Acid-Catalyzed Hydration

$$\text{R--CH=CH}_2 + \text{H}_2\text{O} \xrightarrow{\text{H}^+} \text{R--CH(OH)--CH}_3$$

Concept: Addition of water across the double bond in the presence of an acid catalyst to yield an alcohol. Follows Markovnikov's Rule ($$\text{OH}^-$$adds to the more substituted carbon atom). Proceeds via a discrete carbocation intermediate; therefore, carbocation rearrangements (1,2-hydride or 1,2-methyl shifts) can occur to yield a more stable alcohol.