Chemistry - GOC Question with Solution | TestHub

Removing ${\mathrm{H}}_1$ gives the alkoxide away from chlorine :

Removing ${\mathrm{H}}_2$ gives the alkoxide on the carbon bearing chlorine :

Both charges are on oxygen with no resonance, so compare induction : chlorine is electron-withdrawing and stabilises the negative charge on the neighbouring alkoxide. The second conjugate base is more stable, so the O-H proton next to chlorine, ${\mathrm{H}}_2$, is more acidic.