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JEE Advanced levelSingle correct optionDifficulty 3 of 3co158

1-(4-Methylphenyl)ethan-1-one is subjected to Wolff-Kishner reduction to give X. X is heated with excess alkaline and the mixture is acidified to give Y. Y is

  1. Abenzoic acid
  2. B4-ethylbenzoic acid
  3. C4-methylbenzoic acid
  4. Dbenzene-1,4-dicarboxylic acid

Answer: D

Wolff-Kishner converts into , giving X = 1-ethyl-4-methylbenzene. Hot alkaline oxidises every alkyl side chain bearing a benzylic hydrogen to , so both groups become carboxylic acids: benzene-1,4-dicarboxylic acid.
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