Reactions of Alkenes and Alkynes - What is Hydroboration-Oxidation of Alkene?

8 important questions on Reactions of Alkenes and Alkynes - What is Hydroboration-Oxidation of Alkene?

What is meant with an anti-Markovnikov hydration?

In an anti-Markovnikov hydration, the hydrogen is added to the carbon that is more substituted.

Since Borane can not be prepared pure, in what solution is it commercially available?

BH3 forms a stable Lewis acid-base complex with tetrahydrofuran.

In what way is the addition of borane to alkenes regioselective?

Boron becomes predominantly bonded to the less substituted carbon in an unsymmetrical alkene.
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In what way is the addition of borane to alkenes stereoselective?

Hydrogen and boron add from the same face of the carbon-carbon double bond. Which makes the reaction syn stereoselective.

What is the resemblance between a borane and a carbocation?

Both BH3, BF3 and carbocations have an empty 2p orbital and are electrophiles. The BH3 and BF3 are electrically neutral, this in contradiction to the positive charge on a carbocation.

How is the addition of borane to an alkene initiated?

The reaction is initiated by the coordination of the vacant 2p orbital of boron with the electron pair of the pi bond.

What is the reason the hydroboration-oxidation reaction is regioselective?

Probably because the boron is much larger than the hydrogen and will add to the less hindered carbon.

What is the second step in the hydroboration-oxidation reaction?

This usually is the replacement of the boron with an hydroxyl group or oxidation. This happens when the compound is treated with hydrogen peroxide and sodiumhydroxyl.

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