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haloform reaction
The haloform reaction is a chemical reaction where a haloform (CHX3, where X is a halogen) is produced by the exhaustive halogenation of a methyl ketone (a molecule containing the R–CO–CH3 group) in the presence of a base.〔Chakrabartty, in Trahanovsky, ''Oxidation in Organic Chemistry'', pp 343–370, Academic Press, New York, 1978〕 R may be alkyl or aryl. The reaction can be used to produce chloroform (CHCl3), bromoform (CHBr3), or iodoform (CHI3).
==Scope==
Substrates that successfully undergo the haloform reaction are methyl ketones and secondary alcohols oxidizable to methyl ketones, such as isopropanol. The only primary alcohol and aldehyde to undergo this reaction are ethanol and ethanal, respectively. 1,3-Diketones such as acetylacetone also give the haloform reaction. β-ketoacids such as acetoacetic acid will also give the test upon heating. Acetyl chloride and acetamide don't give this test. The halogen used may be chlorine, bromine, or iodine. Fluoroform (CHF3) cannot be prepared from a methyl ketone by the haloform reaction due to the instability of hypofluorite, but compounds of the type RCOCF3 do cleave with base to produce fluoroform; this is equivalent to the second and third steps in the process shown above.
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