19. Reactions of Aromatics: EAS and Beyond

What products would you expect from the following coupling reactions?

(c)

Provide the reaction for each of the following reaction steps

Beginning from Benzene, synthesize the following compound.

Beginning from Benzene, synthesize the following compound. 

1-Phenylethanol

Beginning from Benzene, synthesize the following compound.

The most common selective herbicide for killing broadleaf weeds is 2,4-dichlorophenoxyacetic acid (2,4-D). Show how you would synthesize 2,4-D from benzene, chloroacetic acid (ClCH₂COOH), and any necessary reagents and solvents.

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

c. p-chlorotoluene

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

b. p-toluenesulfonic acid

Show how you would synthesize the following compounds, starting with benzene or toluene and any necessary acyclic reagents. Assume para is the major product (and separable from ortho) in ortho, para mixtures.

b. 1-phenyl-1-methoxybutane

Show how you would synthesize the following compounds, starting with benzene or toluene and any necessary acyclic reagents. Assume para is the major product (and separable from ortho) in ortho, para mixtures.

a. 1-phenyl-1-bromobutane

Starting from toluene, propose a synthesis of this trisubstituted benzene.

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

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

a. p-tert-butylnitrobenzene

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