Chemistry - GOC Question with Solution | TestHub

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

Removing ${\mathrm{H}}_2$ gives a tertiary carbanion :

The phenoxide carries the negative charge on oxygen and delocalises it into the aromatic ring by resonance; the carbanion carries it on carbon with no resonance. The phenoxide is far more stable, so the O-H proton ${\mathrm{H}}_1$ is more acidic.