Methyl acetate, CH₃COOCH₃
CHEMISTRY · Single correct · A Level · Chemistry · Introduction to organic chemistry · Introduction to organic chemistry
Problem
Methyl acetate, CH₃COOCH₃, undergoes hydrolysis in aqueous solution to form acetic acid and methanol. The reaction is much faster in the presence of H⁺. Which set of elementary steps is most consistent with acid catalysis and satisfies all of the following criteria?
• H⁺ participates but is regenerated.
• The combined steps yield the overall stoichiometry CH₃COOCH₃ + H₂O → CH₃COOH + CH₃OH.
Choose the best option.
(a) (1) H⁺ + H₂O → H₃O⁺ (fast)
(2) CH₃COOCH₃ + H₃O⁺ → CH₃COOH + CH₃OH (slow)
(b) (1) H⁺ + CH₃COOCH₃ ⇌ CH₃COOCH₃H⁺ (fast)
(2) CH₃COOCH₃H⁺ + H₂O → CH₃COOH + CH₃OH + H⁺ (slow)
(c) (1) H⁺ + CH₃COOCH₃ ⇌ CH₃COOH + CH₃⁺ (slow)
(2) CH₃⁺ + H₂O → CH₃OH + H⁺ (fast)
(d) (1) CH₃COOCH₃ + H₂O → CH₃COO⁻ + CH₃OH + H⁺ (fast)
(2) H⁺ + CH₃COO⁻ → CH₃COOH (slow)
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