Thursday, October 26, 2017

organic chemistry - Why is thionyl chloride preferred for preparing alkyl chlorides from alcohols?



Why is thionyl chloride ($\ce{SOCl2}$) preferred for preparing alkyl chlorides from alcohols, as opposed to say $\ce{PCl5}$ or $\ce{PCl3}$ ?



Answer



Thionyl chloride is preferred for preparing alkyl chlorides from alcohols because the by-products formed in the reaction are $\ce{SO2}$ and $\ce{HCl}$ which are in gaseous form and escape into the atmosphere leaving behind pure alkyl chlorides.


$$\ce{CH3CH2-OH + SOCl2 → CH3CH2-Cl + SO2 ↑ + HCl ↑}$$


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