13. Alcohols and Carbonyl Compounds

Develop syntheses for the following compounds. As starting materials, you may use cyclopentanol, alcohols containing no more than four carbon atoms, and any common reagents and solvents.

(e)

What products are obtained from metathesis of each of the following alkenes?

b.

What is the product of each of the following reactions?

b.

What product is obtained from ring-opening metathesis polymerization of each of the following compounds? (Hint: In each case, the product is an unsaturated hydrocarbon with a high molecular weight.)

a.

What compound undergoes metathesis to form each of the following compounds?

a.

What products are obtained from metathesis of each of the following alkenes?

a. CH₃CH₂CH=CH₂

What new products are obtained from metathesis of the following alkyne?

Draw the product of ring-closing metathesis for each of the following compounds:

a.

What starting material is required in order to synthesize each of the following compounds by ring-closing metathesis?

a.

Muscalure is the sex attractant of the common housefly. Flies are lured to traps filled with bait that contain muscalure and an insecticide. Eating the bait is fatal. How could you synthesize muscalure using 1-bromopentane as one of the starting materials?

Using the epoxide shown, addition of an organolithium reagent, when followed by an acid quench, produces only the starting epoxy alcohol. Why? How could the reaction be modified to produce the desired molecule? [Hint: Look back at Section 13.14.]

Predict the product of the following epoxide addition reactions.

(a)

A variety of organometallics, which as strong nucleophiles can react with epoxides, are introduced in Chapter 16. Predict the product of these reactions. [Hint: Assume the carbon–metal bond in each is ionic, with the carbon possessing the negative charge.]

(c)

Give the structures of intermediates A through H in the following synthesis of trans-1-cyclohexyl-2-methoxycyclohexane.

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

(o)