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JEE Main levelSingle correct optionDifficulty 2 of 3g3064

2-Methylcyclohexan-1-one is treated with (lithium diisopropylamide) in THF at (kinetic control). Which proton is removed fastest?

  1. AA hydrogen of the methyl group on C-2
  2. BA hydrogen on C-3
  3. CA hydrogen on C-6 (the on the side away from the methyl group)
  4. DThe hydrogen on C-2 (the bearing the methyl group)

Answer: C

The bulky base at low temperature removes the more accessible, less hindered alpha proton irreversibly. The alpha carbons are C-2 (a hindered methine) and C-6 (a methylene), so C-6 is attacked. This gives the less substituted (kinetic) enolate. The methyl hydrogens and the C-3 hydrogens are not alpha to the carbonyl.
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