This is the second of three ways to add alcohol to a double bond. It is similar in acid-catalyzed hydration in terms of products, but the mechanism is WAY different. 

  • Opening of 3-membered intermediates/molecules always results in anti-addition.

General Reaction:

1. Electrophilic Addition

2. Nucleophilic Substitution (SN2)

3. Reduction (demurcuration)

Problem: Predict the product of the following reaction.