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Chapter Nineteen
Topic: Electrophilic Aromatic Substitution
Section: 19.1
Difficulty Level: Medium
1.
Cyclohexene undergoes addition reaction with bromine, but benzene does not. Instead
benzene undergoes a substitution reaction with bromine. Explain.
2.
Which chemical test would you use to distinguish between ethylbenzene and styrene?
3.
Provide all the resonance structures of the sigma complex, when benzene reacts with an
electrophile (E+).
4.
Which of these is the rate-determining step in the electrophilic aromatic substitution of
benzene?
A)
Formation of an electrophile
B)
Formation of sigma complex.
C)
Loss of proton from sigma complex.
D)
Addition of electrophile & loss of proton
E)
None of these
5.
Provide a stepwise curved arrow mechanism for chlorination of benzene in the presence
of FeCl3.
6.
The electrophile in the sulfonation reaction of benzene is:
A)
SO2+
B)
H2SO4
C)
SO3+
D)
H2SO3
E)
SO3
7.
The electrophile in the nitration reaction of benzene is:
A)
NO2+
B)
HNO3
C)
NO3+
D)
H2SO4
E)
NO2
8.
Predict the product for the following reaction.
SO3H
H3O+
9.
Predict the product for the following reaction.
SO3H
H3O+
10.
Predict the product for the following reaction.
HNO3
SO4
SO3H NO3NO2SO3OH
III III IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
11.
Predict the major product for the following reaction.
(CH3)2CHCH2Cl
AlCl3
CH2CH(CH3)2CHCH2CH3
CH3
C
CH3
CH3
CH3
III III
CH2CH2CH2CH3
IV
A)
I
B)
II
C)
III
D)
IV
E)
none of these
12.
Which one of the following reactions is most likely to give a polysubstituted product?
A)
Friedel-Crafts alkylation
B)
Friedel-Crafts acylation
C)
Nitration
D)
Sulfonation
E)
Halogenation
13.
Which one of the following compounds does not undergo Friedel-Crafts reaction?
A)
Benzene
B)
Chlorobenzene
C)
Nitrobenzene
D)
Toluene
E)
tert-Butylbenzene
14.
Predict the major product for the reaction between benzene and 2-chlorobutane in the
presence of AlCl3.
A)
Chlorobenzene
B)
sec-butylbenzene
C)
ethylbenzene
D)
isopropylbenzene
E)
t-butylbenzene
15.
Predict the major product for the following reaction.
AlCl3
Cl
16.
Predict the major product for the following reaction.
(CH3)3CCH2Cl
AlCl3
CH2C(CH3)3C(CH3)2CH2CH3CH(CH3)CH2CH2CH3CH2CH2CH2CH2CH3
III III IV
CH2CH2CH(CH3)2
v
A)
I
B)
II
C)
III
D)
IV
E)
V
17.
Provide the structure(s) of the intermediate product(s) in the following reaction
sequence
CH3Cl ACl2B
AlCl3AlCl3
C
18.
Predict the major product for the following reaction.
H2SO4
1. KMnO4/NaOH/H2O
2. H3O+
CH2CH2Cl
AlCl3
excess
C(CH3)3
CH2CH3
C(CH3)3
COH
O
COH
COH
O
O
CH2CH(CH3)2
COH
O
COH
CH2CH3
O
III III IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
19.
Provide a stepwise curved arrow mechanism for the following reaction.
AlCl3
Cl
20.
Predict the major product for the following reaction.
H2SO4
21.
Predict the major product for the following reaction.
H2SO4
+
22.
Which one of the following compounds will be most reactive towards bromination
reaction?
A)
nitrobenzene
B)
anisole
C)
acetanilide
D)
benzene
E)
benzaldehyde
23.
Predict the major product for the following reaction and provide a stepwise curved
arrow mechanism for the formation of the product.
Cl AlCl3
+
24.
Predict the structure of the major product for the following reaction.
OH
H2SO4
+
25.
Predict the structure of the major product for the following reaction.
CH3CH2CCl
O
AlCl3
26.
Predict the structure of the major product for the following reaction.
AlCl3
Cl
O
O
OOH
III III
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
27.
Predict the structure of the major product for the following reaction.
CH3CH2CH2COCCH2CH2CH3
AlCl3
O O
28.
Provide the structure of the major products formed in the following reaction sequence.
CH3CH2CH2CCl
O
AlCl3
A
Zn(Hg)
HCl
B
29.
Provide the reagents necessary to carry out the following conversion.
30.
Predict the structure of the product for the following reaction.
O
O
O
1. AlCl3
2. H3O+
+
31.
Predict the structure of the product for the following reaction.
AlCl3
Cl
O
32.
Predict the structure of the product for the following reaction.
Cl
O
AlCl3HCl
Zn(Hg)
O
III III
IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
33.
Predict the major product for the following reaction.
Cl2/FeCl3
Cl
Cl
Cl
Cl
Cl
III III IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
34.
Provide the reagent(s) that are necessary to carry out the following conversion.
t-butylbenzene ⎯⎯→ 4-chloro-1-t-butylbenzene
A)
Cl2, heat
B)
Cl2, FeCl3
C)
SOCl2, pyridine
D)
HCl
E)
PCl3
35.
Predict the major product for the following reaction.
OCH3
Fuming H2SO4
OCH3
SO3H
OCH3
SO3H
OCH3
SO3H
OCH3
III III IV
SO3H
SO3H
A)
I
B)
II
C)
III
D)
IV
E)
I & II
36.
Provide all resonance structures of the sigma complex when aniline reacts with an
electrophile (E+) to yield the para-substituted product.
37.
Predict the major product for the following reaction.
OCCH3
Br2/ FeBr3
O
Br
OCCH3
O
Br
OCCH3
O
OCCH3
O
OCCH3
O
Br
Br
Br
III III IV
A)
I
B)
II
C)
III
D)
IV
E)
I & IV
38.
Which one of the following compounds would be most reactive toward electrophilic
aromatic substitution?
NH2CH3Cl CCH3CF3
O
III III IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
39.
Which one of the following compounds would be least reactive toward electrophilic
aromatic substitution?
NO2OCH3Cl CCH3
O
CF3
III III IV V
A)
I
B)
II
C)
III
D)
IV
E)
V
40.
Arrange the following compounds in order of decreasing reactivity towards electrophilic
aromatic substitution:
NH3Cl OH
O H
III III IV V
A)
V>II>I>III>IV
B)
II>V>III>I>IV
C)
IV>I>III>V>II
D)
III>II>I>IV>V
E)
IV>V>II>I>III
41.
Predict the major product for the following reaction.
COCH3
HNO3/ H2SO4
O
COCH3
NO2
OCOCH3
O
NO2
COCH3
O
NO2
COCH3
NO2
O
NO2
I II III IV
COCH3
O
NO2
O2N
V
A)
I
B)
II
C)
III
D)
IV
E)
V
42.
Predict the major product for the following reaction.
HNO3/H2SO4
