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According to AIITS exam 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 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

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