11. Radical Reactions

Predict the products of the following allylic halogenation reactions.

(c)

Provide the mechanism of the radical reactions shown.

(b)

Draw the products of the following reactions, including all stereoisomers:

e.

Draw the products of the following reactions, including all stereoisomers:

f.

How many allylic substituted bromoalkenes are formed from the reactions in Problems 17 if stereoisomers are included?

What is the major product of the following reactions? Disregard stereoisomers:

d.

How many allylic substituted bromoalkenes are formed from the reactions in Problems 18 if stereoisomers are included?

Propose a mechanism to account for the products formed in the following reaction:

When N-bromosuccinimide is added to hex-1-ene in CCl₄ and a sunlamp is shone on the mixture, three products result.

(a) Give the structures of these three products.

(b) Propose a mechanism that accounts for the formation of these three products

Predict the products of the following reactions.

(c) 2-methylpropene + NBS, light

What reagent would you use to brominate the allylic carbon of cyclohexene?

Predict the major product(s) of the following allylic bromination reactions.

(b)

Predict the major product(s) of the following allylic bromination reactions.

(d)

Two products are formed when methylenecyclohexane reacts with NBS? Show how each is formed. Disregard stereoisomers.

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

1. NBS/∆/peroxide

2. Br₂/CH₂Cl₂