# Hoffmann's rearrangement

In Hoffmann's rearrangement of acid amide...the OH from the basic medium attacked the H ..now my question is...isn't the carbonyl carbon more acidic as it's surrounded by 2 electronegative elements?

• I suppose here $\ce{OH-}$ acts as a base and not as nucleophile. – Suraj S May 14 '17 at 11:19
• why not a nucleophile then? – Salma May 14 '17 at 11:23
• $\ce{OH-}$ cannot act as a nucleophile here, since in that case, leaving ground would be $\ce{NH2-}$, which is stronger than hydroxide. – Pritt says Reinstate Monica May 14 '17 at 12:14
• The arrows should be equilibria ones and yes, the hydroxide will probably act as a nucleophile but it's a product dead-end, shuttling around in equilibrium – Beerhunter Jun 12 '17 at 22:26