Problem

A carboxylic acid has two oxygen atoms, each with two nonbonding pairs of electrons....

A carboxylic acid has two oxygen atoms, each with two nonbonding pairs of electrons.

(a) Draw the resonance forms of a carboxylic acid that is protonated on the hydroxyl oxygen atom.

(b) Compare the resonance forms with those given previously for an acid protonated on the carbonyl oxygen atom.

(c) Explain why the carbonyl oxygen atom of a carboxylic acid is more basic than the hydroxyl oxygen.

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