Wagner-Meerwein rearrangement

Schematic of the Wagner-Meerwein rearrangement. Reagents: alcohol, acid catalyst. Product: olefin.

The Wagner-Meerwein rearrangement is an organic reaction used to convert an alcohol to an olefin using an acid catalyst. The mechanism begins with protonation of the alcohol by the acid which is then released as water to forms a carbocation. A 1,2-shift then occurs to form a more substituted and stabilized carbo-cation. A final deprotonation with water produces the final olefin product and regenerates the acid catalyst.[1][2]


Mechanism of the Wagner-Meerwein rearrangement. 1,2-shift.


Wagner, G. J. Russ. Phys. Chem. Soc. 1899, 31, 690
Meerwein, H. Justus Liebigs Ann. Chem. 1914, 405, 129–175.