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What is the mechanism of the Wagner-Meerwein rearrangement of cyclohexanol to form cyclohexene? Provide a step-by-step explanation including the formation of intermediate carbocation and hydride shift.

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The Wagner-Meerwein rearrangement is a 1,2-rearrangement of a carbocation that involves the migration of an alkyl or aryl group, or a hydrogen atom, to an adjacent carbocation center. In the case of cyclohexanol to cyclohexene, the mechanism involves the following steps:1. Protonation of the alcohol: The reaction starts with the protonation of the hydroxyl group  OH  of cyclohexanol by a strong acid, such as sulfuric acid  H2SO4  or phosphoric acid  H3PO4 . This step generates a good leaving group, water  H2O , and a carbocation on the carbon atom that was previously bonded to the hydroxyl group.Cyclohexanol + H2SO4  Cyclohexyl oxonium ion + H2O2. Formation of the initial carbocation: The water molecule leaves, resulting in the formation of a secondary carbocation at the position where the hydroxyl group was initially attached.Cyclohexyl oxonium ion  Secondary carbocation + H2O3. Hydride shift  1,2-rearrangement : A hydride  H-  from the adjacent carbon atom migrates to the carbocation center, leading to a more stable tertiary carbocation. This step is the key step in the Wagner-Meerwein rearrangement.Secondary carbocation  Tertiary carbocation  via hydride shift 4. Deprotonation and formation of cyclohexene: Finally, a base  such as the bisulfate ion, HSO4-  deprotonates a hydrogen atom from the carbon adjacent to the carbocation center, resulting in the formation of a double bond  C=C  and the desired product, cyclohexene.Tertiary carbocation + HSO4-  Cyclohexene + H2SO4In summary, the Wagner-Meerwein rearrangement of cyclohexanol to cyclohexene involves the protonation of the alcohol, formation of a secondary carbocation, a hydride shift to form a more stable tertiary carbocation, and deprotonation to generate the final product, cyclohexene.
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