MolSynapsequestion bank
MolSynapse / Question bank / General Organic Chemistry III: Reaction Intermediates / Kinetic vs thermodynamic enolate site on drawn ketones
JEE Advanced levelNumerical answerDifficulty 3 of 3g3257

The ketone shown is monomethylated with methyl iodide, one new CH group being introduced on any alpha carbon, so every possible enolate is allowed to react once. Count all distinct stereoisomeric products, counting enantiomers and diastereomers separately (a meso compound counts as one). Give the answer as an integer.

Numerical answer type, tolerance 0.5.

Answer: 4

The ketone shown is 2-methylcyclopentanone with alpha carbons C2 and C5. Methylation at C2 gives 2,2-dimethylcyclopentanone (achiral, 1). Methylation at C5 gives 2,5-dimethylcyclopentanone: the cis isomer is meso (1) and the trans isomer exists as a pair of enantiomers (2). RDKit stereoisomer enumeration gives .
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