Question

The molecule that acts as a nucleophile in the N-acylation reaction used to synthesize acetaminophen is...

The molecule that acts as a nucleophile in the N-acylation reaction used to synthesize acetaminophen is p-aminophenol. (p-aminophenol reacts with acetic anhydride).

What is the most nucleophilic position in the molecule and justify your answer?

The molecule that acts as a nucleophile in the O-acylation reaction used to synthesize aspirin is salicyclic acid. (salicyclic acid reacts with acetic anhydride).

What is the most nucleophilic position in the molecule and justify your answer?

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Homework Answers

Answer #1

In p-aminophenol amine group is more nucleophilic than alcohol. (oxygen is more electronegative than nitrogen therefore it holds its electrons more tightly and are less able to donate them to form a new bond). So in the acetylation of p-amino phenol results acetaminophen.

Hydroxy is more nucleophilic than carboxylate ion (carboxylic acid is strong acid and its conjugate base weak base, phenol is less acidic and its conjugate base is strong base. Strong base means more nucleophilic). So in the acetylation of salicylic acid results aspirin.

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