13. Alcohols and Carbonyl Compounds

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

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

Metathesis of which of the following sets of alkenes leads to the highest yield of a single alkene?

1. 1-butene and 1-pentene 

2. 2-butene and 3-hexene 

3. 2-butene and 1-pentene

Design a synthesis for each of the following, using an intramolecular reaction:

f.