What products would you expect from the following reactions?
(a)
(b)

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

(a)

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

(b) formaldehyde

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)

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

b. 5-methylhex-2-ene

Show how you would add a Grignard reagent to an ester or a nitrile to synthesize

(a) 4-phenylheptan-4-ol.

Grignard reagents add to carbonate esters as they add to other esters.

(a) Predict the major product of the following reaction.

(b) Show how you would synthesize 3-ethylpentan-3-ol using diethyl carbonate and ethyl bromide as your only organic reagents