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Chemistry · Ch 11 — Organic Chemistry: Some Basic Principles

IUPAC Nomenclature — Basic Rules for Hydrocarbons

11.3

IUPAC Nomenclature — Basic Rules for Hydrocarbons

The IUPAC (International Union of Pure and Applied Chemistry) system gives every organic compound exactly one systematic name, built up in a fixed sequence of steps.

Step 1 -- choose the parent chain. Identify the longest continuous chain of carbon atoms in the molecule; this becomes the 'parent chain' and is named with a word stem that states the number of carbon atoms it contains -- meth\text{meth}- (1), eth\text{eth}- (2), prop\text{prop}- (3), but\text{but}- (4), pent\text{pent}- (5), hex\text{hex}- (6), hept\text{hept}- (7), oct\text{oct}- (8), non\text{non}- (9), dec\text{dec}- (10) -- followed by a suffix that states how saturated the chain is: −ane-\text{ane} for a chain with only single bonds, −ene-\text{ene} for one carbon-carbon double bond, and −yne-\text{yne} for one carbon-carbon triple bond.

Step 2 -- number the chain. Number the carbon atoms of the parent chain from whichever end gives the lowest possible locants, applying this order of priority if there is a choice: first to the principal characteristic group (Section 11.4), then to any carbon-carbon multiple bond, and only then to substituent groups.

Step 3 -- name the substituents. Any carbon branch hanging off the parent chain is named as an alkyl substituent, formed by dropping the −ane-\text{ane} ending of the corresponding alkane and adding −yl-\text{yl}: methyl\text{methyl} (−CH3-\text{CH}_3), ethyl\text{ethyl} (−C2H5-\text{C}_2\text{H}_5), propyl\text{propyl}, and so on. Each substituent is written as a prefix to the parent name, preceded by the locant number of the carbon it is attached to.

Step 4 -- combine and order the name. When two or more different substituents are present, they are cited in alphabetical order of their names in the final written name -- never in order of their locant numbers. For instance, in 4-ethyl-2-methylhexane, 'ethyl' (attached at C-4) is written before 'methyl' (attached at C-2) purely because 'e' comes before 'm' alphabetically; the numbering itself is separately chosen (Step 2) to keep the overall set of locants {2,4}\{2,4\} as low as possible, which is lower than the alternative numbering that would give {3,5}\{3,5\} from the other end of the chain. …