Q.Write Haloform reaction.
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Start your 14-day free trial to unlock the full solution →The haloform reaction converts a (or ) compound, on treatment with /, into a haloform () and the sodium salt of a carboxylic acid with one fewer carbon.
Compounds containing a methyl ketone group (), acetaldehyde (), or a secondary alcohol of the type (which is first oxidised in situ by the halogen to the corresponding methyl ketone/aldehyde) react with a halogen (, or ) in the presence of to give a haloform (, or ) and the sodium salt of a carboxylic acid containing one carbon less than the original methyl-ketone chain. This is called the haloform reaction; with iodine it is specifically called the iodoform reaction/test, giving a characteristic yellow precipitate of iodoform, .
Mechanism outline (using acetone + /NaOH as example):
- generates the enolate of acetone; the three hydrogens of the group alpha to the carbonyl are successively replaced by iodine (base-catalysed halogenation of the alpha carbon, repeated three times), giving .
- Hydroxide ion then attacks the carbonyl carbon of this tri-iodo ketone; the strongly electron-withdrawing group makes a good enough leaving group, so the bond cleaves, expelling the trihalomethyl carbanion and leaving (immediately deprotonated by excess to ).
- The carbanion picks up a proton from water/solvent to give the haloform, . …
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