The unusually high stability of the enol form in -dicarbonyl compounds (such as acetylacetone) is pr β Isomerism and Stereochemistry Chemistry Question
Question
The unusually high stability of the enol form in $\beta$ -dicarbonyl compounds (such as acetylacetone) is primarily attributed to which of the following combined structural effects?
Answer: B,C
π‘ Solution & Explanation
The enol form of $\beta$ -dicarbonyls is exceptionally stable because the resulting hydroxyl proton forms a powerful intramolecular hydrogen bond with the adjacent unreacted carbonyl oxygen, creating a stabilizing six-membered chelate ring. Furthermore, the newly formed $C=C$ double bond aligns in direct resonance conjugation with the $C=O$ double bond, vastly lowering the system's overall energy.
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