Question 12.1: What products would you expect from reaction of 4,4-dimethyl...

What products would you expect from reaction of 4,4-dimethylcyclohexene with NBS?

S t r a t e g y

Draw the alkene reactant, and identify the allylic positions. In this case, there are two different allylic positions; we’ll label them A and B. Now abstract an allylic hydrogen from each position to generate the two corresponding allylic radicals. Each of the two allylic radicals can add a Br atom at either end (A or A′; B or B′), to give a mixture of up to four products. Draw and name the products. In the present instance, the “two” products from reaction at positions B and B′ are identical, so a total of only three products are formed in this reaction.