Fundamentals of Organic ChemistryChemistryCarboxylic Acid Derivatives
Identify the correct order of reactivity of the following compounds towards nucleophilic acyl substitution: (I) (II) (III) (IV)
Options
- AIII > II > I > IV
- BIII > IV > II > I
- CII > IV > I > III
- DII > III > IV > I
Correct answer
D. II > III > IV > I
Step-by-step solution
The reactivity of acyl derivatives towards nucleophilic substitution depends on the leaving group ability of the group attached to the carbonyl carbon. The leaving groups in the given compounds are: (I) -NH₂ (II) -Cl (III) -OAc ( -O-CO-CH₃ ) (IV) -OCH₃ A weaker base is a better leaving group. The basic strength of the leaving groups follows the order: Cl^- Therefore, the leaving group ability follows the reverse order: Cl^- > CH₃COO^- > CH₃O^- > NH₂^- Hence, the order of reactivity towards nucleophilic acyl substit