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JEE Advanced levelSingle correct optionDifficulty 3 of 3si214

Benzene is acylated with and anhydrous to give A. A is reduced with Zn-Hg/conc. HCl to give B. B is heated with alkaline and then acidified to give C. C is treated with to give D. D is

  1. A4-bromobenzoic acid
  2. B3-bromobenzoic acid
  3. C2-bromobenzoic acid
  4. Dbenzoyl bromide

Answer: B

A is acetophenone, B is ethylbenzene (Clemmensen), C is benzoic acid (any alkyl side chain with a benzylic H is oxidised to COOH). The carboxyl group is a meta director, so bromination gives 3-bromobenzoic acid.
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