Isomerism and StereochemistryhardMCQ SINGLE⭐ Must-Do

Arrange the following compounds in the strictly decreasing order of their percentage enol content atIsomerism 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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