10. Addition Reactions

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iii) Br₂, H₂O ; (iv) Cl₂, CH₃OH

(f)

At the beginning of Chapter 9, we stated that after finishing Chapters 8 and 9, we would have the ability to make a large variety of functional groups using related reactions. Show the reagent(s) necessary to convert 1-isobutylcyclohexene into the following molecules.

(c)

Using any alkene and any other reagents, how would you prepare the following compounds?

d.

Predict the product of the following reaction.

Predict the product of the following haloalkane syntheses.

(e)

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iv) Cl₂, CH₃OH

(h)

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)

Predict the product of the following reaciton.

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (iv) Cl₂, CH₃OH

(d)

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

c. ethyl alcohol?

d. methyl alcohol?

Which stereoisomer of 3-hexene forms (3S,4S)-4-bromo-3-hexanol and (3R,4R)-4-bromo-3-hexanol when it reacts with Br₂ and H₂O?

1-Methylcyclohexene forms two products when it reacts with bromine in methanol.

a. Draw the mechanism for the formation of the products.

b. Describe their stereochemical relationship—that is, are they enantiomers or diastereomers?

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.

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.

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.