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Keto-enol Tautomerism The carbonyl group is electron withdrawing both by the -I and the -R effect. That makes the carbon more positive and withdraws electron density from the -C-H bond. The -hydrogens become more acidic. The acidity of hydrogens enables carbonyl groups (as in acetone) to undergo keto-enol tautomerism. Tautomers are rapidly interconverted constitutional isomers. They usually have the or -hydrogen atom on the O of the carbonyl group and the C=O double bond relocated between the carbonyl carbon and the -carbon. Tautomeric equilibria are catalyzed by traces of acids or bases that are generally present in most chemical samples. Mechanism for Enol Formation Acid conditions 1) Protonation of the Carbonyl 2) Removal of the -hydrogen Basic conditions 1) Removal of the -hydrogen

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