11. Radical Reactions

Tributyltin hydride (Bu₃SnH) is often used as a 'radical carrier' in radical reactions. Which bond would you expect to be weaker, Sn–H or C–H? How might this relate to radical stability? Explain your answer.

Haloalkanes can be reduced to alkanes using radical reactions involving Bu₃SnH and a catalytic amount of AIBN. Suggest a mechanism for this reaction. [Pay close attention to the bonds formed and broken in developing your mechanism.]

What are the product(s) of each of the following reactions? Disregard stereoisomers.

e.

What are the product(s) of each of the following reactions? Disregard stereoisomers.

d.

How many alkyl halides are obtained from monochlorination of the alkanes in Problem 4 if stereoisomers are included?

h.

How many alkyl halides are obtained from monochlorination of the alkanes in Problem 4 if stereoisomers are included?

g.

How many alkyl halides are obtained from monochlorination of the alkanes in Problem 4 if stereoisomers are included?

f.

How many alkyl halides are obtained from monochlorination of the alkanes in Problem 4 if stereoisomers are included?

e.

How many alkyl halides are obtained from monochlorination of the alkanes in Problem 4 if stereoisomers are included?

b.

How many alkyl halides are obtained from monochlorination of the alkanes in Problem 4 if stereoisomers are included?

a.

How many alkyl chlorides are obtained from monochlorination of the following alkanes? Disregard stereoisomers.

h.

How many alkyl chlorides are obtained from monochlorination of the following alkanes? Disregard stereoisomers.

g.

How many alkyl chlorides are obtained from monochlorination of the following alkanes? Disregard stereoisomers.

f.

How many alkyl chlorides are obtained from monochlorination of the following alkanes? Disregard stereoisomers.

e.

How many alkyl chlorides are obtained from monochlorination of the following alkanes? Disregard stereoisomers.

b.