10. Addition Reactions

Provide the expected product for the reaction of each of the following alkenes with H₂SO₄ and H₂O.

(a)

For each of the products you predicted in Assessment 8.39, provide an arrow-pushing mechanism which rationalizes the formation of each product. Make sure your mechanism accounts for all products formed, including stereoisomers and regioisomers, where applicable.

Provide the alkene that would give the following alcohols under acid-catalyzed hydration conditions.

(a)

The hydration of three C₅H₁₀ alkene isomers can give 2-methylbutan-2-ol. Draw them.

Suggest an arrow-pushing mechanism that accounts for the formation of the following products.

(a)

Predict the products you would get when the following alkenes react under the following conditions: (i) H₂SO₄ , H₂O

(a)

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (iv) H₂SO₄ , H₂O

(b)

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (iv) H₂SO₄ , H₂O

(g)

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (iv) H₂SO₄ , H₂O

(k)

Provide a mechanism for the following reactions occurring with rearrangement.

(a)

Cyclooctene is one of the smaller rings that can form a trans alkene. Would you expect cis-cyclooctene or trans-cyclooctene to react more quickly in an acid-catalyzed hydration reaction?

Devise a synthesis for each compound, starting with methylenecyclohexane and any other reagents you need.

a. 1-methylcyclohexanol

How can the following compounds be prepared from 3,3-dimethyl-1-butene?

b. 3,3-dimethyl-2-butanol

In Chapter 8, we learned about the chemistry of terpenes and the interesting reactions they can undergo. One such reaction is the acid-catalyzed conversion of nerol to terpineol. Suggest a mechanism for this transformation

.

The acid-catalyzed dehydration we learned in this chapter is reversible, as shown below.

(a) Propose a mechanism for the formation of an alcohol from an alkene.