Chemistry Forum

The synthesis of paracetamol was made through mixing p-aminophenol, acetic anhydride and hydrochloric acid. The product in the reaction is paracetamol and hydrochloric acid.

I know that this is a substitute reaction but me and my teacher are divided if it is an SN₁ or SN₂ reaction. I believe it is an SN₂ while my teacher believes it is an SN₁ reaction. I would be greatful if someone could give me a clear answer on if it is SN₁ or SN₂.

Excuse me if the language is not the best. English is not my first language.

It is a hidden Sn₂ reaction at the nitrogen. Its not the same like reaction at carbon. The CH₃CO+ reacts with the free electronpair of the N. The remaing CH₃COO- will capture one H of the Amin and form acetic acid. This acid has to be neutralized by using more Amin as necessary or add othe base like pyridine.