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One potential question for a student studying rearrangement reactions in organic chemistry is: What is the mechanism by which a Wagner-Meerwein rearrangement occurs and give an example of a molecule that undergoes this type of rearrangement?

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The Wagner-Meerwein rearrangement is a type of 1,2-alkyl or aryl shift that occurs in carbocations, leading to the formation of a more stable carbocation. This rearrangement is a crucial step in many organic reactions, such as pinacol rearrangement, demethylation, and dehydration reactions.The mechanism of the Wagner-Meerwein rearrangement involves the following steps:1. Formation of a carbocation: The reaction begins with the generation of a carbocation, which can be formed through various pathways, such as protonation of an alcohol, loss of a leaving group, or addition of an electrophile to a double bond.2. 1,2-alkyl or aryl shift: The key step in the rearrangement is the migration of an alkyl or aryl group from one carbon atom to the adjacent carbocation center. This migration occurs through a concerted process, in which the migrating group forms a partial bond with the carbocation center while simultaneously breaking its bond with the adjacent carbon atom. The driving force for this rearrangement is the formation of a more stable carbocation, such as a tertiary or resonance-stabilized carbocation.3. Termination: The rearranged carbocation can then undergo further reactions, such as deprotonation, nucleophilic attack, or elimination, to form the final product.An example of a molecule that undergoes Wagner-Meerwein rearrangement is 3-methyl-3-pentanol. When treated with a strong acid, such as sulfuric acid, 3-methyl-3-pentanol undergoes dehydration to form a carbocation intermediate. The carbocation then undergoes a 1,2-hydride shift, leading to the formation of a more stable tertiary carbocation. Finally, the carbocation undergoes elimination to form the final product, 3-methyl-2-pentene.
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