fact sheet

How to name hydrocarbons

Hydrocarbons are compounds that contain only Number of Prefix for main Functional group
carbon and hydrogen. Carbon atoms have four carbon atoms chain
valence electrons, allowing them to bond in many
different ways. A carbon atom can bond to two, 1 meth- methyl
three or four other atoms, which means that 2 eth- ethyl
hydrocarbons can form a wide variety of structures. 3 prop- propyl
Aliphatic hydrocarbons form straight chains, alicyclic 4 but- butyl
hydrocarbons form rings of carbon atoms and
aromatic hydrocarbons contain a special structure 5 pent- pentyl
called a benzene ring (C6H6). 6 hex- hexyl
Aliphatic hydrocarbons can be divided into three 7 hept- heptyl
types, based on the number of bonds between 8 oct- octyl
neighbouring carbon atoms. These different types
have different properties due to their bonding. 9 non- nonyl
10 dec- decyl
• Alkanes have only single bonds between carbon
atoms.
• Alkenes contain at least one double bond between
a pair of carbon atoms. Hydrocarbon highest order Suffix / prefix
class bond
• Alkynes have at least one triple bond between
carbon atoms. alkane C C -ane
There are so many different hydrocarbon molecules alkene C C -ene
possible that a special naming system called IUPAC
(International Union of Pure and Applied Chemistry) alkyne -yne
C C
is used to identify them. This naming system has
specific rules so that each molecule has a unique cycloalkane C C cyclo ... ane
name.
1. The first part of the name is based on the length
cycloalkene C C cyclo ... ene
of the longest carbon chain in the molecule. cycloalkyne cyclo ... yne
C C
2. The end of the name is given by the number of
bonds between carbon atoms. If there are only
single bonds the name ends with ‘-ane’, if there
is at least one double bond (and no triple bonds) REPEATING UNITS PREFIX
the name ends in ‘-ene’, and if there is at least 1
one triple bond the name ends in ‘-yne’.
2 di-
3. Functional groups (branches coming off the
3 tri-
longest carbon chain) are named according to
their length and how many there are. 4 tetra-
4. Functional groups are numbered to show where
they are attached to the main chain. Carbon Where there’s more than one double or triple bond
atoms in the main chain are numbered from the in a molecule it’s conventional to add an ‘a’ to the
end closest to the functional groups (or the end prefix. For example, but-1-ene and buta-1,2-diene.
closest to a multiple bond if there is one).

This molecule has only single bonds, so it is an alkane and its name ends in -ane.
CH3
The longest chain has three carbons, so the prefix is prop-.

CH3 C CH3 The molecule has two (di-) single carbon (methyl-) branches, so it is a dimethylpropane.
Both branches come off the second carbon atom in the chain, so it starts 2,2-dimethyl-.
CH3 The full name is 2,2-dimethylpropane.

ast0271 | Hydrocarbon chemistry 3: How to name hydrocarbons (fact sheet) developed for the Department of Education WA
© The University of Western Australia 2011 for conditions of use see spice.wa.edu.au/usage
version 1.2 revised February 2015 page 1 Licensed for NEALS
Examples
Although this looks at first glance to be a heptane, the
H H H C2 H5 H H H methyl group at the left of the chain can be viewed as part
of the backbone.
H C C C C C C C H • The longest chain has eight carbon atoms, so it is an
octane.
CH3 H H CH3 H H H • The molecule has two branches, one with a single carbon
(methyl-) and one with two carbons (ethyl-).
• Both branches are attached to the fourth carbon atom.
• Full name is 4-ethyl-4-methyloctane.

• This molecule has a double bond, so it is an alkene with a

H CH3 H H name ending in -ene.
• The double bond is between the first and second carbon
H C C C C atoms, so it is a but-1-ene.
• Full name is 3,3-dimethylbut-1-ene.
H CH3 H

• This molecule is but-2-yne.

CH3 C C CH3

When a halogen (group 7 or 17 element) is substituted into

H H H a hydrocarbon, the halogen is treated as a functional group
(prefixes are fluoro-, chloro-, bromo- and iodo-).
CH3 C C C Cl • This molecule is 1-chlorobut-1-ene.

H H

• If the chain is numbered from the left this molecule

H H H CH3 H would be called 1-bromo-4-methylpent-3-ene.
• If the chain is numbered from the right it would be
Br C C C C C H 5-bromo-2-methylpent-2-ene.
• The chain is numbered in the direction that gives any
H H H multiple bonds the lowest possible number, so the correct
name is 5-bromo-2-methylpent-2-ene.

ast0271 | Hydrocarbon chemistry 3: How to name hydrocarbons (fact sheet) developed for the Department of Education WA
© The University of Western Australia 2011 for conditions of use see spice.wa.edu.au/usage
version 1.2 revised February 2015 page 2