Allylic Halogenation

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

Remember our friendly addition reaction halogenation? Notice that you achieve a vicinal dihalide in this reaction.  

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

This one added condition will lead to the formation of a mixture of allylic alkyl halides. Here’s the full mechanism:

Example: Predict the product(s) of the following reaction. 

5m