MolSynapsequestion bank
MolSynapse / Question bank / General Organic Chemistry II: Acids and Bases / Tautomerism and enol content
JEE Advanced levelSingle correct optionDifficulty 3 of 3g2200

2-Methylcyclohexanone can enolise toward C-2 or C-6. Counting every distinct enol tautomer, including stereoisomers (enantiomers count separately), the total is

  1. A
  2. B
  3. C
  4. D

Answer: C

Enolisation toward C-2 gives 2-methylcyclohex-1-en-1-ol, which is achiral and has no cis-trans isomerism in the ring. Enolisation toward C-6 gives 6-methylcyclohex-1-en-1-ol, where C-6 carries , , C-1 and C-5, so it is a stereocentre and gives a pair of enantiomers. Total .
Practice General Organic Chemistry II: Acids and Bases More on Tautomerism and enol content

More questions on Tautomerism and enol content