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JEE Advanced levelSingle correct optionDifficulty 3 of 3o1162

Cyclohexanone is treated in sequence with (i) pyrrolidine, trace acid, water removed; (ii) ; (iii) . The final organic product is

  1. Acyclohexyl acetate
  2. B2-acetylcyclohexan-1-one
  3. C1-acetylcyclohexan-1-ol
  4. D1-acetylpyrrolidine only

Answer: B

The enamine carbon attacks the acyl chloride carbon (Stork acylation), giving an acylated iminium ion. Aqueous hydrolysis removes the amine to give the 1,3-diketone 2-acetylcyclohexan-1-one. O-acylation would give an ester, but C-acylation is the observed pathway.
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