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JEE Main levelSingle correct optionDifficulty 2 of 3co024

Cyclohexanone is heated with pyrrolidine (a cyclic secondary amine) and a catalytic amount of acid, with water being removed. The product is

  1. A2-(pyrrolidin-1-yl)cyclohexan-1-one
  2. B1-(cyclohex-1-en-1-yl)pyrrolidine
  3. Ccyclohexanone oxime
  4. D1-(pyrrolidin-1-yl)cyclohexan-1-ol

Answer: B

A secondary amine gives a carbinolamine which cannot form a neutral C=N bond, because nitrogen has no second hydrogen. Loss of water therefore proceeds towards the alpha carbon, giving the enamine.
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