16.

Chemistry of
Benzene: Electrophilic
Aromatic Substitution
16.1 Cl2

AlCl3

a. Hexachlorobenzene
b. Hexachlorocyclohexane
c. 5,6-Dichloro-1,3-cyclohexadiene
d. Chlorobenzene
16.1 Answer
a. Hexachlorobenzene
b. Hexachlorocyclohexane
c. 5,6-Dichloro-1,3-cyclohexadiene
d. Chlorobenzene

One chlorine atom substitutes on the

benzene.
 CH2CH3

16.2 HNO3

H2SO4

a. 2- and 4-nitroethylbenzene
b. 3-Nitroethylbenzene
c. 2- and 4-ethylbenzenesulfonic acid
d. 3-Ethylbenzenesulfonic acid
16.2 Answer
a. 2- and 4-nitroethylbenzene
b. 3-Nitroethylbenzene
c. 2- and 4-ethylbenzenesulfonic acid
d. 3-Ethylbenzenesulfonic acid

The ethyl group is an ortho and para

director.
16.3 What is the major product of the
reaction of nitrobenzene with Br2/FeBr3?

1.
2.

3.

5.
4.
16.3 Answer

3.
16.4 What is the electrophile in the following
aromatic substitution?
Cl

AlCl3

1. 2.

3.

4.
5.
16.4 Answer

5.
 OCH3

16.5 AlCl3

CH3CH2CH2Cl

a. 3-Propylanisole
b. 2- and 4-propylanisole
c. 3-Isopropylanisole
d. 2- and 4-isopropylanisole
16.5 Answer
a. 3-Propylanisole
b. 2- and 4-propylanisole
c. 3-Isopropylanisole
d. 2- and 4-isopropylanisole

The methoxy group is an ortho, para

director. The propyl group rearranges.
16.6 Select the major product of the following
reaction.
KMnO4

H2O

1. 2.

3.

4. 5.
16.6 Answer

4.
 CH2CH3
17.7 Na2Cr2O7

+
CH3 H , heat

CH2CH3
COOH
(a) (b)
COOH
CH3

COOH
CH2CH3
(c) (d)
COOH
CH3
17.7 answer
CH2CH3
COOH
(a) (b)
COOH
CH3

COOH
CH2CH3
(c) (d)
COOH
CH3

Both alkyl groups are oxidized to carboxylic

acids.
 CH3C(=O)Cl H2/Pd
Zn(Hg)
16.7
AlCl3 HCl

a. Ethylbenzene
b. 1-Phenylethanol
c. 2-Phenylethanol
d. Chlorobenzene
16.7 Answer
a. Ethylbenzene
b. 1-Phenylethanol
c. 2-Phenylethanol
d. Chlorobenzene

The Friedel–Crafts reaction produces

acetophenone. The carbonyl is reduced
to form ethylbenzene.
16.8 What is the major product of the following
reaction? CH 3 Br2

HOOC FeBr3

1.
2.

3.

4. 5.
16.8 Answer

3.
16.9 Which series of reactions will convert
benzene into o-nitrobenzoic acid?

1. CH3Br/AlBr3 followed by HNO3/H2SO4 followed by

KMnO4/H2O
2. HNO3/H2SO4 followed by KMnO4/H2O followed by
CH3Br/AlBr3
3. KMnO4/H2O followed by CH3Br/FeBr3 followed by
HNO3/H2SO4
4. CH3Br/AlBr3 followed by KMnO4/H2O followed by
HNO3/H2SO4
5. HNO3/H2SO4 followed by CH3Br/AlBr3 followed by
KMnO4/H2O
16.9 Answer
1. CH3Br/AlBr3 followed by HNO3/H2SO4
followed by KMnO4/H2O

CH3 CH3 COOH

HNO3/H2SO4
NO2 NO2
CH3Br/AlBr3 KMnO4/H2O