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I was wondering why α,β-unsaturated and α-hydroxy acids undergo decarboxylation. Also, I'm aware of neither the products nor mechanism. All I know is that β-keto acids and α-nitro compounds have resonance stabilized anions and have stable transition states.

But α,β-unsaturated have none of those and it isn't that electronegative as its sp2. Someone please help me out; I can't find the answer anywhere else.

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  • $\begingroup$ i cant find the answer anywhere else Strongly disagree: pubs.acs.org/doi/abs/10.1021/ed064p591#/doi/abs/10.1021/… $\endgroup$ – Pritt Balagopal Jun 11 '17 at 12:51
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    $\begingroup$ Im sorry I cant understand it, Im not an undergraduate student can you please explain it to me? Without the oxidative cleavage or free radical hunsdicker reaction. Just how on heating aplha beta unstaurated acids undergo decarboxylation? $\endgroup$ – TheLostGuardian0 Jun 11 '17 at 12:56
  • $\begingroup$ Decarboxylation mechanism involves creating a carbanion at the carbon attached to $\ce{-COOH}$ group. Does this help you decide why? $\endgroup$ – Pritt Balagopal Jun 11 '17 at 12:58
  • $\begingroup$ Related: chemistry.stackexchange.com/questions/53879/… $\endgroup$ – Pritt Balagopal Jun 11 '17 at 13:00
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    $\begingroup$ @PrittBalagopal I noticed you'd linked to a J. Chem. Ed. paper in the comments (DOI: 10.1021/ed064p591). I suspect that the OP doesn't have journal access, it might be more productive to paraphrase what that paper actually says about the reaction in question $\endgroup$ – NotEvans. Jun 11 '17 at 16:23

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