Talk:Hunsdiecker reaction

Reaction mechanism

Is the reaction equation in the Simonini reaction correct? I think the carboxylate should be removed.

I doubt the mechanism given here. Radicals are generally present in such low concentrations that they rarely combine. R. would more likely remove a Br from another molecule. This is also given in most places, such as here and here. — Preceding unsigned comment added by 163.1.173.134 (talk) 19:53, 27 January 2013 (UTC)

Eh, it's plausible if you assume a solvent cage to achieve a sort of "tight ion pair/S_N,i" effect.

With that said, I think the mechanism shown, and which appears in most literature, is probably not quite correct. The Hunsdiecker reaction requires specifically a silver or silver-like counterion, but the mechanism shown only involves silver indiscriminately to form the initial hypohalite. (Unfortunately your links suffer from the same problem.)

If I had to guess, I would propose some sort of oxidative addition to RCO₂-Ag^IIIBr₂ that homolyzes to a carboxyl radical, AgBr, and Br^•. Then we can argue over whether it's a chain reaction or solvent-caged recombination; IMHO it doesn't matter too much. Bernanke's Crossbow (talk) 13:51, 20 April 2025 (UTC)

Wiki Education Foundation-supported course assignment

This article was the subject of a Wiki Education Foundation-supported course assignment, between 22 January 2020 and 15 May 2020. Further details are available on the course page. Student editor(s): Mickey Boray.

Above undated message substituted from Template:Dashboard.wikiedu.org assignment by PrimeBOT (talk) 10:38, 18 January 2022 (UTC)