JEE Main levelSingle correct optionDifficulty 2 of 3g3191
LDA gives the kinetic enolate of an unsymmetrical ketone mainly because
ALDA is a weak base so the enolates equilibrate
Bdiisopropylamine (pKa≈36) is a much weaker acid than the ketone (≈20), so deprotonation is irreversible, and the bulky base removes the more accessible α-H faster
CLDA is small and reaches the most hindered α-H easily
Denolates equilibrate quickly at −78∘C by proton exchange with diisopropylamine
Answer: B
The pKa gap makes the proton transfer essentially one-way, so no equilibration to the stable enolate. The bulky base reacts faster at the less hindered α-position. The enolate formed first is retained.