Chemistry - GOC Question with Solution | TestHub

Removing ${\mathrm{H}}_1$ gives the carboxylate :

Removing ${\mathrm{H}}_2$ gives the alkoxide :

Run through the factors : (1) atom - both charges land on oxygen, no help; (2) resonance - the carboxylate is resonance-stabilised over two oxygens, the alkoxide is not : favours the first; (3) induction - the fluorine stabilises the alkoxide : favours the second; (4) orbital - no help. Resonance beats induction, so the carboxylate is more stable and the carboxylic O-H proton ${\mathrm{H}}_1$ is more acidic.