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Hydroboration-Oxidation

Last updated

Feb 28, 2022
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- Hydride Reagent
- Hydrocarbon

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Alkenes do not undergo hydration upon treatment with water even at very high temperatures. There are two approaches to hydrating alkenes:

Reaction of the alkene with water in the presence of a strong-acid catalyst.
Using an indirect method

Hydroboration-oxidation, sometimes casually called hydroboration for convenience, is a common indirect method used to hydrate alkenes.

net reaction:

The protocol is carried out in two stages:

Stage 1: Hydroboration

The alkene is treated with a source of borane ( diborane or borane-THF complex), which converts the alkene into a trialkylborane.

Stage 2: Oxidation

The trialkylborane is treated with H₂O₂ and a strong base, usually NaOH, in aqueous medium, which converts the trialkylborane into an alcohol.

eg:
Stage 1:

This reaction is an anti-Markovnikov addition and a syn addition.

Stage 2:

Stage 1 + Stage 2 =

The net reaction is an anti-Markovnikov addition:

Stage 1: Hydroboration

Stage 2: Oxidation

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