Carboxylic Acids and their Derivatives - Result Question 55-1
55. Arrange the following in order of their increasing ease of hydrolysis :
$ \mathrm{CH}_3 \mathrm{COOC}_2 \mathrm{H}_5, \mathrm{CH}_3 \mathrm{COCl},\left(\mathrm{CH}_3 \mathrm{CO}\right)_2 \mathrm{O}, \mathrm{CH}_3 \mathrm{CONH}_2 $
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Solution:
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 :
$ \mathrm{CH}_3 \mathrm{CONH}_2<\mathrm{CH}_3 \mathrm{COOC}_2 \mathrm{H}_5<\left(\mathrm{CH}_3 \mathrm{CO}\right)_2 \mathrm{O}<\mathrm{CH}_3 \mathrm{COCl} $
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