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).

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).

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.

North American termite soldiers, when encountering enemy insects, contract their mandibular muscles, expelling a mixture of chemicals that essentially trap their enemies in a glue-like substance. This weapon, built into the face of the termite, is called the fontanellar gun. It releases a mixture of pinene (62%), myrcene (27%), and limonene (11%). pinene myrcene limonene 62% 27% 11%

(a) Identify the isoprene units in pinene, myrcene, and limonene.

North American termite soldiers, when encountering enemy insects, contract their mandibular muscles, expelling a mixture of chemicals that essentially trap their enemies in a glue-like substance. This weapon, built into the face of the termite, is called the fontanellar gun. It releases a mixture of pinene (62%), myrcene (27%), and limonene (11%).

(b) Suggest an acid-catalyzed mechanism by which pinene could be produced from limonene.

Predict the product of each of the following hydroboration–oxidation or oxymercuration–reduction reactions used in the modern synthetic organic chemistry literature (modified to use reagents we are used to seeing).

(c) A similar sequence was featured in the synthesis of muricadienin, a proposed precursor in the biosynthesis of solamin (Org. Lett. 2014, 16, 5886–5889).

The formation of five-membered ring ethers is an important goal in synthetic organic chemistry because tetrahydrofurans are contained within a number of antitumor natural products. Toward that end, a one-pot synthesis of a bis-THF containing compound was developed (Eur. J. Org. Chem. 2010, 6263–6268). Suggest a mechanism for this transformation.