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Chemistry · Ch 12 — Carbonyl Compounds and Carboxylic Acids

Nomenclature of Aldehydes and Ketones

12.1

Nomenclature of Aldehydes and Ketones

Aldehydes and ketones both carry the carbonyl group (>C=O) and are named by the same IUPAC machinery used for other organic families: find the longest carbon chain that includes the carbonyl carbon, replace the alkane's '-e' ending with '-al' for an aldehyde (the carbonyl carbon is always numbered C1, since it must sit at the end of the chain) or '-one' for a ketone (the carbonyl carbon gets the lowest possible locant, cited before the '-one' suffix, since it can sit anywhere along an interior chain). Common names remain in wide use alongside IUPAC names -- formaldehyde (methanal), acetaldehyde (ethanal), acetone (propanone), benzaldehyde (phenylmethanal) -- and are built the same way common names of acids are (see 12.8), by simply substituting a family-ending onto the familiar trivial root. Substituent prefixes (chloro, hydroxy, oxo, phenyl, alkyl branches) are cited exactly as for any other IUPAC name, each with its own locant, and a second carbonyl group present as a substituent elsewhere on the chain is cited as an 'oxo-' pre …

Table 12.1Common names, structures and IUPAC names of representative aldehydes and ketones
Compound (common name)Structural formulaIUPAC name
FormaldehydeH-CHOMethanal
AcetaldehydeCH3-CHOEthanal
AcroleinCH2=CH-CHOProp-2-enal
CrotonaldehydeCH3-CH=CH-CHOBut-2-enal
GlyceraldehydeHOCH2-CH(OH)-CHO2,3-Dihydroxypropanal
BenzaldehydeC6H5-CHOPhenylmethanal
Acetone / Dimethyl ketoneCH3-CO-CH3Propanone
Mesityl oxide(CH3)2C=CH-CO-CH34-Methylpent-3-en-2-one
Methyl phenyl ketoneC6H5-CO-CH31-Phenylethan-1-one (Acetophenone, PIN)
Diphenyl ketoneC6H5-CO-C6H5Diphenylmethanone (Benzophenone, PIN)
-- (an oxo-substituted aldehyde)CH3-CH2-CO-CH2-CHO3-Oxopentanal
Misc evaluate-yourself-1Evaluate Yourself -- IUPAC names and structural/position isomers

Worked out. Book's practice box (no printed solution). (i) Write the IUPAC name for: (a) CH3-CHO; (b) (CH3)2C=CH-CO-CH3; (c) a drawn cyclic ketone; (d) (CH3)2C(OH)-CH2-CHO. Working these through: (a) is simply ethanal; (b) is 4-methylpent-3-en-2-one (identical to the mesityl oxide example above); (d) is 3-hydroxy-3-methylbutanal, numbering from the CHO carbon as C1 so the chain-end aldehyde keeps locant 1 and the hydroxyl/methyl-bearing carbon is C3. (ii) Write all possible structural and position isomers of the ketone C5H10O: the carbonyl can sit at C2 or C3 of a straight pentane chain (pentan-2-one, pentan-3-one) or on a branched, methyl-substituted butane chain (3-methylbutan-2-one), giving three constitutionally distinct ketones of this formula …