Fundamentals of Organic ChemistryChemistryCarboxylic Acid Derivatives
Which of the following statements is incorrect?
Options
- AC ₆ H ₅ COOH + CH ₃ OH H ⁺ C ₆ H ₅ COOCH ₃ + H ₂ O (reaction involves acyl-oxygen fission)
- BCH ₃ COOCH ( CH ₃) C ₂ H ₅ OH ⁻ CH ₃ COO ⁻ + HOCH ( CH ₃) C ₂ H ₅ (configuration of the reactant is retained)
- CCH ₃ COOC ₂ H ₅ OH ⁻ CH ₃ COO ⁻ + C ₂ H ₅ OH (reaction involves acyl-oxygen fission)
Correct answer
A. C ₆ H ₅ COOH + CH ₃ OH H ⁺ C ₆ H ₅ COOCH ₃ + H ₂ O (reaction involves acyl-oxygen fission)
Step-by-step solution
In the reaction shown in option (A), the ester undergoes hydrolysis in the presence of a base ( OH ⁻ ). The base is consumed stoichiometrically to form the carboxylate ion ( R-COO ⁻ ) and is not regenerated at the end of the reaction. Therefore, it is a base-promoted reaction (saponification), not a base-catalyzed reaction. Thus, statement (A) is incorrect. In option (B), Fischer esterification proceeds via the A_ AC 2 mechanism, which involves the cleavage of the acyl-oxygen bond of the carboxylic acid. This state