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NEET levelSingle correct optionDifficulty 1 of 3g3249

The ketone shown is treated with LDA in THF at C (kinetic conditions). Which structure shown is the enolate formed mainly?

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

Answer: A

The ketone shown is 2-methylcyclohexanone. LDA is bulky and strong; at C it removes the more accessible proton from the less substituted alpha carbon (C6) faster than the hindered tertiary C2-H, giving the kinetic enolate with the less substituted C=C. The more substituted enolate is the thermodynamic enolate, which forms under equilibrating conditions.
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