Carboxylic Acids and their Derivatives 2 Question 55
55. Arrange the following in order of their increasing ease of hydrolysis :
$(1986,1 \mathrm{M})$
$$ \mathrm{CH}{3} \mathrm{COOC}{2} \mathrm{H}{5}, \mathrm{CH}{3} \mathrm{COCl},\left(\mathrm{CH}{3} \mathrm{CO}\right){2} \mathrm{O}, \mathrm{CH}{3} \mathrm{CONH}{2} $$
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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 :
$\mathrm{CH}{3} \mathrm{CONH}{2}<\mathrm{CH}{3} \mathrm{COOC}{2} \mathrm{H}{5}<\left(\mathrm{CH}{3} \mathrm{CO}\right){2} \mathrm{O}<\mathrm{CH}{3} \mathrm{COCl}$
