Radical Hydrohalogenation

The presence of radicals in some familiar looking addition reactions can completely change the product. 

Remember our friendly addition reaction hydrohalogenation? Notice that you achieve Markovnikov alkyl halide in this reaction.  

Concept: How Radical Hydrohalogention is different from typical Hydrohalogention.


Now we see this reaction. Note that the only difference is the presence of a radical initiator. 

However, this one added reagent will lead to the formation of an anti-Markovnikov alkyl halide. Here’s the full mechanism:

Example: Provide the complete mechanism for the following radical hydrohalogenation.