Draw the reaction mechanism that shows BH3 adding to the alkene. Why do we get the...

Draw the reaction mechanism that shows BH3 adding to the alkene. Why do we get the anti-Markovnikov product?

Expert Solution

Why it gives anti-markonikov product

First step is the attack of the alkene on BH₃, which then forms a four membered ring intermediate of partial bonds. It is because of this intermediate that hydroboration forms the anti-Markovnikov product. The boron atom is highly electrophilic because of its empty p orbital (ie. it wants electrons), and forms a slight bonding interaction with the pi bond. Since some electron density from the double bond is going towards bonding with the boron, the carbon opposite the boron is slightly electron deficient, left with a slightly positive charge. Positive charges are best stabilized by more highly substituted carbons, so the carbon opposite the boron tends to be the most highly substituted. Once the transition state breaks down, BH2 is attached to the least substituted carbon.

queen_honey_blossom answered 2 years ago

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