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).

Show how you would synthesize each compound using methylenecyclohexane as your starting material.

(a)

Show how you would accomplish the following synthetic conversions.

c. 3-methylpent-1-ene → 3-methylpentan-2-ol

Explain why acid-catalyzed hydration would be a poor choice for the reaction in (c).

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.]

(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 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