13. Alcohols and Carbonyl Compounds

Show how you would synthesize the following compound from alkyl halides, vinyl halides, and aryl halides containing no more than six carbon atoms.

(d) cyclopentyl propyl ketone

Show how you would accomplish the following synthetic

conversions by adding an organolithium reagent to an acid.

(c) pentanoic acid → heptan-3-one

Predict the products of the following reactions:

(c)

(d)

Show how you would accomplish the following synthetic conversions by adding an organolithium reagent to an acid.

(d) phenylacetic acid → 3,3-dimethyl-1-phenylbutan-2-one

Propose structures for intermediates and products (A) through (D).

Devise a synthesis for each compound, starting with methylenecyclohexane and any other reagents you need.

f. 1-(phenylmethyl)cyclohexanol

Show how you would accomplish the following synthetic conversions by adding an organolithium reagent to an acid.

(a)

Show how you would accomplish the following synthetic conversions by adding an organolithium reagent to an acid.

(b)

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)