Mechanism of synthesis of paracetamol by 4-aminophenol

Hi

Can anybody confirm this is the mechanism for synthesis of paracetamol from 4 aminophenol?

If its not, please can you correct me?

Thanks

Reply 1

.Serenity.

Original post by matthewalex

Hi

Can anybody confirm this is the mechanism for synthesis of paracetamol from 4 aminophenol?

If its not, please can you correct me?

Thanks

The nitrogen should have a positive charge in the second step, before the hydrogen comes off of it.

(edited 11 years ago)

Reply 2

EierVonSatan

Original post by matthewalex

Hi

Can anybody confirm this is the mechanism for synthesis of paracetamol from 4 aminophenol?

If its not, please can you correct me?

Thanks

You've got the jist of it but there are a few details that need addressing :smile:

In the first step the curly arrow attacks the C=O bond, which you've drawn. However, the C=O bond breaks then reforms, followed by breaking of the C-O to give you the carboxylate anion.

As above, in the second step the Nitrogen should be carrying a positive charge and the arrow you've drawn is in the opposite direction that it need to be for H⁺ to be removed - recall that the curly arrows represent electron movement :yes: