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JEE Main levelSingle correct optionDifficulty 2 of 3g2179

Cyclohexane-1,3-dione is largely enolic in solution, unlike cyclohexanone, whose enol content is negligible. The chief reason is that the enol

  1. Ahas a strong intramolecular hydrogen bond closing a second ring
  2. Bhas its conjugated with the remaining group
  3. Chas no alpha hydrogen left
  4. Dis aromatic

Answer: B

In the enol of cyclohexane-1,3-dione the is conjugated with the second carbonyl (a vinylogous acid), which stabilises it considerably. The ring geometry holds the hydroxyl and the carbonyl apart, so intramolecular hydrogen bonding is not the cause. The enol is not aromatic. Cyclohexanone has no such conjugation.
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