Multiple Choice
In nucleophilic acyl substitution, which of the following best describes the key mechanistic step that distinguishes it from nucleophilic substitution at alkyl halides?
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22. Carboxylic Acid Derivatives: NAS
Nucleophilic Acyl Substitution
Multiple Choice
Determine the major product for the following reaction.
A
B
C
D
5 Comments
Verified step by step guidance1
Identify the starting material as a carboxylic acid, specifically butanoic acid, which has the structure CH3CH2CH2COOH.
Recognize that the reaction involves two steps: first, treatment with NaOH, and second, reaction with CH3CH2Br.
In the first step, NaOH, a strong base, deprotonates the carboxylic acid to form the carboxylate anion, CH3CH2CH2COO⁻.
In the second step, the carboxylate anion acts as a nucleophile and attacks the electrophilic carbon in CH3CH2Br, resulting in a nucleophilic substitution reaction (SN2 mechanism).
The major product of this reaction is an ester, specifically ethyl butanoate, with the structure CH3CH2CH2COOCH2CH3.
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