According to an internal test series in FIITJEE, it was given that the following compound decarboxylates on heating,
I know that β-keto acids undergo decarboxylation on heating, but I was not sure about the above compound. So, on searching the internet, I found this post, Why are beta-ketoacids better at decarboxylation than gamma or delta? which seems helpful.
As, it says that for γ-keto acids or δ-keto acids, decarboxylation will most likely not happen with a beautiful explanation. So, I drew a possible mechanism and here's what I came up with:
With the help of the reasoning given by @TOLA3HPPA, I can say that decarboxylation will not happen as opposite charges are much separated, but I'm not sure about the mechanism.
Further, while searching on NIST Chemistry Webbook, I've seen an article named,
The Oxidative Bisdecarboxylation of α,β-Dicarboxylic Acids, J. Am. Chem. Soc., 1952, 74, 4370..
which possibly indicates that the above compound undergoes decarboxylation. So, if α,β-dicarboxylic acid undergoes decarboxylation, then what can be the possible mechanism?