Chapter 22, Problem 22.10P

Rank the compounds in each group in order of increasing reactivity in nucleophilic acyl substitution.

a. ${\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{CO}}_{\text{2}}{\text{CH}}_{\text{3}}\text{,}{\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{COCl,}{\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{CONH}}_{\text{2}}$

b. ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CO}}_{\text{2}}\text{H,}{\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{CO}\right)}_{\text{2}}\text{O,}{\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}{\text{CONHCHCH}}_{\text{3}}$