Question

Arrange the following in order of their increasing ease of hydrolysis :
$C{H}_{3}COO{C}_2{H}_5,C{H}_{3}COCI,(C{H}_{3}CO{)}_{2}O,C{H}_{3}CON{H}_2$

Answer 1

Among acid derivatives, the reactivity towards nucleophilic
acyl substitution is in the order of :
Amide < Ester < Anhydride < Acid chloride
Hydrolysis is an example of nucleophilic acyl substitution,
hence the reactivity towards hydrolysis is :
$C{H}_{3}CON{H}_2<C{H}_{3}COO{C}_2{H}_5<(C{H}_{3}CO{)}_{2}O<C{H}_{3}COCl$