Fundamentals of Organic ChemistryChemistryCarboxylic Acid Derivatives
Which of the following statements are true regarding the hydrolysis of acetic anhydride? (I) It is more easily hydrolyzed in an acidic medium than in a neutral medium. (II) It is more easily hydrolyzed in an alkaline medium than in a neutral medium. (III) It is hydrolyzed equally easily in all three media. (IV) It is more easily hydrolyzed in a neutral medium than in an acidic medium. (V) It is more easily hydrolyzed
Options
- A(III) only
- B(IV) and (V)
- C(I) and (II)
- D(I) and (V)
Correct answer
C. (I) and (II)
Step-by-step solution
Hydrolysis of acetic anhydride involves a nucleophilic attack on the carbonyl carbon. In an acidic medium, the carbonyl oxygen gets protonated, which increases the electrophilicity of the carbonyl carbon. This facilitates the nucleophilic attack by water, making the hydrolysis faster than in a neutral medium. Thus, statement (I) is true. In an alkaline medium, the nucleophile is the hydroxide ion ( OH⁻ ), which is a much stronger nucleophile than water. The strong nucleophile attacks the carbonyl carbon more readil