Mechanism of the antiMarkovnikov's addition of HBr Using Hydrogen Peroxide Help Me With Organic Chem

In this video I will discuss the antiMarkovnikov Addition of bromine to an alkene. This mechanism uses preoxide to form bromide radicals that attack the alkene. In the case of an asymmetrical alkene the attack of the bromine radical can form a carbon free radical on the most substituted carbon or the least substituted carbon. From our knowledge of carbon free radical stability we know that forming a free radical on the most substituted carbon is the most stable. This means that the bromine free radical will attack the alkene in such a way as to form the most substituted carbon free radical.

The first step of this mechanism is the homolytic cleavage of the peroxide forming oxygen free radicals. The oxygen free radicals then attack hydrogen bromide. The oxygen free radical removes the hydrogen atom and produces the bromine free radical. The bromine free radical then attacks the least substituted carbon of the alkene resulting in the free radical forming on the most substituted carbon. The carbon free radical then attacks another molecule of hydrogen bromide, removing the hydrogen and forming another bromine free radical. This newly formed bromine free radical will attack another molecule of the alkene thus keeping the radical chain reaction going!

Failing organic chemistry? You do not have to fail Organic Chemistry!

This video is part of a series called How to be Successful in Organic Chemistry. In this series I go over numerous problems that a student could expect to see in there organic chemistry 1 course. Doing organic chemistry practice problems will make you more successful in organic chemistry and biochemistry.

I recommend that you download the problem from the link below and attempt the problem yourself and use this video to correct your work.

Download the problem from this video at the following link:

https://www.dropbox.com/s/is91t20u9rxjmqw/stereochemical%20outcome%20and%20the%20E2%20mechanism.key?dl=0

Good Luck and Good Chemistry!

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https://www.dropbox.com/s/lf44wsvidm99rvo/Mechanism%20of%20the%20antiMarkovnikov%27s%20addition%20of%20HBr%20Using%20Hydrogen%20Peroxide%20.pdf?dl=0