Master Organic Chemistry Reaction Guide

Keto-enol tautomerism

Description: Ketones and other carbonyl compounds containing a hydrogen adjacent to the carbonyl are in equilibrium with a constitutional isomer called an enol.

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Real-World Examples:
Org. Synth. 1952, 32, 97
DOI Link: 10.15227/orgsyn.032.0097

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7 thoughts on “Keto-enol tautomerism

  1. Hi! i read through your notes for keto-enol-tautomerism. I just have a questions, why is 2,4-pentandione is more favourable as an enol? is it because of the conjugation? could you please explain to me why? Thank you.

    1. Two reasons! 1) if one ketone is present as an enol, then it can participate in a hydrogen bond with the other ketone carbonyl, which is a favorable interaction. And yes 2) it is also conjugated, so that has an impact as well.

  2. why when the oxonium ion come form enol the deprotonation for oxygenatom…??

    and if it comes from keto form ( with acid) the deprotonation for alpha proton

    in both cases is the same intermediate??

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