The mechanisms for both acid and base catalyzed hydrolysis of nitriles are clear; enter image description here

(With the subsequent deprotonation from the hydroxyl) and

enter image description here


In both cases, the hydroxyl adds to the carbon while the proton adds to the nitrogen.

I thought up an alternate mechanism, with the proton attaching to the carbon, and the hydroxyl going to the thereby positively-charged nitrogen, yielding an oxime.

Why doesn't this occur? I thought of the fact that the nitrogen atom, with a lone pair, would cause any nearby protons to come straight to it, but I'd like clarification on that.

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    $\begingroup$ Well, nitrogen is the electronegative atom here and it has the lone pair as you mentioned, so its very unlikely that the proton will go to the carbon $\endgroup$ – Shoubhik R Maiti May 2 at 8:57
  • $\begingroup$ Right, that answers it, thanks. $\endgroup$ – harry May 2 at 9:04

Yes, since nitrogen is more electronegative than carbon, and also since it has the lone pair available for taking, the proton is likelier to go to it.


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