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JEE Advanced levelSingle correct optionDifficulty 3 of 3nc110

Nitrobenzene is reduced with and aqueous to give Y. Y is then warmed with dilute to give Z as the major product. Z is

  1. A2-aminophenol
  2. B4-aminophenol
  3. Caniline
  4. Dazoxybenzene

Answer: B

Neutral reduction gives N-phenylhydroxylamine (Y). In warm dilute acid, Y undergoes the Bamberger rearrangement: the protonated hydroxylamine loses water to give a nitrenium-type ion that is attacked by water mainly at the para position, giving 4-aminophenol.
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