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NEET levelSingle correct optionDifficulty 1 of 3g3251

LDA in THF at C is added to the ketone shown. At which position does it remove a proton mainly?

  1. AThe CH group attached to the carbonyl carbon (less hindered).
  2. BThe carbonyl carbon.
  3. CThe isopropyl C-H on the other alpha carbon (more substituted).
  4. DBoth alpha positions equally.

Answer: A

The ketone shown is 3-methylbutan-2-one with two alpha carbons: the CH and the tertiary CH. The bulky base LDA at C acts under kinetic control and removes the more accessible, less hindered proton, giving the less substituted enolate. The carbonyl carbon has no hydrogen, and the two sites are not equivalent.
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