According to AIITS exam answer key, it was given that the following compound decarboxylates on heating:
Then, I read Why are beta-ketoacids better at decarboxylation than gamma or delta? which is related to my question.
It says that for γ-keto acids or δ-keto acids, decarboxylation will 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 separated, but I'm not sure about the mechanism.
How to move on?