11. Radical Reactions

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

3. HBr

4. HBr/peroxide

Show how you would synthesize each compound using methylenecyclopentane as your starting material.

(b)

Propose mechanisms consistent with the following reactions.

(a)

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