Chemistry · Ch 11 — Organic Chemistry: Some Basic Principles
IUPAC Nomenclature of Compounds Containing a Functional Group
IUPAC Nomenclature of Compounds Containing a Functional Group
Many organic molecules carry, in addition to a plain carbon skeleton, one or more functional groups -- specific atoms or groups of atoms, such as , , or , that are chiefly responsible for the molecule's characteristic chemical behaviour. When exactly one kind of functional group is present, it is written as a suffix added to the end of the parent chain name (dropping the final of the parent name before a suffix that itself begins with a vowel, e.g. ), and the parent chain is numbered so as to give this group the lowest possible locant -- overriding, if necessary, the numbering that a double bond or a substituent would otherwise prefer.
When a molecule contains more than one kind of functional group at once, IUPAC rules do not allow every group to be expressed as a suffix simultaneously. Instead, chemists rank functional groups in a fixed order of seniority, and only the single most senior group present -- called the principal characteristic group -- is expressed as the suffix and given the lowest locant; every other functional group present must then be cited only as a prefix. A short, commonly used part of this seniority order, from most to least senior, is: carboxylic acid > ester > amide > nitrile > aldehyde > ketone > alcohol > amine. So, for a molecule containing both an aldehyde and a ketone group, the aldehyde -- being senior to the ketone -- is always chosen as the suffix (), while the ketone's carbonyl is cited only as an - prefix. The table below lists the suffix used when a group is the principal characteristic group, together with the prefix used for the same group whenever it is not senior enough to be the suffix. …
Functional group | Suffix (as principal characteristic group) | Prefix (as substituent) | Example
Carboxylic acid, -COOH | -oic acid | carboxy- | ethanoic acid
Ester, -COOR' | -oate | alkoxycarbonyl- | methyl ethanoate
Amide, -CONH2 | -amide | carbamoyl- | ethanamide
Nitrile, -C#N | -nitrile | cyano- | ethanenitrile
Aldehyde, -CHO | -al | oxo- | ethanal
Ketone, >C=O | -one | oxo- | propan-2-one
Alcohol, -OH | -ol | hydroxy- | ethanol
Amine, -NH2 | -amine | amino- | ethanamine
Alkene, C=C | -ene | (none, part of parent name) | ethene …