In the liquid state, what is the approximate percentage (%) of the enol form present in the tautomer — Isomerism and Stereochemistry Chemistry Question
Question
In the liquid state, what is the approximate percentage (%) of the enol form present in the tautomeric equilibrium mixture of acetylacetone (pentane-2,4-dione)?
Answer: 76
💡 Solution & Explanation
While simple mono-ketones heavily favor the keto form (~99%), $\beta$ -diketones like acetylacetone exhibit a much higher enol content due to resonance stabilization and a stable 6-membered intramolecularly hydrogen-bonded pseudo-ring. In the liquid state, its tautomeric mixture consists of roughly 24% keto form and 76% enol form.
💬Ask on WhatsApp →
Still have doubts about this question?
Send it to our AI chemistry tutor on WhatsApp — gets answered in minutes