Question

Are esters more acidic than amides?

Answer 1

1. The alpha hydrogen of esters $\mathrm{RCOOR}$ is more acidic than the alpha hydrogen present in amides ${\mathrm{RCONH}}_2$.
2. This is because the $-\mathrm{I}$ (inductive effect) of an ester group is much more than that of an amide group.
3. $\mathrm{Oxygen}$ present in esters is more electronegative than $\mathrm{Nitrogen}$ present in amide which reduces the negative charge formed on the compound after the removal of ${\mathrm{H}}^{+}$ from the compound and accounts for its greater $-\mathrm{I}$ effect than amide.