How would you expect phosphorus pentachloride to react with ethanol? How does this reaction resemble the reaction of phosphorus pentachloride with ethanoic acid?

1 Answer
Nov 29, 2016

With alcohol:
PCl_5+ROH rarr O=PCl_3 + RCl + HCl

Explanation:

With acid:

PCl_5+RC(=O)OH rarr O=PCl_3 + RC(=O)Cl + HCl

"Phosphorus pentachloride" is a halogenating agent. It is rarely used these days, as you have to remove the "pockle3" after the reaction. PCl_5 is very water sensitive, and a bit hard to handle. A better alternative might be "thionyl chloride", which you can pour out of a bottle and distill off:

RCO_2H + SOCl_2 + Delta rarr RC(=O)Cl + SO_2uarr + HCluarr