synthesis of paracetamol

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hammaren
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synthesis of paracetamol

Post by hammaren »

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.
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ChenBeier
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Re: synthesis of paracetamol

Post by ChenBeier »

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.
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