Radicals (Stability, Halogenation)

Problem # 1280
 

The structure of 2-methylbutane is shown below.

a) Draw the structures of all possible monochloro products resulting from the free-radical chlorination of 2-methylbutane.

b) Based on statistics alone, what do you expect the major product to be? Is this the same structure as the expected major product? Explain.

c) How would the relative yield of the products differ if bromine was used instead of chlorine?

Problem # 346

For the reaction below, draw the structures of the radical intermediate and the final product.