Specific Classes of Compounds

R-5.6.2 Ketones, thioketones, and their analogues

R- Ketones. The generic term "ketone" refers to compounds containing a carbonyl group, >C=O, joined to two carbon atoms. Ketones are named substitutively by adding a suffix such as "-one", and "-dione" to the name of a parent hydride with elision of the final "e" of the parent hydride, if any, before "o". When a group having priority for citation as principal characteristic group is present, a ketone is described by the prefix "oxo-". Functional class names for monoketones and vicinal diketones, etc., are formed by citing the prefix names for the two groups attached to the carbonyl group(s) in alphabetical order followed by the class name "ketone", "diketone", etc., as a separate word.

Examples to R-

Diketones derived from cyclic parent hydrides having the maximum number of noncumulative double bonds by conversion of two -CH= groups into >CO groups with rearrangement of double bonds to a quinonoid structure may be named alternatively by adding the suffix "-quinone" to the name of the aromatic parent hydride.

Example to R-

Acyl derivatives of benzene or naphthalene have been named by changing the "-ic acid" or "-oic acid" ending of a trivial name of the acid corresponding to the acyl group to "-ophenone" or "-onaphthone". Only the names acetophenone, propiophenone, and benzophenone are retained in these recommendations (see R-9.1, Table 27(a)). Acyl derivatives of cyclic parent hydrides are named by prefixing the substituent name derived from the cyclic parent hydride to the name of the acyclic ketone.

Example to R-

Some trivial names are retained (see R-9.1, Table 27(a)).

R- Chalcogen analogues of ketones are named by using suffixes such as "-thione" and "-selone", and prefix names such as "thioxo-" and "selenoxo-". The use of prefixes such as "thio-" and "seleno-" with the trivial names of ketones, such as acetone, to indicate replacement of the ketonic oxygen atom with a chalcogen atom is not recommended.

Examples to R-

R-5.6.3 Ketenes
R-5.6.4 Acetals, hemiacetals, acylals, and their analogues
R-5.6.5 Acyloins
R-5.6.6 Nitrogenous derivatives of carbonyl compounds

This HTML reproduction is as close as possible to the published version [see IUPAC, Commission on Nomenclature of Organic Chemistry. A Guide to IUPAC Nomenclature of Organic Compounds (Recommendations 1993), 1993, Blackwell Scientific publications, Copyright 1993 IUPAC]. If you need to cite these rules please quote this reference as their source.

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