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JEE Main levelSingle correct optionDifficulty 2 of 3co240

The ketone shown is treated with one equivalent of LDA in THF at -78 C (kinetic control) and the enolate is then quenched with . Which structure is the major product (ignore cis/trans)?

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: B

The drawn compound is 2-methylcyclohexanone. The bulky strong base LDA at low temperature removes the more accessible proton at the less substituted C6 (kinetic enolate); methylation there gives 2,6-dimethylcyclohexanone. Structure A comes from the more substituted (thermodynamic) enolate, C is O-methylation and D is over-alkylation.
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