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?

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  • $\begingroup$ I suppose here $\ce{OH-} $ acts as a base and not as nucleophile. $\endgroup$ – Suraj S May 14 '17 at 11:19
  • $\begingroup$ why not a nucleophile then? $\endgroup$ – Salma May 14 '17 at 11:23
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    $\begingroup$ $\ce{OH-}$ cannot act as a nucleophile here, since in that case, leaving ground would be $\ce{NH2-}$, which is stronger than hydroxide. $\endgroup$ – Pritt says Reinstate Monica May 14 '17 at 12:14
  • $\begingroup$ 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 $\endgroup$ – Beerhunter Jun 12 '17 at 22:26

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