Haloform reaction

Haloform reaction
Named after Adolf Lieben
Reaction type Substitution reaction
Identifiers
Organic Chemistry Portal haloform-reaction
RSC ontology ID RXNO:0000689

In chemistry, the haloform reaction (also referred to as the Lieben haloform reaction) is a chemical reaction in which a haloform (CHX3, where X is a halogen) is produced by the exhaustive halogenation of an acetyl group (R−C(=O)CH3, where R can be either a hydrogen atom, an alkyl or an aryl group), in the presence of a base.[1][2][3] The reaction can be used to transform acetyl groups into carboxyl groups (R−C(=O)OH) or to produce chloroform (CHCl3), bromoform (CHBr3), or iodoform (CHI3). Note that fluoroform (CHF3) can't be prepared in this way.

Haloform reaction scheme
Haloform reaction scheme
  1. ^ March, Jerry; Smith, Michael B. (2007). Knipe, A.C. (ed.). March's Advanced Organic Chemistry Reactions, Mechanisms, and Structure (6th ed.). Hoboken: John Wiley & Sons. p. 484. ISBN 9780470084946.
  2. ^ Reynold C. Fuson and Benton A. Bull (1934). "The Haloform Reaction". Chemical Reviews. 15 (3): 275–309. doi:10.1021/cr60052a001.
  3. ^ Chakrabartty, in Trahanovsky, Oxidation in Organic Chemistry, pp. 343–370, Academic Press, New York, 1978