Does this seem correct? The point is to draw the mechanisnm of which 3-(2-oxocyclohexyl)propanenitrile is synthesized from 1-(cyclohex-1-en-1-yl)pyrrolidine. Synthesis of 2-(2-cyanoethyl) cyclohexanone

  • $\begingroup$ You might want to Google "enamine". The enamine of your second structure in the first line will have the double bond in the less substituted position. $\endgroup$
    – user55119
    Oct 8, 2018 at 19:52

1 Answer 1


The first step is incorrect:

  1. You take electrically neutral cyanoethylene, but on your mechanism it is negatively charged. So you create negative charge of nothing on zeroth step of the mechanism. The same is for positive charge on enamine
  2. You cannot pluck the proton from enamine in this way.


At the first step the electrons of π-orbital of enamine interact with the π*-orbital of acrylonitrile(Michael acceptor) resulting in formation of the bond between alpha-carbon of enamine and beta-carbon of acrylonitrile.

The transformation of iminium to carbonyl occurs via tetrahedral intermediate and not via formation of vinylic carbocation.


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