LANGE'S HANDBOOK OF CHEMISTRY

ORGANIC COMPOUNDS 1.33
by theword ketone. In addition to the preceding nomenclature, acyclic monoacyl derivatives of
cyclic compounds may benamed (3) by prefixing thenameof theacyl group to thenameof the
cyclic compound. For example, the three possible names of
(1) 1-(2-Furyl)-1-propanone
(2) Ethyl 2-furyl ketone
(3) 2-Propionylfuran
When the cyclic component is benzene or naphthalene, the -ic acid or -oic acid of the acid
corresponding to the acyl group is changed to -ophenone or -onaphthone, respectively. For example,
C 6H 59CO9CH 2CH 2CH 3 can be named either butyrophenone (or butanophenone) or phenyl propyl
ketone.
Radicofunctional nomenclature can be used when a carbonyl group is attached directly to carbon
atoms in two ring systems and no other substituent is present having priority for citation.
When the methylene group in polycarbocyclic and heterocyclic ketones is replaced by a keto
group, thechangemay bedenoted by attaching thesuffix -oneto thenameof thering system.
However, when CH in an unsaturated or aromatic system is replaced by a keto group, two alternative
names become possible. First, the maximum number of noncumulative double bonds is added
after introduction of the carbonyl group(s), and any hydrogen that remains to be added is denoted
as indicated hydrogen with the carbonyl group having priority over the indicated hydrogen for lowernumbered
locant. Second, the prefix oxo- is used, with the hydrogenation indicated by hydro prefixes;
hydrogenation is considered to have occurred before the introduction of the carbonyl group. For
example,
(1) 1-(2H)-Naphthalenone
(2) 1-Oxo-1,2-dihydronaphthalene
When another group having higher priority for citation as principal group is also present, the
ketonic oxygen may be expressed by the prefix oxo-, or one can use the name of the carbonylcontaining
radical, as, for example, acyl radicals and oxo-substituted radicals. Examples are
4-(4-Oxohexyl)-1-benzoic acid
1,2,4-Triacetylbenzene
Diketones and tetraketones derived from aromatic compounds by conversion of two or four
CH groups into keto groups, with any necessary rearrangement of double bonds to a quinonoid
structure, are named by adding the suffix -quinone and any necessary affixes.
Polyketones in which two or more contiguous carbonyl groups have rings attached at each end