The Wagner-Meerwein rearrangement uses catalytic acid to convert an alcohol into an olefin. The alcohol is protonated and released as water to form a carbocation. A [1,2]-shift of an adjacent carbon-carbon bond generates a more stable carbocation, followed by loss of a proton to afford the alkene. Both E/Z products are possible in some cases.

  • Reagents: Catalytic Acid
  • Reactant: Alcohol
  • Product: Olefin
  • Type of Reaction: Carbocation Rearrangement
  • Bond Formation: C=C

Lab Tips

  • The initial carbocation can be generated via treatment of an alkyl halide with a Lewis acid, solvolysis of a secondary or tertiary alkyl halide, protonation of an alkene, etc.
  • The [1,2][1,2]-shifts may be necessary to generate the most stable carbocation.
  • Several products may arise if more than one rearrangement pathway is possible.
  • The stereochemistry of the migrating group is retained (Woodward-Hofmann rules).
  • A nucleophile present in the reaction mixture (i.e. the solvent or the conjugate base of the acid used to promote the rearrangement) may capture the carbocation forming a substituted product instead.
Kürti, L., Czakó, B. (2005). Strategic Applications of Named Reactions in Organic Synthesis; Background and Detailed Mechanisms. Burlington, MA: Elsevier Academic Press.


Top Citations

Original Paper

Related Reactions

  • Corey-Kim Oxidation
  • Dess-Martin Oxidation
  • Jones Oxidation

Related Compounds

  • Catalytic Acid
  • Catalytic Acid
By shuhan yang


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