Alkanes

Saturated hydrocarbons (Aliphatic)

Hydrocarbons Contain only C and H atoms.

Saturated Only single bonds.
Aliphatic Fat like.
Can be acyclic (no rings) or cyclic
(cycloalkanes).

Alkanes
Methane, CH4

H C H
H

Ethane, CH3CH3
H H
H C C H
H H

Alkanes
Propane, CH3CH2CH3
H H H
H C C C H
H H H

Butane, CH3CH2CH2CH3
H H H H
H C C C C H
H H H H

Alkanes
Pentane, CH3CH2CH2CH2CH3
Hexane, CH3CH2CH2CH2CH2CH3
Heptane, CH3CH2CH2CH2CH2CH2CH3
Octane, CH3CH2CH2CH2CH2CH2CH2CH3
Nonane, CH3CH2CH2CH2CH2CH2CH2CH2CH3
Decane, CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3

Isomers
Consider Butane C4H10
H H H H
H C C C C H
H H H H
Normal Butane

H
C

H C C C H
H H H
Isobutane

These structures are constitutional isomers

Isomers
Consider Butane C4H10
H H H H
H C C C C H
H H H H
(Normal) Butane n-Butane

H
C

H C C C H
H H H
Isobutane

These structures are constitutional isomers (Have

the same Molecular Formula but differ in the
way the atoms are connected)

Pentanes: C5H12
CH3CH2CH2CH2CH3

n-pentane

CH3
CH3CHCH2CH3

isopentane

CH 3
CH3CCH3
CH 3

neopentane

IUPAC Rules
Rule 1: Find the longest continuous chain of
carbon atoms, and use the name of this chain
as the base name of the compound.
Rule 2: Number the longest chain, beginning
with the end of the chain nearest a
substituent.
Rule 3: Name the groups attached to the
longest chain as alkyl groups. Give the
location of each alkyl group by the number of
the main-chain carbon atom to which it is
attached.
Write the alkyl groups in alphabetical order
regardless of their position on the chain.
Chapter 3

Examples
5

CH3

CH2

CH2

CH
CH3

3-methylpentane

CH3

parent alkane

alkyl group

Examples
5

CH3

CH2

CH2

CH
CH3

3-methylpentane

CH3

parent alkane

alkyl group

Examples
5

CH3

CH2

CH2

CH
CH3

3-methylpentane

CH3

parent alkane

alkyl group

Examples
5

CH3

CH2

CH2

CH
CH3

2-methylpentane

CH3

parent alkane

alkyl group

Examples
5

CH3

CH2

CH2

CH
CH3

CH3

parent alkane

alkyl group

2-methylpentane
Numbers and Words are separated by a hyphen

Common Alkyl Substients

2 Carbon

3 Carbon

Examples
1

CH3

CH

CH

CH3

CH3

CH3

2,3-dimethylbutane

CH3

CH2

CH3

C CH3

CH3
2,2-dimethylbutane

Examples
1

CH3

CH

CH

CH3

CH3

CH3

2,3-dimethylbutane

CH3

CH2

CH3

C CH3

CH3
2,2-dimethylbutane

Examples
1

When the same alkyl CH3 CH CH CH3

group branch chain
CH3 CH3
occurs more than
2,3-dimethylbutane
once, indicate this
repetition by a prefix
(di-, tri-, tetra-, and
CH3
so forth). The prefix 4
3
2
1
CH3 CH2
C CH3
doesnt count
towards alphabetical
CH3
order!
2,2-dimethylbutane

Examples
1

CH3

CH

CH

CH3

CH3

CH3

2,3-dimethylbutane

CH3

CH2

CH3

C CH3

CH3
2,2-dimethylbutane

Examples
1

CH3 CH CH CH3
Include a position
number for each
CH3 CH3
substituent, even it
2,3-dimethylbutane
means repeating a
number more than
CH3
once. (Numbers are
4
3
2
1
separated from other CH
CH2
C CH3
3
numbers by comas)
CH3
2,2-dimethylbutane

Examples
7

CH3

CH
CH3

CH2

CH3
CH
4

CH

CH3
CH
2

CH3

2,3,4,6-tetramethylheptane

CH3

Examples
7

CH3

CH
CH3

CH2

CH3
CH
4

CH

CH3
CH
2

CH3

CH3

2,3,4,6-tetramethylheptane

Note: Number the chain so that the substituents get

the lowest possible numbers.

Examples
7

CH3

CH
CH3

CH2

CH3
CH
4

CH

CH3
CH
2

CH3

CH3

2,3,4,6-tetramethylheptane

Note: Number the chain so that the substituents get

the lowest possible numbers.

Examples
2

CH3

CH2

CH3

CH

CH2

CH2
5

3-methylhexane

CH3
6

When looking for the longest

continuous chain (to give the
base name), look to find all the
different chains of that length.
Often, the longest chain with
the most substituents is not
obvious.

Examples
2

CH3

CH2

CH3

CH

CH2

CH2
5

CH3
6

3-methylhexane

Caution: Be careful to choose the longest chain as

the parent alkane.

Examples
2

CH3

CH2

CH3

CH

CH2

CH2
5

CH3
6

3-methylhexane

Caution: Be careful to choose the longest chain as

the parent alkane.

Problem 3-2
Give a systematic (IUPAC) name for the following
compound.

When substituents are

alphabetized, iso- is used as part of
the alkyl group name, but the
hyphenated prefixes are not.
Thus isobutyl is alphabetized with i,
but n-butyl, tert-butyl, and sec-butyl
are alphabetized with b.
Chapter 3

28