Nomenclature
To name a hydrocarbon, you must
- pick the main chain and number it;
- identify all side branches;
- name each side branch in order;
- name the main chain.
As long as you can do each step individually, putting it all together isn’t that hard. It does require practice, though.
Main chain
- alkane
- [ prefix]ane, where prefix represents the number of carbon atoms in the main chain (see the table below)
- alkene
- #-[ prefix]ene; #,#-[ prefix]diene; #,#,#-[ prefix]triene; etc.; where each # represents the location of a double bond and the part in bold indicates the number of double bonds
- alkyne
- like alkenes, but ending in yne instead of ene
- alicyclic
- like alkanes/alkenes/alkynes, but add cyclo before the prefix
- aromatic
- always benzene
Prefix | atoms |
---|---|
meth | 1 |
eth | 2 |
prop | 3 |
but | 4 |
pent | 5 |
hex | 6 |
hept | 7 |
oct | 8 |
non | 9 |
dec | 10 |
Side branches
Side branches (alkyl groups) are named like #-[ prefix]yl, #,#-di[ prefix]yl, etc., where prefix is the number of carbon atoms in the branch, each # represents the location of the branch on the main chain, and the part in bold indicates the number of this type of branch.
Propyl and butyl groups have non-systematic names for their isomers:
If there are two side branches coming off an aromatic, a classical method can be used instead of numbers: ortho or o- means 1,2; meta or m- means 1,3; and para or p- means 1,4. For example, 1,4-diethylbenzene is the same as p-diethylbenzene.
There are special names for branches that aren’t alkyl groups:
Branch | Name |
---|---|
benzene | phenyl |
F | fluoro |
Cl | chloro |
Br | bromo |
I | iodo |
NO2 | nitro |
NH2 | amino |
OH | hydroxy |
Guidelines
- Always pick the longest main chain possible.
- If there are any double or triple bonds, the main chain must contain all of them, even if this results in a shorter main chain.
- Number the main chain to prefer small numbers, prioritizing the double or triple bonds, then the side branches, and then everything in total (2,2,4 is better than 2,4,4).
- Name side branches in alphabetical order (triethyl comes before dimethyl).
- Numbers separated by commas should be listed in ascending order.
- Put commas between numbers, and hyphens at number–word boundaries.