A synthesis method for alcohols, already studied in the section on alkenes, consists in hydrating the alkene. The addition of -OH can be on the more substituted carbon of the alkene (Markovnikov), or on the less substituted carbon (anti-Markovnikov).
Markovnikov Hydration
In this hydration the hydroxyl group goes to the carbon with more substituents. Aqueous sulfuric reagent or mercury acetate in water is used as the reagent, followed by reduction with sodium borohydride.
Anti-Markovnikov hydration
The hydroxyl group adds to the least substituted carbon. The reagent used is borane in THF followed by oxidation with hydrogen peroxide in a basic medium (hydroboration).
