Alkanes Dr. Shimaa

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Introduction to Organic Chemistry
Organic chemistry is the study of compounds that
contain the element carbon.
• Products such as clothes, foods, medicines,
gasoline, refrigerants, and soaps are composed
almost solely of organic compounds.
• Some organic products can be obtained directly
from natural sources—cotton, wool, and silk.
• Others can be synthetically produced—nylon and
polyester.
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Characteristic Features of Organic
Compounds
• Methane is the main • Ethylene is used as

component of natural starting material in
gas. the preparation of the
plastic polyethylene.
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Compounds
Carbon forms single, double, and triple bonds to
other carbon atoms.
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Compounds
Some compounds have chains of atoms and some
compounds have rings.
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Compounds
Organic compounds may also contain elements
other than carbon and hydrogen.
• Any atom that is not carbon or hydrogen is called
a heteroatom.
• Each heteroatom forms a characteristic number of
bonds, determined by its location in the periodic
table.
• The common heteroatoms (N, O, F, Cl, Br, and I)
also have nonbonding, lone pairs of e−, so that
each atom is surrounded by an octet of e−.
# of bonds + # of lone pairs = 4

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Compounds
The most common multiple bond between carbon
and a heteroatom is a carbon–oxygen double bond.
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Drawing Organic Molecules
Skeletal Structures
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Drawing Organic Molecules
Skeletal Structures
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Functional Groups
• A functional group is an atom or group of atoms
with characteristic chemical and physical
properties.
• A functional group contains a heteroatom, a

multiple bond, or sometimes both.
• The letter R is used to abbreviate the carbon

and hydrogen portion of a molecule.
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Functional Groups
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Functional Groups
Compounds Containing a Single Bond to a
Heteroatom
From Table 10.4:
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Functional Groups
Compounds Containing a C=O group
• Carbonyl groups (carbon–oxygen double bonds)
are present in several different compounds.
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Functional Groups
Compounds Containing a C=O group
From Table 10.5:
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Alkanes
Introduction
Alkanes are hydrocarbons having only C–C and
C–H single bonds.
• Alkanes that contain chains of C atoms but
no rings are acyclic alkanes and have the
general formula CnH2n+2.
• Acyclic alkanes are called saturated alkanes
because they have the maximum number of H
atoms per C atom.
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Alkanes
Introduction
• Cycloalkanes contain C atoms joined in one
or more rings.
• They have the general formula CnH2n.
All alkane molecules have names that end in the

suffix “-ane.”
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Simple Alkanes
Acyclic Alkanes Having
Fewer than Five Carbons
• Methane is a one-carbon alkane.
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Simple Alkanes
• Ethane is a two-carbon alkane.
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Simple Alkanes
• Propane is a three-carbon alkane.
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Simple Alkanes
• Butane is a four-carbon alkane. Four carbons can be
a straight-chain or branched-chain alkane.
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Simple Alkanes
Acyclic Alkanes Having Five or More Carbons
• As the number of C atoms increases, the number
of possible isomers increases.
• Pentane is a five-carbon alkane with three isomers:
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Simple Alkanes
Acyclic Alkanes Having Five or More Carbons
• After pentane, the following names apply:
# of C’s Name Structure
6 hexane CH3CH2CH2CH2CH2CH3
7 heptane CH3CH2CH2CH2CH2CH2CH3
8 octane CH3CH2CH2CH2CH2CH2CH2CH3
9 nonane CH3CH2CH2CH2CH2CH2CH2CH2CH3
10 decane CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3
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An Introduction to Nomenclature
The IUPAC System of Nomenclature
• IUPAC stands for International Union of Pure and

Applied Chemistry.
• The IUPAC system of nomenclature provides a

system of naming organic compounds.
• Using the IUPAC system, each organic compound

gets a unique name.
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Alkane Nomenclature
The names of alkanes with substituents have three parts:
• The parent name indicates the number of C’s in

the longest continuous carbon chain in the
molecule.
• The suffix indicates what functional group is

present.
• The prefix tells the identity, location, and number

of substituents attached to the carbon chain.
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Alkane Nomenclature
Naming Substituents
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Alkane Nomenclature
Naming Substituents
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Alkane Nomenclature
Naming an Acyclic Alkane
HOW TO Name an Alkane Using the IUPAC System
Step [1] Find the parent carbon chain and add the
suffix.
• Find the longest continuous carbon chain, and
name it with an “-ane” ending.
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Alkane Nomenclature
• The longest chain may not be written horizontally.
• It does not matter if the chain is straight or has
bends.
• All three examples below have 6 C’s in their
longest chain:
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Alkane Nomenclature
Step [2] Number the atoms in the carbon chain to

give the first substituent the lower number.
CORRECT INCORRECT 31
Alkane Nomenclature
Step [3] Name and number the substituents.

• Name the substituents as alkyl groups.
• Use the numbers from step [2] to designate their
location.
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Alkane Nomenclature
• Every carbon belongs to either the longest chain

or a substituent, but not both.
• Each substituent needs its own number.
• If two or more substituents are identical, use
prefixes to indicate how many.
# of Substituents Prefix
2 di-
3 tri-
4 tetra- 33
Alkane Nomenclature
• The following compound contains two methyl

groups, so we use the name dimethyl for them.
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Alkane Nomenclature
Step [4] Combine substituent names and numbers +

parent + suffix.
• Alphabetize the substituents, ignoring prefixes.
• Precede the name of each substituent by the

number that indicates its location.
• There must be one number for each substituent.
• Separate numbers by commas and separate
numbers from letters by dashes.
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Alkane Nomenclature
methyl at C2
CH3
CH3 CH CH2 CH2 CH2 CH3
1 2
longest chain is 6 C’s = hexane
2-methylhexane
Answer 36
Alkane Nomenclature
methyl at C2
CH3
CH3 CH CH CH2 CH2 CH3
CH3 methyl at C3
1 2 3
longest chain is 6 C’s = hexane
2,3-dimethylhexane
Answer
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Alkane Nomenclature
Sample Problem 10.8
Give the IUPAC name for the following compound.
ethyl at C5
methyl at CH3 CH3CH2 H
C2
CH3 C CH2CH2 C C CH2CH3
H H CH3 methyl at C6
1 2 5 6
longest chain is 8 C’s = octane
5-ethyl-2,6-dimethyloctane
Answer
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Focus on Health and Medicine
Naming New Drugs
Most drugs have three names:
• Systematic: The IUPAC name—e.g.,

2-[4-(2-methylpropyl)phenyl]propanoic acid
• Generic: The official, internationally approved

name of the drug—e.g., ibuprofen
• Trade: The name assigned by the company that

manufactures the drug—e.g., Motrin or Advil
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Cycloalkanes
Simple Cycloalkanes
Cycloalkanes contain carbon atoms arranged in a ring.
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Cycloalkanes
Simple Cycloalkanes
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Cycloalkanes
Naming Cycloalkanes
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Cycloalkanes
Naming Cycloalkanes
HOW TO Name a Cycloalkane Using the IUPAC System
Step [1] Find the parent cycloalkane.
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Cycloalkanes
Naming Cycloalkanes
Step [2] Name and number the substituents.
• No number is needed for a cycloalkane with a

single substituent.
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Cycloalkanes
Naming Cycloalkanes
For rings with two or more substituents:

• begin numbering at one substituent
• then, proceed around the ring to give the second
substituent the lower number
For two different substituents, number the ring to

assign the lower number to the substituents
alphabetically.
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Cycloalkanes
Naming Cycloalkanes
Place CH3 groups at C1 and C3
1,3-dimethylcyclohexane
(not 1,5-dimethylcyclohexane)
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Cycloalkanes
Naming Cycloalkanes
Earlier letter = lower number
ethyl group at C1
methyl group at C3
1-ethyl-3-methylcyclohexane
(not 3-ethyl-1-methylcyclohexane)
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Focus on the Environment
Fossil Fuels
• Natural gas is composed mostly of methane,
which burns in the presence of oxygen, releasing
energy for cooking and heating.
• Petroleum is a complex mixture of compounds that

must be refined to separate it into usable fractions.
• Gasoline (C5H12–C12H26),
kerosene (C12H26– C16H34), and
diesel fuel (C15H32–C18H38) are some of the
products of petroleum refinement.
• Other portions are used to make plastics, drugs,
fabrics, dyes, and pesticides.
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Physical Properties
• Alkanes contain only nonpolar C–C and C–H
bonds.
• Alkanes exhibit only weak intermolecular forces,

so they have low melting points and boiling points.
• Smaller alkanes are gases at room temperature,

whereas larger alkanes are liquids.
• Alkanes are insoluble in water.
• Alkanes are less dense than water, meaning that

they will float on the surface of water.
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Physical Properties
• As the number of carbons in an alkane increases,
the boiling point increases:
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Combustion
• Alkanes have no functional group, so they undergo

few reactions.
• Combustion is an oxidation reaction.
• In the combustion reaction, alkanes burn in the

presence of O2 gas to form CO2 and H2O.
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Combustion
• The products, CO2 + H2O, are the same, regardless

of the identity of the alkane that undergoes
combustion.
• Combustion of alkanes in the form of natural gas,

gasoline, or heating oil releases energy for heating
homes, powering vehicles, and cooking food.
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Combustion
• If there is not enough O2 to react, incomplete

combustion may occur, and carbon monoxide (CO)
is formed instead of carbon dioxide (CO2).
• Carbon monoxide is a poisonous gas that binds

to hemoglobin in blood, thereby reducing the
amount of O2 that can be transported to cells.
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2

• Methane is the main • Ethylene is used as

# of bonds + # of lone pairs = 4

• A functional group contains a heteroatom, a

• The letter R is used to abbreviate the carbon

From Table 10.5:

All alkane molecules have names that end in the

# of C’s Name Structure

• IUPAC stands for International Union of Pure and

• The IUPAC system of nomenclature provides a

• Using the IUPAC system, each organic compound

• The parent name indicates the number of C’s in

• The suffix indicates what functional group is

• The prefix tells the identity, location, and number

Step [2] Number the atoms in the carbon chain to

Step [3] Name and number the substituents.

• Every carbon belongs to either the longest chain

• The following compound contains two methyl

Step [4] Combine substituent names and numbers +

• Precede the name of each substituent by the

longest chain is 6 C’s = hexane

longest chain is 6 C’s = hexane

• Systematic: The IUPAC name—e.g.,

• Generic: The official, internationally approved

• Trade: The name assigned by the company that

Step [1] Find the parent cycloalkane.

Step [2] Name and number the substituents.

• No number is needed for a cycloalkane with a

For rings with two or more substituents:

For two different substituents, number the ring to

Place CH3 groups at C1 and C3

Earlier letter = lower number

• Petroleum is a complex mixture of compounds that

• Alkanes exhibit only weak intermolecular forces,

• Smaller alkanes are gases at room temperature,

• Alkanes are insoluble in water.

• Alkanes are less dense than water, meaning that

• Alkanes have no functional group, so they undergo

• Combustion is an oxidation reaction.

• In the combustion reaction, alkanes burn in the

• The products, CO2 + H2O, are the same, regardless

• Combustion of alkanes in the form of natural gas,

• If there is not enough O2 to react, incomplete

• Carbon monoxide is a poisonous gas that binds

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