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Cyclohexanone is heated with pyrrolidine (a secondary amine) and a trace of acid with removal of water. The product is

  1. A1-(cyclohex-1-en-1-yl)pyrrolidine
  2. B2-(pyrrolidin-1-yl)cyclohexanone
  3. C1-cyclohexylpyrrolidine
  4. Dcyclohexanol

Answer: A

A secondary amine forms an iminium ion with the ketone. The iminium nitrogen has no N-H to lose, so an alpha proton is lost instead and the enamine is formed.
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