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 3g3256

The ketone shown is treated with LDA in THF at C and then trimethylsilyl chloride. Which structure shown is the silyl enol ether formed under kinetic control?

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

Answer: A

The ketone shown is 4-methylpentan-2-one. LDA at C removes a proton from the less substituted and less hindered CH (kinetic enolate), and the oxygen of this enolate is trapped by the oxophilic silicon of to give the terminal silyl enol ether. Silylation of the CH side would give the more substituted (thermodynamic) silyl enol ether, and Si-C bonded products are not formed from enolates with .
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