Final answer:
The hydroboration-oxidation reaction is a regioselective and stereoselective process that converts alkenes to alcohols, resulting in anti-Markovnikov syn-addition of the borane and subsequent retention of configuration in the alcohol product.
Step-by-step explanation:
The hydroboration-oxidation reaction is a two-step regioselective and stereoselective process used to convert alkenes into alcohols. In the hydroboration step, borane (BH3) or one of its derivatives is added to the alkene in a syn-addition manner, which is the stereoselective component of the reaction. This step proceeds with regioselectivity, typically yielding anti-Markovnikov products; that is, the boron atom attaches to the less-substituted carbon of the alkene, and the resulting organoborane intermediate is then oxidized to an alcohol by hydrogen peroxide (H2O2) in the presence of sodium hydroxide (NaOH) or another base. The oxidation step converts the C-B bond into a C-O bond, giving the corresponding alcohol with retention of configuration from the original syn-addition of boron. For asymmetric alkenes, hydroboration-oxidation provides a predictable outcome based on the aforementioned regioselectivity and stereoselectivity, making it a valuable reaction in organic synthesis for forming alcohols with specific configurations.