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)

What will be the major product obtained from the reaction of Br₂ with 1-butene if the reaction is carried out in

a. dichloromethane?

b. water?

Each of the following reactions has two nucleophiles that could add to the intermediate formed by the reaction of the alkene with an electrophile. What is the major product of each reaction?

a.

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.

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

(h)

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.

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.