How does ethanol react with #PCl_5#?

1 Answer
anor277
Oct 2, 2017

#H_3C-CH_2OH + PCl_5 rarr H_3C-CH_2Cl + O=PCl_3 + HCl#

Explanation:

I don't know how viable this reaction is.....with longer, more valuable alcohols the reaction might be widely used. The hydroxide anion is a POOR leaving group. One way that the organic chemist may address this is to convert the alcohol to an inorganic ester of phosphate (with #PCl_5#), or with #SOCl_2#. These are both potentially halogenating agents as shown.

#H_3C-CH_2OH + SOCl_2 rarr H_3C-CH_2Cl + SO_2 + HCl#

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