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Chemistry · Glossary

What is Hydroboration?

Also known as: anti-Markovnikov orientation

Definition 21.3 University Chemistry — Year 2 · Chapter 21 — Oxidation and Reduction of Alkenes

A hydroboration adds a B–H bond of a borane across a C=C\ce{C=C} bond; followed by oxidation with alkaline hydrogen peroxide, it converts the alkene into an alcohol whose hydroxyl group sits on the less substituted carbon: an anti-Markovnikov orientation.

Hydroboration–oxidation of propene. Borane adds in one step, boron to the terminal carbon and hydrogen to the inner one, both on the same face; oxidation replaces boron by OH with retention of configuration. Propan-1-ol is formed, not the propan-2-ol of acid-catalysed hydration.
Hydroboration–oxidation of propene. Borane adds in one step, boron to the terminal carbon and hydrogen to the inner one, both on the same face; oxidation replaces boron by OH\ce{OH} with retention of configuration. Propan-1-ol is formed, not the propan-2-ol of acid-catalysed hydration.
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