Show how this 1° alcohol can be made from the following:

(b) formaldehyde

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

(a) pentan-3-one from alcohols containing no more than three carbon atoms.

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

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

(a)

For each synthesis, start with bromocyclohexane and predict the products. Assume that an excess of each reactant is added so that all possible reactions that can happen will happen.

(a)

What organocuprate reagent would you use for the following substitutions?

(a)

(b)

What products would you expect from the following reactions?

(a)

(b)

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