Rank the following carboxylic acid derivatives in decreasing order (most to least) of reactivity towards nucleophilic substitution.
A) I IV III II
B) II III IV I
C) I III II IV
D) III IV II I
E) IV I III II

Question

Rank the following carboxylic acid derivatives in decreasing order (most to least) of reactivity towards nucleophilic substitution.  
A) I > IV > III > II 
B) II > III > IV > I 
C) I > III > II > IV 
D) III > IV > II > I 
E) IV > I > III > II

Quizplus · Accepted Answer

Carboxylic acid derivatives can undergo nucleophilic substitution reactions via two mechanisms- nucleophilic acyl substitution and nucleophilic addition-elimination. Nucleophilic acyl substitution follows the order- acid chloride > anhydride > ester > carboxylic acid > amide. Among the given options, option C shows the correct decreasing order of reactivity towards nucleophilic substitution through nucleophilic acyl substitution. Hence, option C is the correct answer.

Rank the Following Carboxylic Acid Derivatives in Decreasing Order (Most