Fundamentals of Organic ChemistryChemistryCarboxylic Acid Derivatives
Which of the following represents the correct order of relative stability of the given acid derivatives towards nucleophilic attack?
Options
- AAcid chloride > Acid anhydride > Ester > Amide
- BAcid chloride > Ester > Acid anhydride > Amide
- CAmide > Acid anhydride > Ester > Acid chloride
- DAmide > Ester > Acid anhydride > Acid chloride
Correct answer
D. Amide > Ester > Acid anhydride > Acid chloride
Step-by-step solution
The reactivity of acid derivatives towards nucleophilic acyl substitution depends on the leaving group ability and the resonance stabilization of the acyl group. The leaving group ability follows the order: Cl ^- > RCOO ^- > RO ^- > NH ₂^- . The resonance stabilization of the carbonyl group by the attached heteroatom follows the order: - NH ₂ > - OR > - OCOR > - Cl . Greater resonance stabilization decreases the positive charge on the carbonyl carbon, leading to lower reactivity and higher stability. Thus, the orde