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.

4. Br₂ in CH₂Cl₂

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.

7. H₂O + H₂SO₄

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

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.

2. BH₃/THF, followed by HO^-, H₂O₂, 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 second-order rate constant (in units of M^-1s^-1) for acid-catalyzed hydration at 25 °C is given for each of the following alkenes:

a. Calculate the relative rates of hydration of the alkenes. (Hint: Divide each rate constant by the smallest rate constant of the series: 3.51 × 10^-8.)

b. Why does (Z)-2-butene react faster than (E)-2-butene?

c. Why does 2-methyl-2-butene react faster than (Z)-2-butene?

d. Why does 2,3-dimethyl-2-butene react faster than 2-methyl-2-butene?

Draw the products of the following reactions. If the products can exist as stereoisomers, show which stereoisomers are formed.

b.

Draw the products of the following reactions. If the products can exist as stereoisomers, show which stereoisomers are formed.

c.

A student was about to turn in the products he had obtained from the reaction of HI with 3,3,3-trifluoropropene when he realized that the labels had fallen off his flasks and he did not know which label belonged to which flask. His friend reminded him of the rule that says the electrophile adds to the sp² carbon bonded to the most hydrogens. In other words, he should label the flask containing the most product 1,1,1-trifluoro-2-iodopropane and label the flask containing the least amount of product 1,1,1-trifluoro-3-iodopropane. Should he follow his friend’s advice?

a. Propose a mechanism for the following reaction (show all curved arrows):

b. Which step is the rate-determining step?

c. What is the electrophile in the first step?

d. What is the nucleophile in the first step?

e. What is the electrophile in the second step?

f. What is the nucleophile in the second step?

Draw the products, including their configurations, obtained from the reaction of 1-ethylcyclohexene with the following reagents:

b. H₂, Pd/C

Draw the products, including their configurations, obtained from the reaction of 1-ethylcyclohexene with the following reagents:

c. R₂BH/THF, followed by HO^–, H₂O₂, H₂O

Which stereoisomer of 3-hexene forms a meso compound when it reacts with Br₂?

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?

Propose a mechanism for each of the following reactions:

b.

What is the major product of each of the following reactions?

a.

What is the major product of each of the following reactions?

b.

Draw the products of the following reactions. If the products can exist as stereoisomers, show which stereoisomers are formed

c. 1-ethylcyclohexene + H₂O + H₂SO₄

Draw the products of the following reactions. If the products can exist as stereoisomers, show which stereoisomers are formed

f. 1,2-dideuteriocyclohexene + H₂, Pd/C

Draw the products of the following reactions. If the products can exist as stereoisomers, show which stereoisomers are formed.

i. (Z)-3,4-dimethyl-3-heptene + H₂, Pd/C

a. What product is obtained from the reaction of HCl with 1-butene? With 2-butene?

b. Which of the two reactions has the greater free energy of activation?

c. Which compound reacts more rapidly with HCl: (Z)-2-butene or (E)-2-butene?

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

c.

d.

For each compound, show the products obtained from ozonolysis, followed by treatment with dimethyl sulfide.

a.

For each compound, show the products obtained from ozonolysis, followed by treatment with dimethyl sulfide.

b.

For each compound, show the products obtained from ozonolysis, followed by treatment with dimethyl sulfide.

c.

For each compound, show the products obtained from ozonolysis, followed by treatment with dimethyl sulfide.

d.

For each compound, show the products obtained from ozonolysis, followed by treatment with dimethyl sulfide.

e.

Which stereoisomer of 3,4-dimethyl-3-hexene forms (3S,4S)-3,4-dimethylhexane and (3R,4R)-3,4-dimethylhexane when it reacts with H₂, Pd/C?