Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Arrange the following compounds in decreasing order of their relative rate of hydrolysis using dilute aqueous NaOH : (I) (II) (III)
Options
- A(III) > (I) > (II)
- B(I) > (III) > (II)
- C(II) > (III) > (I)
- D(I) > (II) > (III)
Correct answer
B. (I) > (III) > (II)
Step-by-step solution
The rate of hydrolysis of acid derivatives depends on the electrophilicity of the carbonyl carbon and the leaving group ability. The given compounds are: (I) Acetyl chloride (acid chloride) (II) Methyl acetate (ester) (III) Acetic anhydride (acid anhydride) The leaving groups for these compounds are Cl^- , CH₃O^- , and CH₃COO^- respectively. A weaker base is a better leaving group. The basic strength of the leaving groups follows the order: CH₃O^- > CH₃COO^- > Cl^- . Therefore, the leaving group ability follows the