Draw the structure for each of the following:

e. 4-bromo-1-chloro-2-methylbenzene

Draw the structure for each of the following:

f. m-chlorostyrene

Draw the structure for each of the following:

g. o-nitroanisole

Draw the structure for each of the following:

h. 2,4-dichloromethylbenzene

Draw the structure for each of the following:

i. m-chlorobenzoic acid

For each of the statements in Column I, choose a substituent from Column II that fits the description for the compound on the right:

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What product is obtained from the reaction of excess benzene with each of the following reagents?

c. dichloromethane + AlCl₃

Draw the product(s) of each of the following reactions:

a. benzoic acid + HNO₃/H₂SO₄

b. isopropylbenzene + Cl₂ + FeCl₃

Draw the product(s) of each of the following reactions:

c. p-xylene + acetyl chloride + AlCl₃ followed by H₂O

Draw the product(s) of each of the following reactions:

d. o-methylaniline + benzenediazonium chloride

Draw the product(s) of each of the following reactions:

h. m-xylene + Na₂Cr₂O₇ + HCl + ∆

Rank the following substituted anilines from most basic to least basic:

For each horizontal row of substituted benzenes, indicate

a. the one that is the most reactive in an electrophilic aromatic substitution reaction.

For each horizontal row of substituted benzenes, indicate

c. the one that yields the highest percentage of meta product in an electrophilic aromatic substitution reaction.

3.

For each horizontal row of substituted benzenes, indicate

c. the one that yields the highest percentage of meta product in an electrophilic aromatic substitution reaction.

For each horizontal row of substituted benzenes, indicate

c. the one that yields the highest percentage of meta product in an electrophilic aromatic substitution reaction.

1.

2.

Show how the following compounds can be synthesized from benzene:

b. m-chloroethylbenzene

Show how the following compounds can be synthesized from benzene:

f. m-hydroxybenzoic acid

Rank each group of compounds from most reactive to least reactive toward electrophilic aromatic substitution:

a. benzene, ethylbenzene, chlorobenzene, nitrobenzene, anisole

Rank each group of compounds from most reactive to least reactive toward electrophilic aromatic substitution:

b. 1-chloro-2,4-dinitrobenzene, 2,4-dinitrophenol, 1-methyl-2,4-dinitrobenzene

Rank each group of compounds from most reactive to least reactive toward electrophilic aromatic substitution:

e. p-methylnitrobenzene, 2-chloro-1-methyl-4-nitrobenzene, 1-methyl-2,4-dinitrobenzene, p-chloromethylbenzene

Rank each group of compounds from most reactive to least reactive toward electrophilic aromatic substitution:

f. bromobenzene, chlorobenzene, fluorobenzene, iodobenzene

What are the products of the following reactions?

c.

d.

What are the products of the following reactions?

f.

For each of the following compounds, indicate the ring carbon(s) that is/are nitrated when the compound is treated with HNO₃/H₂SO₄:

a.

b.

For each of the following compounds, indicate the ring carbon(s) that is/are nitrated when the compound is treated with HNO₃/H₂SO₄:

c.

d.

For each of the following compounds, indicate the ring carbon(s) that is/are nitrated when the compound is treated with HNO₃/H₂SO₄:

e.

f.

Show two pairs of reagents that would each result in formation of the following compound:

Why is anisole nitrated more rapidly than thioanisole under the same conditions?

Describe two ways to prepare anisole from benzene.