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Specifically, I've outlined the arrow pushing heuristic for getting from a carboxylic acid to an acyl chloride in red. Now the mechanism outlined in green is the standard route for what I'm told happens with the release of SO2 gas. However, how stable is this intermediate and is it possible that it undergoes conversion twice as I've drawn in orange?

Two routes

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    $\begingroup$ No. The byproduct of the reaction of thionyl chloride with an acid is unstable and it decomposes very quickly. And even if the compound would be more stable, it would be probably less reactive than thionyl chloride. $\endgroup$ – vapid Sep 9 '16 at 18:36
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    $\begingroup$ Cool, thanks. Why did you put your response as a comment instead of an answer? $\endgroup$ – user19026 Sep 9 '16 at 23:16

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