The solutions to Solved Problem 8-5 showed only how one enantiomer of the product is formed. For each product, show how an equally probable reaction forms the other enantiomer.

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

j. Br₂/CH₃OH

A graduate student attempted to form the iodohydrin of the alkene shown below. Her analysis of the products showed a good yield of an unexpected product. Propose a mechanism to explain the formation of this product.

Using 1,2-dimethylcyclohexene as your starting material, show how you would synthesize the following compounds. (Once you have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.) If a chiral product is shown, assume that it is part of a racemic mixture.

(g)

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

(h)

Predict the major product(s) for each reaction. Include stereochemistry where appropriate.

e. 1-methylcyclopentene + Br₂ in saturated aqueous NaCl

The solutions to Solved Problem 8-6 showed only how one enantiomer of the product is formed. For each product, show how an equally probable reaction forms the other enantiomer.

Predict the major products of the following reactions, and give the structures of any intermediates. Include stereochemistry where appropriate.

(q)

a. Draw the product or products that will be obtained from the reaction of cis-2-butene and trans-2-butene with each of the following reagents. If a product can exist as stereoisomers, show which stereoisomers are formed.

5. Br₂ + H₂O

b. With which reagents do the two alkenes react to form different products?