Master Organic Chemistry Reaction Guide

Elimination of alcohols to give alkenes using POCl3

Description: When treated with phosphorus oxychloride (POCl3) alcohols are converted to alkenes via an elimination reaction.
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6 thoughts on “Elimination of alcohols to give alkenes using POCl3

  1. Please forgive if this is an elementary question, but I am trying to extract information that was last used when a 128k Macintosh was 1600.00. The POCl3 : the electronegativities sandwich the poor little P between a rock and a hard place. The Cl wants the density in 3 directions but the O wants it more by .97. Without getting into the vector analysis, will the Cl’s be pulled upward in the same manner but different direction, as H’s in H2O are bent away the electrons on the O.

    Sorry, for what I think Brother Adrian called, Illigitimus Parenthetica.

    1. Electronegativity: O=3.44, Cl=3.16. As I understand, the chlorines will minimize repulsive forces by settling into the optimal angle from the oxygen. The Cl-Cl angles should be the same, and the Cl-O angle should be slightly larger than Cl-Cl. Exact numbers? Try scientific literature!

    1. Pyridine would significantly improve the rate of reaction. I’d put it in. Need to update this page to show that. Thanks!

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