11. Radical Reactions

Predict the product of the following alkene addition reactions.

(b)

Suggest a mechanism for the following reactions.

(b)

Draw the structures of four six-carbon alkenes that form the same product, whether they react with HBr in the presence of a peroxide or with HBr in the absence of a peroxide.

Draw the major product(s) of the reaction of 1-methylcyclohexene with the following reagents, disregarding stereoisomers:

3. HBr

4. HBr/peroxide

Predict the product of the following alkene addition reactions.

(a)

Provide the expected product for the reaction of each of the following alkenes with (i) HBr and (ii) HBr, H₂O₂

(b)

Provide the expected product for the reaction of each of the following alkenes with (i) HBr and (ii) HBr, H₂O₂.

(e)

Predict the product of the following alkene addition reactions.

(c)

What is the major product of the reaction of 2-methyl-2-butene with each of the following reagents?

c. HBr + peroxide 

d. HCl + peroxide

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

c.

At the beginning of Chapter 9, we stated that after finishing Chapters 8 and 9, we would have the ability to make a large variety of functional groups using related reactions. Show the reagent(s) necessary to convert 1-isobutylcyclohexene into the following molecules.

(f)

Predict the major products of the following reactions, and propose mechanisms to support your predictions.

(b)

HINT: Remember to write out complete structures, including all bonds and charges, when writing a mechanism or determining the course of a reaction.

Show how you would accomplish the following synthetic conversions.

(a) but−1−ene → 1−bromobutane

(b) but−1−ene → 2−bromobutane

Propose a mechanism for the following reaction: