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JEE Advanced levelSingle correct optionDifficulty 3 of 3si026

A compound gives an orange precipitate with 2,4-DNP and a yellow precipitate with , is negative with Tollens and Fehling, and gives benzoic acid on vigorous oxidation. The two organic products of its reaction with are

  1. A and
  2. B and
  3. C and
  4. D and

Answer: A

A carbonyl, ketonic (Tollens negative) compound with and a benzene ring giving benzoic acid is acetophenone, . In the haloform reaction the group is tri-iodinated and the bond is cleaved, giving iodoform and sodium benzoate.
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