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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o1106

Which of the following carbonyl compound / amine pairs give an ENAMINE as the isolable condensation product (with acid catalysis and water removal)?

  1. Apropanal and piperidine
  2. Bcyclohexanone and cyclohexylamine
  3. Cbenzaldehyde and pyrrolidine
  4. Dcyclohexanone and pyrrolidine

Answer: A, D

An enamine needs a secondary amine and a carbonyl compound with an alpha hydrogen to lose after iminium formation. Cyclohexanone + pyrrolidine and propanal + piperidine fit. Cyclohexylamine is a primary amine and gives an imine. Benzaldehyde has no alpha hydrogen, so it cannot give an enamine with pyrrolidine.
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