Predict the product of the following reaction.

Predict the major products of the following reactions.

c. 4−chlorocycloheptene + Hg(OAc)₂ in CH₃OH

d. the product from part (c), treated with NaBH₄

Show how you would accomplish the following synthetic conversions.

a. but-1-ene → 2-methoxybutane

b. 1-iodo-2-methylcyclopentane → 1-methylcyclopentanol

In light of your answer to Assessment 8.73, predict the product of the following oxymercuration–reduction reactions, each of which results in a single product. [Don't worry about the absolute stereochemistry, though these reactions are also stereoselective.]

(b) This reaction sequence was used in the synthesis of (+) -lineatin, a monoterpene aggregation pheromone from the female ambrosia beetle Trypodendron lineatum (Org. Lett. 2004, 6, 1449–1452).

In light of your answer to Assessment 8.73, predict the product of the following oxymercuration–reduction reactions, each of which results in a single product. [Don't worry about the absolute stereochemistry, though these reactions are also stereoselective.]

(c) Oxymercuration–reduction was used in the stereoselective synthesis of the macrolactone core of neopeltolide, a marine macrolide isolated from a Caribbean sponge that has potent anticancer activity (Org. Lett. 2012, 14, 2346–2349).

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)