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JEE Main levelSingle correct optionDifficulty 2 of 3g3069

Propanone is treated with one equivalent of in THF at and then with iodomethane. What is the major product?

  1. APropan-2-ol
  2. B2,2-Dimethylpropanal
  3. CButan-2-one
  4. D2-Methoxyprop-1-ene

Answer: C

converts propanone completely into its enolate . This ambident nucleophile reacts with a soft electrophile like at carbon (C-alkylation), giving . O-alkylation would give the enol ether, which is minor. Propan-2-ol would need a reducing agent.
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