0 votes
44 views
in Organic Chemistry by (138k points)
How does the Wagner-Meerwein rearrangement occur and what are its key characteristics? Explain with the help of a specific example from organic chemistry.

1 Answer

0 votes
by (138k points)
The Wagner-Meerwein rearrangement is a fundamental organic reaction that involves the migration of an alkyl or aryl group from one atom to an adjacent electron-deficient atom, typically a carbocation. This rearrangement is a 1,2-shift and is driven by the formation of a more stable carbocation. The reaction was first reported by Georg Wagner in 1899 and later studied by Hans Meerwein in the early 20th century.Key characteristics of the Wagner-Meerwein rearrangement include:1. The reaction involves the migration of an alkyl or aryl group to an adjacent carbocation.2. The rearrangement is a 1,2-shift, meaning that the migrating group moves from one atom to an adjacent atom.3. The driving force for the rearrangement is the formation of a more stable carbocation.4. The reaction typically occurs under mild conditions and can be promoted by Lewis or Brnsted acids.A specific example of the Wagner-Meerwein rearrangement can be seen in the conversion of a tertiary alcohol to an olefin using a strong acid. In this reaction, the tertiary alcohol is protonated to form a tertiary oxonium ion, which then undergoes a 1,2-alkyl shift to form a more stable carbocation. The carbocation then loses a proton to form the olefin product.Here's a step-by-step description of the reaction using 3-methyl-3-pentanol as an example:1. Protonation of the tertiary alcohol: The tertiary alcohol  3-methyl-3-pentanol  is protonated by a strong acid  e.g., H2SO4  to form a tertiary oxonium ion.2. 1,2-alkyl shift: The oxonium ion undergoes a 1,2-methyl shift, where the methyl group migrates from the carbon adjacent to the oxygen to the positively charged oxygen atom. This migration forms a more stable secondary carbocation.3. Deprotonation: The secondary carbocation loses a proton to form the olefin product  3-methyl-2-pentene .Overall, the Wagner-Meerwein rearrangement is an essential concept in organic chemistry, as it provides a mechanistic understanding of how carbocations can rearrange to form more stable intermediates, ultimately leading to the formation of various organic products.

Related questions

Welcome to Sarvan Science Q&A, where you can ask questions and receive answers from other members of the community.
...