Friday, October 19, 2018

organic chemistry - Which is more stable ? - A carbanion on benzene ring or a carbanion on a vinylic carbon on an aliphatic chain?


I came across a question which asks to work out the stability order for the following species. Can the lone pair on benzene carbanion participate in resonance? - If yes how and how is it more stable than vinylic carbanion ? enter image description here



Answer



The lone pair on the benzene is in the plane of the ring and hence orthogonal to the conjugated $\pi$-system so that it cannot interact with it. It is $\ce{sp^2}$ hybridized just like the vinylic carbanion, which also cannot resonate. Furthermore, both compounds lack an electron withdrawing group, so there is no inductive effect either. Looking at the pKa values for both compounds, which usually gives a good indication about the stability of the anion, we see that there is indeed hardly any difference between them (pKa of benzene ~43 vs pKa of propene ~44 vs pKa of ethylene ~44).


In your question you only show us option (b) and (c). It would be nice if you could show the whole question including all possibilities (also as much as possible in text please, so the search engines can find it!)


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