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Acid-Catalyzed Hydration

Introduction

Reaction

Hydration reaction 1

Regioselectivity:     Markovnikov

Stereospecificity:    syn + anti

Intermediate:          carbocation

Since a carbocation intermediate is formed, the reaction is also susceptible to carbocation rearrangements, as shown below:

Hydration reaction 2

Mechanism

Mechanism without carbocation rearrangement:

Hydration reaction 1 mechanism

Mechanism with a carbocation rearrangement:

Hydration reaction 2 mechanism
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