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JEE Advanced levelSingle correct optionDifficulty 3 of 3g3106

Hexanediamide, , is treated with excess and aqueous . The organic product is

  1. APentane-1,5-diamine
  2. BHexane-1,6-diamine
  3. CButanedioic acid
  4. DButane-1,4-diamine

Answer: D

Each amide group undergoes Hofmann degradation, in which the carbonyl carbon is lost as carbonate and the alkyl group ends up bonded to . Two carbons (both carbonyl carbons) are removed from the six-carbon chain, leaving the four groups with an at each end, i.e. .
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