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JEE Advanced levelSingle correct optionDifficulty 3 of 3si157

Benzene is treated with to give A. A is heated with (excess) and acidified to give B. B is treated with to give C, C with excess to give D, and D with (heat) to give E. E is

  1. Abenzamide
  2. Bphenol
  3. Cbenzylamine
  4. Daniline

Answer: D

A is acetophenone. The haloform reaction cleaves the group to give benzoate, giving benzoic acid (B) after acidification and then benzoyl chloride (C). Ammonia gives benzamide (D). Hofmann bromamide degradation removes the carbonyl carbon, so E is (aniline).
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