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.

(d)

How can the following compounds be prepared from the given starting materials?

c.

What organometallic compound is formed from the reaction of excess methylmagnesium chloride and GaCl₃?

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

Show how you might synthesize the following compounds starting with bromobenzene, and alkyl or alkenyl halides of four carbon atoms or fewer.

a. 3-phenylprop-1-ene

Show how each of the following compounds can be prepared, using the given starting material:

e.

Propose a synthesis to accomplish the following transformation

Show how you would accomplish the following synthetic

conversions by adding an organolithium reagent to an acid.

(c) pentanoic acid → heptan-3-one

Give the structures of the intermediates and products V through Z.

Predict the product of the following reactions.

(b)

Using bromocyclohexane as a starting material, how could you synthesize the following compounds?

d.

Predict the products of the following reactions.

(a) sec-butylmagnesium iodide + D₂O

(b) n-butyllithium + CH₃CH₂OH

(c) isobutylmagnesium bromide + but-1-yne

To practice working through the early parts of a multistep synthesis, devise syntheses of

(b) 3-ethylpentan-2-one from compounds containing no more than three carbon atoms.

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.

(b) 1-chloro-1-ethylcyclopentane

To this point, we have seen four reactions that can be done by Gilman reagents. What are they? What do they have in common?