Fundamentals of Organic ChemistryChemistryCarboxylic Acid Derivatives
Which of the following reactions are feasible? (I) CH ₃ COCl + H ₂ O CH ₃ COOH + HCl (II) CH ₃ COOCH ₃ + HBr CH ₃ COBr + CH ₃ OH (III) CH ₃ CONH ₂ + HBr CH ₃ COBr + NH ₃ (IV) CH ₃ COOCOCH ₃ + H ₂ O 2 CH ₃ COOH
Options
- A(I), (III) and (IV)
- B(I) and (IV)
- C(I), (II), (III) and (IV)
- D(I), (II) and (IV)
Correct answer
B. (I) and (IV)
Step-by-step solution
The feasibility of nucleophilic acyl substitution depends on the leaving group ability. A weaker base is a better leaving group. The order of basic strength of the leaving groups is Cl ⁻ Therefore, the leaving group ability and the reactivity of acid derivatives follow the order: Acid chloride > Acid anhydride > Ester > Amide. A more reactive acid derivative can be converted into a less reactive one, but the reverse is not feasible. (I) CH ₃ COCl + H ₂ O CH ₃ COOH + HCl : Acid chloride is converted to carboxylic ac