My book claims that beta-ketoacids and beta-dicarboxylic acids are better at decarboxylating than their gamma and delta counterparts. Why is that?

I would assume that since gamma and delta keto-acids make a larger ring intermediate (less ring strain) and thus the energy barrier for reaching that intermediate would be lower...


1 Answer 1


It has to do with the stability of the electrons that are ejected from the bond that breaks. In B-ketoacids, the electrons can resonate onto the oxygen and form an enol/enolate intermediate, which is much more stable than forming a carbanion on a gamma or delta ketoacid (because there is nowhere for the electrons to go other than go on the carbon atom that participates in the bond-breaking event).

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