MolSynapsequestion bank
MolSynapse / Question bank / General Organic Chemistry II: Acids and Bases / Tautomerism and enol content
JEE Main levelSingle correct optionDifficulty 2 of 3g2180

Hexane-2,4-dione has a higher enol content in hexane than in water. This is because

  1. Awater forms hydrogen bonds with the enol more strongly than with the keto form, but hexane does not
  2. Bhexane reacts with the keto form and removes it
  3. Cthe chelated cis-enol is less polar than the diketo form, so a non-polar solvent favours it while water stabilises the polar diketo form
  4. Dthe enol content is the same in all solvents because depends only on temperature

Answer: C

The enol with an intramolecular hydrogen bond has its polar groups internally compensated, so it has a small dipole moment. The diketo form is more polar (the dipoles of the two groups add). Polar water solvates the keto form strongly and also competes for the internal hydrogen bond, which lowers enol content. In hexane the chelated enol is favoured.
Practice General Organic Chemistry II: Acids and Bases More on Tautomerism and enol content

More questions on Tautomerism and enol content