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Question 12.9: Acid-Catalyzed Hydration of an Alkene Propose a three-step r...

Acid-Catalyzed Hydration of an Alkene

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: 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: Loss of H ^{+} from the oxonium ion completes the reaction and generates a new H ^{+} catalyst.

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