Q14P - Organic Chemistry (Mcmurry)

Question

Write the mechanism of the reaction between p-hydroxyaniline and acetic anhydride to prepare acetaminophen.

Step-by-Step Solution

Answer

The mechanism involves the following steps:

 

Step 1: Nucleophilic Attack

Step 2:  Deprotonation 

Step 3 : Leaving group removal

Step 1: Reaction for preparation of acetominophen

Acetaminophen can be prepared as from p-hydroxyaniline as

Step 2: Mechanism

The mechanism involves the following steps:

 

Step 1: Nucleophilic Attack

 

Step 2:  Deprotonation 

 

Step 3: Leaving group removal