Draw the products formed when each alkene is treated with BH3 followed by H2 O2, HO ^-. Include

step 1 In this problem, we're given three starting compounds, and we're asked for the product we'd get

Draw the products formed when each alkene is treated with...

Key Concepts

Regioselectivity (Anti?Markovnikov Addition)

During the hydroboration step, the addition of boron occurs preferentially at the less substituted carbon of the double bond. This is because boron, being electrophilic, avoids steric hindrance and leads to the formation of the trialkylborane intermediate on the less hindered side. As a result, after oxidation, the hydroxyl group is placed on the less substituted carbon, which is opposite to what is typically seen in Markovnikov additions.

Hydroboration?Oxidation

This two?step transformation converts alkenes into alcohols. In the first step, borane (BH3) adds to the alkene to form an organoborane intermediate. In the second step, the organoborane is oxidized using hydrogen peroxide (H2O2) in the presence of a base (OH–) to yield the corresponding alcohol. This reaction demonstrates that alkenes can be functionalized to produce alcohols in a straightforward and predictable manner.

Stereospecific Syn Addition

The hydroboration reaction proceeds through a concerted mechanism in which both the hydrogen and the boron atom add to the same face (or side) of the alkene. This syn addition results in a specific stereochemical arrangement of substituents in the intermediate, which is retained during the oxidation step. Consequently, any new stereocenters formed exhibit predictable stereochemistry, with both added groups (after oxidation, the hydroxyl group replacing the boron) being on the same side of the former double bond.

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