Chemistry - GOC Question with Solution | TestHub

Removing ${\mathrm{H}}_1$ gives the alkoxide next to the two methyl groups :

Removing ${\mathrm{H}}_2$ gives the alkoxide next to the $\mathrm{C}{\mathrm{F}}_2$ group :

Both charges are on oxygen with no resonance, so compare induction : the two fluorine atoms withdraw electron density and stabilise the nearby negative charge, while the two methyl groups donate electron density and destabilise it. The second alkoxide is more stable, so ${\mathrm{H}}_2$ is more acidic.