73.7k views
2 votes
Alkenes can be hydrated via the addition of borane to yield alcohols with non-Markovnikov regiochemistry. The boron atom is an electrophile and thus follows Markovnikov's rule in adding to the carbon containing the most hydrogens. Oxidation of the alkylborane with basic peroxide yields the product alcohol. Draw curved arrows to show the movement of electron

1 Answer

6 votes

Answer:

Attached in the pictures.

Step-by-step explanation:

Hello,

In the attached pictures, you're finding the steps concerning to the hydroboration of alkenes.

At first, the addition of the borane to the alkene is initialized and proceeds as a concerted reaction owing to the bond breaking and subsequent formation that is performed at the same time (1st step picture).

Secondly, the Anti Markovnikov addition of boron is carried out. This atom adds to the less substituted carbon of the alkene, which then replaces the hydrogen on the more substituted carbon (2nd step picture).

Then, the oxidation is carried out via the donation of a pair of electrons from the hydrogen peroxide ion, the nucleophile in this reaction, since it is the electron donor to the formed trialkylborane that resulted from aforesaid step (3rd step picture).

Furthermore, a rearrangement of an R group with its pair of bonding electrons to an adjacent oxygen turns out into the removal of a hydroxide ion (4th step picture).

Finally, the trialkylborate reacts with aqueous sodium hydroxide to yield the alcohol and sodium borate as a side product (5th step picture).

Best regards.

Alkenes can be hydrated via the addition of borane to yield alcohols with non-Markovnikov-example-1
Alkenes can be hydrated via the addition of borane to yield alcohols with non-Markovnikov-example-2
Alkenes can be hydrated via the addition of borane to yield alcohols with non-Markovnikov-example-3
Alkenes can be hydrated via the addition of borane to yield alcohols with non-Markovnikov-example-4
Alkenes can be hydrated via the addition of borane to yield alcohols with non-Markovnikov-example-5
User Jecoms
by
5.1k points