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

i. 1-phenyl-2-propanol

What is the major product(s) of each of the following reactions?

a. bromination of p-methylbenzoic acid

What is the major product(s) of each of the following reactions?

b. chlorination of o-benzenedicarboxylic acid

What is the major product(s) of each of the following reactions?

e. nitration of p-methoxybenzaldehyde

f. nitration of p-tert-butylmethylbenzene

Why isn’t FeBr₃ used as a catalyst in the first step of the synthesis of 1,3,5-tribromobenzene?

Explain why a diazonium group on a benzene ring cannot be used to direct an incoming substituent to the meta position.

Show how the following compounds can be synthesized from benzene:

d. m-methylnitrobenzene

What product is formed from the reaction of p-methylphenol with benzenediazonium chloride?

In the mechanism for electrophilic aromatic substitution with a diazonium ion as the electrophile, why does nucleophilic attack occur on the terminal nitrogen of the diazonium ion rather than on the nitrogen that has the formal positive charge?

Draw the structure of the activated benzene ring and the diazonium ion used in the synthesis of each of the following compounds, whose structures can be found on page 607.

b. methyl orange

Which amide bond is hydrolyzed in the first step of the conversion of temozolomide to methyldiazonium?

Diazomethane can be used to convert a carboxylic acid to a methyl ester. Propose a mechanism for this reaction.

Draw resonance contributors for the carbanion that would be formed if meta-chloronitrobenzene were to react with hydroxide ion. Why doesn't the reaction occur?

Rank the following compounds from greatest tendency to least tendency to undergo nucleophilic aromatic substitution:

chlorobenzene 

1-chloro-2,4-dinitrobenzene 

p-chloronitrobenzene

b. Rank the same compounds from greatest tendency to least tendency to undergo electrophilic aromatic substitution.

chlorobenzene, 1-chloro-2,4-dinitrobenzene, p-chloronitrobenzene

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

c. p-bromoanisole

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

d. anisole

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

a.

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

d.

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

e.

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

f.

Draw the structure for each of the following:

d. benzaldehyde

e. anisole

f. styrene

Draw the structure for each of the following:

g. toluene

h. tert-butylbenzene

i. benzyl chloride

Name the following:

c.

Name the following:

d.

Name the following:

e.

f.

Name the following:

g.

h.

i.

Provide the necessary reagents next to the arrows.

Draw the structure for each of the following:

a. m-ethylphenol

Draw the structure for each of the following:

b. p-nitrobenzenesulfonic acid