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According to FIITJEE's Sankalp Test-II answer key, it was given that the following compound decarboxylates on heating:

cyclohexane-1,2-dicarboxylic acid

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:

Proposed reaction mechanism

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.

How to move on?

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  • $\begingroup$ Possible but improbable mechanism. If your final structure is electroneutral (: = negative charge), how do you bond 2 hydrogens to the same carbon? In my experience decarboxylation doesn't occur although anhydride formation may. $\endgroup$ – user55119 Aug 5 at 20:17
  • $\begingroup$ I agree that this is improbable as explained in related post. And, the 2 hydrogens were added automatically by ChemDoodle, the software I used : j $\endgroup$ – rv7 Aug 6 at 17:39
  • $\begingroup$ So much for ChemDoodle! $\endgroup$ – user55119 Aug 6 at 20:09
  • $\begingroup$ Don't forget to manually add any charges to atoms so the implicit hydrogen count can be calculated correctly, such as in this case. Would be cool if ChemDoodle could automatically determine implicit hydrogens based on electron pairs if charges aren't provided though. $\endgroup$ – iclkevin Aug 23 at 20:46

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