19. Reactions of Aromatics: EAS and Beyond

Beginning with benzene, synthesize the following substituted benzenes. The ideal number of steps is indicated.

(d) 

Show how you would synthesize the following aromatic derivatives from benzene.

c. p-chlorotoluene

Tyramine is an alkaloid found in mistletoe and ripe cheese. Dopamine is a neurotransmitter involved in the regulation of the central nervous system.

c. Give two ways to prepare b-phenylethylamine from b-phenylethyl chloride.

FROM THE LITERATURE The following steps were used in the synthesis of the antimalarial thiaplakortone A. Identify the missing reagents, (a) and (b), 

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Predict the product(s) of each of the following multistep reactions.

(a)

Tyramine is an alkaloid found in mistletoe and ripe cheese. Dopamine is a neurotransmitter involved in the regulation of the central nervous system.

e. How can b-phenylethylamine be prepared from benzaldehyde?

Show how you would accomplish the following syntheses.

(a) benzene → n-butylbenzene

Show how each of the following compounds can be synthesized from benzene:

d. anisole

Show how each of the following compounds can be synthesized from benzene:

g. 2-phenylpropene

Fluoxetine, an antidepressant, is better known as Prozac®. Suggest reagents that could be used to make the indicated C–O bond of fluoxetine. [Note that CF₃, an electron-withdrawing group, is para to where the new bond will be formed.]

Propose a synthetic sequence of this trisubstituted benzene starting from toluene.

Predict the major product at the end of each sequence.

(b)

Describe two ways to prepare anisole from benzene.

The antioxidants BHA and BHT are commonly used as food preservatives. Show how BHA and BHT can be made from phenol and hydroquinone

Acetaminophen is the active ingredient in Tylenol. How can acetominophen be synthesized from benzene?