I was dealing with Darzen's Reaction for the preparation of alkyl chlorides. $$\ce{R-OH ->[SOCl2][Pyridine] R-Cl}$$ Now I encountered this as the mechanism of the reaction $$\ce{R-OH + SOCl2 -> RO+HSO^-Cl2 ->[-Cl^-] R-O+HSOCl ->[NC5H5]R-O-SOCl}$$ $$\ce{R-O-SOCl ->[NC5H5][-Cl^-] ROSON+C5H5 ->[Cl^-] R-Cl}$$ My question is that why does the reaction in the second line occur? In other words, why does $\ce{R-O-SOCl -> ROSON+C5H5}$? I am unable to find any reasons to explain why this reaction would be favourable. What major factor allows pyridine to displace the chlorine atom?
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https://chemistry.stackexchange.com/questions/69063/if-socl2-reacts-with-alcohols-via-sni-why-doesnt-pocl3 – Mithoron Apr 20 '23 at 15:04
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@Mithoron Thanks for the post! But could you please elaborate on the stability of $\ce{ R-O-SOCl}$ in comparison to $\ce{ROSON+C5H5}$? – Srish Dutta Apr 21 '23 at 05:15