10. Addition Reactions

Predict the product of the following reaction.

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

(p)

Predict the major products of the following reactions.

a. 1-methylcyclohexene+ aqueous Hg(OAc)₂

b. the product from part (a), treated with NaBH₄

a. Propose a mechanism for the following reaction.

b. Give the structure of the product that results when this intermediate is reduced by sodium borohydride.

Show how you would accomplish the following transformations.

(a)

The first step of oxymercuration–reduction is stereospecific, and yet this fact wasn't emphasized in that discussion. Show the stereospecificity of the first step for the following alkene and then explain why the stereospecificity becomes unimportant after the second step.

A common situation occurs when both carbons of the mercurinium ion are secondary. In a situation like the one shown, to which carbon would you expect water to add? That is, would you expect to produce A or B? Explain your answer.

Provide an arrow-pushing mechanism, accounting also for the stereochemical outcome, of the first step (oxymercuration) of the three reactions in Figure 8.63.

Provide an arrow-pushing mechanism, accounting also for the stereochemical outcome, of the first step (oxymercuration) of the three reactions in Figure 8.63.

Which is more stable, a carbocation or a mercurinium ion? How do you know?

Predict the products you would get when the following alkenes react under the following conditions: (ii) 1. Hg(OAc)₂ , H₂O , 2. NaBH₄

(a)

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (v) 1. Hg(OAc)₂ , H₂O 2. NaBH₄

(g)

Predict the product(s) that would result when the alkenes shown here are allowed to react under the following conditions: (v) 1. Hg(OAc)₂ , H₂O 2. NaBH₄

(k)

Would you expect the following to produce an equal or unequal mixture of stereoisomers?

(a)

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.

(h)