Compiled Lecture in

General Chemistry (Organic Chemistry)

(MIDTERM)

CCJE

Subject Teacher:

Ethelyn M. Pumihic
 ATOMIC STRUCTURES AND LEWIS SYMBOLS

CHAPTER 1

LEARNING OUTCOMES

 Describe atomic structure

 Write Lewis symbols for neutral atoms and ions
 Draw Lewis structures depicting the bonding in simple molecules
 Define the octet rule.

STRUCTURE OF THE ATOM

► Atom – smallest particle of an element

that can exist alone

 Two regions of an atom

► Nucleus
 Center of atom
 Protons and neutrons
► Electron “cloud”
 Area surrounding
nucleus
containing electrons

► Proton – Positive charge (+), 1 atomic mass unit (amu); found in the nucleus
 amu -Approximate mass of a proton or a neutron
► Neutron – Neutral charge (0), 1 amu; found in the nucleus
► Electron – Negative charge (-), mass is VERY small
LEWIS STRUCTURE

In this section, we will explore the typical method for depicting valence shell
electrons and chemical bonds, namely Lewis symbols and Lewis structures.

Lewis Symbols

We use Lewis symbols to describe valence electron configurations of atoms and

monatomic ions. A Lewis symbol consists of an elemental symbol surrounded by one
dot for each of its valence electrons: Valence electron(outermost electron) in an
atom.

Figure 1 shows the Lewis symbols for the elements of the third period of the periodic
table.

Figure 1. Lewis symbols illustrating the number of valence electrons for each element
in the third period of the periodic table.

Lewis symbols can also be used to illustrate the formation of cations from atoms, as
shown here for sodium and calcium:
Likewise, they can be used to show the formation of anions from atoms, as shown
below for chlorine and sulfur:

The Octet Rule

The other halogen molecules (F2, Br2, I2, and At2) form bonds like those in the
chlorine molecule: one single bond between atoms and three lone pairs of electrons
per atom. This allows each halogen atom to have a noble gas electron configuration.
The tendency of main group atoms to form enough bonds to obtain eight valence
electrons is known as the octet rule.

Writing Lewis Structures with the Octet Rule

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 and molecular ions, it is helpful to follow the step-by-
step procedure outlined here:
 1. Determine the total number of valence (outer shell) electrons. For cations,
subtract one electron for each positive charge. For anions, add one electron for
each negative charge.
2. Draw a skeleton structure of the molecule or ion, arranging the atoms around a
central atom. (Generally, the least electronegative element should be placed in
the center.) Connect each atom to the central atom with a single bond (one
electron pair).
3. Distribute the remaining electrons as lone pairs on the terminal atoms (except
hydrogen), completing an octet around each atom.
4. Place all remaining electrons on the central atom.
5. Rearrange the electrons of the outer atoms to make multiple bonds with the
central atom in order to obtain octets wherever possible.

Exercises:

1. Show the Lewis structure of the ff. atoms:

a. Oxygen

b. Xenon

c. Iodine

d. Potassium

e. boron
 CHEMICAL BONDING

Chapter 2

1.3.1. How and why atoms bond

LEARNING OBJECTIVES

Describe ionic bond from covalent bond.

Demonstrate formation of ionic compound and covalent compound.
Atoms can join together by forming a chemical bond, which is a very strong
attraction between two atoms. Chemical bonds are formed when electrons in
different atoms interact with each other to make an arrangement that is more stable
than when the atoms are apart.
What causes atoms to make a chemical bond with other atoms, rather than remaining
as individual atoms?
A clue comes by considering the noble gas elements, the rightmost column of the
periodic table. These elements—helium, neon, argon, krypton, xenon, and radon—do
not form compounds very easily, which suggests that they are especially stable as
lone atoms.
What else do the noble gas elements have in common ?
Except for helium, they all have eight valence electrons. Chemists have concluded
that atoms are especially stable if they have eight electrons in their outermost shell.
This useful rule of thumb is called the octet rule, and it is a key to understanding
why compounds form.
There are two ways for an atom that does not have an octet of valence electrons to
obtain an octet in its outer shell.
1. One way is the transfer of electrons between two atoms until all atoms have
octets. Because some atoms will lose electrons and some atoms will gain
electrons, there is no overall change in the number of electrons, but individual
atoms acquire a nonzero electric charge.
 Those that lose electrons become positively charged, and those that gain
electrons become negatively charged. Charged atoms are called ions.
Because opposite charges attract (while like charges repel), these
oppositely charged ions attract each other, forming ionic bonds. The
resulting compounds are called ionic compounds .
2. The second way for an atom to obtain an octet of electrons is by sharing
electrons with another atom. These shared electrons simultaneously occupy the
outermost shell of more than one atom. The bond made by electron sharing is
 called a covalent bond. Covalent bonding and covalent compounds will be
discussed in detail below.
NOTE: Despite our focus on the octet rule, we must remember that for small atoms,
such as hydrogen, helium, and lithium, the first shell is, or becomes, the outermost
shell and hold only two electrons. Therefore, these atoms satisfy a “duet rule” rather
than the octet rule.
Types of Chemical Bond

1. Ionic bonding is the complete transfer of valence electron(s) between atoms. It is

a type of chemical bond that generates two oppositely charged ions.

In ionic bonds, the metal loses electrons to become a positively charged cation,
whereas the nonmetal accepts those electrons to become a negatively charged anion.
Ionic bonds require an electron donor, often a metal, and an electron acceptor, a
nonmetal.

Ionic bonding is observed because metals have few electrons in their outer-most
orbitals. By losing those electrons, these metals can achieve noble gas configuration
and satisfy the octet rule. Similarly, nonmetals that have close to 8 electrons in their
valence shells tend to readily accept electrons to achieve noble gas configuration.

In ionic bonding, more than 1 electron can be donated or received to satisfy the octet
rule. The charges on the anion and cation correspond to the number of electrons
donated or received.

This sodium atom donates the lone electron in its valence orbital in order to achieve
octet configuration. This creates a positively charged cation due to the loss of
electron.

This flourine atom receives one electron to achieve its octet configuration, which
creates a negatively charged anion.

Example 1: Chloride Salts

In this example, the sodium atom is donating its 1 valence electron to the chlorine
atom. This creates a sodium cation and a chlorine anion. Notice that the net charge of
the resulting compound is 0.

In this example, the magnesium atom is donating both of its valence electrons to
chlorine atoms. Each chlorine atom can only accept 1 electron before it can achieve
its noble gas configuration; therefore, 2 atoms of chlorine are required to accept the
2 electrons donated by the magnesium. Notice that the net charge of the compound
is 0.

Typical of ionic bonds are those in the alkali halides such as sodium chloride, NaCl.

2.Covalent Bonding

Covalent bonding is the sharing of electrons between atoms. This type of bonding
occurs between two atoms of the same element or of elements close to each other in
the periodic table. This bonding occurs primarily between nonmetals.

For example:
Example 1: PCl3

In this example, a phosphorous atom is sharing its three unpaired electrons with
three chlorine atoms. In the end product, all four of these molecules have 8 valence
electrons and satisfy the octet rule.

Hydrogen gas forms the simplest covalent bond in the diatomic hydrogen molecule.
The halogens such as chlorine also exist as diatomic gases by forming covalent bonds.
The nitrogen and oxygen which makes up the bulk of the atmosphere also exhibits
covalent bonding in forming diatomic molecules.

Carbon does not form ionic bonds

because it has 4 valence electrons,
half of an octet. To form ionic bonds,
Carbon molecules must either gain or
lose 4 electrons. This is highly
unfavorable; therefore,
carbon molecules share their 4
valence electrons through single,
double, and triple bonds so that each
atom can achieve noble gas
configurations. Covalent bonds
include interactions of the sigma and
pi orbitals; therefore, covalent bonds lead to formation of single, double, triple, and
quadruple bonds.

Double and Triple Bonds

As previously mentioned, when a pair of atoms shares one pair of electrons, we call
this a single bond. However, a pair of atoms may need to share more than one pair of
electrons in order to achieve the requisite octet. A double bond forms when two
pairs of electrons are shared between a pair of atoms, as between the carbon and
oxygen atoms in CH2O (formaldehyde) and between the two carbon atoms in

C2H4 (ethylene):
A triple bond forms when three electron pairs are shared by a pair of atoms, as in
carbon monoxide (CO) and the cyanide ion (CN –):

Problems

1. Show the Lewis structure of the ff. compounds? Are these compounds ionic or covalent?

2. In the following reactions, indicate whether the reactants and products are ionic or
covalently bonded.

a)

b) Clarification: What is the nature of the bond between sodium and amide? What kind of
bond forms between the anion carbon chain and sodium?

c)
 3. 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:
Show the formation of the ff compounds using Lewis structure..

Glossary

bond length: distance between the nuclei of two bonded atoms at which the lowest potential
energy is achieved
covalent bond: bond formed when electrons are shared between atoms
electronegativity: tendency of an atom to attract electrons in a bond to itself
polar covalent bond: covalent bond between atoms of different electronegativities; a
covalent bond with a positive end and a negative end
pure covalent bond: (also, nonpolar covalent bond) covalent bond between atoms of identical
electronegativities

Electronegativity and bond polarity

Figure 1.6. Polar versus nonpolar covalent bonds. (a) The electrons in the covalent bond are equally shared by
both hydrogen atoms. This is a nonpolar covalent bond. (b) The fluorine atom attracts the electrons in the bond
more than the hydrogen atom does, leading to an imbalance in the electron distribution. This is a polar covalent
bond.
Although we defined covalent bonding as electron sharing, the electrons in a covalent bond
are not always shared equally by the two bonded atoms. Unless the bond connects two atoms
of the same element, there will always be one atom that attracts the electrons in the bond
more strongly than the other atom does, as shown in Figure 1.6. “Polar versus Nonpolar
Covalent Bonds”. When such an imbalance occurs, there is a resulting buildup of some
negative charge (called a partial negative charge and designated δ−) on one side of the bond
and some positive charge (designated δ+) on the other side of the bond.
A covalent bond that has an unequal sharing of electrons, as in part (b) of Figure 1.6., is
called a polar covalent bond. 
A covalent bond that has an equal sharing of electrons (part (a) is called a nonpolar covalent
bond.
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.
There are various numerical scales for rating electronegativity. Figure 1.7.
“Electronegativities of Various Elements” shows one of the most popular—the Pauling scale.
The polarity of a covalent bond can be judged by determining the difference in the
electronegativities of the two atoms making the bond.
The general rule is if the difference in electronegativity 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 electronegativity 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.

When a molecule’s bonds are polar, the substance is usually found to be polar. The polarity of
water has an enormous impact on its physical and chemical properties. (For example, the
boiling point of water [100°C] is high for such a small molecule and is due to the fact that
polar molecules attract each other strongly.)  This aspect will be discussed in more detail
in section 1.8. on intermolecular forces.

Figure 1.7. Electronegativities of Various Elements.  A popular scale for electronegativities

has the value for fluorine atoms set at 4.0, the highest value.
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.
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.

EXAMPLE 2

Describe the electronegativity difference between each pair of atoms and the resulting
polarity (or bond type).

1. C and H
2. H and H
3. Na and Cl
4. O and H

SKILL-BUILDING EXERCISE

1. C and O
2. K and Br
3. N and N
4. Cs and F

CONCEPT REVIEW EXERCISES

1. What does the electronegativity of an atom indicate?

2. What type of bond is formed between two atoms if the difference in
electronegativities is small? Medium? Large?

KEY TAKEAWAYS

 Covalent bonds between different atoms have different bond lengths.

 Covalent bonds can be polar or nonpolar, depending on the electronegativity difference
between the atoms involved.

EXERCISES:

1. Using Figure 1.7. “Electronegativities of Various Elements”, determine which

atom in each pair has the higher electronegativity.
1. H or C
2. O or Br
3. Na or Rb
 4. I or Cl
2. Using Figure 1.7. “Electronegativities of Various Elements”, determine which
atom in each pair has the lower electronegativity.
1. Mg or O
2. S or F
3. Al or Ga
4. O or I
3. Will the electrons be shared equally or unequally across each covalent bond? If
unequally, to which atom are the electrons more strongly drawn?
1. a C–O bond
2. an F–F bond
3. an S–N bond
4. an I–Cl bond
4. Will the electrons be shared equally or unequally across each covalent bond? If
unequally, to which atom are the electrons more strongly drawn?
1. a C–C bond
2. a S–Cl bond
3. an O–H bond
4. an H–H bond

CHAPTER THREE
INTRODUCTION TO ORGANIC CHEMISTRY

LEARNING ACTIVITIES

 Define organic chemistry.
 Identify organic molecules as alkanes, alkenes, alkynes, alcohols, or carboxylic acids.
When methane was mentioned previously, we described it as the simplest organic compound.
In this section, we introduce organic chemistry more formally. Organic chemistry is the study
of the chemistry of carbon 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.

ORGANIC CHEMISTRY

 The study of carbon-containing compounds and their properties. The vast

majority of organic compounds contain chains or rings of carbon atoms.

HYDROCARBONS

 A hydrocarbon is any of a class of organic chemicals made up of only

the elements carbon (C) and hydrogen (H). The carbon atoms join together to form
the framework of the compound, and the hydrogen atoms attach to them in many
different configurations.

 CLASSIFICATIONS OF HYDROCARBONS

1. saturated hydrocarbons—are formed by single bonds. Have relatively few important

chemical properties other than that they undergo combustion and react with halogens.

2. Unsaturated hydrocarbons— hydrocarbons with double or triple bonds—on the other

hand, are quite reactive. In fact, they serve as building blocks for many familiar
plastics—polyethylene, vinyl plastics, acrylics—and other important synthetic
materials (e.g., alcohols, antifreeze, and detergents)


ALKANES, ALKENES AND ALKYNES (ALIPHATIC STRUCTURES)

Learning Objective

 Identify the basic properties of alkanes

 Translate between the structure and the name of an alkene or alkyne compound

  Recognize the properties of alkenes relative to alkanes


Key Points

o Alkanes are saturated hydrocarbons, which means that their carbon backbones
contain no double or triple bonds.
o Due to the valence configuration of carbon, there are a variety of alkane
isomers, which are commonly separated into linear and branched structures.
o Alkanes are used in a number of industrial applications and are found in natural
gas and petroleum.
o ALKANES
 Saturated: C—C bonds are all single bonds.

alkanes [C H ]
n 2n+2

H H
H C C H
H H
Alkanes, also called paraffins, are a class of hydrocarbons that are fully saturated with
hydrogen.

Each alkane has a characteristic, systematic name depending on the number of carbon atoms
in the molecule. These names consist of a stem that indicates the number of carbon atoms in
the chain plus the ending -ane.
The stem meth- means one carbon atom, so methane is an alkane with one carbon atom.
Similarly, the stem eth- means two carbon atoms; ethane is an alkane with two carbon atoms.
Continuing, the stem prop- means three carbon atoms, so propane is an alkane with three
carbon atoms.
The stem but- means four carbon atoms; butane is an alkane with four carbon atoms.
Figure 11 gives the Lewis structures, condensed structural formulas and molecular formulas
of the four simplest alkanes. In the condensed structural formula, the covalent bonds are
understood to exist between each carbon and the hydrogens associated with it, as well as
between carbon atoms.
Figure 11: Formulas and Molecular Models of the Four Simplest Alkanes. The four smallest
alkanes are methane, ethane, propane and butane.

Molecular Structural
Name Isomers
Formula Formula
methane CH4 CH4 1
ethane C2H6 CH3CH3 1
propane C3H8 CH3CH2CH3 1
butane C4H10 CH3CH2CH2CH3 2
pentane C5H12 CH3(CH2)3CH3 3

ALKENES AND ALKYNES are unsaturated hydrocarbons because they are formed by double
or triple bonds.

ALKENES

Key Points

o Alkenes and alkynes are named by identifying the longest chain that contains
the double or triple bond.
o The chain is numbered to minimize the numbers assigned to the double or triple
bond.
o The suffix of the compound is “-ene” for an alkene or “-yne” for an alkyne.

Terms

 Alkenes are unsaturated hydrocarbon containing at least one carbon–carbon double

bond.
 Alkyne are unsaturated hydrocarbon containing at least one carbon—carbon triple
bond between two carbon atoms.
 Stereoisomer is one of a set of the isomers of a compound that exhibits
stereoisomerism.

Alkenes

[C H ]
n 2n

Some hydrocarbons have one or more carbon–carbon double bonds (denoted C=C). These
hydrocarbons are called alkenes. Figure 22 shows the formulas and the molecular models of
the two simplest alkenes. Note that the names of alkenes have the same stem as the alkane
with the same number of carbon atoms in its chain but have the ending -ene. Thus, ethene is
an alkene with two carbon atoms per molecule, and propene is a compound with three carbon
atoms and one double bond.
Figure 22: Formulas and Molecular Models of the Two Simplest Alkenes. Ethene is commonly
called ethylene, while propene is commonly called propylene.

Table 8.1 Physical Properties of Some Selected Alkenes

The first two alkenes in Table 8.1 —ethene and propene, are most often called by their
common names—ethylene and propylene, respectively. Ethylene is a major commercial
chemical. The US chemical industry produces about 25 billion kilograms of ethylene annually,
more than any other synthetic organic chemical. More than half of this ethylene goes into the
manufacture of polyethylene, one of the most familiar plastics. Propylene is also an important
industrial chemical. It is converted to plastics, isopropyl alcohol, and a variety of other
products.

ALKYNES

alkynes [C H ]
n 2n-2

Alkynes are hydrocarbons with a carbon–carbon triple bond (denoted C≡C) as part of their
carbon skeleton. Below is the formula and the molecular model of the simplest alkyne and its
systematic name. Its common name is acetylene. Its chemical formula is C2H2.

Ethyne
The names for alkynes have the same stems as for alkanes but with the ending -yne.

In fact, they serve as building blocks for many familiar plastics—polyethylene, vinyl plastics,
acrylics—and other important synthetic materials (e.g., alcohols, antifreeze, and detergents).

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 7 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.

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 skeleton structure of lycopene

The world would be a much less colorful place without alkenes. Figure 8.4 The bright red
color of tomatoes is due to lycopene.

Exercises:

1. How can you distinguish alkane, alkenes and alkynes from each other

2. Differentiate aromatic hydrocarbons from aliphatic hydrocarbons.

3. Enumerate the uses of the first FIFTEEN alkanes.

4.  Define the term saturation for "hydrocarbons", then determine if the following
compounds are saturated or unsaturated.
 C2H6
 C3H6
 C6H6
 C4H10
 C5H12
3. Discuss the sources of synthetic plastics and natural plastics.
4. Identify the ff. plastics as synthetic or natural. (sample will be given during the quiz
proper.)