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Which one of the following compounds undergoes HVZ reaction?

  • A.\(\mathrm{C_{6}H_{5}COOH}\)
  • B.\(\mathrm{CH_{3}CH_{2}COOH}\)
  • C.\(\mathrm{Cl_{3}C-COOH}\)
  • D.\(\mathrm{CH_{3}CH_{2}CHO}\)
  • E.HCOOH

Answer: B

The compound that undergoes the HVZ reaction is \(\mathrm{CH_{3}CH_{2}COOH}\).

The Hell-Volhard-Zelinsky reaction halogenates a carboxylic acid at the alpha carbon, using Cl2 or Br2 with red phosphorus. It needs a hydrogen on the alpha carbon. Propanoic acid has two, and gives 2-halopropanoic acid.

Benzoic acid and formic acid have no alpha carbon bearing hydrogen, and trichloroacetic acid, Cl3C-COOH, has its alpha hydrogens already replaced. Propanal is an aldehyde, not a carboxylic acid, so the reaction does not apply.

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