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JEE Main levelSingle correct optionDifficulty 2 of 3g3252

The ketone shown is stirred with sodium ethoxide in ethanol at C (equilibrating conditions) and then treated with benzyl bromide. Which structure shown is the major C-alkylation product?

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

Answer: C

The ketone shown is 2-methylcyclopentanone. A weak base at room temperature lets the enolates equilibrate, so the more stable, more substituted (tetrasubstituted) thermodynamic enolate predominates. Its C-alkylation with benzyl bromide at C2 gives 2-benzyl-2-methylcyclopentanone, a quaternary centre; the kinetic product, the O-alkylation product and the dialkylated product are not the major compound.
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