Chemistry · Ch 11 — Organic Chemistry: Some Basic Principles
IUPAC Nomenclature — Basic Rules for Hydrocarbons
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 -- - (1), - (2), - (3), - (4), - (5), - (6), - (7), - (8), - (9), - (10) -- followed by a suffix that states how saturated the chain is: for a chain with only single bonds, for one carbon-carbon double bond, and 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 ending of the corresponding alkane and adding : (), (), , 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 as low as possible, which is lower than the alternative numbering that would give from the other end of the chain. …