10. Addition Reactions

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

(k)

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)

When alkenes react with bromine in water, a halohydrin is produced. When water is replaced with methanol in this reaction, a different product is produced. Suggest a mechanism for the formation of this product.

Explain why water attacks the carbon of the bromonium ion as opposed to the bromonium ion itself in the second step of halohydrin formation.

Suggest an alkene that could be used to make each of the following halohydrins.

(c)

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

(e)

Predict the product of the following haloalkane syntheses.

(e)

Halohydrin formation is a stereospecific reaction. Identify the products of halohydrin formation of the following diastereomeric alkenes to demonstrate this stereospecificity.

In light of your answer to Assessment 9.47, predict the product of the following reactions we have seen previously where an alcohol is substituted for water.

(c)

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

(l)

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)

Retrosynthetic analysis is the process of working backward to develop the synthesis of a new compound. In Chapter 10, we begin developing multistep syntheses in this manner. For now, try to work backward a single step by suggesting an alkene and a reagent that would give products (a)–(i). [Your answers should not include alkenes that undergo rearrangement to give the desired products.]

(i)

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?

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?

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

d.