Nomenclature of Organic

Compounds
A Study Guide

A Level
Chemistry
 Nomenclature of Organic Compounds: A Study Guide

Introduction
1. The Functional Groups
Organic compounds are
named using the IUPAC
A functional group is an atom or group of atoms within a molecule which is
(International Union
responsible for the characteristic properties and reactions of that molecule.
of Pure and Applied
Chemistry) system of
Compounds with the same functional group form a homologous series.
nomenclature.

In the names of organic compounds, functional groups are denoted by prefixes

The name of an
and suffixes which precede or follow the root of the compound’s name.
organic compound is
constructed from the
Table 1 shows information about some common functional groups. In Table 1,
following parts:
R represents a saturated hydrocarbon chain of any length.

1. the functional
Table 1
group(s) present
within the Homologous Functional Group Prefix Suffix Example
compound; Series Structure

alkane a saturated -ane methane

2. the root, which is
hydrocarbon
derived from the
number of carbon alkene C=C -ene propene
atoms in the main
(parent) chain of halogenoalkane R-X fluoro– -ane fluoromethane
the compound; chloro- chloroethane
X is a halogen bromo- bromobutane
3. the position (fluorine, chlorine, iodo- iodooctane
and number bromine or iodine)
of functional
alcohol R-OH hydroxy- -ol ethanol
groups within
hydroxypropanone
the compound.
aldehyde R-CHO oxo- -al methanal
4-oxobutanoic acid

ketone R-CO-R oxo- -one propanone

2-oxobutanoic acid

carboxylic acid R-COOH carboxy- -oic methanoic acid

acid

amine R-NH2 amino- -amine ethylamine

aminopentanoic acid
nitrile R-C≡N cyano- -nitrile ethanenitrile
cyanoethanoic acid

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 Nomenclature of Organic Compounds: A Study Guide

Branched alkanes contain hydrocarbon side chains bonded at various positions along the main chain
of carbon atoms. The main carbon chain is known as the parent chain and can be identified by finding
the longest continuous chain of carbon atoms. Any chains which branch off from the parent chain
are known as alkyl chains. The length of the alkyl chain is denoted in the name of a compound by the
prefixes shown in Table 2.

Table 2

Number of Carbon Atoms in Alkyl Side Chain 1 2 3 4

Nomenclature of Alkyl Chain methyl- ethyl- propyl- butyl-

For example: methylpropane is a saturated hydrocarbon with a parent chain containing three carbon
atoms. It has a side chain bonded to the second carbon in the parent chain, containing one carbon
atom.

Figure 1

Methylpropane

Cyclic compounds are identified by the prefix cyclo-. For example, cyclohexane is a cyclic alkane.

Highest Priority carboxylic acid If an organic compound contains Figure 2

more than one functional group,
nitrile
the main functional group is the
aldehyde one with the highest priority:
ketone The functional group with the
alcohol highest priority determines the
amine suffix which will follow the root
of the molecule in its name.
alkene
Lowest Priority alkyl The prefix for all other functional
groups will precede the root in
alphabetical order.
Cyclohexane

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 Nomenclature of Organic Compounds: A Study Guide

2. The Root

Once the highest priority functional group has been identified, the next step is to find the longest
continuous chain of carbon atoms which includes the main functional group. This is known as the
parent chain. The number of carbon atoms in the parent chain provides the root (sometimes referred
to as the base or the stem) of the compound’s name, shown in Table 3.

Table 3

Number of Root of
Carbon Atoms in Compound Name
the Parent Chain
1 meth
2 eth
3 prop
4 but
5 pent
6 hex

These roots are also used to denote the number of carbon atoms in an alkyl chain in a branched
molecule. For example, a molecule whose parent chain has a side chain containing three
carbon atoms would have the prefix propyl-.

For example: butanone is a ketone with a parent chain containing four carbon atoms.

Figure 3

butanone

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 Nomenclature of Organic Compounds: A Study Guide

3. The Position and Number of Functional Groups

Number the carbon atoms of the parent chain, starting at the end of the chain that is closest to a
functional group.

The positions of functional groups are denoted with hyphens and numbers within the name of
the compound. There should always be a hyphen between a number and a letter in the name of
organic compounds and consecutive numbers should be separated by a comma. For example,
1,4-dichlorobutane and propan-1,3-diol.

The position of each functional group should always be included in the name of a compound unless
there is only one possible position for it, then the number is not necessary.

The molecule in Figure 4 contains the OH (alcohol) functional group, so we use the suffix -ol. There are
four carbon atoms in the parent chain, so we use the root ‘but’. The OH functional group appears at
the end of the parent chain. We must number the carbons in the chain from the end which is closest to
a functional group, so in this case we number the carbon atoms from right to left. It would be possible
for the OH group to be bonded to the second carbon atom in the chain, so we must include the position
number of this group. The molecule in Figure 4 is butan-1-ol.

Figure 4

4 3 2 1

butan-1-ol

If the same functional group is present more than once in the same compound, the number of functional
groups is represented by the prefixes shown in Table 4.

Table 4

Number of Occurrences of Functional Group Prefix

2 di-
3 tri-
4 tetra-
5 penta-
6 hexa-

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 Nomenclature of Organic Compounds: A Study Guide

The molecule in Figure 5 is a halogenoalkane containing chlorine atoms, so the prefix chloro- and the
suffix -ane will be used. It has five carbon atoms in the parent chain, so the root is ‘pent’. There are
chlorine atoms on the second, third and fourth carbon atoms from either end of the chain. It would be
possible for these three chlorine atoms to be in different positions along the parent chain, so we must
include their position in the name of the compound. The compound in Figure 5 is 2,3,4-trichloropentane.

Figure 5

1 2 3 4 5

2,3,4-trichloropentane

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 Nomenclature of Organic Compounds: A Study Guide

Summary

To determine the systematic IUPAC name of an organic compound, follow these steps:

1. Identify the main (highest priority) functional group. This gives you the suffix.
2. Count the number of carbon atoms in the longest continuous chain containing
the main functional group (the parent chain). This gives you the root.
3. Number the carbon atoms in the parent chain, starting at the end that is closest to a functional
group.
4. Use prefixes, in alphabetical order, to indicate any functional groups which are not the main
functional group.
5. Indicate the position and number of each functional group. Be sure to use a hyphen before
and after numbers within the compound’s name and separate numbers with commas.
6. Combine the parts of the name in the order prefix A + prefix B + root + suffix.

Examples

Example A contains the C=C (alkene) functional

1 4 group. This is represented by the suffix -ene.

2 3
There are four carbon atoms in the parent chain, so the root is ‘but’.

The C=C functional group appears between the second and third
carbon atoms in the chain. The lowest number should be used. It would
be possible for the C=C to be between the first and second carbon
atoms, so the functional group position must be included.

Example A is but-2-ene.

Example B is a cyclic saturated hydrocarbon. Saturated hydrocarbons

(alkanes) are named with the suffix -ane. The cyclic nature of this
alkane is denoted by the prefix cyclo-.

There are five carbon atoms in its ring, so the root is ‘pent’.

Example B is cyclopentane.

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 Nomenclature of Organic Compounds: A Study Guide

Example C has two functional groups:

5 4 3 2 1
• a chlorine atom, which is represented with
the prefix chloro- and the suffix -ane;
• and an alkyl side chain, containing one
carbon atom, which is represented
by the prefix methyl-.

The parent chain (the longest carbon chain) contains five carbon atoms, so the root will be ‘pent’.

The carbon atoms should be numbered from right to left, as shown, because the carbon atom on the
right is closest to a functional group.

The methyl group is bonded to the second carbon, so will be denoted by the prefix 2-methyl-.
The chlorine atom is bonded to the third carbon atom, so will be denoted by the prefix 3-chloro-.
Prefixes must be in alphabetical order.

Example C is 3-chloro-2-methylpentane.

Example D contains two functional groups:

• the R-CO-R (ketone) functional group;

• and the OH (alcohol) functional group.

The suffix is determined by the highest priority functional group, in this case the ketone, so the
suffix will be -one.

Since the OH group is of lower priority in this compound it will be represented by its prefix,
hydroxy-.

The parent chain contains three carbon atoms, so the root is ‘prop’.

In a ketone with just three carbon atoms, there is only one possible position for the C=O bond (if
it were at the end of the carbon chain the compound would be an aldehyde instead). Therefore,
no number is needed to indicate its position.

The carbon chain would be numbered starting from whichever end the OH group is bonded to,
the OH group can only be positioned at the first carbon in the chain. So, no number is needed to
indicate its position.

Example D is hydroxypropanone.

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