemical reactions other than
combustion, they serve as a basis of comparison for the properties of many other organic compound families. Let’s consider their
physical properties first.
Table 12.7.1 describes some of the properties of some of the first 10 straight-chain alkanes. Because alkane molecules are
nonpolar, they are insoluble in water, which is a polar solvent, but are soluble in nonpolar and slightly polar solvents. Consequently,
alkanes themselves are commonly used as solvents for organic substances of low polarity, such as fats, oils, and waxes. Nearly all
alkanes have densities less than 1.0 g/mL and are therefore less dense than water (the density of H2O is 1.00 g/mL at 20°C). These
properties explain why oil and grease do not mix with water but rather float on its surface.
Table 12.7.1 : Physical Properties of Some Alkanes
Physical State (at
Molecular Name Formula Melting Point (°C) Boiling Point (°C) Density (20°C)*
20°C)
methane CH4 –182 –164 0.668 g/L gas
ethane C2H6 –183 –89 1.265 g/L gas
propane C3H8 –190 –42 1.867 g/L gas
butane C4H10 –138 –1 2.493 g/L gas
pentane C5H12 –130 36 0.626 g/mL liquid
hexane C6H14 –95 69 0.659 g/mL liquid
octane C8H18 –57 125 0.703 g/mL liquid
decane C10H22 –30 174 0.730 g/mL liquid
*Note the change in units going from gases (grams per liter) to liquids (grams per milliliter). Gas densities are at 1 atm pressure.
Figure 12.7.1 : Oil Spills. Crude oil coats the water’s surface in the Gulf of Mexico after the Deepwater Horizon oil rig sank
following an explosion. The leak was a mile below the surface, making it difficult to estimate the size of the spill. One liter of oil
can create a slick 2.5 hectares (6.3 acres) in size. This and similar spills provide a reminder that hydrocarbons and water don’t mix.
Source: Photo courtesy of NASA Goddard / MODIS Rapid Response Team, NASA.gov, Topics, Earth Features, Oil Spill(opens in
new window) [www.nasa.gov].
Looking Closer: Gas Densities and Fire Hazards
Table 12.7.1 indicates that the first four members of the alkane series are gases at ordinary temperatures. Natural gas is composed
chiefly of methane, which has a density of about 0.67 g/L. The density of air is about 1.29 g/L. Because natural gas is less dense
than air, it rises. When a natural-gas leak is detected and shut off in a room, the gas can be removed by opening an upper window.
On the other hand, bottled gas can be either propane (density 1.88 g/L) or butanes (a mixture of butane and isobutane; density about
2.5 g/L). Both are much heavier than air (density 1.2 g/L). If bottled gas escapes into a building, it collects near the floor. This
presents a much more serious fire hazard than a natural-gas leak because it is more difficult to rid the room of the heavier gas.
Also shown in Table 12.7.1 are the boiling points of the straight-chain alkanes increase with increasing molar mass. This general
rule holds true for the straight-chain homologs of all organic compound families. Larger molecules have greater surface areas and
consequently interact more strongly; more energy is therefore required to separate them. For a given molar mass, the boiling points
of alkanes are relatively low because these nonpolar molecules have only weak dispersion forces to hold them together in the liquid
state.
Looking Closer: An Alkane Basis for Properties of Other Compounds

An understanding of the physical properties of the alkanes is important in that petroleum and natural gas and the many products
derived from them—gasoline, bottled gas, solvents, plastics, and more—are composed primarily of alkanes. This understanding is
also vital because it is the basis for describing the properties of other organic and biological compound families. For example, large
portions of the structures of lipids consist of nonpolar alkyl groups. Lipids include the dietary fats and fatlike compounds called
phospholipids and sphingolipids that serve as structural components of living tissues. These compounds have both polar and
nonpolar groups, enabling them to bridge the gap between water-soluble and water-insoluble phases. This characteristic is essential
for the selective permeability of cell membranes.
Figure 12.7.2 : Tripalmitin (a), a typical fat molecule, has long hydrocarbon chains typical of most lipids. Compare these chains to
hexadecane (b), an alkane with 16 carbon atoms.
Key Takeaway
Alkanes are nonpolar compounds that are low boiling and insoluble in water.
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Understand the reactions of alkanes: combustion and halogenation.
Alkanes are relatively stable, nonpolar molecules, that will not react with acids, bases, or oxidizing or reducing reagents. Alkanes
undergo so few reactions that they are sometimes called paraffins, from the Latin parum affinis, meaning “little affinity.”
However, heat or light can initiate the breaking of C–H or C–C single bonds in reactions called combustion and halogenation.
Combustion
Nothing happens when alkanes are merely mixed with oxygen (O ) at room temperature, but when a flame or spark provides the
2
activation energy, a highly exothermic combustion reaction proceeds vigorously. For methane (CH4), the combustion reaction is as
follows:
C H4 + 2 O2 → C O2 + 2 H2 O + heat (12.8.1)
As a consequence, alkanes are excellent fuels. For example, methane, CH4, is the principal component of natural gas. Butane,
C4H10, used in camping stoves and lighters is an alkane. Gasoline is a liquid mixture of straight- and branched-chain alkanes, each
containing from five to nine carbon atoms, plus various additives to improve its performance as a fuel. Kerosene, diesel oil, and
fuel oil are primarily mixtures of alkanes with higher molecular masses. The main source of these liquid alkane fuels is crude oil, a
complex mixture that is separated by fractional distillation. Fractional distillation takes advantage of differences in the boiling
points of the components of the mixture (Figure 12.8.1). You may recall that boiling point is a function of intermolecular
interactions, which was discussed in an earlier chapter.
Figure 12.8.1 :In a column for the fractional distillation of crude oil, oil heated to about 425 °C in the furnace vaporizes when it
enters the base of the tower. The vapors rise through bubble caps in a series of trays in the tower. As the vapors gradually cool,
fractions of higher, then of lower, boiling points condense to liquids and are drawn off. (credit left: modification of work by Luigi
Chiesa)
If the reactants of combustion reactions are adequately mixed, and there is sufficient oxygen, the only products are carbon dioxide (
C O ), water (H O ), and energy—heat for cooking foods, heating homes, and drying clothes. Because conditions are rarely ideal,
2 2
other unwanted by-products are frequently formed. When the oxygen supply is limited, carbon monoxide (C O) is a by-product:
2C H4 + 3 O2 → 2C O + 4 H2 O (12.8.2)
This reaction is responsible for dozens of deaths each year from unventilated or improperly adjusted gas heaters. (Similar reactions
with similar results occur with kerosene heaters.)
Halogenation
In halogenation reactions, alkanes react with the halogens chlorine (C l ) and bromine (Br ) in the presence of ultraviolet light or
2 2
at high temperatures to yield chlorinated and brominated alkanes. For example, chlorine reacts with excess methane (C H ) to give 4
methyl chloride (C H C l).

3
C H4 + C l2 → C H3 C l + H C l (12.8.3)
With more chlorine, a mixture of products is obtained: CH3Cl, CH2Cl2, CHCl3, and CCl4. Fluorine (F ), the lightest halogen,
2
combines explosively with most hydrocarbons. Iodine (I ) is relatively unreactive. Fluorinated and iodinated alkanes are produced
2
by indirect methods.
A wide variety of interesting and often useful compounds have one or more halogen atoms per molecule. For example, methane
(CH4) can react with chlorine (Cl2), replacing one, two, three, or all four hydrogen atoms with Cl atoms. Several halogenated
products derived from methane and ethane (CH3CH3) are listed in Table 12.8.1, along with some of their uses.
Table 12.8.1 : Some Halogenated Hydrocarbons
Formula Common Name IUPAC Name Some Important Uses
Derived from CH4

refrigerant; the manufacture of
CH3Cl methyl chloride chloromethane silicones, methyl cellulose, and
synthetic rubber
CH2Cl2 methylene chloride dichloromethane laboratory and industrial solvent
CHCl3 chloroform trichloromethane industrial solvent
dry-cleaning solvent and fire

CCl4 carbon tetrachloride tetrachloromethane extinguishers (but no longer
recommended for use)
CBrF3 halon-1301 bromotrifluoromethane fire extinguisher systems
CCl3F chlorofluorocarbon-11 (CFC-11) trichlorofluoromethane foaming plastics
CCl2F2 chlorofluorocarbon-12 (CFC-12) dichlorodifluoromethane refrigerant
Derived from CH3CH3
CH3CH2Cl ethyl chloride chloroethane local anesthetic
ClCH2CH2Cl ethylene dichloride 1,2-dichloroethane solvent for rubber
solvent for cleaning computer

CCl3CH3 methylchloroform 1,1,1-trichloroethane chips and molds for shaping
plastics
 Note To Your Health: Halogenated Hydrocarbons

Once widely used in consumer products, many chlorinated hydrocarbons are suspected carcinogens (cancer-causing
substances) and also are known to cause severe liver damage. An example is carbon tetrachloride (CCl4), once used as a dry-
cleaning solvent and in fire extinguishers but no longer recommended for either use. Even in small amounts, its vapor can
cause serious illness if exposure is prolonged. Moreover, it reacts with water at high temperatures to form deadly phosgene
(COCl2) gas, which makes the use of CCl4 in fire extinguishers particularly dangerous.
Ethyl chloride, in contrast, is used as an external local anesthetic. When sprayed on the skin, it evaporates quickly, cooling the
area enough to make it insensitive to pain. It can also be used as an emergency general anesthetic.
Bromine-containing compounds are widely used in fire extinguishers and as fire retardants on clothing and other materials.
Because they too are toxic and have adverse effects on the environment, scientists are engaged in designing safer substitutes
for them, as for many other halogenated compounds.
 Note To Your Health: Chlorofluorocarbons and The Ozone Layer
Alkanes substituted with both fluorine (F) and chlorine (Cl) atoms have been used as the dispersing gases in aerosol cans, as
foaming agents for plastics, and as refrigerants. Two of the best known of these chlorofluorocarbons (CFCs) are listed in Table
12.8.2.
Chlorofluorocarbons contribute to the greenhouse effect in the lower atmosphere. They also diffuse into the stratosphere,
where they are broken down by ultraviolet (UV) radiation to release Cl atoms. These in turn break down the ozone (O3)
molecules that protect Earth from harmful UV radiation. Worldwide action has reduced the use of CFCs and related
compounds. The CFCs and other Cl- or bromine (Br)-containing ozone-destroying compounds are being replaced with more
benign substances. Hydrofluorocarbons (HFCs), such as CH2FCF3, which have no Cl or Br to form radicals, are one
alternative. Another is hydrochlorofluorocarbons (HCFCs), such as CHCl2CF3. HCFC molecules break down more readily in
the troposphere, and fewer ozone-destroying molecules reach the stratosphere.
Figure 12.8.2: Ozone in the upper atmosphere shields Earth’s surface from UV radiation from the sun, which can cause skin
cancer in humans and is also harmful to other animals and to some plants. Ozone “holes” in the upper atmosphere (the gray,
pink, and purple areas at the center) are large areas of substantial ozone depletion. They occur mainly over Antarctica from late
August through early October and fill in about mid-November. Ozone depletion has also been noted over the Arctic regions.
The largest ozone hole ever observed occurred on 24 September 2006. Source: Image courtesy of NASA,
http://ozonewatch.gsfc.nasa.gov/daily.php?date=2006-09-24.
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12.9: Cycloalkanes
Identify the structures of cycloalkanes.
A cyclic hydrocarbon is a hydrocarbon in which the carbon chain joins to itself in a ring. A cycloalkane is a cyclic hydrocarbon in
which all of the carbon-carbon bonds are single bonds and each carbon is bonded to two hydrogen atoms, they are saturated
compounds. Cycloalkanes have the general formula C H . The simplest of these cyclic hydrocarbons, cyclopropane, has the
n 2 n
formula C3H6, which makes a three-carbon ring.
Figure 12.9.1 : Cyclopropane is the simplest cycloalkane. Its highly strained geometry makes it rather unstable and highly reactive.
The structural formulas of cyclic hydrocarbons can be represented in multiple ways, two of which are shown above. Each atom can
be shown as in the structure on the left from the figure above. A convenient shorthand is to omit the element symbols and only
show the shape, as in the triangle on the right. Carbon atoms are understood to be the vertices of the triangle.
The carbon atoms in cycloalkanes have a bond angle of 109.5 . However, an examination of the cyclopropane structure shows that
o
the triangular structure results in a C−C−C bond angle of 60 . This deviation from the ideal angle is called ring strain and makes
o
cyclopropane a fairly unstable and reactive molecule. Ring strain is decreased for cyclobutane, with a bond angle of 90 , but is still
o
significant. Cyclopentane has a bond angle of about 108 . This minimal ring strain for cyclopentane makes it a more stable
o
compound.
Cyclohexane is a six-carbon cycloalkane, shown below.
All three of the depictions of cyclohexane above are somewhat misleading, because the molecule is not planar. In order to reduce
the ring strain and attain a bond angle of approximately 109.5 , the molecule is actually puckered.
o
The ring structure in cycloalkanes also prevents rotation around the carbon–carbon bonds without breaking open the ring, thus they
are more rigid and less flexible than acyclic alkanes. This property is called restricted rotation.
 Note To Your Health: Cyclopropane as an Anesthetic

With its boiling point of −33°C, cyclopropane is a gas at room temperature. It is also a potent, quick-acting anesthetic with few
undesirable side effects in the body. It is no longer used in surgery, however, because it forms explosive mixtures with air at
nearly all concentrations.
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To name cycloalkanes given their formulas and write formulas for these compounds given their names.
The cycloalkanes—cyclic hydrocarbons with only single bonds—are named by adding the prefix cyclo- to the name of the open-
chain compound having the same number of carbon atoms as there are in the ring. Thus the name for the cyclic compound C4H8 is
cyclobutane. The carbon atoms in cyclic compounds can be represented by line-angle formulas that result in regular geometric
figures. Keep in mind, however, that each corner of the geometric figure represents a carbon atom plus as many hydrogen atoms as
needed to give each carbon atom four bonds.
Some cyclic compounds have substituent groups attached. Example 12.10.1 interprets the name of a cycloalkane with a single
substituent group.
 Example 12.10.1
a. cyclopentane
b. methylcyclobutane
Solution
a. The name cyclopentane indicates a cyclic (cyclo) alkane with five (pent-) carbon atoms. It can be represented as a
pentagon.
The name methylcyclobutane indicates a cyclic alkane with four (but-) carbon atoms in the cyclic part. It can be represented as a
square with a CH3 group attached.
a. cycloheptane
b. ethylcyclohexane
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CHAPTER OVERVIEW
13: Alkenes, Alkynes, and Aromatic Compounds

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1
Identify the difference between saturated and unsaturated hydrocarbons.
Describe the functional groups, alkenes and alkynes.
As noted before, alkenes are hydrocarbons with carbon-to-carbon double bonds (R2C=CR2) and alkynes are hydrocarbons with
carbon-to-carbon triple bonds (R–C≡C–R). Collectively, they are called unsaturated hydrocarbons because they have fewer
hydrogen atoms than does an alkane with the same number of carbon atoms, as is indicated in the following general formulas:
You have likely heard of unsaturated fats. These are complex organic molecules with long chains of carbon atoms, which contain
at least one double bond between carbon atoms. Double and triple bonds give rise to a different geometry around the carbon atom
that participates in them, leading to important differences in molecular shape and properties. The differing geometries are
responsible for the different properties of unsaturated versus saturated fats.
Alkenes
Ethene, C2H4, is the simplest alkene. Each carbon atom in ethene, commonly called ethylene, has a trigonal planar structure. The
second member of the series is propene (propylene) (Figure 13.1.1); the butene isomers follow in the series. Four carbon atoms in
the chain of butene allows for the formation of isomers based on the position of the double bond, as well as a new form of
isomerism.
Figure 13.1.6 : Expanded structures, ball-and-stick structures, and space-filling models for the alkenes ethene, propene, and 1-
butene are shown.
Ethylene (the common industrial name for ethene) is a basic raw material in the production of polyethylene and other important
compounds. Over 135 million tons of ethylene were produced worldwide in 2010 for use in the polymer, petrochemical, and plastic
industries. Ethylene is produced industrially in a process called cracking, in which the long hydrocarbon chains in a petroleum
mixture are broken into smaller molecules.
Alkynes
Hydrocarbon molecules with one or more triple bonds are called alkynes; they make up another series of unsaturated
hydrocarbons. Two carbon atoms joined by a triple bond have bond angles of 180°, giving these types of bonds a linear shape.
The simplest member of the alkyne series is ethyne, C2H2, commonly called acetylene. The Lewis structure for ethyne, a linear
molecule, is:
Acetylene is used in oxyacetylene torches for cutting and welding metals. The flame from such a torch can be very hot. Most
acetylene, however, is converted to chemical intermediates that are used to make vinyl and acrylic plastics, fibers, resins, and a
variety of other products.
Alkynes are similar to alkenes in both physical and chemical properties. For example, alkynes undergo many of the typical addition
reactions of alkenes. The International Union of Pure and Applied Chemistry (IUPAC) names for alkynes parallel those of alkenes,
except that the family ending is -yne rather than -ene.
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Objective 1
Objective 2
Here are some basic rules for naming alkenes from the International Union of Pure and Applied Chemistry (IUPAC):
1. The longest chain of carbon atoms containing the double bond is considered the parent chain. It is named using the same stem
as the alkane having the same number of carbon atoms but ends in -ene to identify it as an alkene. Thus the compound
CH2=CHCH3 is propene.
2. If there are four or more carbon atoms in a chain, we must indicate the position of the double bond. The carbons atoms are
numbered so that the first of the two that are doubly bonded is given the lower of the two possible numbers.The compound
CH3CH=CHCH2CH3, for example, has the double bond between the second and third carbon atoms. Its name is 2-pentene (not
3-pentene).
3. Substituent groups are named as with alkanes, and their position is indicated by a number. Thus, the structure below is 5-
methyl-2-hexene. Note that the numbering of the parent chain is always done in such a way as to give the double bond the
lowest number, even if that causes a substituent to have a higher number. The double bond always has priority in numbering.
 Example 13.2.1
Name each compound.
a.
b.
Solution
a. The longest chain containing the double bond has five carbon atoms, so the compound is a pentene (rule 1). To give the first
carbon atom of the double bond the lowest number (rule 2), we number from the left, so the compound is a 2-pentene. There is
a methyl group on the fourth carbon atom (rule 3), so the compound’s name is 4-methyl-2-pentene.
b. The longest chain containing the double bond has five carbon atoms, so the parent compound is a pentene (rule 1). To give the
first carbon atom of the double bond the lowest number (rule 2), we number from the left, so the compound is a 2-pentene.
There is a methyl group on the third carbon atom (rule 3), so the compound’s name is 3-methyl-2-pentene.
 Exercise 13.2.1
Name each compound.

1. CH3CH2CH2CH2CH2CH=CHCH3
Just as there are cycloalkanes, there are cycloalkenes. These compounds are named like alkenes, but with the prefix cyclo- attached
to the beginning of the parent alkene name.
 Example 13.2.2

1. 3-methyl-2-pentene
2. cyclohexene
Solution
1. First write the parent chain of five carbon atoms: C–C–C–C–C. Then add the double bond between the second and third
carbon atoms:
Now place the methyl group on the third carbon atom and add enough hydrogen atoms to give each carbon atom a total of four
bonds.
First, consider what each of the three parts of the name means. Cyclo means a ring compound, hex means 6 carbon atoms, and -
ene means a double bond.
 Exercise 13.2.2
a. 2-ethyl-1-hexene
b. cyclopentene
The IUPAC nomenclature for alkynes is similar to that for alkenes except that the suffix -yne is used to indicate a triple bond in the
chain. For example, C H C H C ≡ CH is called 1-butyne.
3 2
 Example 13.2.6: Structure of Alkynes
Describe the geometry and hybridization of the carbon atoms in the following molecule:
Solution
Carbon atoms 1 and 4 have four single bonds and are thus tetrahedral with sp3 hybridization. Carbon atoms 2 and 3 are
involved in the triple bond, so they have linear geometries and would be classified as sp hybrids.
 Exercise 13.2.6
Identify the hybridization and bond angles at the carbon atoms in the molecule shown:
Answer
carbon 1: sp, 180°; carbon 2: sp, 180°; carbon 3: sp2, 120°; carbon 4: sp2, 120°; carbon 5: sp3, 109.5°
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Recognize that alkenes that can exist as cis-trans isomers.
Classify isomers as cis or trans.
Draw structures for cis-trans isomers given their names.
There is free rotation about the carbon-to-carbon single bonds (C–C) in alkanes. In contrast, the structure of alkenes requires that
the carbon atoms of a double bond and the two atoms bonded to each carbon atom all lie in a single plane, and that each doubly
bonded carbon atom lies in the center of a triangle. This part of the molecule’s structure is rigid; rotation about doubly bonded
carbon atoms is not possible without rupturing the bond. Look at the two chlorinated hydrocarbons in Figure 13.3.1.
Figure 13.3.1 : Rotation about Bonds. In 1,2-dichloroethane (a), free rotation about the C–C bond allows the two structures to be
interconverted by a twist of one end relative to the other. In 1,2-dichloroethene (b), restricted rotation about the double bond means
that the relative positions of substituent groups above or below the double bond are significant.
In 1,2-dichloroethane (part (a) of Figure 13.3.1), there is free rotation about the C–C bond. The two models shown represent
exactly the same molecule; they are not isomers. You can draw structural formulas that look different, but if you bear in mind the
possibility of this free rotation about single bonds, you should recognize that these two structures represent the same molecule:
In 1,2-dichloroethene (Figure 13.3.1b), however, restricted rotation about the double bond means that the relative positions of
substituent groups above or below the double bond become significant. This leads to a special kind of isomerism. The isomer in
which the two chlorine (Cl) atoms lie on the same side of the molecule is called the cis isomer (Latin cis, meaning “on this side”)
and is named cis-1,2-dichloroethene. The isomer with the two Cl atoms on opposite sides of the molecule is the trans isomer (Latin
trans, meaning “across”) and is named trans-1,2-dichloroethene. These two compounds are cis-trans isomers (or geometric
isomers), compounds that have different configurations (groups permanently in different places in space) because of the presence
of a rigid structure in their molecule.
Consider the alkene with the condensed structural formula CH3CH=CHCH3. We could name it 2-butene, but there are actually two
such compounds; the double bond results in cis-trans isomerism (Figure 13.3.2).
Figure 13.3.2 : Ball-and-Spring Models of (a) Cis-2-Butene and (b) Trans-2-Butene. Cis-trans isomers have different physical,
chemical, and physiological properties.
Cis-2-butene has both methyl groups on the same side of the molecule. Trans-2-butene has the methyl groups on opposite sides of
the molecule. Their structural formulas are as follows:
Figure 13.3.3 : Models of (left) Cis-2-Butene and (right) Trans-2-Butene.
Note, however, that the presence of a double bond does not necessarily lead to cis-trans isomerism (Figure 13.3.4 ). We can draw
two seemingly different propenes:
Figure 13.3.4 : Different views of the propene molecule (flip vertically). These are not isomers.
However, these two structures are not really different from each other. If you could pick up either molecule from the page and flip
it over top to bottom, you would see that the two formulas are identical. Thus there are two requirements for cis-trans isomerism:
1. Rotation must be restricted in the molecule.
2. There must be two nonidentical groups on each doubly bonded carbon atom.
In these propene structures, the second requirement for cis-trans isomerism is not fulfilled. One of the doubly bonded carbon atoms
does have two different groups attached, but the rules require that both carbon atoms have two different groups. In general, the
following statements hold true in cis-trans isomerism:
Alkenes with a C=CH2 unit do not exist as cis-trans isomers.
Alkenes with a C=CR2 unit, where the two R groups are the same, do not exist as cis-trans isomers.
Alkenes of the type R–CH=CH–R can exist as cis and trans isomers; cis if the two R groups are on the same side of the carbon-
to-carbon double bond, and trans if the two R groups are on opposite sides of the carbon-to-carbon double bond.
 Advanced Note: E/Z Isomerization
If a molecule has a C=C bond with one non-hydrogen group attached to each of the carbons, cis/trans nomenclature descried
above is enough to describe it. However, if you have three different groups (or four), then the cis/trans approach is insufficient
to describe the different isomers, since we do not know which two of the three groups are being described. For example, if you
have a C=C bond, with a methyl group and a bromine on one carbon , and an ethyl group on the other, it is neither trans nor cis,
since it is not clear whether the ethyl group is trans to the bromine or the methyl. This is addressed with a more advanced E/Z
nomenclature discussed elsewhere.
Cis-trans isomerism also occurs in cyclic compounds. In ring structures, groups are unable to rotate about any of the ring carbon–
carbon bonds. Therefore, groups can be either on the same side of the ring (cis) or on opposite sides of the ring (trans). For our
purposes here, we represent all cycloalkanes as planar structures, and we indicate the positions of the groups, either above or below
the plane of the ring.
 Example 13.3.1
Which compounds can exist as cis-trans (geometric) isomers? Draw them.

1. CHCl=CHBr
2. CH2=CBrCH3
3. (CH3)2C=CHCH2CH3
4. CH3CH=CHCH2CH3
Solution
All four structures have a double bond and thus meet rule 1 for cis-trans isomerism.
1. This compound meets rule 2; it has two nonidentical groups on each carbon atom (H and Cl on one and H and Br on the
other). It exists as both cis and trans isomers:
This compound has two hydrogen atoms on one of its doubly bonded carbon atoms; it fails rule 2 and does not exist as cis and
trans isomers.
This compound has two methyl (CH3) groups on one of its doubly bonded carbon atoms. It fails rule 2 and does not exist as cis
and trans isomers.
This compound meets rule 2; it has two nonidentical groups on each carbon atom and exists as both cis and trans isomers:
 Exercise 13.3.1
Which compounds can exist as cis-trans isomers? Draw them.

a. CH2=CHCH2CH2CH3
b. CH3CH=CHCH2CH3
c. CH3CH2CH=CHCH2CH3
d.

1. What are cis-trans (geometric) isomers? What two types of compounds can exhibit cis-trans isomerism?
2. Classify each compound as a cis isomer, a trans isomer, or neither.
a.
b.
c.
d.
Answers
1. Cis-trans isomers are compounds that have different configurations (groups permanently in different places in space) because of
the presence of a rigid structure in their molecule. Alkenes and cyclic compounds can exhibit cis-trans isomerism.
2. a. trans (the two hydrogen atoms are on opposite sides)
b. cis (the two hydrogen atoms are on the same side, as are the two ethyl groups)
c. cis (the two ethyl groups are on the same side)
d. neither (fliping the bond does not change the molecule. There are no isomers for this molecule)
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To identify the physical properties of alkenes and describe trends in these properties.
The physical properties of alkenes are similar to those of the alkanes. The table at the start of the chapter shows that the boiling
points of straight-chain alkenes increase with increasing molar mass, just as with alkanes. For molecules with the same number of
carbon atoms and the same general shape, the boiling points usually differ only slightly, just as we would expect for substances
whose molar mass differs by only 2 u (equivalent to two hydrogen atoms). Like other hydrocarbons, the alkenes are insoluble in
water but soluble in organic solvents.
Looking Closer: Environmental Note

Alkenes occur widely in nature. Ripening fruits and vegetables give off ethylene, which triggers further ripening. Fruit processors
artificially introduce ethylene to hasten the ripening process; exposure to as little as 0.1 mg of ethylene for 24 h can ripen 1 kg of
tomatoes. Unfortunately, this process does not exactly duplicate the ripening process, and tomatoes picked green and treated this
way don’t taste much like vine-ripened tomatoes fresh from the garden.
The bright red color of tomatoes is due to lycopene—a polyene.

Other alkenes that occur in nature include 1-octene, a constituent of lemon oil, and octadecene (C18H36) found in fish liver. Dienes
(two double bonds) and polyenes (three or more double bonds) are also common. Butadiene (CH2=CHCH=CH2) is found in coffee.
Lycopene and the carotenes are isomeric polyenes (C40H56) that give the attractive red, orange, and yellow colors to watermelons,
tomatoes, carrots, and other fruits and vegetables. Vitamin A, essential to good vision, is derived from a carotene. The world would
be a much less colorful place without alkenes.
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To write equations for the addition reactions of alkenes with hydrogen, halogens, and water
Alkenes are valued mainly for addition reactions, in which one of the bonds in the double bond is broken. Each of the carbon atoms
in the bond can then attach another atom or group while remaining joined to each other by a single bond. Perhaps the simplest
addition reaction is hydrogenation—a reaction with hydrogen (H2) in the presence of a catalyst such as nickel (Ni) or platinum (Pt).
The product is an alkane having the same carbon skeleton as the alkene.
Alkenes also readily undergo halogenation—the addition of halogens. Indeed, the reaction with bromine (Br2) can be used to test
for alkenes. Bromine solutions are brownish red. When we add a Br2 solution to an alkene, the color of the solution disappears
because the alkene reacts with the bromine:
Another important addition reaction is that between an alkene and water to form an alcohol. This reaction, called hydration,
requires a catalyst—usually a strong acid, such as sulfuric acid (H2SO4):
The hydration reaction is discussed later, where we deal with this reaction in the synthesis of alcohols.
 Example 13.6.1
Write the equation for the reaction between CH3CH=CHCH3 and each substance.
a. H2 (Ni catalyst)
b. Br2
c. H2O (H2SO4 catalyst)
Solution
In each reaction, the reagent adds across the double bond.
a.
 Exercise 13.6.1
Write the equation for each reaction.

a. CH3CH2CH=CH2 with H2 (Ni catalyst)
b. CH3CH=CH2 with Cl2
c. CH3CH2CH=CHCH2CH3 with H2O (H2SO4 catalyst)
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To draw structures for monomers that can undergo addition polymerization and for four-monomer-unit sections of an
addition polymer.
The most important commercial reactions of alkenes are polymerizations, reactions in which small molecules, referred to in general
as monomers (from the Greek monos, meaning “one,” and meros, meaning “parts”), are assembled into giant molecules referred to
as polymers (from the Greek poly, meaning “many,” and meros, meaning “parts”). A polymer is as different from its monomer as a
long strand of spaghetti is from a tiny speck of flour. For example, polyethylene, the familiar waxy material used to make plastic
bags, is made from the monomer ethylene—a gas.
There are two general types of polymerization reactions: addition polymerization and condensation polymerization. In addition
polymerization, the monomers add to one another in such a way that the polymer contains all the atoms of the starting monomers.
Ethylene molecules are joined together in long chains. The polymerization can be represented by the reaction of a few monomer
units:
The bond lines extending at the ends in the formula of the product indicate that the structure extends for many units in each
direction. Notice that all the atoms—two carbon atoms and four hydrogen atoms—of each monomer molecule are incorporated into
the polymer structure. Because displays such as the one above are cumbersome, the polymerization is often abbreviated as follows:
nCH2=CH2 → [ CH2CH2 ] n
Many natural materials—such as proteins, cellulose and starch, and complex silicate minerals—are polymers. Artificial fibers,
films, plastics, semisolid resins, and rubbers are also polymers. More than half the compounds produced by the chemical
industry are synthetic polymers.
Some common addition polymers are listed in Table 13.7.1. Note that all the monomers have carbon-to-carbon double bonds.
Many polymers are mundane (e.g., plastic bags, food wrap, toys, and tableware), but there are also polymers that conduct
electricity, have amazing adhesive properties, or are stronger than steel but much lighter in weight.
Table 13.7.1 : Some Addition Polymers
Monomer Polymer Polymer Name Some Uses
plastic bags, bottles, toys,

CH2=CH2 ~CH2CH2CH2CH2CH2CH2~ polyethylene
electrical insulation
carpeting, bottles, luggage,

CH2=CHCH3 polypropylene
exercise clothing
bags for intravenous solutions,

CH2=CHCl polyvinyl chloride
pipes, tubing, floor coverings
nonstick coatings, electrical

CF2=CF2 ~CF2CF2CF2CF2CF2CF2~ polytetrafluoroethylene
insulation
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organic-and-biological.
To describe the bonding in benzene and the way typical reactions of benzene differ from those of the alkenes.
Next we consider a class of hydrocarbons with molecular formulas like those of unsaturated hydrocarbons, but which, unlike the
alkenes, do not readily undergo addition reactions. These compounds comprise a distinct class, called aromatic hydrocarbons, with
unique structures and properties. We start with the simplest of these compounds. Benzene (C6H6) is of great commercial
importance, but it also has noteworthy health effects.
The formula C6H6 seems to indicate that benzene has a high degree of unsaturation. (Hexane, the saturated hydrocarbon with six
carbon atoms has the formula C6H14—eight more hydrogen atoms than benzene.) However, despite the seeming low level of
saturation, benzene is rather unreactive. It does not, for example, react readily with bromine, which, is a test for unsaturation.
Note
Benzene is a liquid that smells like gasoline, boils at 80°C, and freezes at 5.5°C. It is the aromatic hydrocarbon produced in the
largest volume. It was formerly used to decaffeinate coffee and was a significant component of many consumer products, such
as paint strippers, rubber cements, and home dry-cleaning spot removers. It was removed from many product formulations in
the 1950s, but others continued to use benzene in products until the 1970s when it was associated with leukemia deaths.
Benzene is still important in industry as a precursor in the production of plastics (such as Styrofoam and nylon), drugs,
detergents, synthetic rubber, pesticides, and dyes. It is used as a solvent for such things as cleaning and maintaining printing
equipment and for adhesives such as those used to attach soles to shoes. Benzene is a natural constituent of petroleum
products, but because it is a known carcinogen, its use as an additive in gasoline is now limited.
To explain the surprising properties of benzene, chemists suppose the molecule has a cyclic, hexagonal, planar structure of six
carbon atoms with one hydrogen atom bonded to each. We can write a structure with alternate single and double bonds, either as a
full structural formula or as a line-angle formula:
However, these structures do not explain the unique properties of benzene. Furthermore, experimental evidence indicates that all
the carbon-to-carbon bonds in benzene are equivalent, and the molecule is unusually stable. Chemists often represent benzene as a
hexagon with an inscribed circle:
The inner circle indicates that the valence electrons are shared equally by all six carbon atoms (that is, the electrons are delocalized,
or spread out, over all the carbon atoms). It is understood that each corner of the hexagon is occupied by one carbon atom, and each
carbon atom has one hydrogen atom attached to it. Any other atom or groups of atoms substituted for a hydrogen atom must be
shown bonded to a particular corner of the hexagon. We use this modern symbolism, but many scientists still use the earlier
structure with alternate double and single bonds.
 To Your Health: Benzene and Us
Most of the benzene used commercially comes from petroleum. It is employed as a starting material for the production of
detergents, drugs, dyes, insecticides, and plastics. Once widely used as an organic solvent, benzene is now known to have both
short- and long-term toxic effects. The inhalation of large concentrations can cause nausea and even death due to respiratory or
heart failure, while repeated exposure leads to a progressive disease in which the ability of the bone marrow to make new
blood cells is eventually destroyed. This results in a condition called aplastic anemia, in which there is a decrease in the
numbers of both the red and white blood cells.
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Recognize aromatic compounds from structural formulas.
Name aromatic compounds given formulas.
Write formulas for aromatic compounds given their names.
Historically, benzene-like substances were called aromatic hydrocarbons because they had distinctive aromas. Today, an aromatic
compound is any compound that contains a benzene ring or has certain benzene-like properties (but not necessarily a strong
aroma). You can recognize the aromatic compounds in this text by the presence of one or more benzene rings in their structure.
Some representative aromatic compounds and their uses are listed in Table 13.9.1, where the benzene ring is represented as C6H5.
Table 13.9.1 : Some Representative Aromatic Compounds
Name Structure Typical Uses
starting material for the synthesis of dyes,

aniline C6H5–NH2 drugs, resins, varnishes, perfumes; solvent;
vulcanizing rubber
food preservative; starting material for the
benzoic acid C6H5–COOH synthesis of dyes and other organic
compounds; curing of tobacco
starting material for the synthesis of many
bromobenzene C6H5–Br other aromatic compounds; solvent; motor oil
additive
starting material for the synthesis of aniline;
nitrobenzene C6H5–NO2 solvent for cellulose nitrate; in soaps and shoe
polish
disinfectant; starting material for the synthesis
phenol C6H5–OH
of resins, drugs, and other organic compounds
solvent; gasoline octane booster; starting
material for the synthesis of benzoic acid,
toluene C6H5–CH3
benzaldehyde, and many other organic
compounds
 Example 13.9.1
Which compounds are aromatic?
1.
Solution
1. The compound has a benzene ring (with a chlorine atom substituted for one of the hydrogen atoms); it is aromatic.
2. The compound is cyclic, but it does not have a benzene ring; it is not aromatic.
3. The compound has a benzene ring (with a propyl group substituted for one of the hydrogen atoms); it is aromatic.
4. The compound is cyclic, but it does not have a benzene ring; it is not aromatic.
 Exercise 13.9.1
Which compounds are aromatic?
1.
In the International Union of Pure and Applied Chemistry (IUPAC) system, aromatic hydrocarbons are named as derivatives of
benzene. Figure 13.9.1 shows four examples. In these structures, it is immaterial whether the single substituent is written at the top,
side, or bottom of the ring: a hexagon is symmetrical, and therefore all positions are equivalent.
Figure 13.9.1 : Some Benzene Derivatives. These compounds are named in the usual way with the group that replaces a hydrogen
atom named as a substituent group: Cl as chloro, Br as bromo, I as iodo, NO2 as nitro, and CH3CH2 as ethyl.
Although some compounds are referred to exclusively by IUPAC names, some are more frequently denoted by common names, as
is indicated in Table 13.9.1.
When there is more than one substituent, the corners of the hexagon are no longer equivalent, so we must designate the relative
positions. There are three possible disubstituted benzenes, and we can use numbers to distinguish them (Figure 13.9.2). We start
numbering at the carbon atom to which one of the groups is attached and count toward the carbon atom that bears the other
substituent group by the shortest path.
Figure 13.9.2 : The Three Isomeric Dichlorobenzenes
In Figure 13.9.2, common names are also used: the prefix ortho (o-) for 1,2-disubstitution, meta (m-) for 1,3-disubstitution, and
para (p-) for 1,4-disubstitution. The substituent names are listed in alphabetical order. The first substituent is given the lowest
number. When a common name is used, the carbon atom that bears the group responsible for the name is given the number 1:
 Example 13.9.2
Name each compound using both the common name and the IUPAC name.
1.
Solution
1. The benzene ring has two chlorine atoms (dichloro) in the first and second positions. The compound is o-dichlorobenzene or
1,2-dichlorobenzene.
2. The benzene ring has a methyl (CH3) group. The compound is therefore named as a derivative of toluene. The bromine atom is
on the fourth carbon atom, counting from the methyl group. The compound is p-bromotoluene or 4-bromotoluene.
3. The benzene ring has two nitro (NO2) groups in the first and third positions. It is m-dinitrobenzene or 1,3-dinitrobenzene.
Note: The nitro (NO2) group is a common substituent in aromatic compounds. Many nitro compounds are explosive, most notably
2,4,6-trinitrotoluene (TNT).
 Exercise 13.9.2
Name each compound using both the common name and the IUPAC name.
1.
Sometimes an aromatic group is found as a substituent bonded to a nonaromatic entity or to another aromatic ring. The group of
atoms remaining when a hydrogen atom is removed from an aromatic compound is called an aryl group. The most common aryl
group is derived from benzene (C6H6) by removing one hydrogen atom (C6H5) and is called a phenyl group, from pheno, an old
name for benzene.
Polycyclic Aromatic Hydrocarbons

Some common aromatic hydrocarbons consist of fused benzene rings—rings that share a common side. These compounds are
called polycyclic aromatic hydrocarbons (PAHs).
The three examples shown here are colorless, crystalline solids generally obtained from coal tar. Naphthalene has a pungent odor
and is used in mothballs. Anthracene is used in the manufacture of certain dyes. Steroids, a large group of naturally occurring
substances, contain the phenanthrene structure.
To Your Health: Polycyclic Aromatic Hydrocarbons and Cancer

The intense heating required for distilling coal tar results in the formation of PAHs. For many years, it has been known that workers
in coal-tar refineries are susceptible to a type of skin cancer known as tar cancer. Investigations have shown that a number of PAHs
are carcinogens. One of the most active carcinogenic compounds, benzopyrene, occurs in coal tar and has also been isolated from
cigarette smoke, automobile exhaust gases, and charcoal-broiled steaks. It is estimated that more than 1,000 t of benzopyrene are
emitted into the air over the United States each year. Only a few milligrams of benzopyrene per kilogram of body weight are
required to induce cancer in experimental animals.
Biologically Important Compounds with Benzene Rings

Substances containing the benzene ring are common in both animals and plants, although they are more abundant in the latter.
Plants can synthesize the benzene ring from carbon dioxide, water, and inorganic materials. Animals cannot synthesize it, but they
are dependent on certain aromatic compounds for survival and therefore must obtain them from food. Phenylalanine, tyrosine, and
tryptophan (essential amino acids) and vitamins K, B2 (riboflavin), and B9 (folic acid) all contain the benzene ring. Many important
drugs, a few of which are shown in Table 13.9.2, also feature a benzene ring.
So far we have studied only aromatic compounds with carbon-containing rings. However, many cyclic compounds have an
element other than carbon atoms in the ring. These compounds, called heterocyclic compounds, are discussed later. Some of
these are heterocyclic aromatic compounds.
Table 13.9.2 : Some Drugs That Contain a Benzene Ring

Name Structure
aspirin
acetaminophen
ibuprofen
amphetamine
sulfanilamide
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CHAPTER OVERVIEW
14: Some Compounds with Oxygen, Sulfur, or a Halogen

14.5: Phenols
14.7: Ethers
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1
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1. Give two major types of reactions of alcohols.
2. Describe the result of the oxidation of a primary alcohol.
3. Describe the result of the oxidation of a secondary alcohol.
Chemical reactions in alcohols occur mainly at the functional group, but some involve hydrogen atoms attached to the OH-bearing
carbon atom or to an adjacent carbon atom. Of the three major kinds of alcohol reactions, which are summarized in Figure 14.4.1,
two—dehydration and oxidation—are considered here. The third reaction type—esterification—is covered elsewhere.
Figure 14.4.1 : Reactions of Alcohols. Oxidation and dehydration of alcohols are considered here.
Solution
The first step is to recognize the class of each alcohol as primary, secondary, or tertiary.
 Exercise 14.4.1
Write an equation for the oxidation of each alcohol. Use [O] above the arrow to indicate an oxidizing agent. If no reaction
occurs, write “no reaction” after the arrow.
1.
Summary
Alcohols can be dehydrated to form either alkenes (higher temperature, excess acid) or ethers (lower temperature, excess alcohol).
Primary alcohols are oxidized to form aldehydes. Secondary alcohols are oxidized to form ketones. Tertiary alcohols are not readily
oxidized.
Dehydration
As noted in Figure 14.4.1, an alcohol undergoes dehydration in the presence of a catalyst to form an alkene and water. The
reaction removes the OH group from the alcohol carbon atom and a hydrogen atom from an adjacent carbon atom in the same
molecule:
Under the proper conditions, it is possible for the dehydration to occur between two alcohol molecules. The entire OH group of
one molecule and only the hydrogen atom of the OH group of the second molecule are removed. The two ethyl groups attached
to an oxygen atom form an ether molecule.
(Ethers are discussed in elsewhere) Thus, depending on conditions, one can prepare either alkenes or ethers by the dehydration
of alcohols.
Both dehydration and hydration reactions occur continuously in cellular metabolism, with enzymes serving as catalysts and
at a temperature of about 37°C. The following reaction occurs in the "Embden–Meyerhof" pathway
Although the participating compounds are complex, the reaction is the same: elimination of water from the starting material.
The idea is that if you know the chemistry of a particular functional group, you know the chemistry of hundreds of different
compounds.
Oxidation
Primary and secondary alcohols are readily oxidized. We saw earlier how methanol and ethanol are oxidized by liver enzymes
to form aldehydes. Because a variety of oxidizing agents can bring about oxidation, we can indicate an oxidizing agent without
specifying a particular one by writing an equation with the symbol [O] above the arrow. For example, we write the oxidation of
ethanol—a primary alcohol—to form acetaldehyde—an aldehyde—as follows:
We shall see that aldehydes are even more easily oxidized than alcohols and yield carboxylic acids. Secondary alcohols are
oxidized to ketones. The oxidation of isopropyl alcohol by potassium dichromate (K2Cr2O7) gives acetone, the simplest ketone:
Unlike aldehydes, ketones are relatively resistant to further oxidation, so no special precautions are required to isolate them as
they form. Note that in oxidation of both primary (RCH2OH) and secondary (R2CHOH) alcohols, two hydrogen atoms are
removed from the alcohol molecule, one from the OH group and other from the carbon atom that bears the OH group.
These reactions can also be carried out in the laboratory with chemical oxidizing agents. One such oxidizing agent is
potassium dichromate. The balanced equation (showing only the species involved in the reaction) in this case is as follows:
Alcohol oxidation is important in living organisms. Enzyme-controlled oxidation reactions provide the energy cells need to do
useful work. One step in the metabolism of carbohydrates involves the oxidation of the secondary alcohol group in isocitric acid
to a ketone group:
The overall type of reaction is the same as that in the conversion of isopropyl alcohol to acetone.
Tertiary alcohols (R3COH) are resistant to oxidation because the carbon atom that carries the OH group does not have a
hydrogen atom attached but is instead bonded to other carbon atoms. The oxidation reactions we have described involve the
formation of a carbon-to-oxygen double bond. Thus, the carbon atom bearing the OH group must be able to release one of its
attached atoms to form the double bond. The carbon-to-hydrogen bonding is easily broken under oxidative conditions, but
carbon-to-carbon bonds are not. Therefore tertiary alcohols are not easily oxidized.
 Example 14.4.1
Write an equation for the oxidation of each alcohol. Use [O] above the arrow to indicate an oxidizing agent. If no reaction
occurs, write “no reaction” after the arrow.
a. CH3CH2CH2CH2CH2OH
b.
a. This alcohol has the OH group on a carbon atom that is attached to only one other carbon atom, so it is a primary alcohol.
Oxidation forms first an aldehyde and further oxidation forms a carboxylic acid.
b. This alcohol has the OH group on a carbon atom that is attached to three other carbon atoms, so it is a tertiary alcohol. No
reaction occurs.
c. This alcohol has the OH group on a carbon atom that is attached to two other carbon atoms, so it is a secondary alcohol;
oxidation gives a ketone.
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14.5: Phenols
To describe the structure and uses of some phenols
Compounds in which an OH group is attached directly to an aromatic ring are designated ArOH and called phenols. Phenols differ
from alcohols in that they are slightly acidic in water. They react with aqueous sodium hydroxide (NaOH) to form salts.
ArOH(aq) + NaOH(aq) → ArONa(aq) + H O

2
The parent compound, C6H5OH, is itself called phenol. (An old name, emphasizing its slight acidity, was carbolic acid.) Phenol is
a white crystalline compound that has a distinctive (“hospital smell”) odor.
Figure 14.5.1 : (Left) Structure of Phenol (right) Approximately two grams of phenol in glass vial. Image used with permisison
from Wikipedia
 To Your Health: Phenols and Us

Phenols are widely used as antiseptics (substances that kill microorganisms on living tissue) and as disinfectants (substances
intended to kill microorganisms on inanimate objects such as furniture or floors). The first widely used antiseptic was phenol.
Joseph Lister used it for antiseptic surgery in 1867. Phenol is toxic to humans, however, and can cause severe burns when
applied to the skin. In the bloodstream, it is a systemic poison—that is, one that is carried to and affects all parts of the body. Its
severe side effects led to searches for safer antiseptics, a number of which have been found.
An operation in 1753, painted by Gaspare Traversi, of a surgery before antiseptics were used.
One safer phenolic antiseptic is 4-hexylresorcinol (4-hexyl-1,3-dihydroxybenzene; resorcinol is the common name for 1,3-
dihydroxybenzene, and 4-hexylresorcinol has a hexyl group on the fourth carbon atom of the resorcinol ring). It is much more
powerful than phenol as a germicide and has fewer undesirable side effects. Indeed, it is safe enough to be used as the active
ingredient in some mouthwashes and throat lozenges.
The compound 4-hexylresorcinol is mild enough to be used as the active ingredient in antiseptic preparations for use on the
skin.
Summary
Phenols are compounds in which an OH group is attached directly to an aromatic ring. Many phenols are used as antiseptics.
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14.7: Ethers
Describe the structural difference between an alcohol and an ether that affects physical characteristics and reactivity of
each.
Name simple ethers.
Describe the structure and uses of some ethers.
With the general formula ROR′, an ether may be considered a derivative of water in which both hydrogen atoms are replaced by
alkyl or aryl groups. It may also be considered a derivative of an alcohol (ROH) in which the hydrogen atom of the OH group is
been replaced by a second alkyl or aryl group:
replace both replace H atom
′
HOH −−−−−−−→ ROR ←−−−−−−−− ROH
H atoms of OH group
Simple ethers have simple common names, formed from the names of the groups attached to oxygen atom, followed by the generic
name ether. For example, CH3–O–CH2CH2CH3 is methyl propyl ether. If both groups are the same, the group name should be
preceded by the prefix di-, as in dimethyl ether (CH3–O–CH3) and diethyl ether CH3CH2–O–CH2CH3.
Ether molecules have no hydrogen atom on the oxygen atom (that is, no OH group). Therefore there is no intermolecular hydrogen
bonding between ether molecules, and ethers therefore have quite low boiling points for a given molar mass. Indeed, ethers have
boiling points about the same as those of alkanes of comparable molar mass and much lower than those of the corresponding
alcohols (Table 14.7.1).
Table 14.7.1 : Comparison of Boiling Points of Alkanes, Alcohols, and Ethers
Condensed Structural Intermolecular Hydrogen
Name Molar Mass Boiling Point (°C)
Formula Bonding in Pure Liquid?
CH3CH2CH3 propane 44 –42 no
CH3OCH3 dimethyl ether 46 –25 no
CH3CH2OH ethyl alcohol 46 78 yes
CH3CH2CH2CH2CH3 pentane 72 36 no
CH3CH2OCH2CH3 diethyl ether 74 35 no
CH3CH2CH2CH2OH butyl alcohol 74 117 yes
Ether molecules do have an oxygen atom, however, and engage in hydrogen bonding with water molecules. Consequently, an ether
has about the same solubility in water as the alcohol that is isomeric with it. For example, dimethyl ether and ethanol (both having
the molecular formula C2H6O) are completely soluble in water, whereas diethyl ether and 1-butanol (both C4H10O) are barely
soluble in water (8 g/100 mL of water).
 Example 14.7.1
What is the common name for each ether?
a. CH3CH2CH2OCH2CH2CH3
b.
Solution
a. The carbon groups on either side of the oxygen atom are propyl (CH3CH2CH2) groups, so the compound is dipropyl ether.
b. The three-carbon group is attached by the middle carbon atom, so it is an isopropyl group. The one-carbon group is a methyl
group. The compound is isopropyl methyl ether.
 Exercise 14.7.1
What is the common name for each ether?

a. CH3CH2CH2CH2OCH2CH2CH2CH3
 To Your Health: Ethers as General Anesthetics
A general anesthetic acts on the brain to produce unconsciousness and a general insensitivity to feeling or pain. Diethyl ether
(CH3CH2OCH2CH3) was the first general anesthetic to be used.
William Morton, a Boston dentist, introduced diethyl ether into surgical practice in 1846. This painting shows an operation in
Boston in 1846 in which diethyl ether was used as an anesthetic. Inhalation of ether vapor produces unconsciousness by
depressing the activity of the central nervous system. Source: Painting of William Morton by Ernest Board.
Diethyl ether is relatively safe because there is a fairly wide gap between the dose that produces an effective level of anesthesia and
the lethal dose. However, because it is highly flammable and has the added disadvantage of causing nausea, it has been replaced by
newer inhalant anesthetics, including the fluorine-containing compounds halothane, enflurane, and isoflurane. Unfortunately, the
safety of these compounds for operating room personnel has been questioned. For example, female operating room workers
exposed to halothane suffer a higher rate of miscarriages than women in the general population.
These three modern, inhalant, halogen-containing, anesthetic compounds are less flammable than diethyl ether.
Summary
To give ethers common names, simply name the groups attached to the oxygen atom, followed by the generic name ether. If both
groups are the same, the group name should be preceded by the prefix di-. Ether molecules have no OH group and thus no
intermolecular hydrogen bonding. Ethers therefore have quite low boiling points for a given molar mass. Ether molecules have an
oxygen atom and can engage in hydrogen bonding with water molecules. An ether molecule has about the same solubility in water
as the alcohol that is isomeric with it.
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Identify thiols (mercaptans) by the presence of an SH group.
The mild oxidation of thiols gives disulfides.
Because sulfur is in the same group (6A) of the periodic table as oxygen, the two elements have some similar properties. We might
expect sulfur to form organic compounds related to those of oxygen, and indeed it does. Thiols (also called mercaptans), which are
sulfur analogs of alcohols, have the general formula RSH. Methanethiol (also called methyl mercaptan), has the formula CH3SH.
Ethanethiol (ethyl mercaptan) is the most common odorant for liquid propane (LP) gas.
The mild oxidation of thiols gives compounds called disulfides.
[O]
2RSH −−→ RSSR
The amino acids cysteine [HSCH2CH(NH2)COOH] and methionine [CH3SCH2CH2CH(NH2)COOH] contain sulfur atoms, as do
all proteins that contain these amino acids. Disulfide linkages (–S–S–) between protein chains are extremely important in protein
structure.
Thioethers, which are sulfur analogs of ethers, have the form general formula RSR′. An example is dimethylsulfide (CH3SCH3),
which is responsible for the sometimes unpleasant odor of cooking cabbage and related vegetables. Note that methionine has a
thioether functional group.
 Career Focus: Paramedic

Paramedics are highly trained experts at providing emergency medical treatment. Their critical duties often include rescue
work and emergency medical procedures in a wide variety of settings, sometimes under extremely harsh and difficult
conditions. Like other science-based professions, their work requires knowledge, ingenuity, and complex thinking, as well as a
great deal of technical skill. The recommended courses for preparation in this field include anatomy, physiology, medical
terminology, and—not surprisingly—chemistry. An understanding of basic principles of organic chemistry, for example, is
useful when paramedics have to deal with such traumas as burns from fuel (hydrocarbons) or solvent (alcohols, ethers, esters,
and so on) fires and alcohol and drug overdoses.
To become a paramedic requires 2–4 y of training and usually includes a stint as an emergency medical technician (EMT). An
EMT provides basic care, can administer certain medications and treatments, such as oxygen for respiratory problems and
epinephrine (adrenalin) for allergic reactions, and has some knowledge of common medical conditions. A paramedic, in
contrast, must have extensive knowledge of common medical problems and be trained to administer a wide variety of
emergency drugs.
Paramedics usually work under the direction of a medical doctor with a title such as “medical director.” Some paramedics are
employed by fire departments and may work from a fire engine that carries medical equipment as well as fire-fighting gear.
Some work from hospital-sponsored ambulances and continue to care for their patients after reaching the hospital emergency
room. Still other paramedics work for a government department responsible for emergency health care in a specific
geographical area. Finally, some work for private companies that contract to provide service for a government body.
An experienced paramedic has a broad range of employment options, including training for mountain or ocean rescue, working
with police department special weapons and tactics (SWAT) teams, or working in isolated settings such as on oil rigs. With
their expertise at treating and stabilizing patients before quickly moving them to a hospital, paramedics often provide the first
critical steps in saving an endangered life. The following quotation, inscribed on the Arlington National Cemetery headstone of
Army Lieutenant R. Adams Cowley, who is often called the “father” of shock trauma medicine, serves as the motto for many
paramedic units: “Next to creating a life the finest thing a man can do is save one.” —Abraham Lincoln
Summary
Thiols, thioethers, and disulfides are common in biological compounds.
1. What is the functional group of a thiol? Write the condensed structural formula for ethanethiol (ethyl mercaptan).
2. What is the functional group of a disulfide? Write the condensed structural formula for dipropyl disulfide.
Answers
1. SH; CH3CH2SH
2. –S–S–; CH3CH2CH2SSCH2CH2CH3
Exercises
1. A common natural gas odorant is tert-butyl mercaptan. What is its condensed structural formula?
2. Write the equation for the oxidation of ethanethiol to diethyl disulfide.
Answer
1. (CH3)3CSH
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Identify and name a simple alkyl halide.
The presence of a halogen atom (F, Cl, Br, or I; also, X is used to represent any halogen atom) is one of the simplest functional
groups. Organic compounds that contain a halogen atom are called alkyl halides. We have already seen some examples of alkyl
halides when the addition of halogens across double and triple bonds was introduced in Section 16.3 - "Branched Hydrocarbons;"
the products of these reactions were alkyl halides.
A simple alkyl halide can be named like an ionic salt, first by stating the name of the parent alkane as a substituent group (with the
-yl suffix) and then the name of the halogen as if it were the anion. So CH3Cl has the common name of methyl chloride, while
CH3CH2Br is ethyl bromide and CH3CH2CH2I is propyl iodide. However, this system is not ideal for more complicated alkyl
halides.
The systematic way of naming alkyl halides is to name the halogen as a substituent, just like an alkyl group, and use numbers to
indicate the position of the halogen atom on the main chain. The name of the halogen as a substituent comes from the stem of the
element's name plus the ending -o, so the substituent names are fluoro-, chloro-, bromo- and iodo-. If there is more than one of a
certain halogen, we use numerical prefixes to indicate the number of each kind, just as with alkyl groups. For example, this
molecule
is 2-bromobutane, while this molecule
is 2,3-dichloropentane. If alkyl groups are present, the substituents are listed alphabetically. Numerical prefixes are ignored when
determining the alphabetical ordering of substituent groups.
 Example 14.9.1
Name this molecule.
Solution
The longest carbon chain has five C atoms, so the molecule is a pentane. There are two chlorine substituents located on the
second and third C atoms, with a one-carbon methyl group on the third C atom as well. The correct name for this molecule is
2,3-dichloro-3-methylpentane.
 Exercise 14.9.1
Name this molecule.
Answer
1,1,2-tribromopropane
Most alkyl halides are insoluble in H2O. Smaller alcohols, however, are very soluble in H2O because these molecules can engage
in hydrogen bonding with H2O molecules. For larger molecules, however, the polar OH group is overwhelmed by the nonpolar
alkyl part of the molecule. While methanol is soluble in H2O in all proportions, only about 2.6 g of pentanol will dissolve in 100 g
of H2O. Larger alcohols have an even lower solubility in H2O.
One reaction common to alcohols and alkyl halides is elimination, the removal of the functional group (either X or OH) and an H
atom from an adjacent carbon. The general reaction can be written as follows:
where Z represents either the X or the OH group. The biggest difference between elimination in alkyl halides and elimination in
alcohols is the identity of the catalyst: for alkyl halides, the catalyst is a strong base; for alcohols, the catalyst is a strong acid. For
compounds in which there are H atoms on more than one adjacent carbon, a mixture of products results.
 Example 14.9.3
Predict the organic product(s) of this reaction.
Solution
Under these conditions, an HOH (otherwise known as H2O) molecule will be eliminated, and an alkene will be formed. It does
not matter which adjacent carbon loses the H atom; in either case the product will be
which is propene.
 Exercise 14.9.3
Predict the organic product(s) of this reaction.
Answer
1-butene and 2-butene
Key Takeaways
Alkyl halides have a halogen atom as a functional group.
Alcohols have an OH group as a functional group.
Nomenclature rules allow us to name alkyl halides and alcohols.
In an elimination reaction, a double bond is formed as an HX or an HOH molecule is removed.
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CHAPTER OVERVIEW
15: Aldehydes and Ketones

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1
Identify the aldehyde and ketone functional groups.
There are other functional groups that contain O atoms. Before we introduce them, we define the carbonyl group, which is formed
when an O atom and a C atom are joined by a double bond:
The other two bonds on the C atom are attached to other atoms. It is the identities of these other atoms that define what specific
type of compound an organic molecule is.
If one bond of the carbonyl group is made to an H atom, then the molecule is classified as an aldehyde (If there are two H atoms,
there is only 1 C atom). When naming aldehydes, the main chain of C atoms must include the carbon in the carbonyl group, which
is numbered as position 1 in the carbon chain. The parent name of the hydrocarbon is used, but the suffix -al is appended. (Do not
confuse -al with -ol, which is the suffix used for alcohols.) So we have
Methanal has a common name with which you may be familiar: formaldehyde. The main thing to note about aldehydes is that the
carbonyl group is at the end of a carbon chain.
A carbonyl group in the middle of a carbon chain implies that both remaining bonds of the carbonyl group are made to C atoms.
This type of molecule is called a ketone. Despite the fact that aldehydes and ketones have the same carbonyl group, they have
different chemical and physical properties and are properly grouped as two different types of compounds. The smallest ketone has
three C atoms in it. When naming a ketone, we take the name of the parent hydrocarbon and change the suffix to -one:
The common name for propanone is acetone. With larger ketones, we must use a number to indicate the position of the carbonyl
group, much like a number is used with alkenes and alkynes:
There is another way to name ketones: name the alkyl groups that are attached to the carbonyl group and add the word ketone to the
name. So propanone can also be called dimethyl ketone, while 2-butanone is called methyl ethyl ketone.
 Example 15.1.1
Draw the structure of 2-pentanone.
Solution
This molecule has five C atoms in a chain, with the carbonyl group on the second C atom. Its structure is as follows:
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Use the IUPAC system to name and draw aldehydes and ketones.
Both common and International Union of Pure and Applied Chemistry (IUPAC) names are frequently used for aldehydes and
ketones, with common names predominating for the lower homologs. The common names of aldehydes are taken from the names
of the acids into which the aldehydes can be converted by oxidation.
The stems for the common names of the first four aldehydes are as follows:
1 carbon atom: form-
2 carbon atoms: acet-
3 carbon atoms: propion-
4 carbon atoms: butyr-
Because the carbonyl group in a ketone must be attached to two carbon groups, the simplest ketone has three carbon atoms. It is
widely known as acetone, a unique name unrelated to other common names for ketones.
Generally, the common names of ketones consist of the names of the groups attached to the carbonyl group, followed by the word
ketone. (Note the similarity to the naming of ethers.) Another name for acetone, then, is dimethyl ketone. The ketone with four
carbon atoms is ethyl methyl ketone.
 Example 15.2.1
Classify each compound as an aldehyde or a ketone. Give the common name for each ketone.
1.
Solution
1. This compound has the carbonyl group on an end carbon atom, so it is an aldehyde.
2. This compound has the carbonyl group on an interior carbon atom, so it is a ketone. Both alkyl groups are propyl groups. The
name is therefore dipropyl ketone.
3. This compound has the carbonyl group between two alkyl groups, so it is a ketone. One alkyl group has three carbon atoms and
is attached by the middle carbon atom; it is an isopropyl group. A group with one carbon atom is a methyl group. The name is
therefore isopropyl methyl ketone.
 Exercise 15.2.1
Classify each compound as an aldehyde or a ketone. Give the common name for each ketone.
1.
Here are some simple IUPAC rules for naming aldehydes and ketones:
 Example 15.2.2
Give the IUPAC name for each compound.
a.
Solution
a. There are five carbon atoms in the LCC. The methyl group (CH3) is a substituent on the second carbon atom of the chain; the
aldehyde carbon atom is always C1. The name is derived from pentane. Dropping the -e and adding the ending -al gives
pentanal. The methyl group on the second carbon atom makes the name 2-methylpentanal.
b. There are five carbon atoms in the LCC. The carbonyl carbon atom is C3, and there are methyl groups on C2 and C4. The
IUPAC name is 2,4-dimethyl-3-pentanone.
c. There are six carbon atoms in the ring. The compound is cyclohexanone. No number is needed to indicate the position of the
carbonyl group because all six carbon atoms are equivalent.
 Exercise
Give the IUPAC name for each compound.
a.
 Example 15.2.3

a. 7-chlorooctanal
b. 4-methyl–3-hexanone
Solution
a. The octan- part of the name tells us that the LCC has eight carbon atoms. There is a chlorine (Cl) atom on the seventh
carbon atom; numbering from the carbonyl group and counting the carbonyl carbon atom as C1, we place the Cl atom on
the seventh carbon atom.
The hexan- part of the name tells us that the LCC has six carbon atoms. The 3 means that the carbonyl carbon atom is C3 in this
chain, and the 4 tells us that there is a methyl (CH3) group at C4:
 Exercise

a. 5-bromo-3-iodoheptanal
b. 5-bromo-4-ethyl-2-heptanone
Summary
The common names of aldehydes are taken from the names of the corresponding carboxylic acids: formaldehyde, acetaldehyde,
and so on. The common names of ketones, like those of ethers, consist of the names of the groups attached to the carbonyl group,
followed by the word ketone. Stem names of aldehydes and ketones are derived from those of the parent alkanes, using an -al
ending for an aldehydes and an -one ending for a ketone.
1. The stem names of aldehydes and ketones are derived from those of the parent alkanes, defined by the longest continuous chain
(LCC) of carbon atoms that contains the functional group.
2. For an aldehyde, drop the -e from the alkane name and add the ending -al. Methanal is the IUPAC name for formaldehyde, and
ethanal is the name for acetaldehyde.
3. For a ketone, drop the -e from the alkane name and add the ending -one. Propanone is the IUPAC name for acetone, and
butanone is the name for ethyl methyl ketone.
4. To indicate the position of a substituent on an aldehyde, the carbonyl carbon atom is always considered to be C1; it is
unnecessary to designate this group by number.
5. To indicate the position of a substituent on a ketone, number the chain in the manner that gives the carbonyl carbon atom the
lowest possible number. In cyclic ketones, it is understood that the carbonyl carbon atom is C1.
6. Give the structure and IUPAC name for the compound that has the common name m-bromobenzaldehyde.
7. Give the IUPAC name for glyceraldehyde, (HOCH2CHOHCHO). (Hint: as a substituent, the OH group is named hydroxy.)
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Explain why the boiling points of aldehydes and ketones are higher than those of ethers and alkanes of similar molar
masses but lower than those of comparable alcohols.
Compare the solubilities in water of aldehydes and ketones of four or fewer carbon atoms with the solubilities of
comparable alkanes and alcohols.
Name the typical reactions take place with aldehydes and ketones.
Describe some of the uses of common aldehydes and ketones.
The carbon-to-oxygen double bond is quite polar, more polar than a carbon-to-oxygen single bond. The electronegative oxygen
atom has a much greater attraction for the bonding electron pairs than does the carbon atom. The carbon atom has a partial positive
charge, and the oxygen atom has a partial negative charge:
In aldehydes and ketones, this charge separation leads to dipole-dipole interactions that are great enough to significantly affect the
boiling points. Table 15.3.1 shows that the polar single bonds in ethers have little such effect, whereas hydrogen bonding between
alcohol molecules is even stronger.
Table 15.3.1 : Boiling Points of Compounds Having Similar Molar Masses but Different Types of Intermolecular Forces
Type of Intermolecular
Compound Family Molar Mass Boiling Point (°C)
Forces
CH3CH2CH2CH3 alkane 58 dispersion only –1
CH3OCH2CH3 ether 60 weak dipole 6
CH3CH2CHO aldehyde 58 strong dipole 49
CH3CH2CH2OH alcohol 60 hydrogen bonding 97
Formaldehyde is a gas at room temperature. Acetaldehyde boils at 20°C; in an open vessel, it boils away in a warm room. Most
other common aldehydes are liquids at room temperature.
Although the lower members of the homologous series have pungent odors, many higher aldehydes have pleasant odors and
are used in perfumes and artificial flavorings. As for the ketones, acetone has a pleasant odor, but most of the higher homologs
have rather bland odors.
The oxygen atom of the carbonyl group engages in hydrogen bonding with a water molecule.
The solubility of aldehydes is therefore about the same as that of alcohols and ethers. Formaldehyde, acetaldehyde, and acetone are
soluble in water. As the carbon chain increases in length, solubility in water decreases. The borderline of solubility occurs at about
four carbon atoms per oxygen atom. All aldehydes and ketones are soluble in organic solvents and, in general, are less dense than
water.
Oxidation of Aldehydes and Ketones

Aldehydes and ketones are much alike in many of their reactions, owing to the presence of the carbonyl functional group in both.
They differ greatly, however, in one most important type of reaction: oxidation. Aldehydes are readily oxidized to carboxylic acids,
whereas ketones resist oxidation.
The aldehydes are, in fact, among the most easily oxidized of organic compounds. They are oxidized by oxygen (O2) in air to
carboxylic acids.
2RC H O + O2 → 2RC OOH (15.3.1)
The ease of oxidation helps chemists identify aldehydes. A sufficiently mild oxidizing agent can distinguish aldehydes not only
from ketones but also from alcohols. Tollens’ reagent, for example, is an alkaline solution of silver (Ag+) ion complexed with
ammonia (NH3), which keeps the Ag+ ion in solution.
+
H3 N — Ag — N H3 (15.3.2)
When Tollens’ reagent oxidizes an aldehyde, the Ag+ ion is reduced to free silver (Ag).
Deposited on a clean glass surface, the silver produces a mirror (Figure 15.3.1 ). Ordinary ketones do not react with Tollens’
reagent.
Figure 15.3.1 : Aldehyde Reactions. A reaction related to the Tollens’ reaction is often used to silver mirrors. These ornaments were
silvered by such a reaction. Glucose, a simple sugar with an aldehyde functional group, is used as the reducing agent. Source:
Photo courtesy of Krebs Glas Lauscha, commons.wikimedia.org/wiki/File:Silvering.jpg.
Although ketones resist oxidation by ordinary laboratory oxidizing agents, they undergo combustion, as do aldehydes.
Summary
The polar carbon-to-oxygen double bond causes aldehydes and ketones to have higher boiling points than those of ethers and
alkanes of similar molar masses but lower than those of comparable alcohols that engage in intermolecular hydrogen bonding.
Aldehydes are readily oxidized to carboxylic acids, whereas ketones resist oxidation.
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Objective 1
Objective 2
Formaldehyde has an irritating odor. Because of its reactivity, it is difficult to handle in the gaseous state. For many uses, it is
therefore dissolved in water and sold as a 37% to 40% aqueous solution called formalin. Formaldehyde denatures proteins,
rendering them insoluble in water and resistant to bacterial decay. For this reason, formalin is used in embalming solutions and in
preserving biological specimens.
Aldehydes are the active components in many other familiar substances. Large quantities of formaldehyde are used to make
phenol-formaldehyde resins for gluing the wood sheets in plywood and as adhesives in other building materials. Sometimes the
formaldehyde escapes from the materials and causes health problems in some people. While some people seem unaffected, others
experience coughing, wheezing, eye irritation, and other symptoms.
The odor of green leaves is due in part to a carbonyl compound, cis-3-hexenal, which
with related compounds is used to impart a “green” herbal odor to shampoos and other
products.
Acetaldehyde is an extremely volatile, colorless liquid. It is a starting material for the preparation of many other organic
compounds. Acetaldehyde is formed as a metabolite in the fermentation of sugars and in the detoxification of alcohol in the liver.
Aldehydes are the active components of many other familiar materials (Figure 15.4.2).
Figure 15.4.2 Some Interesting Aldehydes. (a) Benzaldehyde is an oil found in almonds; (b) cinnamaldehyde is oil of cinnamon;
(c) vanillin gives vanilla its flavor; (d) cis-3-hexenal provides an herbal odor; and (e) trans-2-cis-6-nonadienal gives a cucumber
odor.
Acetone is the simplest and most important ketone. Because it is miscible with water as well as with most organic solvents, its chief
use is as an industrial solvent (for example, for paints and lacquers). It is also the chief ingredient in some brands of nail polish
remover.
 To Your Health: Acetone in Blood, Urine, and Breath

Acetone is formed in the human body as a by-product of lipid metabolism. Normally, acetone does not accumulate to an
appreciable extent because it is oxidized to carbon dioxide and water. The normal concentration of acetone in the human body
is less than 1 mg/100 mL of blood. In certain disease states, such as uncontrolled diabetes mellitus, the acetone concentration
rises to higher levels. It is then excreted in the urine, where it is easily detected. In severe cases, its odor can be noted on the
breath.
Ketones are also the active components of other familiar substances, some of which are noted in the accompanying figure.
Some ketones have interesting properties: (a) Butter flavoring comes from 2,3-butanedione; (b) β-ionone is responsible for the
odor of violets; (c) muscone is musk oil, an ingredient in perfumes; and (d) camphor is used in some insect repellents.
Certain steroid hormones have the ketone functional group as a part of their structure. Two examples are progesterone, a hormone
secreted by the ovaries that stimulates the growth of cells in the uterine wall and prepares it for attachment of a fertilized egg, and
testosterone, the main male sex hormone. These and other sex hormones affect our development and our lives in fundamental ways.
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Objective 1
Objective 2
ldehydes and ketones are much alike in many of their reactions, owing to the presence of the carbonyl functional group in both.
They differ greatly, however, in one most important type of reaction: oxidation. Aldehydes are readily oxidized to carboxylic acids,
whereas ketones resist oxidation.
The aldehydes are, in fact, among the most easily oxidized of organic compounds. They are oxidized by oxygen (O2) in air to
carboxylic acids.
2RC H O + O2 → 2RC OOH (15.5.1)
The ease of oxidation helps chemists identify aldehydes. A sufficiently mild oxidizing agent can distinguish aldehydes not only
from ketones but also from alcohols. Tollens’ reagent, for example, is an alkaline solution of silver (Ag+) ion complexed with
ammonia (NH3), which keeps the Ag+ ion in solution.
+
H3 N — Ag — N H3 (15.5.2)
When Tollens’ reagent oxidizes an aldehyde, the Ag+ ion is reduced to free silver (Ag).
Deposited on a clean glass surface, the silver produces a mirror (Figure 15.5.1 ). Ordinary ketones do not react with Tollens’
reagent.
Figure 15.5.1 : Aldehyde Reactions. A reaction related to the Tollens’ reaction is often used to silver mirrors. These ornaments were
silvered by such a reaction. Glucose, a simple sugar with an aldehyde functional group, is used as the reducing agent. Source:
Photo courtesy of Krebs Glas Lauscha, commons.wikimedia.org/wiki/File:Silvering.jpg.
Although ketones resist oxidation by ordinary laboratory oxidizing agents, they undergo combustion, as do aldehydes.
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CHAPTER OVERVIEW
16: Amines
16.6: Amine Salts
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1
Determine the structural feature that classifies amines as primary, secondary, or tertiary.
Amines are classified according to the number of carbon atoms bonded directly to the nitrogen atom. A primary (1°) amine has one
alkyl (or aryl) group on the nitrogen atom, a secondary (2°) amine has two, and a tertiary (3°) amine has three (Figure 16.1.1).
Figure 16.1.1 : The Structure of Amines Compared to Water, an Alcohol, and an Ether
To classify alcohols, we look at the number of carbon atoms bonded to the carbon atom bearing the OH group, not the oxygen
atom itself. Thus, although isopropylamine looks similar to isopropyl alcohol, the former is a primary amine, while the latter is
a secondary alcohol.
The common names for simple aliphatic amines consist of an alphabetic list of alkyl groups attached to the nitrogen atom, followed
by the suffix -amine. (Systematic names are often used by some chemists.) The amino group (NH2) is named as a substituent in
more complicated amines, such as those that incorporate other functional groups or in which the alkyl groups cannot be simply
named.
 Example 16.1.1
Name and classify each compound.
a. CH3CH2CH2NH2
b.
CH3CH2NHCH2CH3
CH3CH2CH2NHCH3
Solution
a. There is only one alkyl group attached to the nitrogen atom, so the amine is primary. A group of three carbon atoms (a propyl
group) is attached to the NH2 group through an end carbon atom, so the name is propylamine.
b. There are two methyl groups and one ethyl group on the nitrogen atom. The compound is ethyldimethylamine, a tertiary amine.
c. There are two ethyl groups attached to the nitrogen atom; the amine is secondary, so the compound is diethylamine.
d. The nitrogen atom has a methyl group and a propyl group, so the compound is methylpropylamine, a secondary amine.
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Objective 1
Objective 2
The common names for simple aliphatic amines consist of an alphabetic list of alkyl groups attached to the nitrogen atom, followed
by the suffix -amine. (Systematic names are often used by some chemists.) The amino group (NH2) is named as a substituent in
more complicated amines, such as those that incorporate other functional groups or in which the alkyl groups cannot be simply
named.
 Example 16.2.1

a. CH3CH2CH2NH2
b.
CH3CH2NHCH2CH3
CH3CH2CH2NHCH3
Solution
a. There is only one alkyl group attached to the nitrogen atom, so the amine is primary. A group of three carbon atoms (a propyl
group) is attached to the NH2 group through an end carbon atom, so the name is propylamine.
b. There are two methyl groups and one ethyl group on the nitrogen atom. The compound is ethyldimethylamine, a tertiary amine.
c. There are two ethyl groups attached to the nitrogen atom; the amine is secondary, so the compound is diethylamine.
d. The nitrogen atom has a methyl group and a propyl group, so the compound is methylpropylamine, a secondary amine.
 Exercise 16.2.1
a.
CH3CH2CH2CH2NH2
CH3CH2CH2NHCH2CH2 CH3
 Example 16.2.2
Draw the structure for each compound and classify.
a. isopropyldimethylamine
b. dipropylamine
Solution
a. The name indicates that there are an isopropyl group (in red) and two methyl groups (in green) attached to the nitrogen
atom; the amine is tertiary.
The name indicates that there are two propyl groups attached to the nitrogen atom; the amine is secondary. (The third bond on
the nitrogen atom goes to a hydrogen atom.) CH3CH2CH2NHCH2CH2CH3
 Exercise 16.2.2
Draw the structure for each compound and classify.

a. ethylisopropylamine
b. diethylpropylamine
The primary amine in which the nitrogen atom is attached directly to a benzene ring has a special name—aniline. Aryl amines are
named as derivatives of aniline.
 Example 16.2.3
Name this compound.
Solution
The benzene ring with an amino (NH2) group is aniline. The compound is named as a derivative of aniline: 3-bromoaniline or m-
bromoaniline.
 Exercise 16.2.3
Name this compound.
 Example 16.2.4
Draw the structure for p-ethylaniline and classify.
Solution
The compound is a derivative of aniline. It is a primary amine having an ethyl group located para to the amino (NH2) group.
 Exercise 16.2.4
Draw the structure for p-isopropylaniline and classify.
 Example 16.2.5
Draw the structure for 2-amino-3-methylpentane.
Solution
Always start with the parent compound: draw the pentane chain. Then attach a methyl group at the third carbon atom and an
amino group at the second carbon atom.
 Exercise 16.2.5
Draw the structure for 2-amino-3-ethyl-1-chloroheptane.
Ammonium (NH4+) ions, in which one or more hydrogen atoms are replaced with alkyl groups, are named in a manner analogous
to that used for simple amines. The alkyl groups are named as substituents, and the parent species is regarded as the NH4+ ion. For
example, CH3NH3+ is the methylammonium ion. The ion formed from aniline (C6H5NH3+) is called the anilinium ion.
 Example 16.2.6
Name each ion.

a. CH3NH3+
b. (CH3)2NH2+
c. (CH3)3NH+
d. (CH3)4N+
Solution
The ions have one, two, three, and four methyl (CH3) groups attached to a nitrogen atom. Their names are as follows:
a. methylammonium ion
b. dimethylammonium ion
c. trimethylammonium ion
d. tetramethylammonium ion
 Exercise 16.2.6
Name each ion.

a. CH3CH2NH3+
b. (CH3CH2)3NH+
c. (CH3CH2CH2)2NH2+
d. (CH3CH2CH2CH2)4N+
Summary
An amine is a derivative of ammonia in which one, two, or all three hydrogen atoms are replaced by hydrocarbon groups. The
amine functional group is as follows:
Amines are classified as primary, secondary, or tertiary by the number of hydrocarbon groups attached to the nitrogen atom.
Amines are named by naming the alkyl groups attached to the nitrogen atom, followed by the suffix -amine.
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Explain why the boiling points of primary and secondary amines are higher than those of alkanes or ethers of similar molar
mass but are lower than those of alcohols.
Compare the boiling points of tertiary amines with alcohols, alkanes, and ethers of similar molar mass.
Compare the solubilities in water of amines of five or fewer carbon atoms with the solubilities of comparable alkanes and
alcohols in water.
Primary and secondary amines have hydrogen atoms bonded to an nitrogen atom and are therefore capable of hydrogen bonding
(part (a) of Figure 16.3.1), although not as strongly as alcohol molecules (which have hydrogen atoms bonded to an oxygen atom,
which is more electronegative than nitrogen). These amines boil at higher temperatures than alkanes but at lower temperatures than
alcohols of comparable molar mass. For example, compare the boiling point of methylamine (CH3NH2; −6°C) with those of ethane
(CH3CH3; −89°C) and methanol (CH3OH; 65°C). Tertiary amines have no hydrogen atom bonded to the nitrogen atom and so
cannot participate in intermolecular hydrogen bonding. They have boiling points comparable to those of ethers (Table 16.3.1).
Figure 16.3.1 : Hydrogen Bonding. (a) Amine molecules are associated through hydrogen bonding. (b) An amine molecule can
form a hydrogen bond with water molecules.
Table 16.3.1 : Physical Properties of Some Amines and Comparable Oxygen-Containing Compounds
Condensed Solubility at 25°C
Name Class Molar Mass Boiling Point (°C)
Structural Formula (g/100 g Water)
butylamine CH3CH2CH2CH2NH2 1° 73 78 miscible
diethylamine (CH3CH2)2NH 2° 73 55 miscible
butyl alcohol CH3CH2CH2CH2OH — 74 118 8
dipropylamine (CH3CH2CH2)2NH 2° 101 111 4
triethylamine (CH3CH2)3N 3° 101 90 14
dipropyl ether (CH3CH2CH2)2O — 102 91 0.25
All three classes of amines can engage in hydrogen bonding with water (Figure ). Amines of low molar mass are quite
16.3.1b
soluble in water; the borderline of solubility in water is at five or six carbon atoms.
 To Your Health: Amines in Death and Life
Amines have “interesting” odors. The simple ones smell very much like ammonia. Higher aliphatic amines smell like decaying
fish. Or perhaps we should put it the other way around: Decaying fish give off odorous amines. The stench of rotting fish is
due in part to two diamines: putrescine and cadaverine. They arise from the decarboxylation of ornithine and lysine,
respectively, amino acids that are found in animal cells.
Aromatic amines generally are quite toxic. They are readily absorbed through the skin, and workers must exercise caution when
handling these compounds. Several aromatic amines, including β-naphthylamine, are potent carcinogens.
Key Takeaways
Primary and secondary amines have higher boiling points than those of alkanes or ethers of similar molar mass because they
can engage in intermolecular hydrogen bonding. Their boiling points are lower than those of alcohols because alcohol
molecules have hydrogen atoms bonded to an oxygen atom, which is more electronegative.
The boiling points of tertiary amines, which cannot engage in hydrogen bonding because they have no hydrogen atom on the
nitrogen atom, are comparable to those of alkanes and ethers of similar molar mass.
Because all three classes of amines can engage in hydrogen bonding with water, amines of low molar mass are quite soluble in
water.

1. Which compound has the higher boiling point, CH3CH2CH2CH2CH2NH2 or CH3CH2CH2CH2CH2CH3? Explain.
2. Which compound is more soluble in water, CH3CH2CH2CH2CH3 or CH3CH2NHCH2CH3? Explain.
Answers
1. CH3CH2CH2CH2CH2NH2 because the nitrogen-to-hydrogen (N–H) bonds can engage in hydrogen bonding;
CH3CH2CH2CH2CH2CH3 cannot engage in hydrogen bonding
2. CH3CH2NHCH2CH3 because amines can engage in hydrogen bonding with water; alkanes cannot engage in hydrogen bonding
Exercises
1. Which compound of each pair has the higher boiling point? Explain.
a. butylamine or pentane
b. CH3NH2 or CH3CH2CH2CH2CH2NH2
2. Which compound of each pair has the higher boiling point? Explain.
a. butylamine or butyl alcohol
b. trimethylamine or propylamine
3. Which compound is more soluble in water—CH3CH2CH3 or CH3CH2NH2? Explain.
4. Which compound is more soluble in water—CH3CH2CH2NH2 or CH3CH2CH2CH2CH2CH2NH2? Explain.
Answers
1. a. butylamine because the N–H bonds can engage in hydrogen bonding; pentane cannot engage in hydrogen bonding
b. CH3CH2CH2CH2CH2NH2 because it has a greater molar mass than CH3NH2
3. CH3CH2NH2 because amines can engage in hydrogen bonding with water; alkanes cannot engage in hydrogen bonding
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Objective 1
Objective 2
Heterocyclic Amines
Looking back at the various cyclic hydrocarbons discussed previously, we see that all the atoms in the rings of these compounds are
carbon atoms. In other cyclic compounds, called heterocyclic compounds (Greek heteros, meaning “other”), nitrogen, oxygen,
sulfur, or some other atom is incorporated in the ring. Many heterocyclic compounds are important in medicine and biochemistry.
Some compose part of the structure of the nucleic acids, which in turn compose the genetic material of cells and direct protein
synthesis.
Many heterocyclic amines occur naturally in plants. Like other amines, these compounds are basic. Such a compound is an
alkaloid, a name that means “like alkalis.” Many alkaloids are physiologically active, including the familiar drugs caffeine,
nicotine, and cocaine.
 To Your Health: Three Well-Known Alkaloids

Caffeine is a stimulant found in coffee, tea, and some soft drinks. Its mechanism of action is not well understood, but it is
thought to block the activity of adenosine, a heterocyclic base that acts as a neurotransmitter, a substance that carries messages
across a tiny gap (synapse) from one nerve cell (neuron) to another cell. The effective dose of caffeine is about 200 mg,
corresponding to about two cups of strong coffee or tea.
Nicotine acts as a stimulant by a different mechanism; it probably mimics the action of the neurotransmitter acetylcholine. People
ingest this drug by smoking or chewing tobacco. Its stimulant effect seems transient, as this initial response is followed by
depression. Nicotine is highly toxic to animals. It is especially deadly when injected; the lethal dose for a human is estimated to be
about 50 mg. Nicotine has also been used in agriculture as a contact insecticide.
Cocaine acts as a stimulant by preventing nerve cells from taking up dopamine, another neurotransmitter, from the synapse. High
levels of dopamine are therefore available to stimulate the pleasure centers of the brain. The enhancement of dopamine action is
thought to be responsible for cocaine’s “high” and its addictive properties. After the binge, dopamine is depleted in less than an
hour. This leaves the user in a pleasureless state and (often) craving more cocaine.
Cocaine is used as the salt cocaine hydrochloride and in the form of broken lumps of the free (unneutralized) base, which is called
crack cocaine.
Because it is soluble in water, cocaine hydrochloride is readily absorbed through the watery mucous membranes of the nose when it
is snorted. Crack cocaine is more volatile than cocaine hydrochloride. It vaporizes at the temperature of a burning cigarette. When
smoked, cocaine reaches the brain in 15 s.
Summary
Amines are bases; they react with acids to form salts. Salts of aniline are properly named as anilinium compounds, but an older
system is used to name drugs: the salts of amine drugs and hydrochloric acid are called “hydrochlorides.” Heterocyclic amines are
cyclic compounds with one or more nitrogen atoms in the ring.
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Name the typical reactions that take place with amines.
Describe heterocyclic amines.
Recall that ammonia (NH3) acts as a base because the nitrogen atom has a lone pair of electrons that can accept a proton. Amines
also have a lone electron pair on their nitrogen atoms and can accept a proton from water to form substituted ammonium (NH4+)
ions and hydroxide (OH−) ions:
As a specific example, methylamine reacts with water to form the methylammonium ion and the OH− ion.
Nearly all amines, including those that are not very soluble in water, will react with strong acids to form salts soluble in water.
Amine salts are named like other salts: the name of the cation is followed by the name of the anion.
 Example 16.5.1
What are the formulas of the acid and base that react to form [CH3NH2CH2CH3]+CH3COO−?
Solution
The cation has two groups—methyl and ethyl—attached to the nitrogen atom. It comes from ethylmethylamine
(CH3NHCH2CH3). The anion is the acetate ion. It comes from acetic acid (CH3COOH).
 Exercise 16.5.1
What are the formulas of the acid and base that react to form (CH3CH2CH2)3NH+I−?
 To Your Health: Amine Salts as Drugs

Salts of aniline are properly named as anilinium compounds, but an older system, still in use for naming drugs, identifies the
salt of aniline and hydrochloric acid as “aniline hydrochloride.” These compounds are ionic—they are salts—and the
properties of the compounds (solubility, for example) are those characteristic of salts. Many drugs that are amines are
converted to hydrochloride salts to increase their solubility in aqueous solution.
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16.6: Amine Salts
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Objective 1
Objective 2
Addictive Alkaloids
Since ancient times, plants have been used for medicinal purposes. One class of substances, called alkaloids, found in many of
these plants has been isolated and found to contain cyclic molecules with an amine functional group. These amines are bases. They
can react with H3O+ in a dilute acid to form an ammonium salt, and this property is used to extract them from the plant:
+ − + −
R N+H O + Cl ⟶ [ R NH ] Cl +H O
3 3 3 2
The name alkaloid means “like an alkali.” Thus, an alkaloid reacts with acid. The free compound can be recovered after extraction
by reaction with a base:
+ − − −
[ R NH ] Cl + OH ⟶ R N + H O + Cl
3 3 2
The structures of many naturally occurring alkaloids have profound physiological and psychotropic effects in humans. Examples of
these drugs include nicotine, morphine, codeine, and heroin. The plant produces these substances, collectively called secondary
plant compounds, as chemical defenses against the numerous pests that attempt to feed on the plant:
Figure 16.7.3 ).
Figure 16.7.3 : Poppies can be used in the production of opium, a plant latex that contains morphine from which other opiates, such
as heroin, can be synthesized. (credit: Karen Roe)
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CHAPTER OVERVIEW
17: Carboxylic Acids and their Derivatives

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1
Objective 1
Objective 2
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Define pK and use it to determine acidity of different carboxylic acids.
a
Describe the reactions between carboxylic acids and strong bases.
Ionization of Carboxylic Acids

Carboxylic acids are named such because they tend to be more acidic than other functional groups in organic chemistry. In dilute
aqueous solutions, they act as weak acids that partially dissociate to produce the corresponding carboxylate anion and hydronium
cation (H3O+). Carboxylate anions are named by replacing the -ic acid ending from the carboxylic acid with -ate, see examples
below.
The extent of dissociation of these weak acids in water is described by K values. Remember that a compound with a smaller K
a a
value will be a weaker acid.

− +
[ RCOO ][ H O ]
− + 3
RC OOH + H2 O ⇌ RC OO + H3 O Ka =
[RCOOH]
When comparing the acidity of organic and biomolecules, it is useful (and more preferable) to use pK values instead of K a a
values, which are calculated by taking the negative log of K : pK = – log K . When using the pK scale, it is important to
a a a a
know that weaker acids have larger and more positive pK values, this is opposite of K values. The pK values of some typical
a a a
carboxylic acids are listed in Table 17.2.1. (Remember that pK is a log expression, which means that every 1 pK unit represents
a a
a 10-fold change in acidity.)

Table 17.2.1 : Comparisons of Carboxylic Acid K and pK Values
a a
Name Compound Ka pKa
formic acid HCOOH 1.8 X 10–4 3.74
acetic acid CH3COOH 1.8 X 10–5 4.74
propanoic acid CH3CH2COOH 1.3 X 10–5 4.89
butanoic acid CH3CH2CH2COOH 1.5 X 10–5 4.82
chloroacetic acid ClCH2COOH 1.4 X 10–3 2.85
trichloroacetic acid Cl3CCOOH 2.3 X 10–1 0.64
hexanoic acid CH3(CH2)4COOH 1.3 X 10–5 4.89
benzoic acid C6H5COOH 6.5 X 10–5 4.19
oxalic acid HOOCCOOH 5.4 X 10–2 1.27

–OOCCOOH 5.2 X 10–5 4.28
glutaric acid HOOC(CH2)3COOH 4.5 X 10–5 4.35

–OOC(CH ) COOH 3.8 X 10–6 5.42
2 3
Neutralization of Carboxylic Acids
Carboxylic acids will react with bases such as sodium hydroxide (NaOH), sodium carbonate (Na2CO3), and sodium bicarbonate
(NaHCO3) to form water and a carboxylic acid salt:
RCOOH + NaOH(aq) → RCOO−Na+(aq) + H2O
2RCOOH + Na2CO3(aq) → 2RCOO−Na+(aq) + H2O + CO2(g)
RCOOH + NaHCO3(aq) → RCOO−Na+(aq) + H2O + CO2(g)
In these reactions, the carboxylic acids act like inorganic acids: they neutralize basic compounds. With solutions of carbonate (
CO
2–
3
) and bicarbonate (H C O ) ions, they also form carbon dioxide gas.
–
3
Carboxylic acid salts are named in the same manner as inorganic salts: the name of the cation is followed by the name of the
organic anion. The name of the anion is obtained by dropping the -ic ending of the acid name and replacing it with the suffix -ate.
This rule applies whether we are using common names or International Union of Pure and Applied Chemistry (IUPAC) names:
 Note
The salts of long-chain carboxylic acids are called soaps.
 Example 17.2.1
Write an equation for each reaction.

1. the ionization of propionic acid in water (H2O)
2. the neutralization of propionic acid with aqueous sodium hydroxide (NaOH)
Solution
Propionic acid has three carbon atoms, so its formula is CH2CH2COOH.
1. Propionic acid ionizes in water to form a propionate ion and a hydronium (H3O+) ion. CH3CH2COOH(aq) + H2O(ℓ) →
CH3CH2COO−(aq) + H3O+(aq)
2. Propionic acid reacts with NaOH(aq) to form sodium propionate and water. CH3CH2COOH(aq) + NaOH(aq) →
CH3CH2COO−Na+(aq) + H2O(ℓ)
 Exercise 17.2.1
Write an equation for each reaction.
a. the ionization of formic acid in water
b. the ionization of p-chlorobenzoic acid in water
 Example 17.2.2
Write an equation for the reaction of decanoic acid with each compound.
a. aqueous sodium hydoxide (NaOH)
b. aqueous sodium bicarbonate (NaHCO3)
Solution
a. Decanoic acid has 10 carbon atoms. It reacts with NaOH to form a salt and water (H2O). CH3(CH2)8COOH + NaOH(aq) →
CH3(CH2)8COO−Na+(aq) + H2O(ℓ)
b. With NaHCO3, the products are a salt, H2O, and carbon dioxide (CO2). CH3(CH2)8COOH + NaHCO3(aq) →
CH3(CH2)8COO−Na+(aq) + H2O(ℓ) + CO2(g)
 Exercise 17.2.3
Write an equation for the reaction of benzoic acid with each compound.
a. aqueous sodium hydroxide (NaOH)
b. aqueous sodium bicarbonate (NaHCO3)
 Note To Your Health: Organic Salts as Preservatives
Some organic salts are used as preservatives in food products. They prevent spoilage by inhibiting the growth of bacteria and
fungi. Calcium and sodium propionate, for example, are added to processed cheese and bakery goods; sodium benzoate is
added to cider, jellies, pickles, and syrups; and sodium sorbate and potassium sorbate are added to fruit juices, sauerkraut, soft
drinks, and wine. Look for them on ingredient labels the next time you shop for groceries.
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To identify and describe the substances from which most esters are prepared.
To identify and describe the substances from which most amides are prepared.
Carboxylic acids will react with alcohols and amines following a similar pattern. In both cases, the –OH group of the carboxylic
acid will be replaced by a different group to form either an ester or an amide, with water formed as a by-product. When the reaction
involves an alcohol, the –OH of the acid is replaced by the –OR' of the alcohol. When the reaction involves an amine, the –OH of
the acid is replaced by the –NH2, or –NHR', or –NR'2 of the amine.
Ester formation
Amide formation
Esterification
Esters are prepared by esterification, a reaction in which a carboxylic acid and an alcohol are heated in the presence of an acid
catalyst:
The reaction is reversible and will reach equilibrium with approximately equivalent amounts of reactants and products. Using
excess amounts of alcohol and continuously removing a product, can drive the reaction towards the product side as per
LeChatelier's principle.
 A Closer Look: Condensation Polymers

A commercially important esterification reaction is condensation polymerization, in which a reaction occurs between a
dicarboxylic acid and a dihydric alcohol (diol), with the elimination of water. Such a reaction yields an ester that contains a
free (unreacted) carboxyl group at one end and a free alcohol group at the other end. Further condensation reactions then occur,
producing polyester polymers.
The most important polyester, polyethylene terephthalate (PET), is made from terephthalic acid and ethylene glycol monomers:
Polyester molecules make excellent fibers and are used in many fabrics. A knitted polyester tube, which is biologically inert, can be
used in surgery to repair or replace diseased sections of blood vessels. PET is used to make bottles for soda pop and other
beverages. It is also formed into films called Mylar. When magnetically coated, Mylar tape is used in audio- and videocassettes.
Synthetic arteries can be made from PET, polytetrafluoroethylene, and other polymers.
Amide Formation
When a carboxylic acid reacts with ammonia (NH3) a primary amide is formed:
When a carboxylic acid reacts with primary or secondary amines, secondary or tertiary amides are produced, respectively.
Need another figure here

Tertiary amines do not have a hydrogen attached to the nitrogen and therefore do not form amides when mixed with carboxylic
acids. However, an acid-base reaction does occur with the amine accepting a proton (acts as a base) and the carboxylic acid
donating a proton. In this case the ammonium and carboxylate salts are formed:
Need another figure here
 Note Polyamides
Just as the reaction of a diol and a diacid forms a polyester, the reaction of a diacid and a diamine yields a polyamide. The two
difunctional monomers often employed are adipic acid and 1,6-hexanediamine. The monomers condense by splitting out water
to form a new product, which is still difunctional and thus can react further to yield a polyamide polymer.
Some polyamides are known as nylons. Nylons are among the most widely used synthetic fibers—for example, they are used
in ropes, sails, carpets, clothing, tires, brushes, and parachutes. They also can be molded into blocks for use in electrical
equipment, gears, bearings, and valves.
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Describe the typical reaction that takes place with esters.
Identify the products of an acidic hydrolysis of an ester.
Identify the products of a basic hydrolysis of an ester.
Esters are neutral compounds, unlike the acids from which they are formed. In typical reactions, the alkoxy (OR′) group of an ester
is replaced by another group. One such reaction is hydrolysis, literally “splitting with water.” The hydrolysis of esters is catalyzed
by either an acid or a base.
Acidic hydrolysis is simply the reverse of esterification. The ester is heated with a large excess of water containing a strong-acid
catalyst. Like esterification, the reaction is reversible and does not go to completion.
As a specific example, butyl acetate and water react to form acetic acid and 1-butanol. The reaction is reversible and does not go to
completion.
 Example 17.4.1
Write an equation for the acidic hydrolysis of ethyl butyrate (CH3CH2CH2COOCH2CH3) and name the products.
Solution
Remember that in acidic hydrolysis, water (HOH) splits the ester bond. The H of HOH joins to the oxygen atom in the OR part
of the original ester, and the OH of HOH joins to the carbonyl carbon atom:
The products are butyric acid (butanoic acid) and ethanol.
 Exercise 17.4.1
Write an equation for the acidic hydrolysis of methyl butanoate and name the products.
When a base (such as sodium hydroxide [NaOH] or potassium hydroxide [KOH]) is used to hydrolyze an ester, the products are a
carboxylate salt and an alcohol. Because soaps are prepared by the alkaline hydrolysis of fats and oils, alkaline hydrolysis of esters
is called saponification (Latin sapon, meaning “soap,” and facere, meaning “to make”). In a saponification reaction, the base is a
reactant, not simply a catalyst. The reaction goes to completion:
As a specific example, ethyl acetate and NaOH react to form sodium acetate and ethanol:
 Example 17.4.2
Write an equation for the hydrolysis of methyl benzoate in a potassium hydroxide solution.
Solution
In basic hydrolysis, the molecule of the base splits the ester linkage. The acid portion of the ester ends up as the salt of the acid
(in this case, the potassium salt). The alcohol portion of the ester ends up as the free alcohol.
 Exercise 17.4.2
Write the equation for the hydrolysis of ethyl propanoate in a sodium hydroxide solution.
Hydrolysis of Amides
Generally, amides resist hydrolysis in plain water, even after prolonged heating. In the presence of added acid or base, however,
hydrolysis proceeds at a moderate rate. In living cells, amide hydrolysis is catalyzed by enzymes. Amide hydrolysis is illustrated in
the following example:
Hydrolysis of an amide in acid solution actually gives a carboxylic acid and the salt of
ammonia or an amine (the ammonia or amine initially formed is neutralized by the acid).
Basic hydrolysis gives a salt of the carboxylic acid and ammonia or an amine.
 Example 17.4.1
Write the equation for the hydrolysis of each compound.
a. butyramide
b. benzamide
Solution
a. The hydrolysis of a simple amide produces an organic acid and ammonia. Butyramide thus yields butyric acid and
ammonia.
The hydrolysis of an amide produces an organic acid and ammonia. Benzamide thus yields benzoic acid and ammonia.
 Exercise 17.4.1
Write the equation for the hydrolysis of each compound.

a. propionamide (propanamide)
b. hexanamide
 Career Focus: Athletic Trainer
Athletic training is an allied health-care profession recognized by the American Medical Association. The athletic trainer’s role
is to recognize, evaluate, and provide immediate care for athletic injuries; prevent athletic injuries by taping, bandaging, and
bracing vulnerable body parts; make referrals to medical doctors when necessary; and rehabilitate injured athletes. Athletic
trainers work in high schools, colleges, and other organizations where athletics programs are found. Athletic trainers usually
have a degree from an accredited athletic training program whose curriculum includes such basic science courses as biology,
chemistry, and physics. These studies provide the necessary background for more applied courses, such as anatomy and
physiology, exercise physiology, kinesiology, and nutrition. Knowledge of chemistry is necessary for understanding
pharmacological and medical terminology. For example, athletic trainers must understand the action of numerous drugs, many
of which are esters, amines, or amides like those mentioned in this chapter.
Athletic trainers may have administrative duties, such as the responsibility for ordering supplies. They also need to be able to
evaluate nutritional supplements because providing the wrong one can get an athlete banned from competition and may bring
sanctions against a school. In short, the athletic trainer is responsible for the overall health and well-being of the athletes in his
or her charge.
Summary
Hydrolysis is a most important reaction of esters. Acidic hydrolysis of an ester gives a carboxylic acid and an alcohol. Basic
hydrolysis of an ester gives a carboxylate salt and an alcohol.
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Describe how polyamides and polyesters are formed.
Animal intestines and silk were used for all guitar strings for centuries, until modern technology and changes in musical taste
brought about significant changes. There are two major types of guitar strings in use today. Steel strings (first developed around
1900) are found on acoustic and electric guitars. They have a bright, crisp sound that lends itself well to diverse music such as jazz,
rock 'n' roll, and bluegrass. Nylon strings are a more recent development. During World War II, the silk and animal products needed
to manufacture steel guitar strings were not available. Nylon quickly proved to be a more-than-adequate substitute. Now nylon
strings are found on all classical guitars. Their sound is somewhat softer than the steel strings, making the tone quality well-suited
for the classical genre of music.
Polymerization - Condensation Polymers

A condensation polymer is a polymer formed by condensation reactions. Monomers of condensation polymers must contain two
functional groups so that each monomer can link up with two other monomers. One type of condensation polymer is called a
polyamide.
One pair of monomers that can form a polyamide is that of adipic acid and hexanediamine. Adipic acid is a carboxylic acid with
two carboxyl groups on either end of the molecule. Hexanediamine has amino groups on either end of a six-carbon chain. When
these molecules react with each other, a molecule of water is eliminated, classifying it as a condensation reaction (see figure
below).
Figure 17.5.2 : Nylon synthesis.

The polymer that results from the repetition of the condensation reaction is a polyamide called nylon-66. Nylon-66 was first
invented in 1935 and has been used in all sorts of products. Polyamides, including Nylon-66, are commonly found in fibers and
clothing, cooking utensils, fishing line, and carpeting—among many other applications.
Figure 17.5.3 : Nylon spatula.

Polyester is another common type of condensation polymer. Recall that esters are formed from the reaction of an alcohol with a
carboxylic acid. When both the acid and alcohol have two functional groups, the ester is capable of being polymerized. One such
polyester is called polyethylene terephthalate (PET) and is formed from the reaction of ethylene glycol with terephthalic acid. The
structure of PET is shown below.
PET is used in tires, photographic film, food packaging, and clothing. Polyester fabric is used in permanent-press clothing. Its
resistance to wrinkling comes from the cross-linking of the polymer strands.
Summary
A condensation polymer is a polymer formed by condensation reactions.
Polyamides and polyesters are common types of condensation polymers.
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Objective 1
Objective 2
Just as carboxylic acids do, inorganic acids such as nitric acid (HNO3), sulfuric acid (H2SO4), and phosphoric acid (H3PO4) also
form esters. The esters of phosphoric acid are especially important in biochemistry. A phosphoric acid molecule can form a
monoalkyl, a dialkyl, or a trialkyl ester by reaction with one, two, or three molecules of an alcohol.
Esters of pyrophosphoric acid and triphosphoric acid are also important in biochemistry.
Esters of these acids are present in every plant and animal cell. They are biochemical intermediates in the transformation of food
into usable energy. The bonds between phosphate units in adenosine triphosphate (ATP) are called phosphoanhydride bonds. These
are high-energy bonds that store energy from the metabolism of foods. Hydrolysis of ATP releases energy as it is needed for
biochemical processes (for instance, for muscle contraction). Phosphate esters are also important structural constituents of
phospholipids and nucleic acids.
The explosive nitroglycerin (glyceryl trinitrate) is an ester formed from glycerol and nitric acid. It is used in medicine to
relieve chest pain in heart disease.
Summary
Inorganic acids such as H3PO4 form esters. The esters of phosphoric acid are especially important in biochemistry.
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CHAPTER OVERVIEW
18: Amino Acids and Proteins

18.3: Amino Acids
18.5: Peptides
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1
Explain what a biomolecule is and list the four main types.
Biochemistry is the study of the molecules of life, (biomolecules); those that structurally make up living organisms and function to
keep them alive. Although the complexity of biomolecules ranges from individual small molecules, such as glycine, to very large
complexes made up of multiple molecules linked together, like ATP synthase, most biomolecules can be categorized into for main
groups based on their structural similarities: carbohydrates, proteins, lipids, or nucleic acids. There are also many other small
molecules and ions that play a wide variety of roles in the cell, ranging chemical messengers (or signals), to toxins produced as a
means of defense against invaders, to coordination complexes that play important rolls in protein function.
Now that you have learned the basics of general and organic chemistry, you are ready to apply your knowledge to understanding
the chemistry of these biomolecules. You will recognize some of the organic functional groups in these biomolecules, which will
help you predict the physical and chemical properties of these new molecules. Living cells are very complex, however, the same
principles that govern chemistry apply to all of biochemistry.
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Lisa Sharpe Elles.
Describe the different structural classes of proteins.
Understand the different functional roles of proteins.
The ability to serve a variety of functions is characteristic of most biomolecules. Nowhere is this versatility better exemplified than
by the proteins. Perhaps because of their many functions, proteins are the most abundant organic molecules in living cells,
constituting more than 50 percent of the mass once water is removed. It is estimated that the human body contains well over a
million different kinds of protein, and even a single-cell organism contains thousands. Each of these is a polymer of amino acids
which has a highly specific composition, a unique molecular weight (usually in the range from 6000 to 1 000 000) and its own
sequence of different amino acids along the polymer chain.
Proteins may be subdivided on the basis of their molecular shape or conformation. In the fibrous proteins, long polymer chains
are arranged parallel or nearly parallel to one another to give long fibers or sheets. This arrangement results in physically tough
materials which do not dissolve in water. The fibrous proteins are fundamental components of structural tissues such as tendons,
bone, hair, horn, leather, claws, and feathers.
By contrast, polymer chains of the globular proteins fold back on themselves to produce compact, nearly spherical shapes. Most
globular proteins are water soluble and hence are relatively mobile within a cell. Some examples are enzymes, antibodies,
hormones, toxins, and substances such as hemoglobin whose function is to transport simple molecules or even electrons from one
place to another. The enzyme trypsin, is a typical globular protein.
Another class of proteins are the membrane proteins, which, as the name would suggest, reside in a cell's lipid bilayer membrane.
Such proteins can act as channels for ions or other molecules unable to pass through the lipid bilayer; as signal transducers, able to
respond to signal molecules on one side of a membrane to begin a molecular response on the other side of the membrane; or as
anchors of other molecules to the cell membrane, to name a few exemplars of membrane protein function. Because these proteins
interface with non-polar portions of the lipid bilayer, they do no maintain function and structure in an aqueous solution, making
them far more difficult to study than globular proteins or fibrous proteins.
Proteins are also classified based on their function as listed in Table 18.2.1 below. As you will see in the following chapters, the
structure and function of a protein are directly related, meaning that if a protein adopts a certain structure, the general function of
that protein can be predicted with a good amount of certainty.
Table 18.2.1 : Classes of Proteins by Function
Type Function Example
Enzymes Catalyze biochemical reactions Amylase – helps digest carbohydrates
Insulin – controls the amount of sugar

Hormone proteins Regulate and coordinate cell functions
(glucose) in the blood
Storage proteins Storage and release of essential substances Myoglobin – stores oxygen in muscle tissue
Hemoglobin – transports oxygen between the

Transport proteins Carries substances through the body
lungs and other tissues
Keratin – main structural component of hair,
Structural proteins Provides structural shape and support
nails, feathers, hooves, etc.
Immunoglobulin – recognizes and binds to
Defense proteins Protects the body against foreign invaders
foreign matter, aiding in destruction
Actin and Myosin – control the movement of
Contractile proteins Mediate contractile processes, i.e., movement
muscles
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18.3: Amino Acids
To recognize amino acids and classify them based on the characteristics of their side chains.
Identify which amino acids are chiral.
The proteins in all living species, from bacteria to humans, are polymers constructed from the same set of 20 amino acids.
Humans can synthesize only about half of the needed amino acids; the remainder must be obtained from the diet and are known as
essential amino acids. However, two additional amino acids have been found in limited quantities in proteins: Selenocysteine was
discovered in 1986, while pyrrolysine was discovered in 2002.
Amino Acid Structure

Every amino acid contains an amino group, (–NH2), a carboxyl group, (–COOH), and a side chain or R group, which are all
attached to the alpha (α -) carbon (the one directly bonded to the carboxyl functional group). Therefore, amino acids are commonly
called alpha-amino (α -amino) acids. Figure 18.3.1 below shows the structure of a generic α -amino acid.
Figure 18.3.1 An α -amino acid. The three parts to an amino acid include the amino group, the carboxyl group, and the side-chain
or R group all attached to the α -carbon. The R group is the part that distinguishes one amino acid from the next.
Amino Acid Side Chains

Amino acid side chains or R groups can range from a single hydrogen atom (as in glycine), to a simple hydrocarbon chain, to a
hydrocarbon containing a functional group. Each R group has differences in size, shape, solubility, and ionization properties, which
contributes to the unique properties of an individual amino acid, and can have an effect on the overall structure and function of a
protein.
Table 18.3.1 below lists the 20 common amino acids along with their names, their three- and one-letter codes, structures, and
distinctive features. The three-letter codes are generally the first three letters of the amino acid name except in a few cases, such as
isoleucine (Ile) and tryptophan (Trp). Similarly, the one-letter code is usually the first letter in the amino acid name, but where the
letter is not unique, a letter that is phonetically similar the amino acid name is used: F for Fenylalanine, R for aRginine, and W for
tWiptophan. This table also groups the amino acids according to whether the side chain at neutral pH is nonpolar, polar uncharged,
positively charged, or negatively charged.
Table 18.3.1 : Common Amino Acids Found in Proteins. (Isoelectric points are explained in a later section.)
Three-letter (one- Systematic (IUPAC) Structural Formula (at
Common Name Isoelectric Point (pI) Distinctive Feature
letter) Code Name pH 6)
Amino acids with a nonpolar R group
the only amino acid

glycine Gly (G) aminoethanoic acid 6.0
lacking a chiral carbon
a methyl group, it is
2-aminopropanoic
alanine Ala (A) 6.0 the second smallest
acid
side chain
2-amino-3- a branched-chain
valine Val (V) 6.0
methylbutanoic acid amino acid
2-amino-4- a branched-chain
leucine Leu (L) 6.0
methylpentanoic acid amino acid
an essential amino
acid because most
2-amino-3-
isoleucine Ile (I) 6.0 animals cannot
methylpentanoic acid
synthesize branched-
chain amino acids
2-amino-3- also classified as an

phenylalanine Phe (F) 5.5
phenylpropanoic acid aromatic amino acid
2-Amino-3-(1H-
also classified as an
tryptophan Trp (W) indol-3-yl)-propanoic 5.9
aromatic amino acid
acid
2-amino-4-
side chain functions as
methionine Met (M) (methylthio)butanoic 5.7
a methyl group donor
acid
contains a secondary
pyrrolidine-2-
proline Pro (P) 6.3 amine group; referred
carboxylic acid
to as an α-imino acid
Amino acids with a polar but neutral R group
2-amino-3-
found at the active site
serine Ser (S) hydroxypropanoic 5.7
of many enzymes
acid
named for its

2-amino-3-
threonine Thr (T) 5.6 similarity to the sugar
hydroxybutanoic acid
threose
2-amino-3- oxidation of two

cysteine Cys (C) mercaptopropanoic 5.0 cysteine molecules
acid yields cystine
2-amino-3-(4-
also classified as an
tyrosine Tyr (Y) hydroxyphenyl)- 5.7
aromatic amino acid
propanoic acid
2-amino-3-
the amide of aspartic
asparagine Asn (N) carbamoylpropanoic 5.4
acid
acid
2-amino-4-
the amide of glutamic
glutamine Gln (Q) carbamoylbutanoic 5.7
acid
acid
Amino acids with a negatively charged R group

carboxyl groups are
2-aminobutanedioic ionized at
aspartic acid Asp (D) 3.0
acid physiological pH; also
known as aspartate
carboxyl groups are

2-aminopentanedioic ionized at
glutamic acid Glu (E) 3.2
acid physiological pH; also
known as glutamate
Amino acids with a positively charged R group
the only amino acid

2-Amino-3-(1H-
whose R group has a
histidine His (H) imidazol-4-yl)- 7.6
pKa (6.0) near
propanoic acid
physiological pH
is somewhat
amphipathic due to the
2,6-diaminohexanoic long hydrocarbon tail
lysine Lys (K) 9.7
acid and positively charged
amino group on the ϵ
carbon
2-amino-5- almost as strong a

arginine Arg (R) guanidinopentanoic 10.8 base as sodium
acid hydroxide
 Note: Interesting Facts About Amino Acids
The first amino acid to be isolated was asparagine in 1806. It was obtained from protein found in asparagus juice (hence the
name). Glycine, the major amino acid found in gelatin, was named for its sweet taste (Greek glykys, meaning “sweet”).
Glutamic acid is named as such because it was first isolated from gluten. The crystalline salt of glutamic acid is called
monosodium glutamate (MSG), which is naturally occuring in some foods but is also added to as a savory or "umami" flavor
enhancer.
In some cases an amino acid found in a protein is actually a derivative of one of the common 20 amino acids (one such
derivative is hydroxyproline). The modification of proline occurs after the amino acid has been assembled into a protein.
Chirality of Amino Acids

Notice in Table 18.3.1 that glycine is the only amino acid whose (\alpha\)-carbon is not chiral, in other words the molecule and the
mirror-image of glycine are identical. All other amino acids have two forms that are mirror images of each other, they are
enantiomers. As you can see in the figure below, the "left-handed" form of the molecule is known as the L-amino acid and the
"right-handed" form is the D-amino acid.
Summary
Amino acids can be classified based on the characteristics of their distinctive side chains as nonpolar, polar but uncharged,
negatively charged, or positively charged. The amino acids found in proteins are L-amino acids.
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To explain how an amino acid can act as both an acid and a base.
The structure of an amino acid allows it to act as both an acid and a base. An amino acid has this ability because at a certain pH
value (different for each amino acid) nearly all the amino acid molecules exist as zwitterions. If acid is added to a solution
containing the zwitterion, the carboxylate group captures a hydrogen (H+) ion, and the amino acid becomes positively charged. If
base is added, ion removal of the H+ ion from the amino group of the zwitterion produces a negatively charged amino acid. In both
circumstances, the amino acid acts to maintain the pH of the system—that is, to remove the added acid (H+) or base (OH−) from
solution.
 Example 18.4.1
a. Draw the structure for the anion formed when glycine (at neutral pH) reacts with a base.
b. Draw the structure for the cation formed when glycine (at neutral pH) reacts with an acid.
Solution
+
a. The base removes H from the protonated amine group.
The acid adds H+ to the carboxylate group.
 Exercise 18.4.1
a. Draw the structure for the cation formed when valine (at neutral pH) reacts with an acid.
b. Draw the structure for the anion formed when valine (at neutral pH) reacts with a base.
The particular pH at which a given amino acid exists in solution as a zwitterion is called the isoelectric point (pI). At its pI, the
positive and negative charges on the amino acid balance, and the molecule as a whole is electrically neutral. The amino acids
whose side chains are always neutral have isoelectric points ranging from 5.0 to 6.5. The basic amino acids (which have positively
charged side chains at neutral pH) have relatively high examples. Acidic amino acids (which have negatively charged side chains at
neutral pH) have quite low examples (Table 18.4.1).
Table 18.4.1 : ExampIes of Some Representative Amino Acids
Amino Acid Classification pI
alanine nonpolar 6.0
valine nonpolar 6.0
serine polar, uncharged 5.7
Amino Acid Classification pI
threonine polar, uncharged 6.5
arginine positively charged (basic) 10.8
histidine positively charged (basic) 7.6
lysine positively charged (basic) 9.8
aspartic acid negatively charged (acidic) 3.0
glutamic acid negatively charged (acidic) 3.2
Amino acids undergo reactions characteristic of carboxylic acids and amines. The reactivity of these functional groups is
particularly important in linking amino acids together to form peptides and proteins, as you will see later in this chapter. Simple
chemical tests that are used to detect amino acids take advantage of the reactivity of these functional groups. An example is the
ninhydrin test in which the amine functional group of α-amino acids reacts with ninhydrin to form purple-colored compounds.
Ninhydrin is used to detect fingerprints because it reacts with amino acids from the proteins in skin cells transferred to the surface
by the individual leaving the fingerprint.
Summary
Amino acids can act as both an acid and a base due to the presence of the amino and carboxyl functional groups. The pH at which a
given amino acid exists in solution as a zwitterion is called the isoelectric point (pI).
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18.5: Peptides
Explain how a peptide is formed from individual amino acids.
Explain why the sequence of amino acids in a protein is important.
Two or more amino acids can join together into chains called peptides. In an earlier chapter, we discussed the reaction between
ammonia and a carboxylic acid to form an amide. In a similar reaction, the amino group on one amino acid molecule reacts with
the carboxyl group on another, releasing a molecule of water and forming an amide linkage:
An amide bond joining two amino acid units is called a peptide bond. Note that the product molecule still has a reactive amino
group on the left and a reactive carboxyl group on the right. These can react with additional amino acids to lengthen the peptide.
The process can continue until thousands of units have joined, resulting in large proteins.
A chain consisting of only two amino acid units is called a dipeptide; a chain consisting of three is a tripeptide. By convention,
peptide and protein structures are depicted with the amino acid whose amino group is free (the amino-terminal or N-terminal end)
on the left and the amino acid with a free carboxyl group (the carboxyl-terminal or C-terminal end) to the right. Individual amino
acids joined in a chain are called residues.
The general term peptide refers to an amino acid chain of unspecified length. However, chains of about 50 amino acids or more are
usually called proteins or polypeptides. In its physiologically active form, a protein may be composed of one or more polypeptide
chains.
Figure 18.5.1 : Space-filling model of bradykinin. (Public Domain; Fvasconcellos)
 Note: Order is Important
For peptides and proteins to be physiologically active, it is not enough that they incorporate certain amounts of specific amino
acids. The order, or sequence, in which the amino acids are connected is also of critical importance. Bradykinin is a nine-amino
acid peptide (Figure 18.5.1) produced in the blood that has the following amino acid sequence:
arg-pro-pro-gly-phe-ser-pro-phe-arg
This peptide lowers blood pressure, stimulates smooth muscle tissue, increases capillary permeability, and causes pain. When
the order of amino acids in bradykinin is reversed,
arg-phe-pro-ser-phe-gly-pro-pro-arg
the peptide resulting from this synthesis shows none of the activity of bradykinin.
Just as millions of different words are spelled with our 26-letter English alphabet, millions of different proteins are made with
the 20 common amino acids. However, just as the English alphabet can be used to write gibberish, amino acids can be put
together in the wrong sequence to produce nonfunctional proteins. Although the correct sequence is ordinarily of utmost
importance, it is not always absolutely required. Just as you can sometimes make sense of incorrectly spelled English words, a
protein with a small percentage of “incorrect” amino acids may continue to function. However, it rarely functions as well as a
protein having the correct sequence. There are also instances in which seemingly minor errors of sequence have disastrous
effects. For example, in some people, every molecule of hemoglobin (a protein in the blood that transports oxygen) has a single
incorrect amino acid unit out of about 300 (a single valine replaces a glutamic acid). That “minor” error is responsible for
sickle cell anemia, an inherited condition that usually is fatal.
Summary
The amino group of one amino acid can react with the carboxyl group on another amino acid to form a peptide bond that links the
two amino acids together. Additional amino acids can be added on through the formation of addition peptide (amide) bonds. A
sequence of amino acids in a peptide or protein is written with the N-terminal amino acid first and the C-terminal amino acid at the
end (writing left to right).

1. Distinguish between the N-terminal amino acid and the C-terminal amino acid of a peptide or protein.
2. Describe the difference between an amino acid and a peptide.
3. Amino acid units in a protein are connected by peptide bonds. What is another name for the functional group linking the amino
acids?
Answers
1. The N-terminal end is the end of a peptide or protein whose amino group is free (not involved in the formation of a peptide
bond), while the C-terminal end has a free carboxyl group.
2. A peptide is composed of two or more amino acids. Amino acids are the building blocks of peptides.
3. amide bond
Exercises
1. Draw the structure for each peptide.
a. gly-val
b. val-gly
2. Draw the structure for cys-val-ala.
3. Identify the C- and N-terminal amino acids for the peptide lys-val-phe-gly-arg-cys.
4. Identify the C- and N-terminal amino acids for the peptide asp-arg-val-tyr-ile-his-pro-phe.
Answers
1. a.
b.
3. C-terminal amino acid: cys; N-terminal amino acid: lys
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Describe primary protein structure.
Explain how sequence can affect function.
Each of the thousands of naturally occurring proteins has its own characteristic amino acid composition and sequence that result in
a unique three-dimensional shape. Since the 1950s, scientists have determined the amino acid sequences and three-dimensional
conformation of numerous proteins and thus obtained important clues on how each protein performs its specific function in the
body.
Levels of Protein Structure

The structure of proteins is generally described as having four organizational levels. The first of these is the primary structure,
which is the number and sequence of amino acids in a protein’s polypeptide chain or chains, beginning with the free amino group
and maintained by the peptide bonds connecting each amino acid to the next. The primary structure of insulin, composed of 51
amino acids, is shown in Figure 18.6.1.
Figure 18.6.1 : Primary Structure of Human Insulin. Human insulin, whose amino acid sequence is shown here, is a hormone that is
required for the proper metabolism of glucose. (CC BY-SA-NC 3.0; anonymous)
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Objective 1
Objective 2
A protein molecule is not a random tangle of polypeptide chains. Instead, the chains are arranged in unique but specific
conformations. The term secondary structure refers to the fixed arrangement of the polypeptide backbone. On the basis of X ray
studies, Linus Pauling and Robert Corey postulated that certain proteins or portions of proteins twist into a spiral or a helix. This
helix is stabilized by intrachain hydrogen bonding between the carbonyl oxygen atom of one amino acid and the amide hydrogen
atom four amino acids up the chain (located on the next turn of the helix) and is known as a right-handed α-helix. X ray data
indicate that this helix makes one turn for every 3.6 amino acids, and the side chains of these amino acids project outward from the
coiled backbone (Figure 18.7.1). The α-keratins, found in hair and wool, are exclusively α-helical in conformation. Some proteins,
such as gamma globulin, chymotrypsin, and cytochrome c, have little or no helical structure. Others, such as hemoglobin and
myoglobin, are helical in certain regions but not in others.
Figure 18.7.1 A Ball-and-Stick Model of an α-Helix. This ball-and-stick model shows the intrachain hydrogen bonding between
carbonyl oxygen atoms and amide hydrogen atoms. Each turn of the helix spans 3.6 amino acids. Note that the side chains
(represented as green spheres) point out from the helix.
Another common type of secondary structure, called the β-pleated sheet conformation, is a sheetlike arrangement in which two or
more extended polypeptide chains (or separate regions on the same chain) are aligned side by side. The aligned segments can run
either parallel or antiparallel—that is, the N-terminals can face in the same direction on adjacent chains or in different directions—
and are connected by interchain hydrogen bonding (Figure 18.7.3). The β-pleated sheet is particularly important in structural
proteins, such as silk fibroin. It is also seen in portions of many enzymes, such as carboxypeptidase A and lysozyme.
Figure 18.7.3 : A Ball-and-Stick Model of the β-Pleated Sheet Structure in Proteins. The side chains extend above or below the
sheet and alternate along the chain. The protein chains are held together by interchain hydrogen bonding.
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Objective 1
Objective 2
Tertiary structure refers to the unique three-dimensional shape of the protein as a whole, which results from the folding and
bending of the protein backbone. The tertiary structure is intimately tied to the proper biochemical functioning of the protein.
Figure 18.8.1 shows a depiction of the three-dimensional structure of insulin.
Figure 18.8.1 : A Ribbon Model of the Three-Dimensional Structure of Insulin. The spiral regions represent sections of the
polypeptide chain that have an α-helical structure, while the broad arrows represent β-pleated sheet structures.
Four major types of attractive interactions determine the shape and stability of the tertiary structure of proteins. You studied several
of them previously.
1. Ionic bonding. Ionic bonds result from electrostatic attractions between positively and negatively charged side chains of amino
acids. For example, the mutual attraction between an aspartic acid carboxylate ion and a lysine ammonium ion helps to maintain
a particular folded area of a protein (part (a) of Figure 18.8.5).
2. Hydrogen bonding. Hydrogen bonding forms between a highly electronegative oxygen atom or a nitrogen atom and a hydrogen
atom attached to another oxygen atom or a nitrogen atom, such as those found in polar amino acid side chains. Hydrogen
bonding (as well as ionic attractions) is extremely important in both the intra- and intermolecular interactions of proteins (part
(b) of Figure 18.8.5).
3. Disulfide linkages. Two cysteine amino acid units may be brought close together as the protein molecule folds. Subsequent
oxidation and linkage of the sulfur atoms in the highly reactive sulfhydryl (SH) groups leads to the formation of cystine (part (c)
of Figure 18.8.2). Intrachain disulfide linkages are found in many proteins, including insulin (yellow bars in Figure 18.8.1) and
have a strong stabilizing effect on the tertiary structure.
4. Dispersion forces. Dispersion forces arise when a normally nonpolar atom becomes momentarily polar due to an uneven
distribution of electrons, leading to an instantaneous dipole that induces a shift of electrons in a neighboring nonpolar atom.
Dispersion forces are weak but can be important when other types of interactions are either missing or minimal (part (d) of
Figure 18.8.2). This is the case with fibroin, the major protein in silk, in which a high proportion of amino acids in the protein
have nonpolar side chains. The term hydrophobic interaction is often misused as a synonym for dispersion forces. Hydrophobic
interactions arise because water molecules engage in hydrogen bonding with other water molecules (or groups in proteins
capable of hydrogen bonding). Because nonpolar groups cannot engage in hydrogen bonding, the protein folds in such a way
that these groups are buried in the interior part of the protein structure, minimizing their contact with water.
Figure 18.8.2 : Tertiary Protein Structure Interactions. Four interactions stabilize the tertiary structure of a protein: (a) ionic
bonding, (b) hydrogen bonding, (c) disulfide linkages, and (d) dispersion forces.
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Objective 1
Objective 2
When a protein contains more than one polypeptide chain, each chain is called a subunit. The arrangement of multiple subunits
represents a fourth level of structure, the quaternary structure of a protein. Hemoglobin, with four polypeptide chains or subunits,
is the most frequently cited example of a protein having quaternary structure (Figure 18.9.1). The quaternary structure of a protein
is produced and stabilized by the same kinds of interactions that produce and maintain the tertiary structure. A schematic
representation of the four levels of protein structure is in Figure 18.9.2.
Figure 18.9.1 The Quaternary Structure of Hemoglobin. Hemoglobin is a protein that transports oxygen throughout the body.
Source: Image from the RCSB PDB (www.pdb.org) of PDB ID 1I3D (R.D. Kidd, H.M. Baker, A.J. Mathews, T. Brittain, E.N.
Baker (2001) Oligomerization and ligand binding in a homotetrameric hemoglobin: two high-resolution crystal structures of
hemoglobin Bart's (gamma(4)), a marker for alpha-thalassemia. Protein Sci. 1739–1749).
Figure 18.9.2 : Levels of Structure in Proteins

The primary structure consists of the specific amino acid sequence. The resulting peptide chain can twist into an α-helix, which is
one type of secondary structure. This helical segment is incorporated into the tertiary structure of the folded polypeptide chain.
The single polypeptide chain is a subunit that constitutes the quaternary structure of a protein, such as hemoglobin that has four
polypeptide chains.
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Objective 1
Objective 2
Protein Hydrolysis
Protein Denaturation
The highly organized structures of proteins are truly masterworks of chemical architecture. But highly organized structures tend to
have a certain delicacy, and this is true of proteins. Denaturation is the term used for any change in the three-dimensional structure
of a protein that renders it incapable of performing its assigned function. A denatured protein cannot do its job. (Sometimes
denaturation is equated with the precipitation or coagulation of a protein; our definition is a bit broader.) A wide variety of reagents
and conditions, such as heat, organic compounds, pH changes, and heavy metal ions can cause protein denaturation (Figure
18.10.1).
Figure 18.10.1: Protein Denaturation Methods

Method Effect on Protein Structure
Heat or UV radiation supplies kinetic energy to protein molecules,

Heat above 50°C or ultraviolet (UV) radiation causing their atoms to vibrate more rapidly and disrupting relatively
weak hydrogen bonding and dispersion forces.
These compounds are capable of engaging in intermolecular hydrogen
Use of organic compounds, such as ethyl alcohol bonding with protein molecules, disrupting intramolecular hydrogen
bonding within the protein.
These ions form strong bonds with the carboxylate anions of the acidic
Salts of heavy metal ions, such as mercury, silver, and lead amino acids or SH groups of cysteine, disrupting ionic bonds and
disulfide linkages.
These reagents combine with positively charged amino groups in
Alkaloid reagents, such as tannic acid (used in tanning leather)
proteins to disrupt ionic bonds.
Anyone who has fried an egg has observed denaturation. The clear egg white turns opaque as the albumin denatures and
coagulates. No one has yet reversed that process. However, given the proper circumstances and enough time, a protein that has
unfolded under sufficiently gentle conditions can refold and may again exhibit biological activity (Figure 18.10.8). Such evidence
suggests that, at least for these proteins, the primary structure determines the secondary and tertiary structure. A given sequence of
amino acids seems to adopt its particular three-dimensional arrangement naturally if conditions are right.
Figure 18.10.8: Denaturation and Renaturation of a Protein. The denaturation (unfolding) and renaturation (refolding) of a protein
is depicted. The red boxes represent stabilizing interactions, such as disulfide linkages, hydrogen bonding, and/or ionic bonds.
The primary structures of proteins are quite sturdy. In general, fairly vigorous conditions are needed to hydrolyze peptide bonds. At
the secondary through quaternary levels, however, proteins are quite vulnerable to attack, though they vary in their vulnerability to
denaturation. The delicately folded globular proteins are much easier to denature than are the tough, fibrous proteins of hair and
skin.
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CHAPTER OVERVIEW
19: Enzymes and Vitamins

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1
Describe how enzymes catalyze biochemical reactions.
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To explain why vitamins are necessary in the diet.
Many enzymes are simple proteins consisting entirely of one or more amino acid chains. Other enzymes contain a nonprotein
component called a cofactor that is necessary for the enzyme’s proper functioning. There are two types of cofactors: inorganic ions
[e.g., zinc or Cu(I) ions] and organic molecules known as coenzymes. Most coenzymes are vitamins or are derived from vitamins.
Vitamins are organic compounds that are essential in very small (trace) amounts for the maintenance of normal metabolism. They
generally cannot be synthesized at adequate levels by the body and must be obtained from the diet. The absence or shortage of a
vitamin may result in a vitamin-deficiency disease. In the first half of the 20th century, a major focus of biochemistry was the
identification, isolation, and characterization of vitamins. Despite accumulating evidence that people needed more than just
carbohydrates, fats, and proteins in their diets for normal growth and health, it was not until the early 1900s that research
established the need for trace nutrients in the diet.
Table 19.2.1 : Fat-Soluble Vitamins and Physiological Functions
Vitamin Physiological Function Effect of Deficiency
formation of vision pigments; differentiation night blindness; continued deficiency leads to

vitamin A (retinol)
of epithelial cells total blindness
increases the body’s ability to absorb calcium osteomalacia (softening of the bones); known
vitamin D (cholecalciferol)
and phosphorus as rickets in children
vitamin E (tocopherol) fat-soluble antioxidant damage to cell membranes
formation of prothrombin, a key enzyme in the

vitamin K (phylloquinone) increases the time required for blood to clot
blood-clotting process
Because organisms differ in their synthetic abilities, a substance that is a vitamin for one species may not be so for another. Over
the past 100 years, scientists have identified and isolated 13 vitamins required in the human diet and have divided them into two
broad categories: the fat-soluble vitamins, which include vitamins A, D, E, and K, and the water-soluble vitamins, which are the B
complex vitamins and vitamin C. All fat-soluble vitamins contain a high proportion of hydrocarbon structural components. There
are one or two oxygen atoms present, but the compounds as a whole are nonpolar. In contrast, water-soluble vitamins contain large
numbers of electronegative oxygen and nitrogen atoms, which can engage in hydrogen bonding with water. Most water-soluble
vitamins act as coenzymes or are required for the synthesis of coenzymes. The fat-soluble vitamins are important for a variety of
physiological functions. The key vitamins and their functions are found in Tables 19.2.1 and 19.2.2.
Table 19.2.2 : Water-Soluble Vitamins and Physiological Functions
Vitamin Coenzyme Coenzyme Function Deficiency Disease
vitamin B1 (thiamine) thiamine pyrophosphate decarboxylation reactions beri-beri
flavin mononucleotide or flavin oxidation-reduction reactions

vitamin B2 (riboflavin) —
adenine dinucleotide involving two hydrogen atoms
nicotinamide adenine dinucleotide

oxidation-reduction reactions
vitamin B3 (niacin) or nicotinamide adenine pellagra
involving the hydride ion (H−)
dinucleotide phosphate
variety of reactions including the

vitamin B6 (pyridoxine) pyridoxal phosphate —
transfer of amino groups
methylcobalamin or intramolecular rearrangement

vitamin B12 (cyanocobalamin) pernicious anemia
deoxyadenoxylcobalamin reactions
biotin biotin carboxylation reactions —
carrier of one-carbon units such as

folic acid tetrahydrofolate anemia
the formyl group
Vitamin Coenzyme Coenzyme Function Deficiency Disease
pantothenic Acid coenzyme A carrier of acyl groups —
antioxidant; formation of
vitamin C (ascorbic acid) none collagen, a protein found in scurvy
tendons, ligaments, and bone
Vitamins C and E, as well as the provitamin β-carotene can act as antioxidants in the body. Antioxidants prevent damage from free
radicals, which are molecules that are highly reactive because they have unpaired electrons. Free radicals are formed not only
through metabolic reactions involving oxygen but also by such environmental factors as radiation and pollution.
β-carotene is known as a provitamin because it can be converted to vitamin A in the body.

Free radicals react most commonly react with lipoproteins and unsaturated fatty acids in cell membranes, removing an electron
from those molecules and thus generating a new free radical. The process becomes a chain reaction that finally leads to the
oxidative degradation of the affected compounds. Antioxidants react with free radicals to stop these chain reactions by forming a
more stable molecule or, in the case of vitamin E, a free radical that is much less reactive (vitamin E is converted back to its
original form through interaction with vitamin C).
Summary
Vitamins are organic compounds that are essential in very small amounts for the maintenance of normal metabolism. Vitamins are
divided into two broad categories: fat-soluble vitamins and water-soluble vitamins. Most water-soluble vitamins are needed for the
formation of coenzymes, which are organic molecules needed by some enzymes for catalytic activity.
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Objective 1
Objective 2
Hundreds of enzymes have been purified and studied in an effort to understand how they work so effectively and with such
specificity. The resulting knowledge has been used to design drugs that inhibit or activate particular enzymes. An example is the
intensive research to improve the treatment of or find a cure for acquired immunodeficiency syndrome (AIDS). AIDS is caused by
the human immunodeficiency virus (HIV). Researchers are studying the enzymes produced by this virus and are developing drugs
intended to block the action of those enzymes without interfering with enzymes produced by the human body. Several of these
drugs have now been approved for use by AIDS patients.
Enzyme Nomenclature
Most enzymes can be recognized because they have the family name ending –ase. However, the first enzymes to be discovered
were named according to their source or method of discovery. The enzyme pepsin, which aids in the hydrolysis of proteins, is
found in the digestive juices of the stomach (Greek pepsis, meaning “digestion”). Papain, another enzyme that hydrolyzes protein
(in fact, it is used in meat tenderizers), is isolated from papayas.
In addition to the family name, more systematic enzyme names will give two sepcific pieces of information: the first part is the
substrate upon which the enzyme acts, and the second part is the type of reaction it catalyzes. For example, alcohol dehydrogenase
(Figure 19.3.1) catalyzes the oxidation of an alcohol to an aldehyde.
Enzyme Classification
As more enzymes were discovered, chemists recognized the need for a more systematic and chemically informative identification
scheme. In the current numbering and naming scheme, under the oversight of the Nomenclature Commission of the International
Union of Biochemistry, enzymes are arranged into six groups according to the general type of reaction they catalyze (Table 19.3.1),
with subgroups and secondary subgroups that specify the reaction more precisely.
Each enzyme is assigned a four-digit number, preceded by the prefix EC—for enzyme classification—that indicates its group,
subgroup, and so forth. This is demonstrated in Table 19.3.2 for alcohol dehydrogenase.
Table 19.3.1 : Classes of Enzymes
Main Class Type of Reaction Catalyzed Subclasses Examples
Dehydrogenases catalyze
Oxidoreductases oxidation-reduction reactions oxidation-reduction reactions Alcohol dehydrogenase
involving hydrogen.
Oxidases catalyze oxidation by

addition of O2 to a substrate.
Reductases catalyze reactions in

which a substrate is reduced.
transfer reactions of functional Transaminases catalyze the

Transferases
groups transfer of amino group.
Kinases catalyze the transfer of a

Phosphofructokinase
phosphate group.
reactions that use water to break a Lipases catalyze the hydrolysis of

Hydrolases
chemical bond lipids
Main Class Type of Reaction Catalyzed Subclasses Examples
Proteases catalyze the hydrolysis

of proteins
Amylases catalyze the hydrolysis

of carbohydrates
Nucleases catalyze the hydrolysis

of DNA and RNA
reactions in which functional

Decarboxylases catalyze the
Lyases groups are added or removed
removal of carboxyl groups.
without hydrolysis
Deaminases catalyze the removal

of amino groups.
Dehydratases catalyze the

removal of water.
Hydratases catalyze the addition

Fumarase
of water.
Isomerases may catalyze the

reactions in which a compound is
Isomerases conversion of an aldose to a Triose Phosphate Isomerase
converted to its isomer
ketose.
Mutases catalyze reactions in

which a functional group is
transferred from one atom in a
substrate to another.
reactions in which new bonds are Synthetases catalyze reactions in

Ligases formed between carbon and which two smaller molecules are
another atom; energy is required linked to form a larger one.
Carboxylases catalyze the

Pyruvate Carboxylase
addition of CO2 using ATP
Table 19.3.2 : Assignment of an Enzyme Classification Number

Alcohol Dehydrogenase: EC 1.1.1.1
The first digit indicates that this enzyme is an oxidoreductase; that is, an enzyme that catalyzes an oxidation-reduction reaction.
The second digit indicates that this oxidoreductase catalyzes a reaction involving a primary or secondary alcohol.
The third digit indicates that either the coenzyme NAD+ or NADP+ is required for this reaction.
The fourth digit indicates that this was the first enzyme isolated, characterized, and named using this system of nomenclature.
The systematic name for this enzyme is alcohol:NAD+ oxidoreductase, while the recommended or common name is alcohol dehydrogenase.
Reaction catalyzed:
Figure 19.3.1 : Structure of the alcohol dehydrogenase protein (E.C.1.1.1.1) (EE ISOZYME) complexed wtih nicotinamide
adenini dinulceotide (NAD) and zinc (PDB: 1CDO).
Summary
An enzyme is a biological catalyst, a substance that increases the rate of a chemical reaction without being changed or consumed in
the reaction. A systematic process is used to name and classify enzymes.
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To describe the interaction between an enzyme and its substrate.
Enzyme-catalyzed reactions occur in at least two steps. In the first step, an enzyme (E) and the substrate molecule or molecules (S)
collide and react to form an intermediate compound called the enzyme-substrate (ES) complex. (This step is reversible because the
complex can break apart into the original substrate or substrates and the free enzyme.) Once the ES complex forms, the enzyme is
able to catalyze the formation of product (P), which is then released from the enzyme surface:
E + S ↔ ES (19.4.1)
ES → E + P (19.4.2)
Hydrogen bonding and other electrostatic interactions hold the enzyme and substrate together in the complex. The structural
features or functional groups on the enzyme that participate in these interactions are located in a cleft or pocket on the enzyme
surface. This pocket, where the enzyme combines with the substrate and transforms the substrate to product is called the active site
of the enzyme (Figure 19.4.1).
Figure 19.4.1 : Substrate Binding to the Active Site of an Enzyme. The enzyme dihydrofolate reductase is shown with one of its
substrates: NADP+ (a) unbound and (b) bound. The NADP+ (shown in red) binds to a pocket that is complementary to it in shape
and ionic properties.
Models of Enzyme-Substrate Interaction

The active site of an enzyme possesses a unique conformation (including correctly positioned bonding groups) that is
complementary to the structure of the substrate, so that the enzyme and substrate molecules fit together in much the same manner
as a key fits into a tumbler lock. In fact, an early model describing the formation of the enzyme-substrate complex was called the
lock-and-key model (Figure 19.4.2). This model portrayed the enzyme as conformationally rigid and able to bond only to
substrates that exactly fit the active site.
Figure 19.4.2 : The Lock-and-Key Model of Enzyme Action. (a) Because the substrate and the active site of the enzyme have
complementary structures and bonding groups, they fit together as a key fits a lock. (b) The catalytic reaction occurs while the two
are bonded together in the enzyme-substrate complex.
Working out the precise three-dimensional structures of numerous enzymes has enabled chemists to refine the original lock-and-
key model of enzyme actions. They discovered that the binding of a substrate often leads to a large conformational change in the
enzyme, as well as to changes in the structure of the substrate or substrates. The current theory, known as the induced-fit model,
says that enzymes can undergo a change in conformation when they bind substrate molecules, and the active site has a shape
complementary to that of the substrate only after the substrate is bound, as shown for hexokinase in Figure 19.4.3. After catalysis,
the enzyme resumes its original structure.
Figure 19.4.3 : The Induced-Fit Model of Enzyme Action. (a) The enzyme hexokinase without its substrate (glucose, shown in red)
is bound to the active site. (b) The enzyme conformation changes dramatically when the substrate binds to it, resulting in additional
interactions between hexokinase and glucose.
The structural changes that occur when an enzyme and a substrate join together bring specific parts of a substrate into alignment
with specific parts of the enzyme’s active site. Amino acid side chains in or near the binding site can then act as acid or base
catalysts, provide binding sites for the transfer of functional groups from one substrate to another or aid in the rearrangement of a
substrate. The participating amino acids, which are usually widely separated in the primary sequence of the protein, are brought
close together in the active site as a result of the folding and bending of the polypeptide chain or chains when the protein acquires
its tertiary and quaternary structure. Binding to enzymes brings reactants close to each other and aligns them properly, which has
the same effect as increasing the concentration of the reacting compounds.
 Example 19.4.1
a. What type of interaction would occur between an OH group present on a substrate molecule and a functional group in the
active site of an enzyme?
b. Suggest an amino acid whose side chain might be in the active site of an enzyme and form the type of interaction you just
identified.
Solution
a. An OH group would most likely engage in hydrogen bonding with an appropriate functional group present in the active site
of an enzyme.
b. Several amino acid side chains would be able to engage in hydrogen bonding with an OH group. One example would be
asparagine, which has an amide functional group.
 Exercise 19.4.1
a. What type of interaction would occur between an COO− group present on a substrate molecule and a functional group in
the active site of an enzyme?
b. Suggest an amino acid whose side chain might be in the active site of an enzyme and form the type of interaction you just
identified.
One characteristic that distinguishes an enzyme from all other types of catalysts is its substrate specificity. An inorganic acid such
as sulfuric acid can be used to increase the reaction rates of many different reactions, such as the hydrolysis of disaccharides,
polysaccharides, lipids, and proteins, with complete impartiality. In contrast, enzymes are much more specific. Some enzymes act
on a single substrate, while other enzymes act on any of a group of related molecules containing a similar functional group or
chemical bond. Some enzymes even distinguish between D- and L-stereoisomers, binding one stereoisomer but not the other.
Urease, for example, is an enzyme that catalyzes the hydrolysis of a single substrate—urea—but not the closely related compounds
methyl urea, thiourea, or biuret. The enzyme carboxypeptidase, on the other hand, is far less specific. It catalyzes the removal of
nearly any amino acid from the carboxyl end of any peptide or protein.
Enzyme specificity results from the uniqueness of the active site in each different enzyme because of the identity, charge, and
spatial orientation of the functional groups located there. It regulates cell chemistry so that the proper reactions occur in the proper
place at the proper time. Clearly, it is crucial to the proper functioning of the living cell.
Summary
A substrate binds to a specific region on an enzyme known as the active site, where the substrate can be converted to product. The
substrate binds to the enzyme primarily through hydrogen bonding and other electrostatic interactions. The induced-fit model says
that an enzyme can undergo a conformational change when binding a substrate. Enzymes exhibit varying degrees of substrate
specificity.
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To describe how pH, temperature, and the concentration of an enzyme and its substrate influence enzyme activity.
The single most important property of enzymes is the ability to increase the rates of reactions occurring in living organisms, a
property known as catalytic activity. Because most enzymes are proteins, their activity is affected by factors that disrupt protein
structure, as well as by factors that affect catalysts in general. Factors that disrupt protein structure include temperature and pH;
factors that affect catalysts in general include reactant or substrate concentration and catalyst or enzyme concentration. The activity
of an enzyme can be measured by monitoring either the rate at which a substrate disappears or the rate at which a product forms.
Substrate Concentration
In the presence of a given amount of enzyme, the rate of an enzymatic reaction increases as the substrate concentration increases
until a limiting rate is reached, after which further increase in the substrate concentration produces no significant change in the
reaction rate (part (a) of Figure 19.5.1). At this point, so much substrate is present that essentially all of the enzyme active sites
have substrate bound to them. In other words, the enzyme molecules are saturated with substrate. The excess substrate molecules
cannot react until the substrate already bound to the enzymes has reacted and been released (or been released without reacting).
Figure 19.5.1 : Concentration versus Reaction Rate. (a) This graph shows the effect of substrate concentration on the rate of a
reaction that is catalyzed by a fixed amount of enzyme. (b) This graph shows the effect of enzyme concentration on the reaction
rate at a constant level of substrate.
Let’s consider an analogy. Ten taxis (enzyme molecules) are waiting at a taxi stand to take people (substrate) on a 10-minute trip to
a concert hall, one passenger at a time. If only 5 people are present at the stand, the rate of their arrival at the concert hall is 5
people in 10 minutes. If the number of people at the stand is increased to 10, the rate increases to 10 arrivals in 10 minutes. With 20
people at the stand, the rate would still be 10 arrivals in 10 minutes. The taxis have been “saturated.” If the taxis could carry 2 or 3
passengers each, the same principle would apply. The rate would simply be higher (20 or 30 people in 10 minutes) before it leveled
off.
Enzyme Concentration
When the concentration of the enzyme is significantly lower than the concentration of the substrate (as when the number of taxis is
far lower than the number of waiting passengers), the rate of an enzyme-catalyzed reaction is directly dependent on the enzyme
concentration (part (b) of Figure 19.5.1). This is true for any catalyst; the reaction rate increases as the concentration of the catalyst
is increased.
Effect of Temperature on Activity

A general rule of thumb for most chemical reactions is that a temperature rise of 10°C approximately doubles the reaction rate. To
some extent, this rule holds for all enzymatic reactions. After a certain point, however, an increase in temperature causes a decrease
in the enzyme reaction rate, due to denaturation of the protein structure and disruption of the active site (part (a) of Figure 19.5.2).
For many proteins, denaturation occurs between 45°C and 55°C. Furthermore, even though an enzyme may appear to have a
maximum reaction rate between 40°C and 50°C, most biochemical reactions are carried out at lower temperatures because enzymes
are not stable at these higher temperatures and will denature after a few minutes.
Figure 19.5.2 : Temperature and pH versus Concentration. (a) This graph depicts the effect of temperature on the rate of a reaction
that is catalyzed by a fixed amount of enzyme. (b) This graph depicts the effect of pH on the rate of a reaction that is catalyzed by a
fixed amount of enzyme.
At 0°C and 100°C, the rate of enzyme-catalyzed reactions is nearly zero. This fact has several practical applications. We sterilize
objects by placing them in boiling water, which denatures the enzymes of any bacteria that may be in or on them. We preserve our
food by refrigerating or freezing it, which slows enzyme activity. When animals go into hibernation in winter, their body
temperature drops, decreasing the rates of their metabolic processes to levels that can be maintained by the amount of energy stored
in the fat reserves in the animals’ tissues.
Effect of Hydrogen Ion Concentration (pH) on Activity

Because most enzymes are proteins, they are sensitive to changes in the hydrogen ion concentration or pH. Enzymes may be
denatured by extreme levels of hydrogen ions (whether high or low); any change in pH, even a small one, alters the degree of
ionization of an enzyme’s acidic and basic side groups and the substrate components as well. Ionizable side groups located in the
active site must have a certain charge for the enzyme to bind its substrate. Neutralization of even one of these charges alters an
enzyme’s catalytic activity.
An enzyme exhibits maximum activity over the narrow pH range in which a molecule exists in its properly charged form. The
median value of this pH range is called the optimum pH of the enzyme (part (b) of Figure 19.5.2). With the notable exception of
gastric juice (the fluids secreted in the stomach), most body fluids have pH values between 6 and 8. Not surprisingly, most enzymes
exhibit optimal activity in this pH range. However, a few enzymes have optimum pH values outside this range. For example, the
optimum pH for pepsin, an enzyme that is active in the stomach, is 2.0.
Summary
Initially, an increase in substrate concentration leads to an increase in the rate of an enzyme-catalyzed reaction. As the enzyme
molecules become saturated with substrate, this increase in reaction rate levels off. The rate of an enzyme-catalyzed reaction
increases with an increase in the concentration of an enzyme. At low temperatures, an increase in temperature increases the rate of
an enzyme-catalyzed reaction. At higher temperatures, the protein is denatured, and the rate of the reaction dramatically decreases.
An enzyme has an optimum pH range in which it exhibits maximum activity.

1. The concentration of substrate X is low. What happens to the rate of the enzyme-catalyzed reaction if the concentration of X is
doubled?
2. What effect does an increase in the enzyme concentration have on the rate of an enzyme-catalyzed reaction?
Answers
1. If the concentration of the substrate is low, increasing its concentration will increase the rate of the reaction.
2. An increase in the amount of enzyme will increase the rate of the reaction (provided sufficient substrate is present).
Exercises
1. In non-enzyme-catalyzed reactions, the reaction rate increases as the concentration of reactant is increased. In an enzyme-
catalyzed reaction, the reaction rate initially increases as the substrate concentration is increased but then begins to level off, so
that the increase in reaction rate becomes less and less as the substrate concentration increases. Explain this difference.
2. Why do enzymes become inactive at very high temperatures?
3. An enzyme has an optimum pH of 7.4. What is most likely to happen to the activity of the enzyme if the pH drops to 6.3?
Explain.
4. An enzyme has an optimum pH of 7.2. What is most likely to happen to the activity of the enzyme if the pH increases to 8.5?
Explain.
Answers
1. In an enzyme-catalyzed reaction, the substrate binds to the enzyme to form an enzyme-substrate complex. If more substrate is
present than enzyme, all of the enzyme binding sites will have substrate bound, and further increases in substrate concentration
cannot increase the rate.
3. The activity will decrease; a pH of 6.3 is more acidic than 7.4, and one or more key groups in the active site may bind a
hydrogen ion, changing the charge on that group.
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Explain what an enzyme inhibitor is.
Distinguish between reversible and irreversible inhibitors.
Distinguish between competitive, noncompetitive, and uncompetitive inhibitors.
Previously, we noted that enzymes can be inactivated at high temperatures and by changes in pH. These are nonspecific factors that
would inactivate any enzyme. The activity of enzymes can also be regulated by more specific inhibitors that slow or stop catalysis.
Enzyme inhibition can either be reversible or irreversible. In reversible inhibition, the inhibitor can bind (usually non-covalently)
and dissociate, allowing enzyme activity to return back to its original, uninhibited level. Irreversible inhibitors bind to the enzyme
permanently and thus permanently inhibit enzyme activity.
Reversible Inhibition
Reversible enzyme inhibition can be competitive, noncompetitive, or uncompetitive, depending on where the inhibitor binds to the
enzyme, substrate, or enzyme-substrate complex.
Competitive inhibition is when an inhibitor reversibly binds to an enzyme at the enzyme active site; competing with the substrate
for binding. A competitive inhibitor must be a molecule that is structurally similar to the substrate molecule, allowing it to interact
with the enzyme active site through similar non-covalent interactions, but it does not, or cannot, undergo the same chemical
reaction. When the inhibitor is bound to the active site, it blocks the correct substrate from binding and catalysis from occurring.
However, as a reversible inhibitor, it can disassociate from the enzyme eventually allowing for the correct substrate to bind and the
catalysis to occur. Because the inhibitor and substrate are in competition for the same active site, inhibition is concentration-
dependent. As shown in the below plot of rate of reaction vs. substrate concentration (Figure 19.6.1), the competitive inhibitor
slows the rate of reaction, but at higher substrate concentrations, the normal maximum rate can be reached.
Figure 19.6.1 : Plots of reaction rate vs. substrate concentration with and without inhibitors. Competitive inhibitors bind reversibly
at the active site and therefore, compete with the substrate for binding. As substrate concentration increases, it can outcompete the
inhibitor allowing enzyme activity to reach a normal maximum (green line). A noncompetive inhibitor binds at a site separate from
the active site, the enzyme activity can only reach a lower than normal maximum reaction rate even as substrate concentration
increases (blue line). Uncompetitive inhibition is not represented on this plot, but would be similar to the noncompetitive inhibitor,
reaching a lower maximum rate. (Figure from OpenStax Biology)
Studies of competitive inhibition have provided helpful information about certain enzyme-substrate complexes and the interactions
of specific groups at the active sites. As a result, pharmaceutical companies have synthesized drugs that competitively inhibit
metabolic processes in bacteria and certain cancer cells. Many drugs are competitive inhibitors of specific enzymes.
A classic example of competitive inhibition is the effect of malonate on the enzyme activity of succinate dehydrogenase (Figure
19.6.2). Malonate and succinate are the anions of dicarboxylic acids and contain three and four carbon atoms, respectively. The
malonate molecule binds to the active site because the spacing of its carboxyl groups is not greatly different from that of succinate.
However, no catalytic reaction occurs because malonate does not have a CH2CH2 group to convert to CH=CH. This reaction will
also be discussed in connection with the Krebs cycle and energy production in a later chapter.
Figure 19.6.2 : Competitive Inhibition. (a) Succinate binds to the enzyme succinate dehydrogenase. A dehydrogenation reaction
occurs, and the product—fumarate—is released from the enzyme. (b) Malonate, a competitive inhibitor, also binds to the active site
of succinate dehydrogenase. In this case, however, no subsequent reaction occurs while malonate remains bound to the enzyme.
In uncompetitive inhibition, the inhibitor can only bind the enzyme when the substrate is already bound, in other words it binds
the enzyme-substrate complex but not the enzyme alone. The maximum reaction rate in the presence of an uncompetitive inhibitor
is lowered, however, unlike with competitive inhibition, the rate cannot be increased by adding more substrate. This type of
inhibition is most commonly seen when the enzyme reaction involves two substrates and as long as the concentration of inhibitor
remains constant, the maximum reaction rate does not change.
A noncompetitive inhibitor can bind to either the free enzyme or the enzyme-substrate complex because its binding site on the
enzyme is distinct from the active site. Binding of this kind of inhibitor alters the three-dimensional conformation of the enzyme,
changing the configuration of the active site with one of two results. Either the enzyme-substrate complex does not form at its
normal rate, or, once formed, it does not yield products at the normal rate (see Figure 19.6.1). Because the inhibitor does not
structurally resemble the substrate, nor is it competing with the substrate for the active site, the addition of excess substrate does
not reverse the inhibitory effect.
Chemotherapy is the strategic use of chemicals (that is, drugs) to destroy infectious microorganisms or cancer cells without causing
excessive damage to the other, healthy cells of the host. From bacteria to humans, the metabolic pathways of all living organisms
are quite similar, so the search for safe and effective chemotherapeutic agents is a formidable task. Many well-established
chemotherapeutic drugs function by inhibiting a critical enzyme in the cells of the invading organism.
An antibiotic is a compound that kills bacteria; it may come from a natural source such as molds or be synthesized with a structure
analogous to a naturally occurring antibacterial compound. Antibiotics constitute no well-defined class of chemically related
substances, but many of them work by effectively inhibiting a variety of enzymes essential to bacterial growth.
 To Your Health: Penicillin
Penicillin, one of the most widely used antibiotics in the world, was fortuitously discovered by Alexander Fleming in 1928,
when he noticed antibacterial properties in a mold growing on a bacterial culture plate. In 1938, Ernst Chain and Howard
Florey began an intensive effort to isolate penicillin from the mold and study its properties. The large quantities of penicillin
needed for this research became available through development of a corn-based nutrient medium that the mold loved and
through the discovery of a higher-yielding strain of mold at a United States Department of Agriculture research center near
Peoria, Illinois. Even so, it was not until 1944 that large quantities of penicillin were being produced and made available for the
treatment of bacterial infections.
Penicillin functions by interfering with the synthesis of cell walls of reproducing bacteria. It does so by inhibiting an enzyme—
transpeptidase—that catalyzes the last step in bacterial cell-wall biosynthesis. The defective walls cause bacterial cells to burst.
Human cells are not affected because they have cell membranes, not cell walls.
Several naturally occurring penicillins have been isolated. They are distinguished by different R groups connected to a
common structure: a four-member cyclic amide (called a lactam ring) fused to a five-member ring. The addition of appropriate
organic compounds to the culture medium leads to the production of the different kinds of penicillin.
The penicillins are effective against gram-positive bacteria (bacteria capable of being stained by Gram’s stain) and a few gram-
negative bacteria (including the intestinal bacterium Escherichia coli). They are effective in the treatment of diphtheria,
gonorrhea, pneumonia, syphilis, many pus infections, and certain types of boils. Penicillin G was the earliest penicillin to be
used on a wide scale. However, it cannot be administered orally because it is quite unstable; the acidic pH of the stomach
converts it to an inactive derivative. The major oral penicillins—penicillin V, ampicillin, and amoxicillin—on the other hand,
are acid stable.
Some strains of bacteria become resistant to penicillin through a mutation that allows them to synthesize an enzyme—penicillinase
—that breaks the antibiotic down (by cleavage of the amide linkage in the lactam ring). To combat these strains, scientists have
synthesized penicillin analogs (such as methicillin) that are not inactivated by penicillinase.
Some people (perhaps 5% of the population) are allergic to penicillin and therefore must be treated with other antibiotics. Their
allergic reaction can be so severe that a fatal coma may occur if penicillin is inadvertently administered to them. Fortunately,
several other antibiotics have been discovered. Most, including aureomycin and streptomycin, are the products of microbial
synthesis. Others, such as the semisynthetic penicillins and tetracyclines, are made by chemical modifications of antibiotics; and
some, like chloramphenicol, are manufactured entirely by chemical synthesis. They are as effective as penicillin in destroying
infectious microorganisms. Many of these antibiotics exert their effects by blocking protein synthesis in microorganisms.
Initially, antibiotics were considered miracle drugs, substantially reducing the number of deaths from blood poisoning, pneumonia,
and other infectious diseases. Some seven decades ago, a person with a major infection almost always died. Today, such deaths are
rare. Seven decades ago, pneumonia was a dreaded killer of people of all ages. Today, it kills only the very old or those ill from
other causes. Antibiotics have indeed worked miracles in our time, but even miracle drugs have limitations. Not long after the
drugs were first used, disease organisms began to develop strains resistant to them. In a race to stay ahead of resistant bacterial
strains, scientists continue to seek new antibiotics. The penicillins have now been partially displaced by related compounds, such as
the cephalosporins and vancomycin. Unfortunately, some strains of bacteria have already shown resistance to these antibiotics.
Irreversible Inhibition
An irreversible inhibitor inactivates an enzyme by bonding covalently to a particular group at the active site. When the inhibitor
is bound, the enzyme active site is blocked, the substrate does not bind, and catalysis cannot occur, similar to competitive
inhibition. The difference here is that the inhibition is irreversible, meaning that the inhibitor remains bound and does not
dissociate from the enzyme because the enzyme-inhibitor covalent bonds are not easily broken. In the presence of an irreversible
inhibitor, the substrate cannot bind the active site at all, nor can high substrate concentrations outcompete the inhibitor, hence the
enzyme is completely inactivated. Many of the known irreversible inhibitors are poisons because they inactivate an enzyme
completely. Some examples are provided in Table 19.6.1 below.
Table 19.6.1 : Poisons as Enzyme Inhibitors
Poison Formula Example of Enzyme Inhibited Action
glyceraldehyde 3-phosphate
arsenate AsO
3 −
substitutes for phosphate
4
dehydrogenase
iodoacetate ICH COO

2
−
triose phosphate dehydrogenase binds to cysteine SH group
diisopropylfluoro-phosphate
acetylcholinesterase binds to serine OH group
(DIFP; a nerve poison)
Summary
An irreversible inhibitor inactivates an enzyme by bonding covalently to a particular group at the active site. A reversible inhibitor
inactivates an enzyme through noncovalent, reversible interactions. A competitive inhibitor competes with the substrate for binding
at the active site of the enzyme. A noncompetitive inhibitor binds at a site distinct from the active site.

1. What are the characteristics of an irreversible inhibitor?
2. In what ways does a competitive inhibitor differ from a noncompetitive inhibitor?
Answers
1. It inactivates an enzyme by bonding covalently to a particular group at the active site.
2. A competitive inhibitor structurally resembles the substrate for a given enzyme and competes with the substrate for binding at
the active site of the enzyme. A noncompetitive inhibitor binds at a site distinct from the active site and can bind to either the
free enzyme or the enzyme-substrate complex.
Exercises
1. What amino acid is present in the active site of all enzymes that are irreversibly inhibited by nerve gases such as DIFP?
2. Oxaloacetate (OOCCH2COCOO) inhibits succinate dehydrogenase. Would you expect oxaloacetate to be a competitive or
noncompetitive inhibitor? Explain.
Answer
1. serine
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Objective 1
Objective 2
In the previous section you learned about the different types of enzyme inhibitors and how they can be used to slow or stop enzyme
activity by binding to an enzyme or enzyme-substrate complex. All of these inhibitor types, except noncompetitive inhibitors, work
by binding to enzyme active sites. Noncompetitive inhibitors, however, work by binding to an enzyme at a location other than the
active site, an allosteric site. Inhibitors and other molecules, called activators, that bind to enzymes at allosteric sites are considered
an important part of enzyme regulation called allosteric control. In this section, we will take a look at allosteric control and
feedback control, two ways in which enzyme activity is regulated differently.
Allosteric Control
Allosteric enzymes have both a binding site, for substrate binding and catalysis, and an allosteric site, for regulation of enzyme
activity. When a regulator molecule binds to the allosteric site of an enzyme, usually by noncovalent interactions, a conformational
change occurs in the enzyme active site, which affects substrate binding and reaction rates. Allosteric regulation of enzyme activity
can be either positive, increasing reaction rates, or negative, decreasing reaction rates.
When an enzyme binds a negative regulator (or inhibitor), it will undergo a change in the active site in a way that prevents substrate
binding, thereby lowering the reaction rate. As illustrated in the left-hand panel in Figure 19.7.1, the active site changes (becomes
smaller in this case) and the substrate can no longer bind. Positive regulators (activators) bind to allosteric sites and cause
conformational changes that open up an active site to promote substrate binding, allowing catalysis or increasing the reaction rate.
The right panel of Figure 19.7.1 shows an enzyme that will only bind substrate when the active site is formed after the allosteric
activator binds.
Some enzymes will have more than one allosteric site that can interact with one another, which allows for highly-controlled or
finely-tuned reaction rates.
Figure 19.7.1 : Allosteric inhibitors and activators: Allosteric inhibitors modify the active site of the enzyme so that substrate
binding is reduced or prevented. In contrast, allosteric activators modify the active site of the enzyme so that the affinity for the
substrate increases.
Feedback Control
Many biological processes involve the sequential action of multiple enzymes, a reaction pathway, in which the product of one
reaction is the substrate for the next enzyme and so on until the final product is formed. Positive or negative regulation of these
pathways often occurs by feedback control, where a product from one of the steps in the path feedback to an earlier step in the
process to increase or decrease production. It may help to visualize a factory assembly line with each person responsible for one
step (catalytic reaction) in making a perfect box of 12 donuts. If the last person in the line, who is responsible for putting 12 donuts
in the box, falls behind, donuts will start to pile up. In order to not waste donuts or have less than full boxes at the end, it would be
beneficial to signal to the other people to slow down or take a break. The process is similar in biochemical pathways: if too much
product is being formed, the pathway needs to be turned off so energy and resources are not wasted.
Consider the pathway shown below in which substrate A is converted to product D through three enzymes and two intermediate
products (B and C):
Enzyme 1 Enzyme 2 Enzyme 3
A −−−−−→ B −−−−−→ C −−−−−→ D
If there is a lot of product D formed, there would be enough to bind to Enzyme 1, which would inhibit formation of products B, and
subsequently product C, and D. This type of feedback control is useful to prevent waste of substrate A and any energy that is
needed for the activity of Enzymes 1-3. As you will see in later chapters, there are many different types of feedback control that can
both negatively and positively regulate pathways. Typically, feedback control occurs at points in pathways where it would be
energetically unfavorable to proceede if the final product is not needed.
Feedback inhibition is used to regulate the synthesis of many amino acids. For example, bacteria synthesize isoleucine from
threonine in a series of five enzyme-catalyzed steps. As the concentration of isoleucine increases, some of it binds as a
noncompetitive inhibitor to the first enzyme of the series (threonine deaminase), thus bringing about a decrease in the amount of
isoleucine being formed (Figure 19.7.2).
Figure 19.7.2 : Feedback Inhibition of Threonine Deaminase by Isoleucine. Threonine deaminase is the first enzyme in the
conversion of threonine to isoleucine. Isoleucine inhibits threonine deaminase through feedback inhibition.
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CHAPTER OVERVIEW
20: Carbohydrates
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Define what is meant by anomers and describe how they are formed.
Explain what is meant by mutarotation.
So far we have represented monosaccharides as linear molecules, but many of them also adopt cyclic structures. This conversion
occurs because of the ability of aldehydes and ketones to react with alcohols:
You might wonder why the aldehyde reacts with the OH group on the fifth carbon atom rather than the OH group on the second
carbon atom next to it. Recall that cyclic alkanes containing five or six carbon atoms in the ring are the most stable. The same is
true for monosaccharides that form cyclic structures: rings consisting of five or six carbon atoms are the most stable.
Figure 20.3.1 : Cyclization of D-Glucose. D-Glucose can be represented with a Fischer projection (a) or three dimensionally (b). By
reacting the OH group on the fifth carbon atom with the aldehyde group, the cyclic monosaccharide (c) is produced.
When a straight-chain monosaccharide, such as any of the structures shown in Figure 20.3.1, forms a cyclic structure, the carbonyl
oxygen atom may be pushed either up or down, giving rise to two stereoisomers, as shown in Figure 20.3.2. The structure shown
on the left side of Figure 20.3.2, with the OH group on the first carbon atom projected downward, represent what is called the
alpha (α) form. The structures on the right side, with the OH group on the first carbon atom pointed upward, is the beta (β) form.
These two stereoisomers of a cyclic monosaccharide are known as anomers; they differ in structure around the anomeric carbon—
that is, the carbon atom that was the carbonyl carbon atom in the straight-chain form.
It is possible to obtain a sample of crystalline glucose in which all the molecules have the α structure or all have the β structure.
The α form melts at 146°C and has a specific rotation of +112°, while the β form melts at 150°C and has a specific rotation of
+18.7°. When the sample is dissolved in water, however, a mixture is soon produced containing both anomers as well as the
straight-chain form, in dynamic equilibrium (part (a) of Figure 20.3.2). You can start with a pure crystalline sample of glucose
consisting entirely of either anomer, but as soon as the molecules dissolve in water, they open to form the carbonyl group and then
reclose to form either the α or the β anomer. The opening and closing repeats continuously in an ongoing interconversion between
anomeric forms and is referred to as mutarotation (Latin mutare, meaning “to change”). At equilibrium, the mixture consists of
about 36% α-D-glucose, 64% β-D-glucose, and less than 0.02% of the open-chain aldehyde form. The observed rotation of this
solution is +52.7°.
Figure 20.3.2 : Monosaccharides. In an aqueous solution, monosaccharides exist as an equilibrium mixture of three forms. The
interconversion between the forms is known as mutarotation, which is shown for D-glucose (a) and D-fructose (b).
Even though only a small percentage of the molecules are in the open-chain aldehyde form at any time, the solution will
nevertheless exhibit the characteristic reactions of an aldehyde. As the small amount of free aldehyde is used up in a reaction, there
is a shift in the equilibrium to yield more aldehyde. Thus, all the molecules may eventually react, even though very little free
aldehyde is present at a time.
Commonly, (e.g., in Figures 20.3.1 and 20.3.2) the cyclic forms of sugars are depicted using a convention first suggested by Walter
N. Haworth, an English chemist. The molecules are drawn as planar hexagons with a darkened edge representing the side facing
toward the viewer. The structure is simplified to show only the functional groups attached to the carbon atoms. Any group written
to the right in a Fischer projection appears below the plane of the ring in a Haworth projection, and any group written to the left in
a Fischer projection appears above the plane in a Haworth projection.
The difference between the α and the β forms of sugars may seem trivial, but such structural differences are often crucial in
biochemical reactions. This explains why we can get energy from the starch in potatoes and other plants but not from cellulose,
even though both starch and cellulose are polysaccharides composed of glucose molecules linked together.
Summary
Monosaccharides that contain five or more carbons atoms form cyclic structures in aqueous solution. Two cyclic stereoisomers can
form from each straight-chain monosaccharide; these are known as anomers. In an aqueous solution, an equilibrium mixture forms
between the two anomers and the straight-chain structure of a monosaccharide in a process known as mutarotation.
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To identify the structures of D-glucose, D-galactose, and D-fructose and describe how they differ from each other.
Although a variety of monosaccharides are found in living organisms, three hexoses are particularly abundant: D-glucose, D-
galactose, and D-fructose (Figure 20.4.1). Glucose and galactose are both aldohexoses, while fructose is a ketohexose.
Figure 20.4.1 : Structures of Three Important Hexoses. Each hexose is pictured with a food source in which it is commonly found.
Source: Photos © Thinkstock.
Glucose
D-Glucose, generally referred to as simply glucose, is the most abundant sugar found in nature; most of the carbohydrates we eat
are eventually converted to it in a series of biochemical reactions that produce energy for our cells. It is also known by three other
names: dextrose, from the fact that it rotates plane-polarized light in a clockwise (dextrorotatory) direction; corn sugar because in
the United States cornstarch is used in the commercial process that produces glucose from the hydrolysis of starch; and blood sugar
because it is the carbohydrate found in the circulatory system of animals. Normal blood sugar values range from 70 to 105 mg
glucose/dL plasma, and normal urine may contain anywhere from a trace to 20 mg glucose/dL urine.
Figure 20.4.2 : Fischer projection of D-glucose

The Fischer projection of D-glucose is given in Figure 20.4.2. Glucose is a D sugar because the OH group on the fifth carbon atom
(the chiral center farthest from the carbonyl group) is on the right. In fact, all the OH groups except the one on the third carbon
atom are to the right.
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Identify the structures of sucrose, lactose, and maltose.
Identify the monosaccharides that are needed to form sucrose, lactose, and maltose
Reducing Sugars
Sugar Alcohols
Disaccharide Formation
Previously, you learned that monosaccharides can form cyclic structures by the reaction of the carbonyl group with an OH group.
These cyclic molecules can in turn react with another alcohol. Disaccharides (C12H22O11) are sugars composed of two
monosaccharide units that are joined by a carbon–oxygen-carbon linkage known as a glycosidic linkage. This linkage is formed
from the reaction of the anomeric carbon of one cyclic monosaccharide with the OH group of a second monosaccharide.
The disaccharides differ from one another in their monosaccharide constituents and in the specific type of glycosidic linkage
connecting them. There are three common disaccharides: maltose, lactose, and sucrose. All three are white crystalline solids at
room temperature and are soluble in water. We’ll consider each sugar in more detail.
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Objective 1
Objective 2
Maltose
Maltose occurs to a limited extent in sprouting grain. It is formed most often by the partial hydrolysis of starch and glycogen. In the
manufacture of beer, maltose is liberated by the action of malt (germinating barley) on starch; for this reason, it is often referred to
as malt sugar. Maltose is about 30% as sweet as sucrose. The human body is unable to metabolize maltose or any other
disaccharide directly from the diet because the molecules are too large to pass through the cell membranes of the intestinal wall.
Therefore, an ingested disaccharide must first be broken down by hydrolysis into its two constituent monosaccharide units.
In the body, such hydrolysis reactions are catalyzed by enzymes such as maltase. The same reactions can be carried out in the
laboratory with dilute acid as a catalyst, although in that case the rate is much slower, and high temperatures are required. Whether
it occurs in the body or a glass beaker, the hydrolysis of maltose produces two molecules of D-glucose.
+
H or maltase
maltose −−−−−−−−→ 2 D-glucose (16.6.2)
Maltose is a reducing sugar. Thus, its two glucose molecules must be linked in such a way as to leave one anomeric carbon that can
open to form an aldehyde group. The glucose units in maltose are joined in a head-to-tail fashion through an α-linkage from the
first carbon atom of one glucose molecule to the fourth carbon atom of the second glucose molecule (that is, an α-1,4-glycosidic
linkage; see Figure 20.6.1). The bond from the anomeric carbon of the first monosaccharide unit is directed downward, which is
why this is known as an α-glycosidic linkage. The OH group on the anomeric carbon of the second glucose can be in either the α or
the β position, as shown in Figure 20.6.1.
Figure 20.6.1 : An Equilibrium Mixture of Maltose Isomers
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To compare and contrast the structures and uses of starch, glycogen, and cellulose.
The polysaccharides are the most abundant carbohydrates in nature and serve a variety of functions, such as energy storage or as
components of plant cell walls. Polysaccharides are very large polymers composed of tens to thousands of monosaccharides joined
together by glycosidic linkages. The three most abundant polysaccharides are starch, glycogen, and cellulose. These three are
referred to as homopolymers because each yields only one type of monosaccharide (glucose) after complete hydrolysis.
Heteropolymers may contain sugar acids, amino sugars, or noncarbohydrate substances in addition to monosaccharides.
Heteropolymers are common in nature (gums, pectins, and other substances) but will not be discussed further in this textbook. The
polysaccharides are nonreducing carbohydrates, are not sweet tasting, and do not undergo mutarotation.
Starch
Starch is the most important source of carbohydrates in the human diet and accounts for more than 50% of our carbohydrate intake.
It occurs in plants in the form of granules, and these are particularly abundant in seeds (especially the cereal grains) and tubers,
where they serve as a storage form of carbohydrates. The breakdown of starch to glucose nourishes the plant during periods of
reduced photosynthetic activity. We often think of potatoes as a “starchy” food, yet other plants contain a much greater percentage
of starch (potatoes 15%, wheat 55%, corn 65%, and rice 75%). Commercial starch is a white powder.
Starch is a mixture of two polymers: amylose and amylopectin. Natural starches consist of about 10%–30% amylose and 70%–90%
amylopectin. Amylose is a linear polysaccharide composed entirely of D-glucose units joined by the α-1,4-glycosidic linkages we
saw in maltose (part (a) of Figure 20.7.1). Experimental evidence indicates that amylose is not a straight chain of glucose units but
instead is coiled like a spring, with six glucose monomers per turn (part (b) of Figure 20.7.1). When coiled in this fashion, amylose
has just enough room in its core to accommodate an iodine molecule. The characteristic blue-violet color that appears when starch
is treated with iodine is due to the formation of the amylose-iodine complex. This color test is sensitive enough to detect even
minute amounts of starch in solution.
Figure 20.7.1 : Amylose. (a) Amylose is a linear chain of α-D-glucose units joined together by α-1,4-glycosidic bonds. (b) Because
of hydrogen bonding, amylose acquires a spiral structure that contains six glucose units per turn.
Amylopectin is a branched-chain polysaccharide composed of glucose units linked primarily by α-1,4-glycosidic bonds but with
occasional α-1,6-glycosidic bonds, which are responsible for the branching. A molecule of amylopectin may contain many
thousands of glucose units with branch points occurring about every 25–30 units (Figure 20.7.2). The helical structure of
amylopectin is disrupted by the branching of the chain, so instead of the deep blue-violet color amylose gives with iodine,
amylopectin produces a less intense reddish brown.
Figure 20.7.2 : Representation of the Branching in Amylopectin and Glycogen. Both amylopectin and glycogen contain branch
points that are linked through α-1,6-linkages. These branch points occur more often in glycogen.
Dextrins are glucose polysaccharides of intermediate size. The shine and stiffness imparted to clothing by starch are due to the
presence of dextrins formed when clothing is ironed. Because of their characteristic stickiness with wetting, dextrins are used as
adhesives on stamps, envelopes, and labels; as binders to hold pills and tablets together; and as pastes. Dextrins are more easily
digested than starch and are therefore used extensively in the commercial preparation of infant foods.
The complete hydrolysis of starch yields, in successive stages, glucose:
starch → dextrins → maltose → glucose
In the human body, several enzymes known collectively as amylases degrade starch sequentially into usable glucose units.
Glycogen
Glycogen is the energy reserve carbohydrate of animals. Practically all mammalian cells contain some stored carbohydrates in
the form of glycogen, but it is especially abundant in the liver (4%–8% by weight of tissue) and in skeletal muscle cells (0.5%–
1.0%). Like starch in plants, glycogen is found as granules in liver and muscle cells. When fasting, animals draw on these
glycogen reserves during the first day without food to obtain the glucose needed to maintain metabolic balance.
Glycogen is structurally quite similar to amylopectin, although glycogen is more highly branched (8–12 glucose units between
branches) and the branches are shorter. When treated with iodine, glycogen gives a reddish brown color. Glycogen can be
broken down into its D-glucose subunits by acid hydrolysis or by the same enzymes that catalyze the breakdown of starch. In
animals, the enzyme phosphorylase catalyzes the breakdown of glycogen to phosphate esters of glucose.
About 70% of the total glycogen in the body is stored in muscle cells. Although the
percentage of glycogen (by weight) is higher in the liver, the much greater mass of
skeletal muscle stores a greater total amount of glycogen.
Cellulose
Cellulose, a fibrous carbohydrate found in all plants, is the structural component of plant cell walls. Because the earth is
covered with vegetation, cellulose is the most abundant of all carbohydrates, accounting for over 50% of all the carbon found in
the vegetable kingdom. Cotton fibrils and filter paper are almost entirely cellulose (about 95%), wood is about 50% cellulose,
and the dry weight of leaves is about 10%–20% cellulose. The largest use of cellulose is in the manufacture of paper and paper
products. Although the use of noncellulose synthetic fibers is increasing, rayon (made from cellulose) and cotton still account
for over 70% of textile production.
Like amylose, cellulose is a linear polymer of glucose. It differs, however, in that the glucose units are joined by β-1,4-
glycosidic linkages, producing a more extended structure than amylose (part (a) of Figure 20.7.3). This extreme linearity allows
a great deal of hydrogen bonding between OH groups on adjacent chains, causing them to pack closely into fibers (part (b) of
Figure 20.7.3). As a result, cellulose exhibits little interaction with water or any other solvent. Cotton and wood, for example,
are completely insoluble in water and have considerable mechanical strength. Because cellulose does not have a helical
structure, it does not bind to iodine to form a colored product.
Figure 20.7.3 : Cellulose. (a) There is extensive hydrogen bonding in the structure of cellulose. (b) In this electron micrograph
of the cell wall of an alga, the wall consists of successive layers of cellulose fibers in parallel arrangement.
Cellulose yields D-glucose after complete acid hydrolysis, yet humans are unable to metabolize cellulose as a source of glucose.
Our digestive juices lack enzymes that can hydrolyze the β-glycosidic linkages found in cellulose, so although we can eat
potatoes, we cannot eat grass. However, certain microorganisms can digest cellulose because they make the enzyme cellulase,
which catalyzes the hydrolysis of cellulose. The presence of these microorganisms in the digestive tracts of herbivorous animals
(such as cows, horses, and sheep) allows these animals to degrade the cellulose from plant material into glucose for energy.
Termites also contain cellulase-secreting microorganisms and thus can subsist on a wood diet. This example once again
demonstrates the extreme stereospecificity of biochemical processes.
 Career Focus: Certified Diabetes Educator
Certified diabetes educators come from a variety of health professions, such as nursing and dietetics, and specialize in the
education and treatment of patients with diabetes. A diabetes educator will work with patients to manage their diabetes.
This involves teaching the patient to monitor blood sugar levels, make good food choices, develop and maintain an exercise
program, and take medication, if required.
A certified diabetes educator at Naval Medical Center Portsmouth (left) and a registered dietician at the medical center
(center), provide nutritional information to a diabetes patient and her mother at the Diabetes Boot Camp.
Diabetes educators also work with hospital or nursing home staff to improve the care of diabetic patients. Educators must
be willing to spend time attending meetings and reading the current literature to maintain their knowledge of diabetes
medications, nutrition, and blood monitoring devices so that they can pass this information to their patients.
Summary
Starch is a storage form of energy in plants. It contains two polymers composed of glucose units: amylose (linear) and
amylopectin (branched). Glycogen is a storage form of energy in animals. It is a branched polymer composed of glucose units.
It is more highly branched than amylopectin. Cellulose is a structural polymer of glucose units found in plants. It is a linear
polymer with the glucose units linked through β-1,4-glycosidic bonds.

Answers
Exercises
Answers
1. What purposes do starch and cellulose serve in plants?
2. What purpose does glycogen serve in animals?
3. Starch is the storage form of glucose (energy) in plants, while cellulose is a structural component of the plant cell wall.
4. Glycogen is the storage form of glucose (energy) in animals.
5. What monosaccharide is obtained from the hydrolysis of each carbohydrate?
a. starch
b. cellulose
c. glycogen
6. For each carbohydrate listed in Exercise 1, indicate whether it is found in plants or mammals.
7. Describe the similarities and differences between amylose and cellulose.
8. Describe the similarities and differences between amylopectin and glycogen.
9. a. glucose
b. glucose
c. glucose
10. Amylose and cellulose are both linear polymers of glucose units, but the glycosidic linkages between the glucose units
differ. The linkages in amylose are α-1,4-glycosidic linkages, while the linkages in cellulose they are β-1,4-glycosidic
linkages.
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CHAPTER OVERVIEW
21: The Generation of Biochemical Energy

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1
Objective 1
Objective 2
Life requires energy. Animals, for example, require heat energy to maintain body temperature, mechanical energy to move their
limbs, and chemical energy to synthesize the compounds needed by their cells. Living cells remain organized and functioning
properly only through a continual supply of energy. But only specific forms of energy can be used. Supplying a plant with energy
by holding it in a flame will not prolong its life. On the other hand, a green plant is able to absorb radiant energy from the sun, the
most abundant source of energy for life on the earth. Plants use this energy first to form glucose and then to make other
carbohydrates, as well as lipids and proteins. Unlike plants, animals cannot directly use the sun’s energy to synthesize new
compounds. They must eat plants or other animals to get carbohydrates, fats, and proteins and the chemical energy stored in them.
Once digested and transported to the cells, the nutrient molecules can be used in either of two ways: as building blocks for making
new cell parts or repairing old ones or “burned” for energy.
Figure 21.1.2 : Some Energy Transformations in Living Systems. Plants and animals exist in a cycle; each requires products of the
other.
The thousands of coordinated chemical reactions that keep cells alive are referred to collectively as metabolism. In general,
metabolic reactions are divided into two classes: the breaking down of molecules to obtain energy is catabolism, and the building
of new molecules needed by living systems is anabolism.
 Definition: Metabolite
Any chemical compound that participates in a metabolic reaction is a metabolite.
Most of the energy required by animals is generated from lipids and carbohydrates. These fuels must be oxidized, or “burned,” for
the energy to be released. The oxidation process ultimately converts the lipid or carbohydrate to carbon dioxide (CO2) and water
(H2O).
Carbohydrate:
C H O +6 O → 6 CO + 6 H O + 670 kcal
6 12 6 2 2 2
Lipid:
C H O + 23 O → 16 CO + 16 H O + 2 , 385 kcal
16 32 2 2 2 2
These two equations summarize the biological combustion of a carbohydrate and a lipid by the cell through respiration.
Respiration is the collective name for all metabolic processes in which gaseous oxygen is used to oxidize organic matter to carbon
dioxide, water, and energy.
Like the combustion of the common fuels we burn in our homes and cars (wood, coal, gasoline), respiration uses oxygen from the
air to break down complex organic substances to carbon dioxide and water. But the energy released in the burning of wood is
manifested entirely in the form of heat, and excess heat energy is not only useless but also injurious to the living cell. Living
organisms instead conserve much of the energy respiration releases by channeling it into a series of stepwise reactions that produce
adenosine triphosphate (ATP) or other compounds that ultimately lead to the synthesis of ATP. The remainder of the energy is
released as heat and manifested as body temperature.
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Describe the two types of cell: prokaryotic and eukaryotic.
Explain the function of each cellular component.
Cells fall into one of two broad categories: prokaryotic and eukaryotic. Only the predominantly single-celled organisms of the
domains Bacteria and Archaea are classified as prokaryotes (pro- = “before”; -kary- = “nucleus”). Cells of animals, plants, fungi,
and protists are all eukaryotes (eu- = “true”) and are made up of eukaryotic cells.
Components of Prokaryotic Cells

All cells share four common components: 1) a plasma membrane, an outer covering that separates the cell’s interior from its
surrounding environment; 2) cytoplasm, consisting of a jelly-like cytosol within the cell in which other cellular components are
found; 3) DNA, the genetic material of the cell; and 4) ribosomes, which synthesize proteins. However, prokaryotes differ from
eukaryotic cells in several ways.
A prokaryote is a simple, mostly single-celled (unicellular) organism that lacks a nucleus, or any other membrane-bound organelle.
We will shortly come to see that this is significantly different in eukaryotes. Prokaryotic DNA is found in a central part of the cell:
the nucleoid (Figure 21.2.1).
Figure 21.2.1 : This figure shows the generalized structure of a prokaryotic cell. All prokaryotes have chromosomal DNA localized
in a nucleoid, ribosomes, a cell membrane, and a cell wall. The other structures shown are present in some, but not all, bacteria.
Unlike prokaryotic cells, eukaryotic cells have: 1) a membrane-bound nucleus; 2) numerous membrane-bound organelles such as
the endoplasmic reticulum, Golgi apparatus, chloroplasts, mitochondria, and others; and 3) several, rod-shaped chromosomes.
Because a eukaryotic cell’s nucleus is surrounded by a membrane, it is often said to have a “true nucleus.” The word “organelle”
means “little organ,” and, as already mentioned, organelles have specialized cellular functions, just as the organs of your body have
specialized functions.
At this point, it should be clear to you that eukaryotic cells have a more complex structure than prokaryotic cells. Organelles allow
different functions to be compartmentalized in different areas of the cell. Before turning to organelles, let’s first examine two
important components of the cell: the plasma membrane and the cytoplasm.
Figure 21.2.2: These figures show the major organelles and other cell components of a general eukaryotic cell.
Mitochondria (singular = mitochondrion) are often called the “powerhouses” or “energy factories” of a cell because they are
responsible for making adenosine triphosphate (ATP), the cell’s main energy-carrying molecule. ATP represents the short-term
stored energy of the cell. Cellular respiration is the process of making ATP using the chemical energy found in glucose and other
nutrients. In mitochondria, this process uses oxygen and produces carbon dioxide as a waste product. In fact, the carbon dioxide
that you exhale with every breath comes from the cellular reactions that produce carbon dioxide as a byproduct.
Mitochondria are oval-shaped, double membrane organelles (Figure 21.2.3) that have their own ribosomes and DNA. Each
membrane is a phospholipid bilayer embedded with proteins. The inner layer has folds called cristae. The area surrounded by the
folds is called the mitochondrial matrix. The cristae and the matrix have different roles in cellular respiration.
Figure 21.2.3 : This electron micrograph shows a mitochondrion as viewed with a transmission electron microscope. This organelle
has an outer membrane and an inner membrane. The inner membrane contains folds, called cristae, which increase its surface area.
The space between the two membranes is called the intermembrane space, and the space inside the inner membrane is called the
mitochondrial matrix. ATP synthesis takes place on the inner membrane. (credit: modification of work by Matthew Britton; scale-
bar data from Matt Russell)
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Describe the stages of catabolism from food to ATP.
Metabolism describes all of the chemical reactions that take place in an organism. A metabolic pathway is a series of
interconnected biochemical reactions that convert a substrate molecule or molecules, step-by-step, through a series of metabolic
intermediates, eventually yielding a final product or products. In the case of sugar metabolism, the first metabolic pathway
synthesized sugar from smaller molecules, and the other pathway broke sugar down into smaller molecules. These two opposite
processes—the first requiring energy and the second producing energy—are referred to as anabolic (building) and catabolic
(breaking down) pathways, respectively. Consequently, metabolism is composed of building (anabolism) and degradation
(catabolism).
It is important to know that the chemical reactions of metabolic pathways don’t take place spontaneously. Each reaction step is
facilitated, or catalyzed, by enzymes. Enzymes are important for catalyzing all types of biological reactions—those that require
energy as well as those that release energy. See a simple graphic below, (Figure 21.3.1).
Figure 21.3.1 : Anabolic pathways are those that require energy to synthesize larger molecules. Catabolic pathways are those that
generate energy by breaking down larger molecules. Both types of pathways are required for maintaining the cell’s energy balance.
We can think of catabolism as occurring in three stages (Figure 21.3.1). In stage I, carbohydrates, fats, and proteins are broken
down into their individual monomer units: carbohydrates into simple sugars, fats into fatty acids and glycerol, and proteins into
amino acids. One part of stage I of catabolism is the breakdown of food molecules by hydrolysis reactions into the individual
monomer units—which occurs in the mouth, stomach, and small intestine—and is referred to as digestion.
In stage II, these monomer units (or building blocks) are further broken down through different reaction pathways, one of which
produces ATP, to form a common end product, Acetyl-coenzyme A, that can then be used in stage III to produce even more ATP.
In this chapter, we will look at each stage of catabolism—as an overview and in detail.
Figure 21.3.1 : Energy Conversions. The conversion of food into cellular energy (as ATP) occurs in three stages.
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To describe the importance of ATP as a source of energy in living organisms.
Adenosine triphosphate (ATP), a nucleotide composed of adenine, ribose, and three phosphate groups, is perhaps the most
important of the so-called energy-rich compounds in a cell. Its concentration in the cell varies from 0.5 to 2.5 mg/mL of cell fluid.
Energy-rich compounds are substances having particular structural features that lead to a release of energy after hydrolysis. As a
result, these compounds are able to supply energy for biochemical processes that require energy. The structural feature important in
ATP is the phosphoric acid anhydride, or pyrophosphate, linkage:
The pyrophosphate bond, symbolized by a squiggle (~), is hydrolyzed when ATP is converted to adenosine diphosphate (ADP). In
this hydrolysis reaction, the products contain less energy than the reactants; there is a release of energy (> 7 kcal/mol). One reason
for the amount of energy released is that hydrolysis relieves the electron-electron repulsions experienced by the negatively charged
phosphate groups when they are bonded to each other (Figure 20.1.1).
Figure 21.4.1 : Hydrolysis of ATP to Form ADP

Energy is released because the products (ADP and phosphate ion) have less energy than the reactants [ATP and water (H2O)].
The general equation for ATP hydrolysis is as follows:
AT P + H2 O → ADP + Pi + 7.4 kcal/mol
If the hydrolysis of ATP releases energy, its synthesis (from ADP) requires energy. In the cell, ATP is produced by those processes
that supply energy to the organism (absorption of radiant energy from the sun in green plants and breakdown of food in animals),
and it is hydrolyzed by those processes that require energy (the syntheses of carbohydrates, lipids, proteins; the transmission of
nerve impulses; muscle contractions). In fact, ATP is the principal medium of energy exchange in biological systems. Many
scientists call it the energy currency of cells.
Pi is the symbol for the inorganic phosphate anions H 2PO

−
4
and HP O 2−
4
.
ATP is not the only high-energy compound needed for metabolism. Several others are listed in Table 21.4.1. Notice, however, that
the energy released when ATP is hydrolyzed is approximately midway between those of the high-energy and the low-energy
phosphate compounds. This means that the hydrolysis of ATP can provide energy for the phosphorylation of the compounds below
it in the table. For example, the hydrolysis of ATP provides sufficient energy for the phosphorylation of glucose to form glucose 1-
phosphate. By the same token, the hydrolysis of compounds, such as creatine phosphate, that appear above ATP in the table can
provide the energy needed to resynthesize ATP from ADP.
Table 21.4.1 : Energy Released by Hydrolysis of Some Phosphate Compounds
Type Example Energy Released (kcal/mol)
acyl phosphate
1,3-bisphosphoglycerate (BPG) −11.8
acetyl phosphate −11.3
guanidine phosphates
creatine phosphate −10.3
arginine phosphate −9.1
pyrophosphates PPi* → 2Pi −7.8
ATP → AMP + PPi −7.7
ATP → ADP + Pi −7.5
ADP → AMP + Pi −7.5
glucose 1-phosphate −5.0

sugar phosphates
fructose 6-phosphate −3.8
AMP → adenosine + Pi −3.4
glucose 6-phosphate −3.3
glycerol 3-phosphate −2.2
*PPi is the pyrophosphate ion.
Summary
The hydrolysis of ATP releases energy that can be used for cellular processes that require energy.
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Describe the reactions of the citric acid cycle.
Describe the function of the citric acid cycle and identify the products produced.
The acetyl group enters a cyclic sequence of reactions known collectively as the citric acid cycle (or Krebs cycle or tricarboxylic
acid [TCA] cycle). The cyclical design of this complex series of reactions, which bring about the oxidation of the acetyl group of
acetyl-CoA to carbon dioxide and water, was first proposed by Hans Krebs in 1937. (He was awarded the 1953 Nobel Prize in
Physiology or Medicine.) Acetyl-CoA’s entrance into the citric acid cycle is the beginning of stage III of catabolism. The citric acid
cycle produces adenosine triphosphate (ATP), reduced nicotinamide adenine dinucleotide (NADH), reduced flavin adenine
dinucleotide (FADH2), and metabolic intermediates for the synthesis of needed compounds.
Steps of the Citric Acid Cycle

At first glance, the citric acid cycle appears rather complex (Figure 21.7.1). All the reactions, however, are familiar types in
organic chemistry: hydration, oxidation, decarboxylation, and hydrolysis. Each reaction of the citric acid cycle is numbered, and in
Figure 21.7.1, the two acetyl carbon atoms are highlighted in red. Each intermediate in the cycle is a carboxylic acid, existing as an
anion at physiological pH. All the reactions occur within the mitochondria, which are small organelles within the cells of plants and
animals.
Figure 21.7.1 : Reactions of the Citric Acid Cycle

1. In the first step, acetyl-CoA enters the citric acid cycle, and the acetyl group is transferred onto oxaloacetate, yielding citrate.
Note that this step releases coenzyme A. The reaction is catalyzed by citrate synthase.
2. In the next step, aconitase catalyzes the isomerization of citrate to isocitrate. In this reaction, a tertiary alcohol, which cannot be
oxidized, is converted to a secondary alcohol, which can be oxidized in the next step.
3. Isocitrate then undergoes a reaction known as oxidative decarboxylation because the alcohol is oxidized and the molecule is
shortened by one carbon atom with the release of carbon dioxide (decarboxylation). The reaction is catalyzed by isocitrate
dehydrogenase, and the product of the reaction is α-ketoglutarate. An important reaction linked to this is the reduction of the
coenzyme nicotinamide adenine dinucleotide (NAD+) to NADH. The NADH is ultimately reoxidized, and the energy released
is used in the synthesis of ATP, as we shall see.
4. The fourth step is another oxidative decarboxylation. This time α-ketoglutarate is converted to succinyl-CoA, and another
molecule of NAD+ is reduced to NADH. The α-ketoglutarate dehydrogenase complex catalyzes this reaction. This is the only
irreversible reaction in the citric acid cycle. As such, it prevents the cycle from operating in the reverse direction, in which
acetyl-CoA would be synthesized from carbon dioxide.
So far, in the first four steps, two carbon atoms have entered the cycle as an acetyl group, and two carbon atoms have been
released as molecules of carbon dioxide. The remaining reactions of the citric acid cycle use the four carbon atoms of the
succinyl group to resynthesize a molecule of oxaloacetate, which is the compound needed to combine with an incoming acetyl
group and begin another round of the cycle.
In the fifth reaction, the energy released by the hydrolysis of the high-energy thioester bond of succinyl-CoA is used to form
guanosine triphosphate (GTP) from guanosine diphosphate (GDP) and inorganic phosphate in a reaction catalyzed by succinyl-CoA
synthetase. This step is the only reaction in the citric acid cycle that directly forms a high-energy phosphate compound. GTP can
readily transfer its terminal phosphate group to adenosine diphosphate (ADP) to generate ATP in the presence of nucleoside
diphosphokinase.
Succinate dehydrogenase then catalyzes the removal of two hydrogen atoms from succinate, forming fumarate. This oxidation-
reduction reaction uses flavin adenine dinucleotide (FAD), rather than NAD+, as the oxidizing agent. Succinate dehydrogenase is
the only enzyme of the citric acid cycle located within the inner mitochondrial membrane. We will see soon the importance of this.
In the following step, a molecule of water is added to the double bond of fumarate to form L-malate in a reaction catalyzed by
fumarase.
One revolution of the cycle is completed with the oxidation of L-malate to oxaloacetate, brought about by malate dehydrogenase.
This is the third oxidation-reduction reaction that uses NAD+ as the oxidizing agent. Oxaloacetate can accept an acetyl group from
acetyl-CoA, allowing the cycle to begin again.
The Citric Acid Cycle: An Overview
Video: "The Citric Acid Cycle: An Overview". In the matrix of the mitochondrion, the Citric Acid Cycle uses Acetyl CoA molecules
to produce energy through eight chemical reactions. This animation provides an overview of the pathway and its products. NDSU
VCell Production's animation; for more information please see http://vcell.ndsu.edu/animations.
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Summarize the electron transport chain.
Recognize that electron transport chain is the third and final stage of aerobic cellular respiration.
Identify the products of the citric acid cycle.
What do trains, trucks, boats, and planes all have in common? They are ways to transport. And they all use a lot of energy. To make
ATP, energy must be "transported" - first from glucose to NADH, and then somehow passed to ATP. How is this done? With an
electron transport chain, the third stage of aerobic respiration. This third stage uses energy to make energy.
The Electron Transport Chain: ATP for Life in the Fast Lane
At the end of the Krebs Cycle, energy from the chemical bonds of glucose is stored in diverse energy carrier molecules: four ATPs,
but also two FADH and ten NADH molecules. The primary task of the last stage of cellular respiration, the electron transport
2
chain, is to transfer energy from the electron carriers to even more ATP molecules, the "batteries" which power work within the
cell.
Pathways for making ATP in stage 3 of aerobic respiration closely resemble the electron transport chains used in photosynthesis. In
both electron transport chains, energy carrier molecules are arranged in sequence within a membrane so that energy-carrying
electrons cascade from one to another, losing a little energy in each step. In both photosynthesis and aerobic respiration, the energy
lost is harnessed to pump hydrogen ions into a compartment, creating an electrochemical gradient or chemiosmotic gradient
across the enclosing membrane. And in both processes, the energy stored in the chemiosmotic gradient is used with ATP synthase
to build ATP.
For aerobic respiration, the electron transport chain or "respiratory chain" is embedded in the inner membrane of the mitochondria
(see figure below). The FADH and NADH molecules produced in glycolysis and the Krebs Cycle, donate high-energy electrons to
2
energy carrier molecules within the membrane. As they pass from one carrier to another, the energy they lose is used to pump
hydrogen ions into the mitochondrial intermembrane space, creating an electrochemical gradient. Hydrogen ions flow "down" the
gradient - from outer to inner compartment - through the ion channel/enzyme ATP synthase, which transfers their energy to ATP.
Note the paradox that it requires energy to create and maintain a concentration gradient of hydrogen ions that are then used by ATP
synthase to create stored energy (ATP). In broad terms, it takes energy to make energy. Coupling the electron transport chain to
ATP synthesis with a hydrogen ion gradient is chemiosmosis, first described by Nobel laureate Peter D. Mitchell. This process, the
use of energy to phosphorylate ADP and produce ATP is also known as oxidative phosphorylation.
Figure 21.8.1 : The third stage of cellular respiration uses the energy stored during the earlier stages in NADH and FADH to make
2
ATP. Electron transport chains embedded in the mitochondrial inner membrane capture high-energy electrons from the carrier
molecules and use them to concentrate hydrogen ions in the intermembrane space. Hydrogen ions flow down their electrochemical
gradient back into the matrix through ATP synthase channels which capture their energy to convert ADP to ATP. Notice that the
process regenerates NAD , supplying the electron acceptor molecule needed in glycolysis. (CC BY-NC 3.0; Mariana Ruiz
+
Villarreal (LadyofHats) for the CK-12 Foundation).

After passing through the electron transport chain, low-energy electrons and low-energy hydrogen ions combine with oxygen to
form water. Thus, oxygen's role is to drive the entire set of ATP-producing reactions within the mitochondrion by accepting "spent"
hydrogens. Oxygen is the final electron acceptor, no part of the process - from the Krebs Cycle through the electron transport
chain- can happen without oxygen.
The electron transport chain can convert the energy from one glucose molecule's worth of F ADH and N ADH + H into as 2
+
many as 34 ATP. When the four ATP produced in glycolysis and the Krebs Cycle are added, the total of 38 ATP fits the overall
equation for aerobic cellular respiration:
6O + C H O + 38 ADP + 39 Pi → 38 ATP + 6 CO +6 H O (21.8.1)

2 6 12 6 2 2


stored chemical energy
stored chemical energy
Aerobic respiration is complete. If oxygen is available, cellular respiration transfers the energy from one molecule of glucose to 38
molecules of ATP, releasing carbon dioxide and water as waste. "Deliverable" food energy has become energy which can be used
for work within the cell - transport within the cell, pumping ions and molecules across membranes, and building large organic
molecules. Can you see how this could lead to "life in the fast lane" compared to anaerobic respiration (glycolysis alone)?
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CHAPTER OVERVIEW
22: Carbohydrate Metabolism

22.3: Glycolysis
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1
Describe digestion of carbohydrates.
The first stage of catabolism is digestion, in which food molecules are broken down into smaller molecules. Carbohydrate
digestion begins in the mouth (Figure 22.1.1) where salivary α -amylase attacks the α -glycosidic linkages in starch, the main
carbohydrate ingested by humans. Cleavage of the glycosidic linkages produces a mixture of dextrins, maltose, and glucose. The
α -amylase mixed into the food remains active as the food passes through the esophagus, but it is rapidly inactivated in the acidic
environment of the stomach.
Figure 22.1.1 : The Principal Events and Sites of Carbohydrate Digestion

The primary site of carbohydrate digestion is the small intestine. The secretion of α -amylase in the small intestine converts any
remaining starch molecules, as well as the dextrins, to maltose. Maltose is then cleaved into two glucose molecules by maltase.
Disaccharides such as sucrose and lactose are not digested until they reach the small intestine, where they are acted on by sucrase
and lactase, respectively. The major products of the complete hydrolysis of disaccharides and polysaccharides are three
monosaccharide units: glucose, fructose, and galactose. These are absorbed through the wall of the small intestine into the
bloodstream.
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22.3: Glycolysis
Objective 1
Objective 2
Glycolysis is the catabolic process in which glucose is converted into pyruvate via ten enzymatic steps. There are three regulatory
steps, each of which is highly regulated.
Introduction
There are two phases of Glycolysis:
1. the "priming phase" because it requires an input of energy in the form of 2 ATPs per glucose molecule and
2. the "pay off phase" because energy is released in the form of 4 ATPs, 2 per glyceraldehyde molecule.
The end result of Glycolysis is two new pyruvate molecules which can then be fed into the Citric Acid cycle (also known as the
Kreb's Cycle) if oxygen is present, or can be reduced to lactate or ethanol in the absence of of oxygen using a process known as
Fermentation. Glycolysis occurs within almost all living cells and is the primary source of Acetyl-CoA, which is the molecule
responsible for the majority of energy output under aerobic conditions. The structures of Glycolysis intermediates can be found in
the following diagram:
Hexokinase
Pyruvate
Mg ++
Pyruvate kinase Phosphoglucose
ATP Mg ++ isomerase
Glucose ATP
ADP Glucose 6-phosphate
ADP
+ Enolase
H
Mg ++
Fructose 6-phosphate Phosphofructokinase
×2 Mg ++
Phosphoenolpyruvate H2 O
H2 O ATP
2-phosphoglycerate Phosphoglycerate
mutase
ADP
Fructose 1,6-biphosphate
Legend Fructose bisphosphate aldolase

Phosphoglycerate
Hydrogen 3-phosphoglycerate kinase
Adenosine Mg ++
Glyceraldehyde 3-phosphate
Carbon ATP triphosphate
Glyceraldehyde phosphate
Oxygen
dehydrogenase
Adenosine
Phosphate group ADP diphosphate Mg ++
ATP Triosephosphate isomerase
H2 PO4 Inorganic phosphate Irreversible reaction
(highly exergonic) ADP
Mg++ Magnesium ion (cofactor) +
Reversible reaction NAD+
NAD+
NADH, H
Nicotinamide adenine H2 PO4
dinucleotide 1,3-biphosphoglycerate
Hexokinase Enzyme Dihydroxyacetone phosphate
Figure 1: Glycolysis pathway. from Wikipedia (CCBY-SA 3.0; YassineMrabet).
Phase 1: The "Priming Step"

The first phase of Glycolysis requires an input of energy in the form of ATP (adenosine triphosphate).
1. alpha-D-Glucose is phosphorolated at the 6 carbon by ATP via the enzyme Hexokinase (Class: Transferase) to yield alpha-D-
Glucose-6-phosphate (G-6-P). This is a regulatory step which is negatively regulated by the presence of glucose-6-phosphate.
2. alpha-D-Glucose-6-phosphate is then converted into D-Fructose-6-phosphate (F-6-P) by Phosphoglucoisomerase (Class:
Isomerase)
3. D-Fructose-6-phosphate is once again phosphorolated this time at the 1 carbon position by ATP via the enzyme
Phosphofructokinase (Class: Transferase) to yield D-Fructose-1,6-bisphosphate (FBP). This is the committed step of glycolysis
because of its large ΔG value.
4. D-Fructose-1,6-bisphosphate is then cleaved into two, three carbon molecules; Dihydroxyacetone phosphate (DHAP) and D-
Glyceraldehyde-3-phosphate (G-3-P) by the enzyme Fructose bisphosphate aldolase (Class: Lyase)
5. Because the next portion of Glycolysis requires the molecule D-Glyceraldehyde-3-phosphate to continue Dihydroxyacetone
phosphate is converted into D-Glyceraldehyde-3-phosphate by the enzyme Triose phosphate isomerase (Class: Isomerase)
Phase 2: The "Pay Off Step"

The second phase of Glycolysis where 4 molecules of ATP are produced per molecule of glucose. Enzymes appear in red:
1. D-Glyceraldehyde-3-phosphate is phosphorolated at the 1 carbon by the enzyme Glyceraldehyde-3-phosphate dehodrogenase to
yield the high energy molecule 1,3-Bisphosphoglycerate (BPG)
2. ADP is then phosphorolated at the expense of 1,3-Bisphosphoglycerate by the enzyme Phosphoglycerate kinase (Class:
Transferase) to yield ATP and 3-Phosphoglycerate (3-PG)
3. 3-Phosphoglycerate is then converted into 2-Phosphoglycerate by Phosphoglycerate mutase in preparation to yield another high
energy molecule
4. 2-Phosphoglycerate is then converted to phosphoenolpyruvate (PEP) by Enolase. H2O, potassium, and magnesium are all
released as a result.
5. ADP is once again phosphorolated, this time at the expense of PEP by the enzyme pyruvate kinase to yield another molecule of
ATP and and pyruvate. This step is regulated by the energy in the cell. The higher the energy of the cell the more inhibited
pyruvate kinase becomes. Indicators of high energy levels within the cell are high concentrations of ATP, Acetyl-CoA, Alanine,
and cAMP.
Because Glucose is split to yield two molecules of D-Glyceraldehyde-3-phosphate, each step in the "Pay Off" phase occurs twice
per molecule of glucose.
References
1. Garrett, H., Reginald and Charles Grisham. Biochemistry. Boston: Twayne Publishers, 2008.
2. Raven, Peter. Biology. Boston: Twayne Publishers, 2005.
Problems
1. What is the net yield of Glycolysis as far as ATP?
2. Name the enzymes that are key regulatory sites in Glycolysis.
3. Why are the enzymes in the previous question targets for regulation?
4. Why is the priming phase necessary?
5. Draw the entire pathway for glycolysis including enzymes, reactants and products for each step.

Darik Benson, (University California Davis)
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CHAPTER OVERVIEW
23: Lipids
23.6: Steroids
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1
Define lipids and recognize the different classes.
Fats and oils, found in many of the foods we eat, belong to a class of biomolecules known as lipids. Gram for gram, they pack
more than twice the caloric content of carbohydrates: the oxidation of fats and oils supplies about 9 kcal of energy for every gram
oxidized, whereas the oxidation of carbohydrates supplies only 4 kcal/g. Although the high caloric content of fats may be bad news
for the dieter, it says something about the efficiency of nature’s designs. Our bodies use carbohydrates, primarily in the form of
glucose, for our immediate energy needs. Our capacity for storing carbohydrates for later use is limited to tucking away a bit of
glycogen in the liver or in muscle tissue. We store our reserve energy in lipid form, which requires far less space than the same
amount of energy stored in carbohydrate form. Lipids have other biological functions besides energy storage. They are a major
component of the membranes of the 10 trillion cells in our bodies. They serve as protective padding and insulation for vital organs.
Furthermore, without lipids in our diets, we would be deficient in the fat-soluble vitamins A, D, E, and K.
Lipids are not defined by the presence of specific functional groups, as carbohydrates are, but by a physical property—solubility.
Compounds isolated from body tissues are classified as lipids if they are more soluble in organic solvents, such as
dichloromethane, than in water. By this criterion, the lipid category includes not only fats and oils, which are esters of the
trihydroxy alcohol glycerol and fatty acids, but also compounds that incorporate functional groups derived from phosphoric acid,
carbohydrates, or amino alcohols, as well as steroid compounds such as cholesterol (Figure 23.1.1 presents one scheme for
classifying the various kinds of lipids). We will discuss the various kinds of lipids by considering one subclass at a time and
pointing out structural similarities and differences as we go.
Figure 23.1.1 : Lipid Organization Based on Structural Relationships
Lipids Formed from Fatty Acids

Fatty acids are carboxylic acids with 12-22 carbon atoms connected in a long, unbranched chain. As shown in the diagram above,
most lipids are classified as esters or amides of fatty acids.
Waxes are esters formed from long-chain fatty acids and long-chain alcohols. Most natural waxes are mixtures of such esters.
Triacylglycerol (triglycerides) are esters of glycerol, a trialcohol, and three fatty acids. Many organisms store energy in this
form.
Glycerophospholipids are esters of glycerol formed from two fatty acid chains and a charged phosphate.
Figure 23.1.2: Esters of Fatty Acids: Triglycerides, Waxes, and Glycerophospholipids.
Sphingolipids are fatty acid amides formed from a fatty acid attached to an amino alcohol backbone, called sphingosine, along
with either a phosphate (sphingomyelin) or a carbohydrate (glycolipid). These along with glycerophospholipids are important
for the structure and function of cellular membranes.
Other Lipids
Not all lipids contain fatty acid groups:
Sterols (also classified as steroids) all contain the steroid nucleus, which is four fused rings. Cholesterol is the most commonly
known sterol and is also an important lipid in cell membranes.
Eicosanoids are important chemical messengers that include prostaglandins, which have a five-member ring and a carboxylic
acid chain.
Chemical diagram Prostaglandin - Wikipedia
Figure 23.1.3: Other Lipids: Cholesterol contains the steroid nucleus (top) and a prostaglandin (bottom).
In the next sections of this chapter you will learn more about the structure, properties, and functions of each of these types of lipid.
 To Your Health: Prostaglandins
Prostaglandins are chemical messengers synthesized in the cells in which their physiological activity is expressed. They are
unsaturated fatty acids containing 20 carbon atoms and are synthesized from arachidonic acid—a polyunsaturated fatty acid—
when needed by a particular cell. They are called prostaglandins because they were originally isolated from semen found in the
prostate gland. It is now known that they are synthesized in nearly all mammalian tissues and affect almost all organs in the
body. The five major classes of prostaglandins are designated as PGA, PGB, PGE, PGF, and PGI. Subscripts are attached at the
end of these abbreviations to denote the number of double bonds outside the five-carbon ring in a given prostaglandin.
The prostaglandins are among the most potent biological substances known. Slight structural differences give them highly
distinct biological effects; however, all prostaglandins exhibit some ability to induce smooth muscle contraction, lower blood
pressure, and contribute to the inflammatory response. Aspirin and other nonsteroidal anti-inflammatory agents, such as
ibuprofen, obstruct the synthesis of prostaglandins by inhibiting cyclooxygenase, the enzyme needed for the initial step in the
conversion of arachidonic acid to prostaglandins.
Their wide range of physiological activity has led to the synthesis of hundreds of prostaglandins and their analogs. Derivatives
of PGE2 are now used in the United States to induce labor. Other prostaglandins have been employed clinically to lower or
increase blood pressure, inhibit stomach secretions, relieve nasal congestion, relieve asthma, and prevent the formation of
blood clots, which are associated with heart attacks and strokes.
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To recognize the structures of common fatty acids and classify them as saturated, monounsaturated, or polyunsaturated.
Describe characteristics of fatty acid esters.
Fatty acids are carboxylic acids that are structural components of fats, oils, and all other categories of lipids, except steroids. More
than 70 have been identified in nature. They usually contain an even number of carbon atoms (typically 12–20), are generally
unbranched, and can be classified by the presence and number of carbon-to-carbon double bonds. Thus, Fatty acids may be
saturated, containing all carbon-carbon single bonds, or unsaturated, containing at least one or more carbon-carbon double
bonds. Saturated fatty acids are saturated with hydrogens; in other words, the number of hydrogen atoms attached to the carbon
skeleton is maximized. Stearic acid is an example of a saturated fatty acid (Figure 23.2.1).
When the hydrocarbon chain contains a double bond, there are less hydrogens attached to the carbon skeleton and the fatty acid is
said to be unsaturated. Oleic acid is an example of a monounsaturated fatty acid (Figure 23.2.1), because it contains one double
bond. A fatty acid with two or more double bonds is a polyunsaturated fat. The atoms or groups around the double bonds in
unsaturated fatty acids can be arranged in either the cis or trans isomeric form, compare cis vs. trans oleic acid in (Figure 23.2.1).
Naturally occurring fatty acids are generally in the cis configuration.
Figure 23.2.1: Saturated fatty acids have hydrocarbon chains connected by single bonds only. Unsaturated fatty acids have one or
more double bonds. Each double bond may be in a cis or trans configuration. In the cis configuration, both hydrogens are on the
same side of the hydrocarbon chain. In the trans configuration, the hydrogens are on opposite sides. A cis double bond causes a
kink in the chain.
Table 23.2.1lists some common fatty acids. Chemists use a shorthand notation for fatty acids rather than the common name
because they are all carboxylic acids with different numbers of carbons and degree of unsaturation (number of double bonds).
This notation gives the number of carbons followed by the number of double bonds present. For example: palmitic acid, a 16
carbon saturated fatty acid, would be represented by C16:0 and palmitoleic acid, a 16 carbon monounsaturated fatty acid, would be
C16:1.
Table 23.2.1 : Some Common Fatty Acids Found in Natural Fats
Number of Number of Double Condensed Shorthand
Name Melting Point (°C) Source
Carbons Bonds Structural Formula Notation
CH3(CH2)10COO
lauric acid 12 0 44 C12:0 palm kernel oil
H
CH3(CH2)12COO
myristic acid 14 0 58 C14:0 oil of nutmeg
H
CH3(CH2)14COO
palmitic acid 16 0 63 C16:0 palm oil
H
CH3(CH2)5CH=C
palmitoleic acid 16 1 0.5 C16:1 macadamia oil
H(CH2)7COOH
CH3(CH2)16COO
stearic acid 18 0 70 C18:0 cocoa butter
H
CH3(CH2)7CH=C
oleic acid 18 1 16 C18:1 olive oil
H(CH2)7COOH
CH3(CH2)3(CH2C
linoleic acid 18 2 H=CH)2(CH2)7C −5 C18:2 canola oil
OOH
CH3(CH2CH=CH
α -linolenic acid 18 3 −11 C18:3 flaxseed
)3(CH2)7COOH
CH3(CH2)4(CH2C
arachidonic acid 20 4 H=CH)4(CH2)2C −50 C20:4 liver
OOH
Two polyunsaturated fatty acids—linoleic and α -linolenic acids—are termed essential fatty acids because humans must obtain
them from their diets. Both substances are required for normal growth and development, but the human body does not synthesize
them. The body uses linoleic acid to synthesize many of the other unsaturated fatty acids, such as arachidonic acid, a precursor for
the synthesis of prostaglandins. In addition, the essential fatty acids are necessary for the efficient transport and metabolism of
cholesterol. The average daily diet should contain about 4–6 g of the essential fatty acids.
Waxes
Waxes are esters formed from long-chain fatty acids and long-chain alcohols. Most natural waxes are mixtures of such esters. Plant
waxes on the surfaces of leaves, stems, flowers, and fruits protect the plant from dehydration and invasion by harmful
microorganisms. Carnauba wax, used extensively in floor waxes, automobile waxes, and furniture polish, is largely myricyl
cerotate, obtained from the leaves of certain Brazilian palm trees. Animals also produce waxes that serve as protective coatings,
keeping the surfaces of feathers, skin, and hair pliable and water repellent. In fact, if the waxy coating on the feathers of a water
bird is dissolved as a result of the bird swimming in an oil slick, the feathers become wet and heavy, and the bird, unable to
maintain its buoyancy, drowns.
Triacylglycerols
Animal fats and vegetable oils are called triacylcylgerols (or triglycerides) because they are esters composed of three fatty acid
units joined to glycerol, a trihydroxy alcohol:
If all three OH groups on the glycerol molecule are esterified with the same fatty acid, the resulting ester is called a simple
triglyceride. Although simple triglycerides have been synthesized in the laboratory, they rarely occur in nature. Instead, a typical
triacylglycerols obtained from naturally occurring fats and oils contains two or three different fatty acid components and is thus
termed a mixed triglyceride.
Tristearin
a simple triglyceride
a mixed triglyceride
A triacylglycerol is called a fat if it is a solid at 25 °C; it is called an oil if it is a liquid at that temperature. These differences in
melting points reflect differences in the degree of unsaturation and number of carbon atoms in the constituent fatty acids.
Triglycerides obtained from animal sources are usually solids, while those of plant origin are generally oils. Therefore, we
commonly speak of animal fats and vegetable oils.
No single formula can be written to represent the naturally occurring fats and oils because they are highly complex mixtures of
triglycerides in which many different fatty acids are represented. Table 23.2.2 shows the fatty acid compositions of some common
fats and oils. The composition of any given fat or oil can vary depending on the plant or animal species it comes from as well as on
dietetic and climatic factors. To cite just one example, lard from corn-fed hogs is more highly saturated than lard from peanut-fed
hogs. Palmitic acid is the most abundant of the saturated fatty acids, while oleic acid is the most abundant unsaturated fatty acid.
Table 23.2.2 : Average Fatty Acid Composition of Some Common Fats and Oils (%)*
Myristic Palmitic Linolenic
Source Lauric (C12:0) Stearic (C18:0) Oleic (C18:1) Linoleic (C18:2)
(C14:0) (C16:0) (C18:3)
Fats
*Totals less than 100% indicate the presence of fatty acids with fewer than 12 carbon atoms or more than 18 carbon atoms.
†Coconut oil is highly saturated. It contains an unusually high percentage of the low-melting C8, C10, and C12 saturated fatty acids.
Myristic Palmitic Linolenic
Source Lauric (C12:0) Stearic (C18:0) Oleic (C18:1) Linoleic (C18:2)
(C14:0) (C16:0) (C18:3)
butter (cow) 3 11 27 12 29 2 1
tallow 3 24 19 43 3 1
lard 2 26 14 44 10
Oils
canola oil 4 2 62 22 10
coconut oil† 47 18 9 3 6 2
corn oil 11 2 28 58 1
olive oil 13 3 71 10 1
peanut oil 11 2 48 32
soybean oil 11 4 24 54 7
*Totals less than 100% indicate the presence of fatty acids with fewer than 12 carbon atoms or more than 18 carbon atoms.
†Coconut oil is highly saturated. It contains an unusually high percentage of the low-melting C8, C10, and C12 saturated fatty acids.
Terms such as saturated fat or unsaturated oil are often used to describe the fats or oils obtained from foods. Saturated fats contain
a high proportion of saturated fatty acids, while unsaturated oils contain a high proportion of unsaturated fatty acids. The high
consumption of saturated fats is a factor, along with the high consumption of cholesterol, in increased risks of heart disease.
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23.6: Steroids
To identify the functions of steroids produced in mammals.
All the lipids discussed so far are saponifiable, reacting with aqueous alkali to yield simpler components, such as glycerol, fatty
acids, amino alcohols, and sugars. Lipid samples extracted from cellular material, however, also contain a small but important
fraction that does not react with alkali. The most important nonsaponifiable lipids are the steroids. These compounds include the
bile salts, cholesterol and related compounds, and certain hormones (such as cortisone and the sex hormones).
Figure 23.6.1 Steroids. (a) The four-fused-ring steroid skeleton uses letter designations for each ring and the numbering of the
carbon atoms. (b) The cholesterol molecule follows this pattern.
Steroids occur in plants, animals, yeasts, and molds but not in bacteria. They may exist in free form or combined with fatty acids or
carbohydrates. All steroids have a characteristic structural component consisting of four fused rings. Chemists identify the rings by
capital letters and number the carbon atoms as shown in Figure 23.6.1a. Slight variations in this structure or in the atoms or groups
attached to it produce profound differences in biological activity.
Cholesterol
Cholesterol (Figure 23.6.1b) does not occur in plants, but it is the most abundant steroid in the human body (240 g is a typical
amount). Excess cholesterol is believed to be a primary factor in the development of atherosclerosis and heart disease, which are
major health problems in the United States today. About half of the body’s cholesterol is interspersed in the lipid bilayer of cell
membranes. Much of the rest is converted to cholic acid, which is used in the formation of bile salts. Cholesterol is also a precursor
in the synthesis of sex hormones, adrenal hormones, and vitamin D.
Excess cholesterol not metabolized by the body is released from the liver and transported by the blood to the gallbladder. Normally,
it stays in solution there until being secreted into the intestine (as a component of bile) to be eliminated. Sometimes, however,
cholesterol in the gallbladder precipitates in the form of gallstones (Figure 23.6.2). Indeed, the name cholesterol is derived from
the Greek chole, meaning “bile,” and stereos, meaning “solid.”
Figure 23.6.2 : Numerous small gallstones made up largely of cholesterol, all removed in one patient. Grid scale 1 mm
 To Your Health: Cholesterol and Heart Disease

Heart disease is the leading cause of death in the United States for both men and women. The Centers for Disease Control and
Prevention reported that heart disease claimed 631,636 lives in the United States (26% of all reported deaths) in 2006.
Scientists agree that elevated cholesterol levels in the blood, as well as high blood pressure, obesity, diabetes, and cigarette
smoking, are associated with an increased risk of heart disease. A long-term investigation by the National Institutes of Health
showed that among men ages 30 to 49, the incidence of heart disease was five times greater for those whose cholesterol levels
were above 260 mg/100 mL of serum than for those with cholesterol levels of 200 mg/100 mL or less. The cholesterol content
of blood varies considerably with age, diet, and sex. Young adults average about 170 mg of cholesterol per 100 mL of blood,
whereas males at age 55 may have cholesterol levels at 250 mg/100 mL or higher because the rate of cholesterol breakdown
decreases with age. Females tend to have lower blood cholesterol levels than males.
To understand the link between heart disease and cholesterol levels, it is important to understand how cholesterol and other
lipids are transported in the body. Lipids, such as cholesterol, are not soluble in water and therefore cannot be transported in the
blood (an aqueous medium) unless they are complexed with proteins that are soluble in water, forming assemblages called
lipoproteins. Lipoproteins are classified according to their density, which is dependent on the relative amounts of protein and
lipid they contain. Lipids are less dense than proteins, so lipoproteins containing a greater proportion of lipid are less dense
than those containing a greater proportion of protein.
Research on cholesterol and its role in heart disease has focused on serum levels of low-density lipoproteins (LDLs) and high-
density lipoproteins (HDLs). One of the most fascinating discoveries is that high levels of HDLs reduce a person’s risk of
developing heart disease, whereas high levels of LDLs increase that risk. Thus the serum LDL:HDL ratio is a better predictor of
heart disease risk than the overall level of serum cholesterol. Persons who, because of hereditary or dietary factors, have high
LDL:HDL ratios in their blood have a higher incidence of heart disease.
How do HDLs reduce the risk of developing heart disease? No one knows for sure, but one role of HDLs appears to be the
transport of excess cholesterol to the liver, where it can be metabolized. Therefore, HDLs aid in removing cholesterol from blood
and from the smooth muscle cells of the arterial wall.
Dietary modifications and increased physical activity can help lower total cholesterol and improve the LDL:HDL ratio. The
average American consumes about 600 mg of cholesterol from animal products each day and also synthesizes approximately 1 g of
cholesterol each day, mostly in the liver. The amount of cholesterol synthesized is controlled by the cholesterol level in the blood;
when the blood cholesterol level exceeds 150 mg/100 mL, the rate of cholesterol biosynthesis is halved. Hence, if cholesterol is
present in the diet, a feedback mechanism suppresses its synthesis in the liver. However, the ratio of suppression is not a 1:1 ratio;
the reduction in biosynthesis does not equal the amount of cholesterol ingested. Thus, dietary substitutions of unsaturated fat for
saturated fat, as well as a reduction in consumption of trans fatty acids, is recommended to help lower serum cholesterol and the
risk of heart disease.
Steroid Hormones
Hormones are chemical messengers that are released in one tissue and transported through the circulatory system to one or more
other tissues. One group of hormones is known as steroid hormones because these hormones are synthesized from cholesterol,
which is also a steroid. There are two main groups of steroid hormones: adrenocortical hormones and sex hormones.
The adrenocortical hormones, such as aldosterone and cortisol (Table 23.6.1), are produced by the adrenal gland, which is located
adjacent to each kidney. Aldosterone acts on most cells in the body, but it is particularly effective at enhancing the rate of
reabsorption of sodium ions in the kidney tubules and increasing the secretion of potassium ions and/or hydrogen ions by the
tubules. Because the concentration of sodium ions is the major factor influencing water retention in tissues, aldosterone promotes
water retention and reduces urine output. Cortisol regulates several key metabolic reactions (for example, increasing glucose
production and mobilizing fatty acids and amino acids). It also inhibits the inflammatory response of tissue to injury or stress.
Cortisol and its analogs are therefore used pharmacologically as immunosuppressants after transplant operations and in the
treatment of severe skin allergies and autoimmune diseases, such as rheumatoid arthritis.
Table 23.6.1 : Representative Steroid Hormones and Their Physiological Effects
Hormone Effect
regulates salt metabolism; stimulates kidneys to retain sodium and

excrete potassium
stimulates the conversion of proteins to carbohydrates
regulates the menstrual cycle; maintains pregnancy
stimulates female sex characteristics; regulates changes during the

menstrual cycle
stimulates and maintains male sex characteristics
The sex hormones are a class of steroid hormones secreted by the gonads (ovaries or testes), the placenta, and the adrenal glands.
Testosterone and androstenedione are the primary male sex hormones, or androgens, controlling the primary sexual characteristics
of males, or the development of the male genital organs and the continuous production of sperm. Androgens are also responsible
for the development of secondary male characteristics, such as facial hair, deep voice, and muscle strength. Two kinds of sex
hormones are of particular importance in females: progesterone, which prepares the uterus for pregnancy and prevents the further
release of eggs from the ovaries during pregnancy, and the estrogens, which are mainly responsible for the development of female
secondary sexual characteristics, such as breast development and increased deposition of fat tissue in the breasts, the buttocks, and
the thighs. Both males and females produce androgens and estrogens, differing in the amounts of secreted hormones rather than in
the presence or absence of one or the other.
Sex hormones, both natural and synthetic, are sometimes used therapeutically. For example, a woman who has had her ovaries
removed may be given female hormones to compensate. Some of the earliest chemical compounds employed in cancer
chemotherapy were sex hormones. For example, estrogens are one treatment option for prostate cancer because they block the
release and activity of testosterone. Testosterone enhances prostate cancer growth. Sex hormones are also administered in
preparation for sex-change operations, to promote the development of the proper secondary sexual characteristics. Oral
contraceptives are synthetic derivatives of the female sex hormones; they work by preventing ovulation.
Bile Salts
Bile is a yellowish green liquid (pH 7.8–8.6) produced in the liver. The most important constituents of bile are bile salts, which are
sodium salts of amidelike combinations of bile acids, such as cholic acid (part (a) of Figure 23.6.3) and an amine such as the amino
acid glycine (part (b) of Figure 23.6.3). They are synthesized from cholesterol in the liver, stored in the gallbladder, and then
secreted in bile into the small intestine. In the gallbladder, the composition of bile gradually changes as water is absorbed and the
other components become more concentrated.
Figure 23.6.3 Bile Acids. (a) Cholic acid is an example of a bile acid. (b) Sodium glycocholate is a bile salt synthesized from
cholic acid and glycine.
Because they contain both hydrophobic and hydrophilic groups, bile salts are highly effective detergents and emulsifying agents;
they break down large fat globules into smaller ones and keep those smaller globules suspended in the aqueous digestive
environment. Enzymes can then hydrolyze fat molecules more efficiently. Thus, the major function of bile salts is to aid in the
digestion of dietary lipids.
Surgical removal is often advised for a gallbladder that becomes infected, inflamed, or perforated. This surgery does not
seriously affect digestion because bile is still produced by the liver, but the liver’s bile is more dilute and its secretion into the
small intestine is not as closely tied to the arrival of food.
Summary
Steroids have a four-fused-ring structure and have a variety of functions. Cholesterol is a steroid found in mammals that is needed
for the formation of cell membranes, bile acids, and several hormones. Bile salts are secreted into the small intestine to aid in the
digestion of fats.
23.6: Steroids is shared under a CC BY-NC-SA 3.0 license and was authored, remixed, and/or curated by LibreTexts.
17.4: Steroids by Anonymous is licensed CC BY-NC-SA 4.0. Original source: https://2012books.lardbucket.org/books/introduction-to-
Identify the distinguishing characteristics of membrane lipids.
Describe membrane components and how they are arranged.
All living cells are surrounded by a cell membrane. Plant cells (Figure 23.7.1A) and animal cells (Figure 23.7.1B) contain a cell
nucleus that is also surrounded by a membrane and holds the genetic information for the cell. Everything between the cell
membrane and the nuclear membrane—including intracellular fluids and various subcellular components such as the mitochondria
and ribosomes—is called the cytoplasm. The membranes of all cells have a fundamentally similar structure, but membrane function
varies tremendously from one organism to another and even from one cell to another within a single organism. This diversity arises
mainly from the presence of different proteins and lipids in the membrane.
Figure 23.7.1 : (A) An Idealized Plant Cell. Not all the structures shown here occur in every type of plant cell. (B) An Idealized
Animal Cell. The structures shown here will seldom all be found in a single animal cell.
The lipids in cell membranes are highly polar but have dual characteristics: part of the lipid is ionic and therefore dissolves in
water, whereas the rest has a hydrocarbon structure and therefore dissolves in nonpolar substances. Often, the ionic part is referred
to as hydrophilic, meaning “water loving,” and the nonpolar part as hydrophobic, meaning “water fearing” (repelled by water).
Molecules that have both polar and nonpolar parts are called amphipathic. When allowed to float freely in water, lipids
spontaneously cluster together in different arrangements: micelles, liposomes, monolayers, or bilayers (Figure 23.7.2).
Figure 23.7.2 : Aggregation of Membrane Lipids. In polar solvents like water, amphipathic lipids will aggregate the polar heads and
nonpolar tails forming monolayers, bilayers, micelles, and liposomes.
Micelles are aggregations in which the lipids’ hydrocarbon tails—being hydrophobic—are directed toward the center of the
assemblage and away from the surrounding water while the hydrophilic heads are directed outward, in contact with the water. Each
micelle may contain thousands of lipid molecules. Polar lipids may also form a monolayer, a layer one molecule thick on the
surface of the water. The polar heads face into water, and the nonpolar tails stick up into the air. Bilayers are double layers of lipids
arranged so that the hydrophobic tails are sandwiched between an inner surface and an outer surface consisting of hydrophilic
heads. The hydrophilic heads are in contact with water on either side of the bilayer, whereas the tails, sequestered inside the bilayer,
are prevented from having contact with the water. Bilayers like this make up every cell membrane (Figure 23.7.3).
Figure 23.7.3 : Schematic Diagram of a Cell Membrane. The membrane enclosing a typical animal cell is a phospholipid bilayer
with embedded cholesterol and protein molecules. Short oligosaccharide chains are attached to the outer surface.
In the bilayer interior, the hydrophobic tails (that is, the fatty acid portions of lipid molecules) interact by means of dispersion
forces. The interactions are weakened by the presence of unsaturated fatty acids. As a result, the membrane components are free to
mill about to some extent, and the membrane is described as fluid.
Membrane Proteins
If membranes were composed only of lipids, very few ions or polar molecules could pass through their hydrophobic “sandwich
filling” to enter or leave any cell. However, certain charged and polar species do cross the membrane, aided by proteins that move
about in the lipid bilayer. The two major classes of proteins in the cell membrane are integral proteins, which span the hydrophobic
interior of the bilayer, and peripheral proteins, which are more loosely associated with the surface of the lipid bilayer (Figure
23.7.3). Peripheral proteins may be attached to integral proteins, to the polar head groups of phospholipids, or to both by hydrogen
bonding and electrostatic forces.
Transport Across Cell Membranes

Plasma membranes must allow certain substances to enter and leave a cell, and prevent some harmful materials from entering and
some essential materials from leaving. In other words, plasma membranes are selectively permeable—they allow some substances
to pass through, but not others. If they were to lose this selectivity, the cell would no longer be able to sustain itself, and it would be
destroyed. Some cells require larger amounts of specific substances than do other cells; they must have a way of obtaining these
materials from extracellular fluids. This may happen passively, as certain materials move back and forth, or the cell may have
special mechanisms that facilitate transport. Some materials are so important to a cell that it spends some of its energy, hydrolyzing
adenosine triphosphate (ATP), to obtain these materials. Red blood cells use some of their energy doing just that. All cells spend
the majority of their energy to maintain an imbalance of sodium and potassium ions between the interior and exterior of the cell.
There are two primary modes of transport across membranes. Passive transport is a naturally occurring phenomenon and does not
require the cell to exert any of its energy to accomplish the movement. In passive transport, substances move from an area of higher
concentration to an area of lower concentration. Active transport mechanisms require the use of the cell’s energy, usually in the
form of adenosine triphosphate (ATP). If a substance must move into the cell against its concentration gradient—that is, if the
concentration of the substance inside the cell is greater than its concentration in the extracellular fluid (and vice versa)—the cell
must use energy to move the substance.
File:Passive vs Active Membrane Transport.svg
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CHAPTER OVERVIEW
24: Lipid Metabolism

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1
Describe the process of digestion of lipids and their transport into the bloodstream.
Lipid digestion begins in the upper portion of the small intestine. A hormone secreted in this region stimulates the gallbladder to
discharge bile into the duodenum. The principal constituents of bile are the bile salts, which emulsify large, water-insoluble lipid
droplets, disrupting some of the hydrophobic interactions holding the lipid molecules together and suspending the resulting smaller
globules (micelles) in the aqueous digestive medium. These changes greatly increase the surface area of the lipid particles, allowing
for more intimate contact with the lipases and thus rapid digestion of the fats. Another hormone promotes the secretion of
pancreatic juice, which contains these enzymes.
Figure 24.1.1 : The Principal Events and Sites of Lipid (Primarily Triglyceride) Digestion
The lipases in pancreatic juice catalyze the digestion of triglycerides first to diglycerides and then to 2‑monoglycerides and fatty
acids:
Figure 24.1.2 : Digestion of triglycerides.

The large and hydrophobic long-chain fatty acids and monoacylglycerides are not so easily suspended in the watery intestinal
chyme. However, bile salts and lecithin resolve this issue by enclosing them in a micelle, which is a tiny sphere with polar
(hydrophilic) ends facing the watery environment and hydrophobic tails turned to the interior, creating a receptive environment for
the long-chain fatty acids. The core also includes cholesterol and fat-soluble vitamins. Without micelles, lipids would sit on the
surface of chyme and never come in contact with the absorptive surfaces of the epithelial cells. Micelles can easily squeeze
between microvilli and get very near the luminal cell surface. At this point, lipid substances exit the micelle and are absorbed via
simple diffusion.
The free fatty acids and monoacylglycerides that enter the epithelial cells are reincorporated into triglycerides. The triglycerides are
mixed with phospholipids and cholesterol, and surrounded with a protein coat. This new complex, called a chylomicron, (see
Figure 24.1.3), is a water-soluble lipoprotein.
File:2512 Chylomicrons Contain Triglycerides Cholesterol Molecules and Other Lipids.jpg
Figure 24.1.3 : Lipoproteins (chylomicrons) package triacylglycrols and cholesterol for transport to cells.
After being processed by the Golgi apparatus, chylomicrons are released from the cell. Too big to pass through the basement
membranes of blood capillaries, chylomicrons instead enter the large pores of lacteals. The lacteals come together to form the
lymphatic vessels. The chylomicrons are transported in the lymphatic vessels and empty through the thoracic duct into the
circulatory system (Figure 24.1.4).
Figure 24.1.4 : Pathways of Lipids
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Describe the difference in composition and function between the five classes of lipoproteins.
During times of feasting, lipids enter the body's metabolic pathways through the process of digestion. Any excess energy will be
stored in adipose tissues. If food has not been eaten for a while, fasting, lipids mobilized from stored adipose tissue and synthesized
in the liver can be used for energy. Transportation of nonpolar lipids through the bloodstream requires binding to water-soluble
proteins like serum albumin or packaging in lipoproteins. There are five categories of lipoprotein defined by their composition and
density, or the ratio of lipid to protein. Chylomicrons, which have the highest lipid to protein ratio, have the lowest-density, are
responsible for transporting lipids from digestion into the blood and eventually to the liver. Following is a list of the remaining four
lipoproteins and their functions:
Very low-density lipoproteins (VLDLs) (0.96-1.006 g/cm3) are made in the liver from remnants of chylomicrons and transport
triglycerides from the liver to various tissues in the body for energy or storage. As the VLDLs travel through the circulatory
system, the lipoprotein lipase strips the VLDL of triglycerides. As triglyceride removal persists, the VLDLs become
intermediate-density lipoproteins.
Intermediate-density lipoproteins (IDLs) (1.007-1.019 g/cm3) transport a variety of fats and cholesterol left from VLDLs from
the tissues to the liver where they are transformed into low-density lipoprotein.
Low-density lipoproteins (LDLs) (1.020-1.062 g/cm3) carry cholesterol and other lipids from the liver to tissue throughout the
body. LDLs are comprised of very small amounts of triglycerides, and house over 50 percent cholesterol and cholesterol esters.
Once inside the cell, the LDL is taken apart and its cholesterol is released and used for membrane formation, steroid synthesis,
or if in excess forming arterial plaques.
High-density lipoproteins (HDLs) (1.063-1.210 g/cm3) are responsible for carrying cholesterol out of the bloodstream and into
the liver, where it is either reused or removed from the body with bile.
Figure 24.2.1 : Lipoprotein Classes The classification of the major types of lipoproteins are based on their densities. Density range
is shown as well as lipid (red) and protein (blue) content. (Diagram not to scale) / CC BY 3.0
 Note To Your Health: Good vs. Bad Cholesterol
You are probably familiar with HDL and LDL being referred to as "good cholesterol" and "bad cholesterol," respectively. This
is an oversimplification to help the public interpret their blood lipid values, because cholesterol is cholesterol; it's not good or
bad. LDL and HDL are lipoproteins, and as a result you can't consume good or bad cholesterol, you consume cholesterol. A
more appropriate descriptor for these lipoproteins would be HDL "good cholesterol transporter" and LDL "bad cholesterol
transporter."
For healthy total blood cholesterol, the desired range you would want to maintain is under 200 mg/dL. More specifically, when
looking at individual lipid profiles, a low amount of LDL and a high amount of HDL prevents excess buildup of cholesterol in
the arteries and wards off potential health hazards. An LDL level of less than 100 milligrams per deciliter is ideal while an
LDL level above 160 mg/dL would be considered high. In contrast, a low value of HDL is a telltale sign that a person is living
with major risks for disease. Values of less than 40 mg/dL for men and 50 mg/dL for women mark a risk factor for developing
heart disease. In short, elevated LDL blood lipid profiles indicate an increased risk of heart attack, while elevated HDL blood
lipid profiles indicate a reduced risk.The University of Maryland Medical Center reports that omega-3 fatty acids promote
lower total cholesterol and lower triglycerides in people with high cholesterol.[1]
It is suggested that people consume omega-3 fatty acids such as alpha-linolenic acid in their diets regularly. Polyunsaturated
fatty acids are especially beneficial to consume because they both lower LDL and elevate HDL, thus contributing to healthy
blood cholesterol levels. The study also reveals that saturated and trans fatty acids serve as catalysts for the increase of LDL
cholesterol. Additionally, trans fatty acids decrease HDL levels, which can impact negatively on total blood cholesterol.
1. Omega-3 fatty acids. University of Maryland Medical Center. http://www.umm.edu/altmed/articles/omega-3-000316.htm.

Updated August 5, 2015. Accessed September 28, 2017. ↵
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Identify the main metabolic pathways of triacylglycerols.
In the body, triacylglycerols are essential for long-term energy storage as well as for insulation and protection. Triacylglycerols can
be ingested directly or synthesized from extra dietary protein or carbohydrates. Figure 24.3.1 is a summary of the metabolic
pathways of triacylglycerols that will be discussed in more detail in the following sections.
Dietary Triacylglycerols
Dietary triacylglycerols are transported through the bloodstream in chylomicrons. When a chylomicron encounters the enzyme
lipoprotein lipase, triacylglycerols are broken down by hydrolysis into fatty acids and glycerol. These breakdown products then
pass through capillary walls to be used for energy by cells or stored in adipose tissue as fat. Liver cells combine the remaining
chylomicron remnants with proteins, forming lipoproteins that transport cholesterol in the blood.
Stored Triacylglycerols
When energy is needed, lipases in adipose tissue (fat cells) are activated to hydrolyze stored triacylglycerols into fatty acids and
glycerol and release them into the bloodstream. Once the fatty acids reach their destination (muscle or liver cells) they are used to
generate acetyl-CoA and eventually ATP.
Figure 24.3.1 : Overview of Triacylglycerol Metabolism
Glycerol from Triacylglycerols

The hydrolysis of triacylglycerols produce fatty acids, that are used for energy, and glycerol. The glycerol can be used to regenerate
triacylglycerol or it can enter glycolysis or gluconeogenesis in the form dihydroxyacetone phosphate (DHAP).
Figure 24.3.2 : Conversion of Glycerol to DHAP: Lipid metabolism and carbohydrate metabolism are linked through glycerol and
DHAP.
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Describe the steps of fatty acid oxidation.
Calculate the yield of ATP from fatty acid oxidation.
Fatty acids released in the digestion of triglycerides and other lipids are broken down in a series of sequential reactions
accompanied by the gradual release of usable energy.
Activation of Fatty Acids

Fatty acid oxidation is initiated in the cytosol. There the fatty acids, which like carbohydrates are relatively inert, must first be
activated by conversion to an energy-rich fatty acid derivative of coenzyme A called fatty acyl-coenzyme A (CoA). The activation
is catalyzed by acyl-CoA synthetase. For each molecule of fatty acid activated, one molecule of coenzyme A and one molecule of
adenosine triphosphate (ATP) are used, equaling a net utilization of the two high-energy bonds in one ATP molecule (which is
therefore converted to adenosine monophosphate [AMP] rather than adenosine diphosphate [ADP]):
Transport into the Mitochondrial Matrix

The fatty acyl-CoA cannot cross the membrane by diffusion and therefore must be transported into the mitochondrial matrix using
a carrier molecule known as carnitine. At the outer mitochondrial membrane, fatty acyl-CoA is attached to the hydroxyl group of
carnitine in a transesterification reaction catalyzed by carnitine acyltransferase I (also called carnitine palmitoyl transferase I,
CPTI). The acyl-carnitine derivative is transported into the mitochondrial matrix by facilitated diffusion through a translocase
protein (carnitine-acylcarnitine translocase). Once in the matrix, the acyl-carnitine is converted back to the fatty acyl-CoA and
carnitine in a reaction catalyzed by carnitine acyltransferase II (also called carnitine palmitoyl transferase II, CPTI).
Figure 24.5.1 : Movement of Acyl-CoAs into the Mitochondrial Matrix
Oxidation of Fatty Acyl-CoA

Once inside the mitochondria the fatty acyl-CoA can enter into beta-oxidation, which is a four-step cycle that removes carbons
from the fatty acid two at a time to form acetyl-CoA (which eventually yields energy in the form of ATP).
STEP 1: First β-oxidation (dehydrogenation of an alkane)
A fatty acyl-CoA is oxidized by the enzyme, Acyl-CoA dehydrogenase, to yield a trans double bond between the α - and β- carbons
(the first and second carbons attached to the carbonyl group). The coenzyme FAD is reduced by accepting two hydrogen atoms and
their electrons forming FADH2, which moves into the electron transport chain.
STEP 2: Hydration (addition of water across the double bond)

The trans alkene is then hydrated with the help of Enoyl-CoA hydratase. The hydroxyl group is placed on the β-carbon.
STEP 3: Second β -oxidation (oxidation of an alcohol)

The alcohol of the hydroxyacly-CoA is then oxidized to a carbonyl with the help of β-hydroxyacyl-CoA dehydrogenase and the
coenzyme by NAD+.
STEP 4: Thiolytic Cleavage

The enzyme thiolase (acyl-CoA acetyltransferase) cleaves off the acetyl-CoA and attaches a new coenzyme A to the chain to yield
an acyl-CoA that is two carbons shorter than before. The acyl-CoA will continue through the cycle and start back at step 1. The
cleaved acetyl-CoA can then enter into the the citric acid cycle and electron transport chain because it is already within the
mitochondria.
Additional steps are required for unsaturated fatty acids and those with an even number of carbons. The amount of energy released
by a fatty acid is determined by the amount of ATP produced from the acetyl-CoA entering the citric acid cycle and from the
reduced coenzymes NADH and FADH2 entering the electron transport chain.
ATP Yield from Fatty Acid Oxidation

The amount of ATP obtained from fatty acid oxidation depends on the size of the fatty acid being oxidized. For our purposes here.
we’ll study palmitic acid, a saturated fatty acid with 16 carbon atoms, as a typical fatty acid in the human diet. Calculating its
energy yield provides a model for determining the ATP yield of all other fatty acids.
The breakdown of 1 mol of palmitic acid requires 1 mol of ATP (for activation) and forms 8 mol of acetyl-CoA. Recall from that
each mole of acetyl-CoA metabolized by the citric acid cycle yields 10 mol of ATP. The complete degradation of 1 mol of palmitic
acid requires the β-oxidation reactions to be repeated seven times. Thus, 7 mol of NADH and 7 mol of FADH2 are produced.
Reoxidation of these coenzymes through respiration yields 2.5–3 and 1.5–2 mol of ATP, respectively. The energy calculations can
be summarized as follows:
1 mol of ATP is split to AMP and 2Pi −2 ATP
8 mol of acetyl-CoA formed (8 × 12) 96 ATP
7 mol of FADH2 formed (7 × 2) 14 ATP
7 mol of NADH formed (7 × 3) 21 ATP
Total 129 ATP
The number of times β-oxidation is repeated for a fatty acid containing n carbon atoms is
n/2 – 1 because the final turn yields two acetyl-CoA molecules.
The combustion of 1 mol of palmitic acid releases a considerable amount of energy:
C16 H32 O2 + 23 O2 → 16C O2 + 16 H2 O + 2, 340 kcal
The percentage of this energy that is conserved by the cell in the form of ATP is as follows:
energy conserved (129 ATP)(7.4 kcal/ATP)
× 100 = × 100 = 41%
total energy available 2, 340 kcal
The efficiency of fatty acid metabolism is comparable to that of carbohydrate metabolism, which we calculated to be 42%.
The oxidation of fatty acids produces large quantities of water. This water, which sustains
migratory birds and animals (such as the camel) for long periods of time.
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Describe the structure and function of ketone bodies.
In the liver, most of the acetyl-CoA obtained from fatty acid oxidation is oxidized by the citric acid cycle. However, some of the
acetyl-CoA is used to synthesize a group of compounds known as ketone bodies: acetoacetate, β-hydroxybutyrate, and acetone.
Two acetyl-CoA molecules combine, in a reversal of the final step of β-oxidation, to produce acetoacetyl-CoA. The acetoacetyl-
CoA reacts with another molecule of acetyl-CoA and water to form β-hydroxy-β-methylglutaryl-CoA, which is then cleaved to
acetoacetate and acetyl-CoA. Most of the acetoacetate is reduced to β-hydroxybutyrate, while a small amount is decarboxylated to
carbon dioxide and acetone.
The acetoacetate and β-hydroxybutyrate synthesized by the liver are released into the blood for use as a metabolic fuel (to be
converted back to acetyl-CoA) by other tissues, particularly the kidney and the heart. Thus, during prolonged starvation, ketone
bodies provide about 70% of the energy requirements of the brain. Under normal conditions, the kidneys excrete about 20 mg of
ketone bodies each day, and the blood levels are maintained at about 1 mg of ketone bodies per 100 mL of blood.
In starvation, diabetes mellitus, and certain other physiological conditions in which cells do not receive sufficient amounts of
carbohydrate, the rate of fatty acid oxidation increases to provide energy. This leads to an increase in the concentration of acetyl-
CoA. The increased acetyl-CoA cannot be oxidized by the citric acid cycle because of a decrease in the concentration of
oxaloacetate, which is diverted to glucose synthesis. In response, the rate of ketone body formation in the liver increases further, to
a level much higher than can be used by other tissues. The excess ketone bodies accumulate in the blood and the urine, a condition
referred to as ketosis. When the acetone in the blood reaches the lungs, its volatility causes it to be expelled in the breath. The sweet
smell of acetone, a characteristic of ketosis, is frequently noticed on the breath of severely diabetic patients.
Because two of the three kinds of ketone bodies are weak acids, their presence in the blood in excessive amounts overwhelms the
blood buffers and causes a marked decrease in blood pH (to 6.9 from a normal value of 7.4). This decrease in pH leads to a serious
condition known as acidosis. One of the effects of acidosis is a decrease in the ability of hemoglobin to transport oxygen in the
blood. In moderate to severe acidosis, breathing becomes labored and very painful. The body also loses fluids and becomes
dehydrated as the kidneys attempt to get rid of the acids by eliminating large quantities of water. The lowered oxygen supply and
dehydration lead to depression; even mild acidosis leads to lethargy, loss of appetite, and a generally run-down feeling. Untreated
patients may go into a coma. At that point, prompt treatment is necessary if the person’s life is to be saved.
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Describe how fatty acids are synthesized and compare to fatty acid break-down.
Lipogenesis or the synthesis of fatty acids occurs in the cytoplasm and endoplasmic reticulum of the cell and is chemically similar
to the beta-oxidation process, but with a couple of key differences. The first of these occur in preparing substrates for the reactions
that grow the fatty acid. Transport of acetyl-CoA from the mitochondria occurs when it begins to build up. Two molecules can play
roles in moving it to the cytoplasm – citrate and acetylcarnitine. Joining of oxaloacetate with acetyl-CoA in the mitochondrion
creates citrate which moves across the membrane, followed by action of citrate lyase in the cytoplasm of the cell to release acetyl-
CoA and oxaloacetate. Additionally, when free acetyl-CoA accumulates in the mitochondrion, it may combine with carnitine and
be transported out to the cytoplasm.
The fatty acid chain is built two carbons at a time (opposite of beta-oxidation), beginning with two acetyl-CoA molecules. One is
converted to malonyl-CoA by carboxylation, catalyzed by the enzyme acetyl-CoA carboxylase (ACC), the only regulatory enzyme
of fatty acid synthesis (Figure 24.7.1). Next, both acetyl-CoA molecules have their CoA portions replaced by a carrier protein
known as ACP (acyl-carrier protein) to form acetyl-ACP and malonyl-ACP. Joining of a fatty acyl-ACP (in this case, acetyl-ACP)
with malonyl-ACP splits out the carboxyl that was added and creates the intermediate at the upper right in the figure at left.
F
igure 24.7.1 : Fatty Acid Synthesis
From this point forward, the chemical reactions resemble those of beta oxidation reversed. First, the ketone is reduced to a
hydroxyl using NADPH. In contrast to the hydroxylated intermediate of beta oxidation, the beta intermediate here is in the D-
configuration. Next, water is removed from carbons 2 and 3 of the hydroxyl intermediate to produce a trans doubled bonded
molecule. Last, the double bond is hydrogenated to yield a saturated intermediate. The process cycles with the addition of another
malonyl-ACP to the growing chain until ultimately an intermediate with 16 carbons is produced (palmitoyl-CoA). At this point, the
cytoplasmic synthesis ceases.
Enzymes of Fatty Acid Synthesis
Acetyl-CoA carboxylase, which catalyzes synthesis of malonyl-CoA, is the only regulated enzyme in fatty acid synthesis. Its
regulation involves both allosteric control and covalent modification. The enzyme is known to be phosphorylated by both AMP
Kinase and Protein Kinase A. Dephosphorylation is stimulated by phosphatases activated by insulin binding. Dephosphorylation
activates the enzyme and favors its assembly into a long polymer, while phosphorylation reverses the process.Citrate acts as an
allosteric activator and may also favor polymerization. Palmitoyl-CoA allosterically inactivates it.
Figure 24.7.2 : Fatty Acid Synthase (FAS) revised model with positions of polypeptides, three catalytic domains and their
corresponding reactions, visualization by Kosi Gramatikoff. Note that FAS is only active as a homodimer rather than the monomer
pictured. (Public Domain; Kosigrim)
In animals, six different catalytic activities necessary for the remaining catalytic actions to fully make palmitoyl-CoA are contained
in a single complex called Fatty Acid Synthase (Figure 24.7.2). These include transacylases for swapping CoA with ACP on
acetyl-CoA and malonyl-CoA; a synthase to catalyze addition of the two carbon unit from the three carbon malonyl-ACP in the
first step of the elongation process; a reductase to reduce the ketone; a dehydrase to catalyze removal of water, and a reductase to
reduce the trans double bond. In bacteria, these activities are found on separate enzymes and are not part of a complex.
Elongation of Fatty Acids

Elongation to make fatty acids longer than 16 carbons occurs in the endoplasmic reticulum and is catalyzed by enzymes described
as elongases. Mitochondria also can elongate fatty acids, but their starting materials are generally shorter than 16 carbons long. The
mechanisms in both environments are similar to those in the cytoplasm (a malonyl group is used to add two carbons, for example),
but CoA is attached to the intermediates, not ACP. Further, whereas cytoplasmic synthesis employs the fatty acid synthase complex
(Figure 24.7.2), the enzymes in these organelles are separable and not part of a complex.
Desaturation of Fatty Acids

Fatty acids are synthesized in the saturated form and desaturation occurs later. Enzymes called desaturases catalyze the formation
of cis double bonds in mature fatty acids. These enzymes are found in the endoplasmic reticulum. Animals are limited in the
desaturated fatty acids they can make, due to an inability to catalyze reactions beyond carbons 9 and 10. Thus, humans can make
oleic acid, but cannot synthesis linoleic acid or linolenic acid. Consequently, these two must be provided in the diet and are referred
to as essential fatty acids.
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CHAPTER OVERVIEW
25: Protein and Amino Acid Metabolism

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List the steps of protein digestion.
Protein digestion begins in the stomach (Figure 25.1.1), where the action of gastric juice hydrolyzes about 10% of the peptide
bonds. Gastric juice is a mixture of water (more than 99%), inorganic ions, hydrochloric acid, and various enzymes and other
proteins.
Figure 25.1.1 : The Principal Events and Sites of Protein Digestion

The hydrochloric acid (HCl) in gastric juice is secreted by glands in the stomach lining. The pH of freshly secreted gastric juice is
about 1.0, but the contents of the stomach may raise the pH to between 1.5 and 2.5. HCl helps to denature food proteins; that is, it
unfolds the protein molecules to expose their chains to more efficient enzyme action. The principal digestive component of gastric
juice is pepsinogen, an inactive enzyme produced in cells located in the stomach wall. When food enters the stomach after a period
of fasting, pepsinogen is converted to its active form—pepsin—in a series of steps initiated by the drop in pH. Pepsin catalyzes the
hydrolysis of peptide linkages within protein molecules. It has a fairly broad specificity but acts preferentially on linkages
involving the aromatic amino acids tryptophan, tyrosine, and phenylalanine, as well as methionine and leucine.
Protein digestion is completed in the small intestine. Pancreatic juice, carried from the pancreas via the pancreatic duct, contains
inactive enzymes such as trypsinogen and chymotrypsinogen. They are activated in the small intestine as follows (Figure 25.1.2):
The intestinal mucosal cells secrete the proteolytic enzyme enteropeptidase, which converts trypsinogen to trypsin; trypsin then
activates chymotrypsinogen to chymotrypsin (and also completes the activation of trypsinogen). Both of these active enzymes
catalyze the hydrolysis of peptide bonds in protein chains. Chymotrypsin preferentially attacks peptide bonds involving the
carboxyl groups of the aromatic amino acids (phenylalanine, tryptophan, and tyrosine). Trypsin attacks peptide bonds involving the
carboxyl groups of the basic amino acids (lysine and arginine). Pancreatic juice also contains procarboxypeptidase, which is
cleaved by trypsin to carboxypeptidase. The latter is an enzyme that catalyzes the hydrolysis of peptide linkages at the free
carboxyl end of the peptide chain, resulting in the stepwise liberation of free amino acids from the carboxyl end of the polypeptide.
Figure 25.1.2 : Activation of Some Pancreatic Enzymes in the Small Intestine
Aminopeptidases in the intestinal juice remove amino acids from the N-terminal end of peptides and proteins possessing a free
amino group. Figure 25.1.3 illustrates the specificity of these protein-digesting enzymes. The amino acids that are released by
protein digestion are absorbed across the intestinal wall into the circulatory system, where they can be used for protein synthesis.
Figure 25.1.3 : Hydrolysis of a Peptide by Several Peptidases

This diagram illustrates where in a peptide the different peptidases we have discussed would catalyze hydrolysis the peptide bonds.
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Objective 1
Objective 2
Once the proteins in the diet have been hydrolyzed, the free amino acids join the non-essential amino acid synthesized in the liver
and the amino acids recycled from the body's own proteins, constituting the amino acid pool now available for metabolic
processes. Most of the amino acid pool is used for the synthesis of protein and other nitrogen-containing compounds such as DNA
bases, neurotransmitters, hormones, etc. Under certain metabolic situations, amino acids can also be used as a source of energy by
the body. It is worth mentioning that the human body cannot store amino acids. If the amino acids in the amino acid pool are not
used for biological processes, they are degraded and the nitrogen excreted in the urine as urea.
Protein turnover
A balance between protein synthesis and protein degradation is required for good health and normal protein metabolism. Not all the
amino acids needed for the biological function of the body need to be incorporated through the diet. When the proteins already
present in the metabolism have complete their lifespan, they are also recycled. Protein turnover refers to the replacement of older
proteins as they are broken down within the cell. Different types of proteins have very different turnover rates, depending on their
particular function. Structural proteins such as college tend to have long half-life periods (in the range of years), while enzymatic
protein have a shorter life span to adapt to the metabolic requirements of the body.
Example protein half-lives
Name Half-Life
Collagen 117 years
Eye lens crystallin >70 years
Replication factor C subunit 1 9 hours
40S ribosomal protein S8 3 hours
Ornithine decarboxylase 11 minutes
Once the protein have been hydrolyzed and amino acids recycled, these amino acids are added to the amino acid pool for further
utilization.
 Note To Your Health: Complete and Incomplete Proteins

Amino acids are classified into three groups namely: essential amino acids and nonessential amino acids
ESSENTIAL AMINO ACIDS
Essential amino acids cannot be made by the body. As a result, they must come from food.
The 9 essential amino acids are: histidine, isoleucine, leucine, lysine, methionine, phenylalanine, threonine, tryptophan, and
valine.
NONESSENTIAL AMINO ACIDS
Nonessential means that our bodies produce an amino acid, even if we do not get it from the food we eat. Nonessential amino
acids include: alanine, arginine, asparagine, aspartic acid, cysteine, glutamic acid, glutamine, glycine, proline, serine, and
tyrosine.
Based on this classification of amino acids, proteins can also be classified as either complete or incomplete. Complete
proteins provide adequate amounts of all nine essential amino acids. Animal proteins such as meat, fish, milk, and eggs are
good examples of complete proteins. Incomplete proteins do not contain adequate amounts of one or more of the essential
amino acids. For example, if a protein doesn't provide enough of the essential amino acid leucine it would be considered
incomplete. Leucine would be referred to as the limiting amino acid, because there is not enough of it for the protein to be
complete. Most plant foods are incomplete proteins, with a few exceptions such as soy. Table 25.2.1 shows the limiting amino
acids in some plant foods.
Table 25.2.1 Limiting Amino Acids in Some Common Plant Foods.
Even though most plant foods do not contain complete proteins, it does
not mean that they should be sworn off as protein sources. It is possible
to pair foods containing incomplete proteins with different limiting
amino acids to provide adequate amounts of the essential amino acids.
These two proteins are called complementary proteins, because they
supply the amino acid(s) missing in the other protein. A simple analogy
would be that of a 4 piece puzzle. If one person has 2 pieces of a puzzle,
and another person has 2 remaining pieces, neither of them have a
complete puzzle. But when they are combined, the two individuals
create a complete puzzle.
Two examples of complementary proteins are shown below.
Figure 25.2.1 .Two complementary protein examples
It should be noted that complementary proteins do not need
to be consumed at the same time or meal. It is currently
recommended that essential amino acids be met on a daily
basis, meaning that if a grain is consumed at one meal, a
legume could be consumed at a later meal, and the proteins
would still complement one another.
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Describe how nitrogen is conserved from amino acids.
The liver is the principal site of amino acid metabolism, but other tissues, such as the kidney, the small intestine, muscles, and
adipose tissue, take part. Generally, the first step in the breakdown of amino acids is the separation of the amino group from the
carbon skeleton, usually by a transamination reaction. The carbon skeletons resulting from the deaminated amino acids are used
to form either glucose or fats, or they are converted to a metabolic intermediate that can be oxidized by the citric acid cycle. The
latter alternative, amino acid catabolism, is more likely to occur when glucose levels are low—for example, when a person is
fasting or starving.
Transamination
Transamination is an exchange of functional groups between any amino acid (except lysine, proline, and threonine) and an α-keto
acid. The amino group is usually transferred to the keto carbon atom of pyruvate, oxaloacetate, or α-ketoglutarate, converting the
alpha-keto acid to alanine, aspartate, or glutamate, respectively. Transamination reactions are catalyzed by specific transaminases
(also called aminotransferases), which require pyridoxal phosphate as a coenzyme.
Figure 25.3.1 ): Transamination involves the interchange of an amino group and keto group.
In an alpha -keto acid, the carbonyl or keto group is located on the carbon atom adjacent
to the carboxyl group of the acid.
Figure 25.3.2: Alanine aminotransferase (ALT) catalyzes the transfer of an amino group from alanine to alpha -ketoglutarate,
forming pyruvate and glutamate.
Oxidative Deamination
In the breakdown of amino acids for energy, the final acceptor of the alpha-amino group is alpha-ketoglutarate, forming
glutamate. Glutamate can then undergo oxidative deamination, in which it loses its amino group as an ammonium (NH4+) ion and
is oxidized back to alpha-ketoglutarate (ready to accept another amino group):
This reaction occurs primarily in liver mitochondria. Most of the NH4+ ion formed by oxidative deamination of glutamate is
converted to urea and excreted in the urine in a series of reactions known as the urea cycle.
The synthesis of glutamate occurs in animal cells by reversing the reaction catalyzed by glutamate dehydrogenase. For this reaction
nicotinamide adenine dinucleotide phosphate (NADPH) acts as the reducing agent. The synthesis of glutamate is significant
because it is one of the few reactions in animals that can incorporate inorganic nitrogen (NH4+) into an α-keto acid to form an
amino acid. The amino group can then be passed on through transamination reactions, to produce other amino acids from the
appropriate α-keto acids.
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Describe the urea cycle reactions.
Deamination of amino acids results in the production of ammonia (as well as the ammonium ion, NH4+). Ammonia is an
extremely toxic base and its accumulation in the body would quickly be fatal. Animals that live in aquatic environments tend to
release ammonia into the water. Terrestrial organisms have evolved other mechanisms to excrete nitrogenous wastes. These animals
must detoxify ammonia by converting it into a relatively nontoxic form such as urea or uric acid. Mammals, including humans,
produce urea through the urea cycle, whereas reptiles and many terrestrial invertebrates produce uric acid. Animals that secrete
urea as the primary nitrogenous waste material are called ureotelic animals.
The Urea Cycle

The urea cycle is the primary mechanism by which mammals convert ammonia to urea. Urea is made in the liver and excreted in
urine. The overall chemical reaction by which ammonia is converted to urea is 2 NH3 (ammonia) + CO2 + 3 ATP + H2O → H2N-
CO-NH2 (urea) + 2 ADP + 4 Pi + AMP.
The urea cycle utilizes five intermediate steps, catalyzed by five different enzymes, to convert ammonia to urea, as shown in Figure
25.4.1. The amino acid L-ornithine gets converted into different intermediates before being regenerated at the end of the urea
cycle. Hence, the urea cycle is also referred to as the ornithine cycle. The enzyme ornithine transcarbamylase catalyzes a key step
in the urea cycle and its deficiency can lead to accumulation of toxic levels of ammonia in the body. The first two reactions occur
in the mitochondria and the last three reactions occur in the cytosol. Urea concentration in the blood, called blood urea nitrogen or
BUN, is used as an indicator of kidney function.
Figure 25.4.1 : The urea cycle converts ammonia to urea.
 Note Everyday Connection: Gout
Mammals use uric acid crystals as an antioxidant in their cells. However, too much uric acid tends to form kidney stones and
may also cause a painful condition called gout, where uric acid crystals accumulate in the joints, as illustrated in Figure 25.4.2.
Food choices that reduce the amount of nitrogenous bases in the diet help reduce the risk of gout. For example, tea, coffee, and
chocolate have purine-like compounds, called xanthines, and should be avoided by people with gout and kidney stones.
Figure 25.4.2: Gout causes the inflammation visible in this person’s left big toe joint. (credit: "Gonzosft"/Wikimedia
Commons)
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Objective 1
Objective 2
Any amino acid can be converted into an intermediate of the citric acid cycle. Once the amino group is removed, usually by
transamination, the α-keto acid that remains is catabolized by a pathway unique to that acid and consisting of one or more
reactions. For example, phenylalanine undergoes a series of six reactions before it splits into fumarate and acetoacetate. Fumarate
is an intermediate in the citric acid cycle, while acetoacetate must be converted to acetoacetyl-coenzymeA (CoA) and then to
acetyl-CoA before it enters the citric acid cycle.
File:Amino acid catabolism revised.png
Figure 25.5.1 : Fates of the Carbon Skeletons of Amino Acids (https://commons.wikimedia.org/wiki/F...sm_revised.png)

Those amino acids that can form any of the intermediates of carbohydrate metabolism can subsequently be converted to glucose via
a metabolic pathway known as gluconeogenesis. These amino acids are called glucogenic amino acids. Amino acids that are
converted to acetoacetyl-CoA or acetyl-CoA, which can be used for the synthesis of ketone bodies but not glucose, are called
ketogenic amino acids. Some amino acids fall into both categories. Leucine and lysine are the only amino acids that are exclusively
ketogenic. Figure 25.5.1 summarizes the ultimate fates of the carbon skeletons of the 20 amino acids.
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Objective 1
Objective 2
In humans, only half of the standard amino acids (Glu, Gln, Pro, Asp, Asn, Ala, Gly, Ser, Tyr, Cys) can be synthesized (Figure
25.6.12 and 13), and are thus classified the nonessential amino acids. Within this group, the first three, glutamate, glutamine, and
proline, have a shared anabolic pathway. It begins with glutamate dehydrogenase, which adds ammonia to α-ketoglutarate in the
presence of NADPH to form glutamate. This is a key reaction for all amino acid synthesis: glutamate is a nitrogen (amino group)
donor for the production of all the other amino acids.
Glutamine synthetase catalyzes the formation of glutamine from glutamate and ammonia. This is an important biochemical reaction
for a completely different reason: it is the primary route for ammonia detoxification.
Proline is synthesized from glutamate in a two-step process that begins with the reduction of glutamate to a semialdehyde form that
spontaneously cyclizes to D-pyrroline-5-carboxylate. This is reduced by pyrroline carboxylate reductase to proline.
Alanine and Aspartate are the products of glutamate-based transamination of pyruvate and oxaloacetate, respectively.
Asparagine is synthesized through one of two known pathways. In bacteria, an asparagine synthetase combines aspartate and
ammonia. However, in mammals, the aspartate gets its amino group from glutamine.
The synthesis of serine begins with the metabolic intermediate 3-phosphoglycerate (glycolysis). Phosphoglycerate dehydrogenase
oxidizes it to 3-phosphohydroxypyruvate. An amino group is donated by glutamate in a reaction catalyzed by phosphoserine
transaminase, forming 3-phosphoserine, and finally the phosphate is removed by phosphoserine phosphatase to produce serine.
Serine is the immediate precursor to glycine, which is formed by serine hydroxymethyltransferase. This enzyme requires the
coenzyme tetrahydrofolate (THF), which is a derivative of vitamin B9 (folic acid).
Serine is also a precursor for cysteine, although the synthesis of cysteine actually begins with the essential amino acid methionine.
Methionine is converted to S-adenosylmethionine by methionine adenosyltransferase. This is then converted to S-
adenosylhomocysteine by a member of the SAM-dependent methylase family. The sugar is removed by adenosylhomocysteinase,
and the resultant homocysteine is connected by cystathionine synthase to the serine molecule to form cystathionine. Finally,
cystathionine-g-lyase catalyzes the production of cysteine.
Tyrosine is another amino acid that depends on an essential amino acid as a precursor. In this case, phenylalanine oxygenase
reduces phenylalanine to produce the tyrosine.
In general, the synthesis of essential amino acids, usually in microorganisms, is much more complex than for the nonessential
amino acids and is best left to a full-fledged biochemistry course.
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CHAPTER OVERVIEW
26: Nucleic Acids and Protein Synthesis

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CHAPTER OVERVIEW
27: Genomics
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CHAPTER OVERVIEW
28: Chemical Messengers- Hormones, Neurotransmitters, and Drugs

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CHAPTER OVERVIEW
29: Body Fluids

29.2: Fluid Balance
29.3: Blood
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29.2: Fluid Balance
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29.3: Blood
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Describe how normal urine consists of water, urea, salts and pigment
Urine is a liquid byproduct of the body secreted by the kidneys through a process called urination and excreted through the urethra.
The normal chemical composition of urine is mainly water content, but it also includes nitrogenous molecules, such as urea, as well
as creatinine and other metabolic waste components. Other substances may be excreted in urine due to injury or infection of the
glomeruli of the kidneys, which can alter the ability of the nephron to reabsorb or filter the different components of blood plasma.
Normal Chemical Composition of Urine

Urine is an aqueous solution of greater than 95% water, with a minimum of these remaining constituents, in order of decreasing
concentration:
Urea 9.3 g/L.
Chloride 1.87 g/L.
Sodium 1.17 g/L.
Potassium 0.750 g/L.
Creatinine 0.670 g/L .
Other dissolved ions, inorganic and organic compounds (proteins, hormones, metabolites).
Urine is sterile until it reaches the urethra, where epithelial cells lining the urethra are colonized by facultatively anaerobic gram-
negative rods and cocci. Urea is essentially a processed form of ammonia that is non-toxic to mammals, unlike ammonia, which
can be highly toxic. It is processed from ammonia and carbon dioxide in the liver.
 Abnormal Types of Urine

There are several conditions that can cause abnormal components to be excreted in urine or present as abnormal characteristics
of urine. They are mostly referred to by the suffix -uria. Some of the more common types of abnormal urine include:
Proteinuria—Protein content in urine, often due to leaky or damaged glomeruli.
Oliguria—An abnormally small amount of urine, often due to shock or kidney damage.
Polyuria—An abnormally large amount of urine, often caused by diabetes.
Dysuria—Painful or uncomfortable urination, often from urinary tract infections.
Hematuria—Red blood cells in urine, from infection or injury.
Glycosuria—Glucose in urine, due to excess plasma glucose in diabetes, beyond the amount able to be reabsorbed in the
proximal convoluted tubule.
Summary
Urine is a liquid by-product of the body secreted by the kidneys through a process called urination and excreted through the
urethra. It is an aqueous solution of greater than 95% water. Other constituents include urea, chloride, sodium, potassium,
creatinine and other dissolved ions, and inorganic and organic compounds. Urea is a non-toxic molecule made of toxic ammonia
and carbon dioxide. Any abnormal constituents found in urine are an indication of disease.
References
1. "Boundless." http://www.boundless.com/Boundless Learning CC BY-SA 3.0.
2. "red blood cell." http://en.wiktionary.org/wiki/red_blood_cellWiktionary CC BY-SA 3.0.
3. "diabetes." en.wiktionary.org/wiki/diabetesWiktionary CC BY-SA 3.0.
4. "urine." en.wiktionary.org/wiki/urineWiktionary CC BY-SA 3.0.

Boundless (www.boundless.com)
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Index
A H P
Absolute Temperature half life (nuclear) parent isotope
8.6: Charles’s Law- The Relation between Volume 11.5: Radioactive Half-Life 11.1: Nuclear Reactions
and Temperature partial pressures
atomic number I 8.11: Partial Pressure and Dalton's Law
2.2: Elements and Atomic Number Phospholipids
impulse
8.3: Gases and the Kinetic-Molecular Theory 23.5: Phospholipids and Glycolipids
B isotope Postulates of the Kinetic Theory
band of stability 2.3: Isotopes and Atomic Weight 8.3: Gases and the Kinetic-Molecular Theory
becquerel (unit) K R
11.7: Detecting and Measuring Radiation rad (unit)
kelvin
bile 8.6: Charles’s Law- The Relation between Volume 11.7: Detecting and Measuring Radiation
24.1: Digestion of Triacylglycerols and Temperature radioisotope
ketoacidosis 11.3: Stable and Unstable Isotopes
C 24.6: Ketone Bodies and Ketoacidosis rem (unit)
change phase Ketone bodies 11.7: Detecting and Measuring Radiation
1.2: States of Matter 24.6: Ketone Bodies and Ketoacidosis roentgen (units)
Charles's Law kilogram (unit) 11.7: Detecting and Measuring Radiation
8.6: Charles’s Law- The Relation between Volume 1.7: Measuring Mass, Length, and Volume rounding
and Temperature kinetic molecular theory 1.9: Rounding Off Numbers
chylomicrons 8.3: Gases and the Kinetic-Molecular Theory
24.2: Lipoproteins for Lipid Transport kinetic theory S
colligative properties 8.3: Gases and the Kinetic-Molecular Theory scientific notation
9.10: Osmosis and Osmotic Pressure KT 1.6: Physical Quantities - Units and Scientific
curie (unit) 8.3: Gases and the Kinetic-Molecular Theory Notation
11.7: Detecting and Measuring Radiation sievert (unit)
L 11.7: Detecting and Measuring Radiation
D Le Chatelier's Principle significant figures
Dalton 7.9: Le Chatelier’s Principle- The Effect of Changing 1.8: Measurement and Significant Figures
8.11: Partial Pressure and Dalton's Law Conditions on Equilibria specific gravity
Dalton’s law Lewis diagram 1.12: Density and Specific Gravity
8.11: Partial Pressure and Dalton's Law 2.9: Electron-Dot Symbols
Dalton’s law of partial pressures Lipoproteins T
8.11: Partial Pressure and Dalton's Law 24.2: Lipoproteins for Lipid Transport transamination
daughter isotope liter (unit) 25.3: Amino Acid Catabolism - The Amino Group
11.1: Nuclear Reactions 1.7: Measuring Mass, Length, and Volume triacylglycerols
density 24.1: Digestion of Triacylglycerols
1.12: Density and Specific Gravity M tritium
deuterium mass 2.3: Isotopes and Atomic Weight
2.3: Isotopes and Atomic Weight 1.7: Measuring Mass, Length, and Volume
dynamic equilibrium mass number U
7.9: Le Chatelier’s Principle- The Effect of Changing 2.2: Elements and Atomic Number
Conditions on Equilibria
units
meter (unit) 1.6: Physical Quantities - Units and Scientific
1.7: Measuring Mass, Length, and Volume Notation
E molar mass urea cycle
electron configuration 6.2: Gram-Mole Conversions 25.4: The Urea Cycle
N V
G noble gas configuration vapor pressure
Glycolipids 2.7: Electron Configurations 8.11: Partial Pressure and Dalton's Law
23.5: Phospholipids and Glycolipids nuclide vapor pressure depression
glycolysis 11.1: Nuclear Reactions 9.10: Osmosis and Osmotic Pressure
22.3: Glycolysis 11.3: Stable and Unstable Isotopes volume
gray (unit) 1.7: Measuring Mass, Length, and Volume
Glossary
Sample Word 1 | Sample Definition 1
Detailed Licensing
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19.6: Enzyme Regulation - Inhibition - CC BY-NC-SA Glycogenolysis - CC BY-NC-SA 3.0
3.0 22.9: Gluconeogenesis- Glucose Synthesis from
19.7: Enzyme Regulation- Allosteric Control and Noncarbohydrates - CC BY-NC-SA 3.0
Feedback Inhibition - CC BY-NC-SA 3.0 23: Lipids - CC BY-NC-SA 3.0
19.8: Enzyme Regulation - Covalent Modification 23.1: Structure and Classification of Lipids - CC BY-
and Genetic Control - CC BY-NC-SA 3.0 NC-SA 3.0
19.9: Vitamins, Antioxidants, and Minerals - CC BY- 23.2: Fatty Acids and Their Esters - CC BY-NC-SA
NC-SA 3.0 3.0
20: Carbohydrates - CC BY-NC-SA 3.0 23.3: Properties of Fats and Oils - CC BY-NC-SA 3.0
20.1: An Introduction to Carbohydrates - CC BY-NC- 23.4: Chemical Reactions of Triacylglycerols - CC
SA 3.0 BY-NC-SA 3.0
20.2: Handedness of Carbohydrates - CC BY-NC-SA 23.5: Phospholipids and Glycolipids - CC BY-NC-SA
3.0 3.0
20.3: Structure of Glucose and Other 23.6: Steroids - CC BY-NC-SA 3.0
Monosaccharides - CC BY-NC-SA 3.0 23.7: Cell Membranes- Structure and Transport - CC
20.4: Some Important Monosaccharides - CC BY-NC- BY-NC-SA 3.0
SA 3.0 24: Lipid Metabolism - CC BY-NC-SA 3.0
20.5: Reactions of Monosaccharides - CC BY-NC-SA 24.1: Digestion of Triacylglycerols - CC BY-NC-SA
3.0 3.0
20.6: Common Disaccharides - CC BY-NC-SA 3.0 24.2: Lipoproteins for Lipid Transport - CC BY-NC-
20.7: Some Important Polysaccharides Based on SA 3.0
Glucose - CC BY-NC-SA 3.0
24.3: Triacylglycerol Metabolism - An Overview - 27.1: Mapping the Human Genome - CC BY-NC-SA
CC BY-NC-SA 3.0 3.0
24.4: Storage and Mobilization of Triacylglycerols - 27.2: DNA and Chromosomes - CC BY-NC-SA 3.0
CC BY-NC-SA 3.0 27.3: Mutations and Polymorphisms - CC BY-NC-SA
24.5: Oxidation of Fatty Acids - CC BY-NC-SA 3.0 3.0
24.6: Ketone Bodies and Ketoacidosis - CC BY-NC- 27.4: Recombinant DNA - CC BY-NC-SA 3.0
SA 3.0 27.5: Genomics- Using What We Know - CC BY-NC-
24.7: Biosynthesis of Fatty Acids - CC BY-NC-SA 3.0 SA 3.0
25: Protein and Amino Acid Metabolism - CC BY-NC-SA 28: Chemical Messengers- Hormones, Neurotransmitters,
3.0 and Drugs - CC BY-NC-SA 3.0
25.1: Digestion of Proteins - CC BY-NC-SA 3.0 28.1: Messenger Molecules - CC BY-NC-SA 3.0
25.2: Amino Acid Metabolism - An Overview - CC 28.2: Hormones and the Endocrine System - CC BY-
BY-NC-SA 3.0 NC-SA 3.0
25.3: Amino Acid Catabolism - The Amino Group - 28.3: How Hormones Work - Epinephrine and Fight-
CC BY-NC-SA 3.0 or-Flight - CC BY-NC-SA 3.0
25.4: The Urea Cycle - CC BY-NC-SA 3.0 28.4: Amino Acid Derivatives and Polypeptides as
25.5: Amino Acid Catabolism - The Carbon Atoms - Hormones - CC BY-NC-SA 3.0
CC BY-NC-SA 3.0 28.5: Neurotransmitters - CC BY-NC-SA 3.0
25.6: Biosynthesis of Nonessential Amino Acids - CC 28.6: How Neurotransmitters Work- Acetylcholine,
BY-NC-SA 3.0 Its Agonists and Antagonists - CC BY-NC-SA 3.0
26: Nucleic Acids and Protein Synthesis - CC BY-NC-SA 28.7: Histamines, Antihistamines, and Important
3.0 Neurotransmitters - CC BY-NC-SA 3.0
26.1: DNA, Chromosomes, and Genes - CC BY-NC- 29: Body Fluids - CC BY-NC-SA 3.0
SA 3.0 29.1: Body Water and Its Solutes - CC BY-NC-SA 3.0
26.2: Composition of Nucleic Acids - CC BY-NC-SA 29.2: Fluid Balance - CC BY-NC-SA 3.0
3.0 29.3: Blood - CC BY-NC-SA 3.0
26.3: The Structure of Nucleic Acid Chains - CC BY- 29.4: Plasma Proteins, White Blood Cells, and
NC-SA 3.0 Immunity - CC BY-NC-SA 3.0
26.4: Base Pairing in DNA- The Watson-Crick Model 29.5: Blood Clotting - CC BY-NC-SA 3.0
- CC BY-NC-SA 3.0 29.6: Red Blood Cells and Blood Gases - CC BY-NC-
26.5: Nucleic Acids and Heredity - CC BY-NC-SA 3.0 SA 3.0
26.6: Replication of DNA - CC BY-NC-SA 3.0 29.7: The Kidney and Urine Formation - CC BY-NC-
26.7: Structure and Function of RNA - CC BY-NC-SA SA 3.0
3.0 29.8: Urine Composition and Function - CC BY-NC-
26.8: Transcription - RNA Synthesis - CC BY-NC-SA SA 3.0
3.0 Back Matter - CC BY-NC-SA 3.0
26.9: The Genetic Code - CC BY-NC-SA 3.0 Index - CC BY-NC-SA 3.0
26.10: Translation- tRNA and Protein Synthesis - CC Glossary - CC BY-NC-SA 3.0
BY-NC-SA 3.0 Detailed Licensing - Undeclared
27: Genomics - CC BY-NC-SA 3.0

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FUNDAMENTALS OF

Textmap McMurry et al.

1: Matter and Measurements

2: Atoms and the Periodic Table

5: Classification and Balancing of Chemical Reactions

6: Chemical Reactions - Mole and Mass Relationships

7: Chemical Reactions - Energy, Rates, and Equilibrium

8: Gases, Liquids, and Solids

10: Acids and Bases

11: Nuclear Chemistry

12: Introduction to Organic Chemistry - Alkanes

14: Some Compounds with Oxygen, Sulfur, or a Halogen

15: Aldehydes and Ketones

17: Carboxylic Acids and their Derivatives

19: Enzymes and Vitamins

21: The Generation of Biochemical Energy

22: Carbohydrate Metabolism

24: Lipid Metabolism

25: Protein and Amino Acid Metabolism

26: Nucleic Acids and Protein Synthesis

29: Body Fluids

1: Matter and Measurements

Physical and Chemical Properties and Changes

solid to liquid melting, fusion

solid to gas sublimation

liquid to gas boiling, evaporation

liquid to solid solidification, freezing

gas to liquid condensation

gas to solid deposition

Classify each of the following changes as physical or chemical:

Classify each of the following changes as physical or chemical:

particles move in random motion

particles move in random motion particles are free to move over

Compressibility highly compressible weakly compressible weakly compressible

State of Matter Depends on the External Conditions

-500 1.05 100.5

Contributors and Attributions

Allison Soult, Ph.D. (Department of Chemistry, University of Kentucky)

How would a chemist categorize each example of matter?

How would a chemist categorize each example of matter?

Contributors and Attributions

Elemental Names and Symbols

Today, new elements are usually named after famous scientists.

arsenic As mercury Hg*

copper Cu* silver Ag*

fluorine F sodium Na*

gold Au* strontium Sr

hydrogen H tin Sn*

lead Pb* zinc Zn

Elements in Nature and the Human Body

Element Percentage Element Percentage

oxygen 46.1 oxygen 61

silicon 28.2 carbon 23

aluminum 8.23 hydrogen 10

iron 5.53 nitrogen 2.6

calcium 4.15 calcium 1.4

sodium 2.36 phosphorus 1.1

magnesium 2.33 sulfur 0.20

potassium 2.09 potassium 0.20

titanium 0.565 sodium 0.14

hydrogen 0.14 chlorine 0.12

phosphorus 0.105 magnesium 0.027

all others 0.174 silicon 0.026