Find the most acidic hydrogen in each of the following and write a chemical equation for t...

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.