Acid-Catalyzed Hydration

This is the first of three ways to add alcohol to a double bond. Similar to hydrohalogenation in terms of mechanism, however it will require a protonation and deprotonation step since it is acid-catalyzed. 

This reaction uses the same reagents as acid-catalyzed dehydration, so how do you know which reaction to use? Just look at what you are starting with:

General Reaction:

Note: The squiggly line on the product just means “indeterminate stereochemistry”. We aren’t sure where that –H will add, so we’ll just draw it on a squiggly line. 

Concept: A worked-example of the acid-catalyzed hydration mechanism.     


Problem: Predict the product of the following reaction.