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Nomenclature of Alkanes ( )

Chemists have developed a method of nomenclature that assigns a systematic, unique name to
each possible compound. The system presently used is called the IUPAC system, an
abbreviation for the International Union of Pure and Applied Chemistry.

The nomenclature of all other classes of compounds is based on the names of the alkane series.
The names of the first ten straight-chain (unbranched) alkanes is shown in the table below.

No. carbons Name Formula Structure No. isomers


1 methane CH4 CH4 1

2 ethane C2H6 CH3CH3 1

3 propane C3H8 CH3CH2CH3 1

4 butane C4H10 CH3CH2CH2CH3 2

5 pentane C5H12 CH3CH2CH2CH2CH3 3

6 hexane C6H14 CH3(CH2)4CH3 5

7 heptane C7H16 CH3(CH2)5CH3 9

8 octane C8H18 CH3(CH2)6CH3 18

9 nonane C9H20 CH3(CH2)7CH3 35

10 decane C10H22 CH3(CH2)8CH3 75

Removal of a terminal hydrogen from an alkane generates an alkyl group.

Below are the names of some common alkyl groups.

H3C CH
H3C H3C CH2 H3C CH2 CH2 H3C CH CH3
methyl ethyl propyl (or n-propyl) isopropyl CH3

CH3 CH3
H3C CH2 CH2 CH2 H3C CH CH2 H3C CH2 CH CH3 H3C C CH3

butyl (or n-butyl) isobutyl sec-butyl tert-butyl

n = normal indicates a straight chain alkane (all 1 and 2 carbons)


The IUPAC rules for naming alkanes are given below and will be illustrated by naming the
alkane below:

CH3
CH2
H3C CH2 CH2 CH CH CH3
H2C CH3

Rule 1: Selecting and Naming the Longest Chain.

Name the compound as a derivative of the alkane represented by the longest chain or continuous
sequence of carbon atoms. In the above compound, the longest chain contains 7 carbons (do you
see it?). The compound is therefore named as a heptane, and is considered to be a derivative of
this parent compound. The name must end in the suffix ane to indicate the compound is a
member of the alkane series. Except for the first four members of the alkane series, the prefix of
the name donates the number of carbon atoms in the chain. Thus, for example, hept indicates 7
carbons.

Rule 2: Numbering the Longest Carbon Chain.

Number the carbon atoms of the longest chain so that the branching group(s) are on the lowest
numbered carbon atoms.

Rule 3: Locating the Branching Groups.

The location of the branching hydrocarbon groups is indicated by the number of the carbon atom
of the parent chain to which they are attached. Thus, in our illustrative compound, we find a CH3
group on C-3 and a CH3CH2 group on C-4.

Rule 4: Naming the Branched Groups.

Each branched group is named according to the number of carbons on its longest chain. To name
the group, replace the suffix ane by yl. Thus, CH3 is called methyl since it stems from
methane, and CH3CH2 is named ethyl from ethane.

Rule 5: Arranging the Names of the Branched Groups.

The names of these groups are prefixed alphabetically with the number of the carbon atom to
which each group is attached. Thus, the name of the compound illustrated above is:

_____________________________
Rule 6: Punctuation.

The rules of punctuation are:

1. words are run together


2. a dash is used to separate a number from a word
3. a comma is used to separate numbers.

The following examples further illustrate the method:

CH3 CH3 CH2 CH3 CH3


CH3 CH2 CH2 C CH3 H3C CH C CH CH3
CH3 CH3
2,2-dimethylpentane 2,3,3,4-tetramethylhexane

Note the repetition of numbers when a group appears twice on the same carbon, and the use of
di- and tri- to indicate the number of times the groups appears in as a branch.

A problem that is sometimes encountered is to draw all of the isomers with a certain molecular
formula. This is done on the next page for the formula C7H16. This is easy to do if it is done
systematically. The best way is to start with the longest possible carbon chain (seven in this
case), draw it, then proceed to all possible structures with six carbons in the chain, etc. One way
to insure that you do not duplicate a structure is to give it an IUPAC name. If two structures
have the same correct IUPAC name, then the are simply two representations of the same
compound.
Constitutional isomers of heptane: C7H16

Constitutional isomers have the same molecular formula, but differ in way in their atoms are
connected.

H3C CH2 CH2 CH2 CH2 CH2 CH3 heptane

CH3
CH3 CH2 CH2 CH2 CH CH3 2-methylhexane

CH3
3-methylhexane
CH3 CH2 CH2 CH CH2 CH3

CH3
CH2
CH3 CH2 CH CH2 CH3 3-ethylpentane

CH3
CH3 CH2 CH2 C CH3 2,2-dimethylpentane
CH3

CH3 CH3

CH3 CH2 CH CH CH3 2,3-dimethylpentane

CH3 CH3

CH3 CH CH2 CH CH3 2,4-dimethylpentane

CH3
CH3 CH2 C CH2 CH3 3,3-dimethylpentane
CH3

CH3 CH3

CH3 CH C CH3 2,2,3-trimethylbutane

CH3

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