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JEE Advanced levelSingle correct optionDifficulty 3 of 3o1092

Cyclohexanone is treated with (i) pyrrolidine, cat., remove water; (ii) ; (iii) aqueous . The final product is

  1. A2-methylcyclohexanone
  2. B2,6-dimethylcyclohexanone as the only product
  3. CN-methylpyrrolidine
  4. D1-methylcyclohexan-1-ol

Answer: A

Step (i) gives the enamine. The nucleophilic enamine beta-carbon (ring carbon 2) is alkylated by to give an iminium salt (Stork enamine alkylation). Aqueous acid hydrolyses the iminium to the ketone, giving 2-methylcyclohexanone and recovering pyrrolidine.
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