What about other bases such as Group 1 or Group 2 hydroxides? Does it have to do something with the mechanism?

I don't understand the mechanism either:

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What is NaOH supposed to with the acetate ion? I thought the acetate ion would be produced when NaOH reacted with acetic acid after which the reaction would proceed as follows:

Mechanism of decarboxylation


1 Answer 1


Decarboxylation can be effected by pretty much any base strong enough to produce the anion plus a high enough temperature. I've used DBU to effect an aromatic decarboxylation. The role of the $\ce{NaOH}$ is this reaction is to capture the $\ce{CO2}$ as sodium carbonate.

  • $\begingroup$ So does NaOH act as a protonic acid over here (by donating H+ to the alkyle anion) and then capture the CO2 as Na2CO3? If yes, then isn't that quite odd that NaOH donates a proton? $\endgroup$
    – Pranoy De
    Mar 23, 2017 at 19:35
  • $\begingroup$ Draw out the whole equation. 2NaOH + CO2 gives Na2CO3 + H2O which provides your proton source $\endgroup$
    – Waylander
    Mar 23, 2017 at 20:07
  • $\begingroup$ Yes, I understand. $\endgroup$
    – Pranoy De
    Mar 23, 2017 at 20:29

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