13. Alcohols and Carbonyl Compounds

Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).

(p)

Predict the major products of the following reactions.

(g)

Draw the organic products you would expect to isolate from the following reactions (after hydrolysis).

(a)

(b)

Predict the products of the following reactions.

(d)

(e)

Suggest the most appropriate method for each of the following laboratory syntheses. In each case, suggest both a chromium reagent and a chromium-free reagent.

(d) cyclopentanol → 1-ethylcyclopentanol (two steps)

(e) cyclopentylmethanol → 1-cyclopentylpropan-1-ol (two steps)

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.

(d)

Show how you would synthesize the following compounds from any starting materials containing no more than six carbon atoms.

(b)

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.