What is the major product obtained from the reaction of HBr with each of the following?

b.

Which is more highly regioselective: reaction of an alkene with BH₃ or with 9-BBN?

What is the major product obtained from hydroboration–oxidation of the following alkenes?

a. 2-methyl-2-butene

What will be the product of the preceding reaction if HBr is used in place of Br₂?

How does the first step in the reaction of propene with Br₂ differ from the first step in the reaction of propene with HBr?

To understand why Br⁻ adds to a carbon of the bromonium ion rather than to the positively charged ­bromine, draw the product that would be obtained if Br⁻ did add to bromine.

Why are Na⁺ and K⁺ unable to form covalent bonds?

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.

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?

b.

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?

c.

What is the product of the addition of I—Cl to 1-butene? (Hint: Chlorine is more electronegative than iodine [Table 1.3].)

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?

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?

Draw structures for the following:

a. 2-propyloxirane

b. cyclohexene oxide

Draw structures for the following:

c. 2,2,3,3-tetramethyloxirane

Draw structures for the following:

d. 2,3-epoxy-2-methylpentane

What alkene would you treat with a peroxyacid in order to obtain each of the epoxides in Problem 27?

a. 2-propyloxirane

b. cyclohexene oxide

What alkene would you treat with a peroxyacid in order to obtain each of the epoxides in Problem 27?

c. 2,2,3,3-tetramethyloxirane

d. 2,3-epoxy-2-methylpentane

Identify each of the following reactions as an oxidation reaction, a reduction reaction, or neither.

a.

b.

What products are formed when the following compounds react with ozone and then with dimethyl sulfide?

a.

What products are formed when the following compounds react with ozone and then with dimethyl sulfide?

b.

What products are formed when the following compounds react with ozone and then with dimethyl sulfide?

c.

d.

What products are formed when the following compounds react with ozone and then with dimethyl sulfide?

e.

f.

What alkene would give only a ketone with three carbons as a product of oxidative cleavage?

What alkenes would give only an aldehyde with four carbons as a product of oxidative cleavage

What aspect of the structure of the alkene does ozonolysis not tell you?

The following products were obtained from the oxidative cleavage of a diene. What is the structure of the diene?

The following product was obtained from the ozonolysis of an alkene followed by treatment with dimethyl sulfide. What is the structure of the alkene?

a.

The following product was obtained from the ozonolysis of an alkene followed by treatment with dimethyl sulfide. What is the structure of the alkene?

b.

The following product was obtained from the ozonolysis of an alkene followed by treatment with dimethyl sulfide. What is the structure of the alkene?

c.