chapter 15 test bank chem 200

Package Title: Solomons Test Bank
Course Title: Solomons 11e
Chapter Number: 15

Question Type: Multiple Choice

1) Which of these is the rate-determining step in the nitration of benzene?
a) Protonation of nitric acid by sulfuric acid
b) Protonation of sulfuric acid by nitric acid
c) Loss of a water molecule by the protonated species to produce the nitronium ion
d) Addition of the nitronium to benzene to produce the arenium ion
e) Loss of a proton by the arenium ion to form nitrobenzene
Answer: D
Topic: Mechanisms and Intermediates
Section: 15.2
Difficulty Level: Medium

2) Which of these is the rate-determining step in the sulfonation of benzene?
a) Formation of SO3 from sulfuric acid
b) Protonation of SO3 sulfuric acid
c) Addition of SO3H+ to benzene to form the arenium ion
d) Loss of a proton from the arenium ion to form benzenesulfonic acid
e) None of these choices.
Answer: C
Topic: Mechanisms and Intermediates
Section: 15.2
Difficulty Level: Medium

3) Which of these is the rate-determining step in the bromination of benzene?
a) Complexation of bromine with the iron(III) bromide catalyst
b) Formation of Br+ ion

c) Addition of Br+ to benzene to form the arenium ion
d) Loss of a proton from the arenium ion to form bromobenzene
e) None of these choices.

1


Answer: C
Topic: Mechanisms and Intermediates
Section: 15.2
Difficulty Level: Medium

4) Which of the following structures contribute(s) to the resonance hybrid of the intermediate
formed when bromobenzene undergoes para-chlorination?
..
..
..
..
: Br :
: Br +
: Br :
: Br :
+
+
+
H Cl

H Cl

H Cl

H Cl

I

II

III

IV

a) I
b) II
c) III
d) IV
e) All of these choices.
Answer: E
Topic: Mechanisms and Intermediates
Section: 15.11
Difficulty Level: Medium

5) Which of the following structures contribute(s) to the resonance hybrid of the intermediate
formed when chlorobenzene undergoes para-chlorination?
..
..
..
..
: Cl :
: Cl +
: Cl :

: Cl :
+
+
+
H Cl

H Cl

H Cl

H Cl

I

II

III

IV

a) I
b) II
c) III
d) IV
e) All of these choices.
Answer: E
Topic: Mechanisms and Intermediates
2

Section: 15.11
Difficulty Level: Medium

6) Which of the following structures contribute(s) to the resonance hybrid of the intermediate
formed when acetanilide undergoes para-bromination?
+NCOCH
:NHCOCH3
: NHCOCH3
: NHCOCH3
3
+
+
+
H Br

H Br

H Br

H Br

I

II

III

IV

a) I

b) II
c) III
d) IV
e) All of these choices.
Answer: E
Topic: Mechanisms and Intermediates
Section: 15.11
Difficulty Level: Medium

7) Which of the following contributors to the resonance stabilized hybrid formed when aniline
undergoes para-chlorination would be exceptionally stable?
+NH2
: NH2
: NH2
: NH2
+
+
+
H Cl

H Cl

H Cl

H Cl

I

II

III

IV

a) I
b) II
c) III
d) IV
e) None of these choices.
Answer: B
Topic: Mechanisms and Intermediates
Section: 15.11
Difficulty Level: Medium

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8) Consider the structures given below. Which of them would be a relatively stable contributor
to the hybrid formed when toluene undergoes para bromination?

a) I
b) II
c) III
d) IV
e) V
Answer: C
Topic: Mechanisms and Intermediates
Section: 15.11
Difficulty Level: Medium

9) Which of the following structures does not contribute to the resonance hybrid of the
intermediate formed when nitrobenzene undergoes meta-chlorination?
..
..
..
..
..
..
:O : O:
: O : O:
: O : O:
N

N

+

H
Cl

I

+

N

+H

H
Cl

II

Cl

III

a) I
b) II
c) III
d) None of these contribute.
e) All of these contribute.
Answer: E
Topic: Mechanisms and Intermediates
Section: 15.11
Difficulty Level: Medium

10) Consider the resonance forms shown for the arenium ionformed from the bromination of
acetanilide. Which resonance form contributes most to the overall resonance hybrid?
4


H
I

Br

O

HN

HN

HN

Br

O

O

O

H
II

Br

HN

H

H

Br
IV

III

a) I

b) II
c) III
d) IV
e) All contribute equally.
Answer: C
Topic: Mechanisms and Intermediates
Section: 15.11
Difficulty Level: Medium

11) Consider the resonance forms shown for the arenium ionformed from the bromination of
acetanilide. Which resonance form contributes most to the overall resonance hybrid?

a) I
b) II
c) III
d) IV
e) All contribute equally.
Answer: D
5


Topic: Mechanisms and Intermediates
Section: 15.11
Difficulty Level: Medium

12) The electrophilic bromination or chlorination of benzene requires, in addition to the halogen:
a) a hydroxide ion.
b) a Lewis base.
c) a Lewis acid.
d) peroxide.

e) ultraviolet light.
Answer: C
Topic: Other EAS Considerations
Section: 15.3
Difficulty Level: Easy

13) In electrophilic aromatic substitution, the attacking species (the electrophile) necessarily is a:
a) neutral species.
b) positively charged species.
c) lewis acid.
d) proton.
e) carbocation.
Answer: C
Topic: Other EAS Considerations
Section: 15.2
Difficulty Level: Medium

14) Which of these liquids would be unsuitable as an inert solvent for a Friedel-Crafts reaction?
a) Chlorobenzene
b) Nitrobenzene
c) Acetophenone
d) (Trifluoromethyl) benzene
e) All of these choices could be used.
Answer: A

6


Topic: Other EAS Considerations
Section: 15.8

Difficulty Level: Medium

15) Undesired polysubstitution of an aromatic nucleus is most likely to be encountered in the
case of:
a) Friedel-Crafts alkylation
b) Friedel-Crafts acylation
c) Nitration
d) Sulfonation
e) Chlorination
Answer: A
Topic: Other EAS Considerations
Section: 15.8
Difficulty Level: Medium

16) This substituent deactivates the benzene ring towards electrophilic substitution but directs the
incoming group chiefly to the ortho and para positions.
a) -OCH2CH3
b) -NO2
c) -F
d) -CF3
e) -NHCOCH3
Answer: C
Topic: Other EAS Considerations
Section: 15.10 and 15.11
Difficulty Level: Medium

17) This molecule does not normally participate as a reactant in a Friedel-Crafts reaction.
a) Benzene
b) Chlorobenzene
c) Nitrobenzene

d) Toluene
e) tert-Butylbenzene
Answer: C
7


Topic: Other EAS Considerations
Section: 15.8
Difficulty Level: Medium

18) Which one of these molecules can be a reactant in a Friedel-Crafts reaction?
a) Aniline
b) Nitrobenzene
c) Chloroethene
d) Bromobenzene
e) p-Bromonitrobenzene
Answer: D
Topic: Other EAS Considerations
Section: 15.8
Difficulty Level: Medium

19) Which one of these molecules can be a reactant in a Friedel-Crafts reaction?
a) Aniline
b) Benzenesulfonic acid
c) Chloroethene
d) Bromobenzene
e) p-Bromonitrobenzene
Answer: D
Topic: Other EAS Considerations
Section: 15.8

Difficulty Level: Medium

20) Which reagent would you use as the basis for a simple chemical test that would distinguish
between toluene and vinylbenzene (C6H5CH=CH2)?
a) NaOH/H2O
b) Br2/CCl4
c) NaBH4
d) HCl/H2O
e) NaI in acetone
Answer: B
8


Topic: Functional Group Tests
Sections: 14.2, 14.3 and 15.3
Difficulty Level: Medium

21) Which reagent or test could you use to distinguish between phenylacetylene and
vinylbenzene?
a) NaOH/H2O
b) Br2/CCl4
c) IR Spectroscopy
d) CrO3/H2SO4
e) Concd. H2SO4
Answer: C
Topic: Nomenclature, Functional Group Tests
Section: 14.2, 14.11 and 15.3
Difficulty Level: Medium

22) What is the chief product of the Friedel-Crafts alkylation of benzene with 1-butene and HF?

a) butylbenzene
b) 2-phenylbutane
c) 2-methyl-1-phenylpropane
d) t-butylbenzene
e) 2,2-diphenylbutane
Answer: B
Topic: Nomenclature, Reaction Products
Section: 14.2 and 15.6
Difficulty Level: Hard

23) What is the chief product of the Friedel-Crafts alkylation of benzene with 1-butene and
AlCl3?
a) butylbenzene
b) 2-phenylbutane
c) 2-methyl-1-phenylpropane
d) t-butylbenzene
e) 2,2-diphenylbutane

9


Answer: B
Topic: Nomenclature, Reaction Products
Section: 14.2 and 15.6
Difficulty Level: Hard

24) A mixture of chlorobenzene (1 mol) and acetanilide (1mol) is allowed to react with Br2 (0.5
mol) in the presence of trace amounts of FeBr3. What is the principal product of the competing
reactions?
a) 1-bromo-4-chlorobenzene

b) 1-bromo-2-chlorobenzene
c) 1-bromo-3-chlorobenzene
d) 4-bromoacetanilide
e) 3-bromoacetanilide
Answer: D
Topic: Nomenclature, Reaction Products
Section: 14.2, 15.3, and 15.8
Difficulty Level: Hard

25) A mixture of chlorobenzene (1 mol) and anisole (1mol) is allowed to react with Br2 (0.5 mol)
in the presence of trace amounts of FeBr3. What is the principal product of the competing
reactions?
a) 1-bromo-4-chlorobenzene
b) 1-bromo-2-chlorobenzene
c) 1-bromo-3-chlorobenzene
d) 4-bromoanisole
e) 3-bromoanisole
Answer: D
Topic: Nomenclature, Reaction Products
Section: 14.2, 15.3, and 15.8
Difficulty Level: Hard

26) Which of the following reactions could be used to synthesize tert-butylbenzene?
a) C6H6 + CH2=C(CH3)2

H2SO4

10

b) C6H6 + (CH3)3COH
c) C6H6 + (CH3)3CCl
d) All of these choices.
e) None of these choices.

H2SO4
AlCl3

Answer: D
Topic: Synthesis
Section: 15.6
Difficulty Level: Easy

27) Which of the following reactions could be used to synthesize tert-butylbenzene?
a) C6H6 + CH2=C(CH3)2

H2SO4

b)
c) C6H6 + (CH3)3CCl
d) All of these choices.
e) None of these choices.

AlCl3

Answer: D
Topic: Synthesis
Section: 15.6
Difficulty Level: Easy

28) Which of the following reactions could be used to synthesize tert-butylbenzene?

a)
b)
c) C6H6 + (CH3)3CCl
d) All of these choices.
e) None of these choices.

AlCl3

Answer: D
Topic: Synthesis
11


Section: 15.6
Difficulty Level: Easy

29) Consider the following reaction: what is the expected product?
NH2

Br2, H2O

?

Cl
Cl

NH2
Br

Br

H2 N

Cl

Br

Br

Cl

NH2

II

I

Br

Br

III

NH2

NH2
Br

Br
Br

Cl

Cl

IV

V

a) I
b) II
c) III
d) IV
e) V
Answer: B
Topic: Synthesis
Section: 15.3
Difficulty Level: Easy

30) Which of the following reactions would yield isopropylbenzene as the major product?
CH3CHCH3

Benzene

b)

OH

H2SO4
CH3CHCH3

Benzene

c)

Cl

AlCl3

12


Benzene

CH3CH2CH2Cl

AlCl3
d)
e) All of these choices.
Answer: E
Topic: Synthesis
Section: 15.6
Difficulty Level: Medium

31) Which of the following reactions would yield isopropylbenzene as the major product?

a)
CH3CHCH3

Benzene

b)

OH

H2SO4
CH3CHCH3

Benzene

c)

Cl

AlCl3
CH3CH2CH2Cl

Benzene
AlCl3
d)
e) All of these choices.
Answer: E
Topic: Synthesis
Section: 15.6
Difficulty Level: Medium

32) Which of the following reactions would yield isopropylbenzene as the major product?

a)

13


b)
CH3CHCH3

Benzene

c)

Benzene

Cl

AlCl3
CH3CH2CH2Cl

AlCl3
d)
e) All of these choices.
Answer: E
Topic: Synthesis
Section: 15.6
Difficulty Level: Medium

33) Which of the following reactions would produce isopropylbenzene?
Cl

Benzene

a)
Benzene

b)

AlCl3
HF
OH

Benzene
H2SO4

c)

Br

Benzene

AlCl3
d)
e) All of these choices.
Answer: E
Topic: Synthesis
Section: 15.6
Difficulty Level: Medium

34) Which of these is a satisfactory synthesis of 1-chloro-2-phenylethane?
14

a) C6H5CH2CH3 + Cl2, Fe ⎯⎯→
b) C6H5CH2CH3 + Cl2, 400°C ⎯⎯→
c) C6H5CH2CH2OH + SOCl2 ⎯⎯→
d) C6H5CH=CH2 + HCl, peroxide ⎯⎯→
e) C6H6 + CH3CH2Cl, AlCl3 ⎯⎯→
Answer: C
Topic: Synthesis
Sections: 11.9 and 15.6
Difficulty Level: Medium

35) Which of these is a satisfactory synthesis of 1-chloro-2-phenylethane?
a) C6H5CH2CH3 + Cl2, Fe ⎯⎯→
b) C6H5CH2CH3 + Cl2, 400°C ⎯⎯→
c) C6H5CH2CH2OH + PCl5 ⎯⎯→
d) C6H5CH=CH2 + HCl, peroxide ⎯⎯→
e) C6H6 + CH3CH2Cl, AlCl3 ⎯⎯→
Answer: C
Topic: Synthesis
Sections: 11.9 and 15.6
Difficulty Level: Medium

36) Which of the following reactions would produce cumene?
Cl

Benzene

a)
Benzene

b)

AlCl3
HF
OH

Benzene
H2SO4

c)

Br

Benzene

AlCl3
d)
e) All of these choices.
Answer: E
15


Topic: Synthesis
Section: 15.6
Difficulty Level: Hard

37) Which of the following reactions would yield cumene as the major product?

Benzene

a)

CH3CH

CH2

H2SO4
CH3CHCH3

Benzene

b)

OH

H2SO4
CH3CHCH3

Benzene

c)

Benzene

Cl

AlCl3
CH3CH2CH2Cl

AlCl3

d)
e) All of these choices.
Answer: E
Topic: Synthesis
Section: 15.6
Difficulty Level: Hard

38) Which of the following reactions would give the product(s) indicated in substantial amounts
(i.e., in greater than 50% yield)?
NH2

NH2

+ CH3Cl

I

AlCl3

NH2

and

CH3

CH3
NH2

II

NH2

+ CH3Cl

AlCl3
CH3

III

+ CH3CH2CH2Cl

CH2CH2CH3

AlCl3

16


a) I
b) II
c) III
d) All of these choices.
e) None of these choices.
Answer: E
Topic: Reaction Products
Section: 15.6 and 15.8
Difficulty Level: Easy

39) What would you expect to be the major product obtained from the following reaction?
O

excess
HN

AlCl3

?

CH3Cl

O

O

O

HN

HN

HN

I

II

III

O

O

HN

HN

IV

V

a) I
b) II
c) III
d) IV
e) V
Answer: E
Topic: Reaction Products
Section: 15.6 and 15.8
Difficulty Level: Medium

40) What would you expect to be the major product obtained from the following reaction?
17


O2N

O

AlCl3

+

O2 N
O

I

II
O2N

O

O2N

O2N
O

?

Cl

III

O2 N

IV

V

O

O

a) I
b) II
c) III
d) IV
e) V
Answer: A
Topic: Reaction Products
Section: 15.7 and 15.8
Difficulty Level: Medium

41) The major product(s) of the following reaction,

18


O
O

AlCl3

+

?

Cl

O

O

O
O

O

O

I
O

II

III
O

IV

O

V
O

would be:
a) I
b) II
c) III
d) IV
e) V

Answer: E
Topic: Reaction Products
Section: 15.7 and 15.8
Difficulty Level: Medium

42) What might be predicted to happen when the following substance undergoes Friedel-Crafts
acylation?
O2N

CH2

A

B

a) Substitution occurs in ring B, p- to the methylene group.
b) Substitution occurs in ring A, o- to the nitro group.
c) Substitution occurs in ring A, o- to the methylene group.
d) Substitution occurs in ring B, m- to the methylene group.
e) None of these choices. No reaction will occur.
Answer: A
Topic: Reaction Products

19


Section: 15.7 and 15.8
Difficulty Level: Medium

43) What would be the product of the following reaction sequence?

OH
i) SOCl2
?
ii) C6H6, AlCl3
O
iii) Zn(Hg), HCl, heat
O

O

OH
OH

II

I

IV

III

V

a) I
b) II
c) III
d) IV
e) V
Answer: E
Topic: Reaction Products

Section: 15.7 and 15.9
Difficulty Level: Medium

44) What would be the product of the following reaction sequence?

20


OH

i) SOCl 2
ii) C6H6, AlCl3
iii) H2NNH2/KOH

O

?

O

O

OH
OH

II

I

III

V

IV
a) I
b) II
c) III
d) IV
e) V
Answer: E
Topic: Reaction Products
Section: 15.7 and 15.9
Difficulty Level: Medium

45) What would be the product of the following reaction sequence?
OH
O

i) PCl5
ii) C6H6, AlCl3
iii) Zn(Hg), HCl, heat

O

?

OH

O
OH

I

II

IV

III

V

a) I

21


b) II
c) III
d) IV
e) V
Answer: E
Topic: Reaction Products
Section: 15.7 and 15.9
Difficulty Level: Medium

46) What would be the product of the following reaction sequence?

a) I
b) II
c) III

d) IV
e) V
Answer: E
Topic: Reaction Products
Section: 15.7 and 15.9
Difficulty Level: Medium

47) What would be the product of the following reaction sequence?

22


OH

O

i) SOCl2
ii) C6H6, AlCl3
iii) Zn(Hg), HCl, heat

?

O

OH

II

I

III
O

OH

IV

V

a) I
b) II
c) III
d) IV
e) V
Answer: B
Topic: Reaction Products
Section: 15.7 and 15.9
Difficulty Level: Medium

48) What would be the product of the following reaction sequence?

23


a) I
b) II
c) III
d) IV
e) V
Answer: B

Topic: Reaction Products
Section: 15.7 and 15.9
Difficulty Level: Medium

49) Which would be the product of the following reaction sequence?
O
i) SOCl2
?
OH ii) benzene, AlCl3
iii) Zn(Hg), HCl

SO2

CO2

CH2

I

II

III

O

IV

V

24

a) I
b) II
c) III
d) IV
e) V
Answer: C
Topic: Reaction Products
Section: 15.7 and 15.9
Difficulty Level: Medium

50) Which would be the product of the following reaction sequence?

a) I
b) II
c) III
d) IV
e) V
Answer: C
Topic: Reaction Products
Section: 15.7 and 15.9
Difficulty Level: Medium

51) Which would be the product of the following reaction sequence?

25