JEE Main · 2022 · 26 Jun 2022 · Shift 1 · General Organic Chemistry

Which will have the highest enol content?

(A)(see structure)
(B)(see structure)
(C)(see structure)
✓ Correct
(D)(see structure)

Answer: (C)

Solution

The compound in option (C) is 1,3,5-cyclohexanetrione. Its enol form is 1,3,5-trihydroxybenzene (phloroglucinol), which is aromatic with three hydroxyl groups on a benzene ring. Due to the exceptional stability gained from aromaticity, this compound exists predominantly in the enol form. The other options lack this aromatic stabilization in their enol forms, so they have much lower enol content.

Structure enol form (aromatic) — enol form (aromatic)

JEE Main · 2022 · 26 Jun 2022 · Shift 1 · Single correct option

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