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Is the mechanism similar to the reaction of $\ce{SOCl2}$ with alcohols?
If not, then how is it different? We have been taught about the latter at school but my friend quizzed me about $\ce{SO2Cl2}$.

Please give the detailed reaction mechanism.

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  • $\begingroup$ I was asking on high school level, we have been taught the reaction of Thionyl Chloride with alcohols to give a carbon with double-bonded =O and -Cl ( sorry I don't know the name for the functional group). How does SO2Cl2 react with alcohols, or other functional groups? @Mithoron $\endgroup$
    – sidgrand98
    Jun 29, 2015 at 16:44

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According to this article a mixture of products is formed, with alkylchlorsulfonates $\ce{Cl-SO2-O-R}$ being dominant products. These molecules are resistant to abstraction of sulfur trioxide, probably because trioxide is a very strong Lewis acid, unlike dioxide.

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SO2Cl2 is source of Cl2 gas rather than Cl-. So it doesn't react the same with alcohols. It will form HCl when in contact with water - so a lot of its chemistry with organic molecules will originate from that process. Used with a radical initiator it will convert certain functional groups to alkyl chlorides.

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