10. Addition Reactions

Predict the product of the following reaction.

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?

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?

What is the product of the reaction of maleate and H₂O when H₂SO4 is used as a catalyst instead of fumarase?

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.

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 major product obtained from the acid-catalyzed hydration of each of the following alkenes?

d.

What is the major product obtained from the acid-catalyzed hydration of each of the following alkenes?

a. CH₃CH₂CH₂CH=CH₂

When the following compound is hydrated in the presence of acid, the unreacted alkene is found to have retained the deuterium atoms. What does this tell you about the mechanism for hydration?

Predict the major products of the following reactions, and give the structures of any intermediates. Include stereochemistry where appropriate. n

(n)

Predict the products of the following hydration reactions.

a. 1−methylcyclopentene + dilute acid