Arrange the following compounds in the strictly decreasing order of their percentage enol content at — Isomerism and Stereochemistry Chemistry Question
Question
Arrange the following compounds in the strictly decreasing order of their percentage enol content at equilibrium: (I) Acetone, (II) Acetylacetone, (III) Phenol.
Answer: C
💡 Solution & Explanation
The enol form of phenol (III) is ~100% because it generates a highly stable $6\pi$ aromatic ring. Acetylacetone (II) is a $\beta$-diketone with exceptionally high enol content (~76%) due to internal H-bonding and extended conjugation. Acetone (I) is a simple mono-ketone where the keto form is vastly more stable. Thus, III > II > I.
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