Pro Tip!
Benzamide is less easily hydrolysed because of difference of positive charge density on carbonyl carbon. In hydrolysis reaction, hydroxyl ion (OH–) attacks on the carbonyl carbon, so we need to check out the positive charge density on carbonyl carbon.
Solution
We know that the nitrogen is less electronegative as compared to oxygen. So, nitrogen can donate a pair of electron more readily as compared to oxygen.
In case of benzamide the magnitude of positive charge on carbonyl carbon is less than that in case of methyl benzoate.
During the hydrolysis reaction, the attack on hydroxyl ion (OH–) on carbonyl carbon is difficult in case of benzamide as compared to that of methyl benzoate.
Hence, benzamide is less easily hydrolysed than methyl benzoate.
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