MolSynapsequestion bank
MolSynapse / Question bank / General Organic Chemistry III: Reaction Intermediates / Reaction energy profiles, kinetic vs thermodynamic control
JEE Main levelOne or more correct optionsDifficulty 2 of 3g3198

For 2-methylcyclohexan-1-one, which statements are correct?

  1. ALDA is a weaker base than NaOEt, which is why it gives the kinetic enolate
  2. BThe more substituted enolate is the kinetic enolate
  3. CNaOEt in EtOH, under equilibrating conditions, gives mainly the more substituted enolate
  4. DLDA in THF at gives mainly the less substituted enolate

Answer: C, D

Irreversible deprotonation with the bulky, strong base LDA gives the less substituted kinetic enolate. A weaker base in a protic solvent equilibrates the enolates, giving the more substituted thermodynamic one. LDA (conjugate acid pKa about 36) is a much stronger base than NaOEt (about 16).
Practice General Organic Chemistry III: Reaction Intermediates More on Reaction energy profiles, kinetic vs thermodynamic control
Previous questionNext question

More questions on Reaction energy profiles, kinetic vs thermodynamic control