Consider the compound 2,4-pentanedione. How many highly acidic -hydrogens are actively involved in d β Isomerism and Stereochemistry Chemistry Question
Question
Consider the compound 2,4-pentanedione. How many highly acidic $\alpha$ -hydrogens are actively involved in driving the formation of its exceptionally stable enol tautomer?
Answer: 2
π‘ Solution & Explanation
2,4-pentanedione (acetylacetone) has an active methylene group ($-CH_2-$) at carbon-3 flanked by two strongly electron-withdrawing carbonyl groups. These 2 $\alpha$ -hydrogens are highly acidic and actively participate in the rapid 1,3-shift (keto-enol tautomerism) to form a stable, conjugated enol ring via intramolecular hydrogen bonding.
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