MolSynapsequestion bank
MolSynapse / Question bank / General Organic Chemistry III: Reaction Intermediates / Reaction energy profiles, kinetic vs thermodynamic control
JEE Main levelSingle correct optionDifficulty 2 of 3g3191

LDA gives the kinetic enolate of an unsymmetrical ketone mainly because

  1. ALDA is a weak base so the enolates equilibrate
  2. Bdiisopropylamine () is a much weaker acid than the ketone (), so deprotonation is irreversible, and the bulky base removes the more accessible -H faster
  3. CLDA is small and reaches the most hindered -H easily
  4. Denolates equilibrate quickly at 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 -position. The enolate formed first is retained.
Practice General Organic Chemistry III: Reaction Intermediates More on Reaction energy profiles, kinetic vs thermodynamic control

More questions on Reaction energy profiles, kinetic vs thermodynamic control