11. Radical Reactions

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

a.

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

f.

What are the answers to Problem 29 when the same compounds are treated with Br₂ at 125 °C?

c.

What is the major product obtained from treating an excess of each of the following compounds with Cl₂ in the presence of ultraviolet light at room temperature? Disregard stereoisomers.

c.

What alkyl halide will be obtained in greatest yield? Ignore stereoisomers.

a.

What alkyl halide will be obtained in greatest yield? Ignore stereoisomers.

b.

What hydrocarbon with molecular formula C₄H₁₀ forms only two monochlorinated products? Both products are achiral.

What hydrocarbon with the same molecular formula as in part a forms three monochlorinated products? One is achiral and two are chiral.

Explain why iodine (I₂) does not react with ethane, even though I₂ is more easily cleaved homolytically than the other halogens.

Write the initiation, propagation, and termination steps for the monochlorination of cyclohexane.

Provide an arrow-pushing mechanism for the following alkane bromination. [Don't forget to use fishhook arrows to represent the movement of single electrons.]

If a small amount of a moderately nonpolar poisonous compound was added to a pond, why would it be safer to drink the water than it would be to eat the fish that live there?

Predict the major monohalogenation product(s) of the following reactions. Indicate whether you think the reaction will be selective and justify your position.

(c)

Predict the product(s) of the following halogenation reactions. Only one equivalent of the halogen is used in each case. If the reaction proceeds selectively, indicate this by only drawing the major product. If the reaction is not selective, draw all possible products.

(e)

Predict the product(s) of the following halogenation reactions. Only one equivalent of the halogen is used in each case. If the reaction proceeds selectively, indicate this by only drawing the major product. If the reaction is not selective, draw all possible products.

(f)