Predict the products of the following allylic halogenation reactions.
(d)

Propose mechanisms to account for the observed products in the following reactions.

(b)

Show the products you expect when each compound reacts with NBS with light shining on the reaction.

(a)

(b)

In the presence of a small amount of bromine, cyclohexene undergoes the following light-promoted reaction:

a. Propose a mechanism for this reaction.

When methylenecyclohexane is treated with a low concentration of bromine under irradiation by a sunlamp, two substitution products are formed.

a. Propose structures for these two products. (b) Propose a mechanism to account for their formation.

In the following allylic radicals, identify the carbon where the new C–Br bond is most likely to form in the second propagation step.

(a)

In the presence of a small amount of bromine, cyclohexene undergoes the following light-promoted reaction:

d. Explain why cyclohexene reacts with bromine much faster than cyclohexane, which must be heated to react.

In the presence of a small amount of bromine, the following light-promoted reaction has been observed.

a. Write a mechanism for this reaction. Your mechanism should explain how both products are formed. (Hint: Notice which H atom has been lost in both products.)

The fact that allylic halogenation results in formation of the most stable alkene suggests that it is under thermodynamic control. Thus, the second propagation step must be reversible. Suggest an arrow-pushing mechanism by which the less stable allylic halide might equilibrate to the more stable allylic halide.