Question 12.9: Propose a three-step reaction mechanism for the acid catalyz...
Propose a three-step reaction mechanism for the acid catalyzed hydration of methylenecyclohexane to give 1 methylcyclohexanol.
Strategy
The reaction mechanism for the acid-catalyzed hydration of methylenecyclohexane is similar to the three-step mechanism proposed for the acidcatalyzed hydration of propene.
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Step 1: Add a proton. Reaction of the carbon–carbon double bond with H^+ gives a 3° carbocation intermediate.
Step 2: Reaction of the carbocation intermediate with water completes the valence shell of carbon and gives an oxonium ion.
Step 3: Take a proton away. Loss of H^+ from the oxonium ion completes the reaction and generates a new H^+ catalyst.
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