MCAT Organic Chemistry Question 134: Answer and Explanation

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Question: 134

14. Which reactant could be combined with butanol to form butyl acetate?

A. (CH₃CO)₂O and catalytic acid
B. (CH₃CH₂CO)₂O and catalytic acid
C. CH₃CH₂CONH₂ and catalytic acid
D. CH₃CONH₂ and catalytic acid

Correct Answer: A

Explanation:

In order to prepare butyl acetate from butanol, we need to perform a nucleophilic acyl substitution reaction. If the product is an ester, we need to start with a reactant that is more reactive than the ester itself, or the reaction will not proceed. Anhydrides are more reactive than esters, but amides are less reactive, eliminating choices (C) and (D). Reaction with propanoic anhydride, as in choice (B), would result in butyl propanoate.

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