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JEE Advanced levelSingle correct optionDifficulty 3 of 3g3074

Propanone is stirred with but-3-en-2-one () in the presence of aqueous and the mixture is heated. A Michael addition is followed by an intramolecular aldol condensation. The final cyclic product is

  1. ACyclohexane-1,3-dione
  2. B3-Methylcyclopent-2-en-1-one
  3. C3-Methylcyclohex-2-en-1-one
  4. D2-Methylcyclohex-2-en-1-one

Answer: C

The propanone enolate adds to the beta carbon ( end) of the enone, giving (heptane-2,6-dione). A terminal enolate then attacks the carbonyl at the other end, closing a six-membered ring (C-1 to C-6 of the chain). Dehydration gives the conjugated enone with the methyl on the beta carbon, i.e. 3-methylcyclohex-2-en-1-one.
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