Find the most acidic hydrogen in each of the following and write a chemical equation for the proton-transfer process that occurs on reaction with hydroxide ion. Use curved arrows to show electron flow and label the acid, base, conjugate acid, and conjugate base.
(a) tert-Butyl methyl ketone
(b) 3-Methylbutanal
(c) Cyclohexanone
Sample Solution (a) The only α hydrogens in tert-butyl methyl ketone are those of the methyl group attached to the carbonyl. Only α hydrogens are acidic enough to be removed by hydroxide. None of the hydrogens of the tert-butyl group are α hydrogens.
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