MolSynapsequestion bank
MolSynapse / Question bank / General Organic Chemistry III: Reaction Intermediates / Kinetic vs thermodynamic enolate site on drawn ketones
JEE Advanced levelSingle correct optionDifficulty 3 of 3g3258

The ketone shown is treated with LDA in THF at C. Which structure shown is the enolate formed under kinetic control?

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: C

The ketone shown is cyclohex-2-enone. The alpha' protons at C6 are the only alpha protons that are removed quickly by LDA at low temperature, giving the cross-conjugated kinetic enolate (C1=C6 with the C2=C3 bond retained). The extended, fully conjugated dienolate formed by removal of a gamma proton at C4 is the thermodynamic enolate, and the other structures are not enolates.
Practice General Organic Chemistry III: Reaction Intermediates More on Kinetic vs thermodynamic enolate site on drawn ketones

More questions on Kinetic vs thermodynamic enolate site on drawn ketones