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When a secondary alcohol reacts with SOCl2 (or even PCl5), does the reaction proceed via SN2 or SNi?

SchrodingerCat2023
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  • see https://chemistry.stackexchange.com/questions/171573/reaction-of-pcl5-with-alcohol/171575#171575 for PCl5 – Waylander Feb 25 '23 at 07:40
  • Also see: https://chemistry.stackexchange.com/questions/69063/if-socl2-reacts-with-alcohols-via-sni-why-doesnt-pocl3 – Nilay Ghosh Feb 26 '23 at 05:30

1 Answers1

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For SOCl2 it depends on the reaction conditions- if a base such as pyridine is present the reaction goes with inversion, in the absence of base it goes with retention

Full explanation here

Waylander
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