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Package title: Solomons Test Bank

Course Title: Solomons 11e


Chapter Number: 14

Question type: Multiple choice

1) The correct name for the compound shown below is:

HO
Cl

a) m-chorophenol
b) o-chorophenol
c) p-chorophenol
d) o-chorobenzyl alcohol
e) 2-chlorophenyl alcohol
Answer: B
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Easy

2) The correct name for the compound shown below is:


Br

NH 2

a) m-bromoaniline
b) o-bromoaniline
c) p-bromoaniline
d) o-bromobenzyl amine
e) 3-bromophenyl amine
Answer: A
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Easy

3) The correct name for the compound shown below is:


OCH3
O2N

a) o-nitroanisole
b) m-nitroanisole
c) p-nitroanisole
d) p-nitrotoluene
e) 4-nitrophenol
Answer: C
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Easy

4) The correct name for the compound shown below is:

Br
CH 3

a) 3-bromobenzene
b) 4-bromobenzene
c) m-bromobenzene
d) o-bromotoluene
e) Bromomethylbenzene
Answer: D
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Easy

5) Which of the following is NOT 2-bromo-5-nitrobenzoic acid?

Br

Br
HO

OH

O2N

NO2

NO2

HO
Br

II

III
HO

Br

Br

HO
O

NO2

IV

NO2

a) I
b) II
c) III
d) IV
e) V
Answer: D
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Easy

6) Toluene is the name commonly assigned to:


a) Hydroxybenzene
b) Aminobenzene
c) Methylbenzene
d) Ethylbenzene
e) Methoxybenzene
Answer: C
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Easy

7) Anisole is the name commonly assigned to:


a) Hydroxybenzene
b) Aminobenzene
c) Methylbenzene
d) Ethylbenzene
3

e) Methoxybenzene
Answer: E
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium

8) Phenol is the name commonly assigned to:


a) Hydroxybenzene
b) Aminobenzene
c) Methylbenzene
d) Ethylbenzene
e) Methoxybenzene
Answer: A
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium

9) Aniline is the name commonly assigned to:


a) Hydroxybenzene
b) Aminobenzene
c) Methylbenzene
d) Ethylbenzene
e) Methoxybenzene
Answer: B
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium

10) Xylene is the name commonly assigned to:


a) Hydroxybenzene
b) Aminobenzene
c) Dimethylbenzene
d) Ethylbenzene
e) Methoxybenzene
4

Answer: C
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium

11) Cumene is the name commonly assigned to:


a) Hydroxybenzene
b) Aminobenzene
c) Ethylbenzene
d) Isopropylbenzene
e) Isobutylbenzene
Answer: D
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium

12) The correct name for the compound shown below is:
Br
Br
NH2

a) 3,4-Dibromoaniline
b) 2,4-Dibromoaniline
c) 2,5-Dibromoaniline
d) 3,6-Dibromoaniline
e) 2,6-Dibromoaniline
Answer: C
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium

13) 2-Bromo-4-nitroaniline is:

Br

Br
NH2
Br

NO2

NO2
NH2

NO2

II

H2N

III

OCH3

Br

Br

H3CO
NO2

NO2

IV

a) I
b) II
c) III
d) IV
e) V
Answer: C
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium

14) 2-Bromo-5-nitroaniline is:


Br

Br
NH2
Br

NO2

NO2
NH2

NO2

II

H2N

III

OCH3
Br

Br
H3CO

NO2

NO2

IV

a) I
b) II
c) III
d) IV
e) V

Answer: B
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium

15) 2-Bromo-4-nitroaniline is:


Br

Br
NH2
Br

NO2

NO2
NH2

NO2

II

H2N

III

OCH3
Br

Br
H3CO

NO2

NO2

IV

a) I
b) II
c) III
d) IV
e) V
Answer: C
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium

16) m-chlorobenzenesulfonic acid is:

Cl
Cl

SO 3HCl

SO3 H
Cl

SO 3H

II
HO3 S

HOOC

III
HOOC

Cl

Cl

IV

a) I
b) II
c) III
d) IV
e) V
Answer: D
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium

17) 4-Bromo-2-nitroaniline is:


Br

Br
NH2
Br

NO2

NO2
NH2

NO2

II

H2N

III

OCH3
Br

Br
H3CO

NO2

NO2

IV

a) I
b) II
c) III
d) IV
e) V
8

Answer: A
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium

18) 4-Amino-2-chlorophenol is:


Cl

OH

Cl

Cl
NH2

NO2

II

H2N

III

OH

OH

Cl

Cl

NH2

NO2

IV

a) I
b) II
c) III
d) IV
e) V
Answer: D
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium

19) 3-bromo-4-nitroacetophenone is:


Br

O
Br

H
O2 N

O 2N

O 2N

Br

II

III
O

O
O 2N

O 2N

Br

Br

IV

V
9

a) I
b) II
c) III
d) IV
e) V
Answer: C
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium

20) 4-Chloro-3-nitro-benzaldehyde is:


Cl

OH

Cl

Cl
NH2

NO2

II

H2N

III

OH
Cl

OH
Cl

NH2

NO2

IV

a) I
b) II
c) III
d) IV
e) V
Answer: B
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium

21) 4-Amino-2-chlorobenzaldehyde is:

10

Cl

OH

Cl

Cl
NH2

NO2

II

H2N

III

OH

OH

Cl

Cl

NH2

NO2

IV

a) I
b) II
c) III
d) IV
e) V
Answer: C
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium

22) 4-Amino-2-bromoanisole is:


Br

Br

Br

OCH3

H3CO
NH2

NO2

II

H2N

III

OCH3
Br

OCH3
Br

NH2

NO2

IV

a) I
b) II
c) III
d) IV
e) V
Answer: D
Topic: Nomenclature and Isomerism
11

Section: 14.2
Difficulty Level: Medium

23) 4-Bromomethyl-2-nitroanisole is:


Br

Br

Br

OCH3

H3CO
NH2

NO2

II

H2N

III

OCH3

OCH3

Br

Br

NH2

NO2

IV

a) I
b) II
c) III
d) IV
e) V
Answer: B
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium

24) 3-chloro-4-nitrobenzoic acid is:


Cl

O
Cl

H
O2 N

O 2N

O 2N

Cl

OH

II

III
O

O
O 2N

O 2N

Cl

Cl

IV

a) I
12

b) II
c) III
d) IV
e) V
Answer: B
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium

25) In theory, a single molecule of this compound will rotate plane-polarized light.
a) Butylbenzene
b) Isobutylbenzene
c) sec-Butylbenzene
d) tert-Butylbenzene
e) None of these choices.
Answer: C
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium

26) Which dichlorobenzene might theoretically yield three mononitro products?


a) o-Dichlorobenzene
b) m-Dichlorobenzene
c) p-Dichlorobenzene
d) None of these choices.
e) All of these choices.
Answer: B
Topic: Nomenclature and Isomerism
Section: 14.2 and 14.3
Difficulty Level: Medium

27) Which dibromobenzene can yield only one mononitro derivative?


a) o-Dibromobenzene
b) m-Dibromobenzene
13

c) p-Dibromobenzene
d) More than one of these choices.
e) None of these choices.
Answer: C
Topic: Nomenclature and Isomerism
Section: 14.2 and 14.3
Difficulty Level: Medium

28) If thiophene is an aromatic molecule and reacts similarly to benzene, how many (neutral)
monobromothiophenes could be obtained in the following reaction?
S

Br2
FeBr3

a) 1
b) 2
c) 3
d) 4
e) 5
Answer: B
Topic: Nomenclature and Isomerism
Section: 14.3
Difficulty Level: Medium

29) Which of these is the single best representation for naphthalene?

II

IV

III

a) I
b) II
c) III
d) IV
e) V
14

Answer: A
Topic: Nomenclature and Isomerism
Section: 14.8
Difficulty Level: Medium

30) How many dichloronaphthalenes are possible?


a) 7
b) 8
c) 9
d) 10
e) 12
Answer: D
Topic: Nomenclature and Isomerism
Section: 14.2 and 14.8
Difficulty Level: Hard

31) How many monochloronaphthalenes are possible?


a) 2
b) 3
c) 4
d) 5
e) 6
Answer: A
Topic: Nomenclature and Isomerism
Section: 14.2 and 14.8
Difficulty Level: Hard

32) The complete name for the following compound is:


CH3

a) sec-Hexylbenzene
b) 2-Phenylhexane
c) (R)-2-Phenylhexane
15

d) (S)-2-Phenylhexane
e) Butylmethylphenylmethane
Answer: D
Topic: Nomenclature and Isomerism
Section: 5.7 and 14.2
Difficulty Level: Hard

33) The complete name for the following compound is:


CH3

a) sec-Hexylbenzene
b) 2-Phenylhexane
c) (R)-2-Phenylhexane
d) (S)-2-Phenylhexane
e) Butylmethylphenylmethane
Answer: C
Topic: Nomenclature and Isomerism
Section: 5.7 and 14.2
Difficulty Level: Hard

34) Which dibromobenzene can, in theory, yield three mononitro derivatives?


a) o-Dibromobenzene
b) m-Dibromobenzene
c) p-Dibromobenzene
d) All of these choices.
e) None of these choices.
Answer: B
Topic: Nomenclature and Isomerism
Section: 14.3
Difficulty Level: Hard

35) Which dihydroxybenzene can yield only one mononitro derivative?


16

a) o-Dihydroxybenzene
b) m-Dihydroxybenzene
c) p- Dihydroxybenzene
d) More than one of these choices.
e) None of these choices.
Answer: C
Topic: Nomenclature and Isomerism
Section: 14.2 and 14.3
Difficulty Level: Hard

36) How many different dibromophenols are possible?


a) 8
b) 7
c) 6
d) 5
e) 4
Answer: C
Topic: Nomenclature and Isomerism
Section: 14.2 and 14.3
Difficulty Level: Hard

37) How many different dichloronitrobenzenes are possible?


a) 8
b) 7
c) 6
d) 5
e) 4
Answer: C
Topic: Nomenclature and Isomerism
Section: 14.2 and 14.3
Difficulty Level: Hard

38) How many different dihydroxybromobenzenes are possible?

17

a) 8
b) 7
c) 6
d) 5
e) 4
Answer: C
Topic: Nomenclature and Isomerism
Section: 14.2 and 14.3
Difficulty Level: Hard

39) Which is the only one of these reagents which will react with benzene under the specified
conditions?
a) Cl2, FeCl3, heat
b) H2, 25C
c) Br2/CCl4, 25C, dark
d) KMnO4/H2O, 25C
e) H3O+, heat
Answer: A
Topic: Chemical Tests and Reactions
Section: 14.3
Difficulty Level: Easy

40) Which reagent(s) would serve as the basis for a simple chemical test that would distinguish
between benzene and 1-hexene?
a) NaOH in H2O
b) Br2 in CCl4
c) AgNO3 in C2H5OH
d) NaHSO3 in H2O
e) None of these choices.
Answer: B
Topic: Chemical Tests and Reactions
Section: 14.3
Difficulty Level: Medium

41) Which reagent(s) would serve as the basis for a simple chemical test that would distinguish
18

between benzene and cyclohexene?


a) NaOH in H2O
b) Br2 in CCl4
c) AgNO3 in C2H5OH
d) NaHSO3 in H2O
e) None of these choices.
Answer: B
Topic: Chemical Tests and Reactions
Section: 14.3
Difficulty Level: Medium

42) Which reagent(s) would serve as the basis for a simple chemical test that would distinguish
between ethylbenzene and vinylcyclohexane?
a) H2CrO4
b) LAH
c) NaBH4, H2O
d) KMnO4, OH, H2O
e) Two of these choices.
Answer: D
Topic: Chemical Tests and Reactions
Section: 14.3
Difficulty Level: Medium

43) Which reagent(s) would serve as the basis for a simple chemical test that would distinguish
between ethylbenzene and vinylcyclohexane?
a) H2CrO4
b) LAH
c) NaBH4, H2O
d) O3/Zn, H+
e) Two of these choices.
Answer: D
Topic: Chemical Tests and Reactions
Section: 14.3
Difficulty Level: Medium

19

44) Which reagent(s) would serve as the basis for a simple chemical test that would distinguish
between naphthalene and 2,4,6-decatriene?
a) NaOH in H2O
b) KMnO4, OH, H2O
c) NaBH4, H2O
d) H2CrO4
e) None of these choices.
Answer: B
Topic: Chemical Tests and Reactions
Section: 14.3
Difficulty Level: Medium

45) Why would 1,3-cyclohexadiene undergo dehydrogenation readily?


a) It is easily reduced.
b) Hydrogen is a small molecule.
c) 1,3-Cyclohexadiene has no resonance energy.
d) It would gain considerable stability by becoming benzene.
e) It would not undergo dehydrogenation.
Answer: D
Topic: Explanations and Predictions
Section: 14.5
Difficulty Level: Medium
46) Recalling that benzene has a resonance energy of 152 kJ mol-1 and naphthalene has a
resonance energy of 255 kJ mol-1, predict the positions which would be occupied by bromine
when phenanthrene (below) undergoes addition of Br2.

7
1

8
10

a) 1, 2
b) 1, 4
c) 3, 4
d) 7, 8
20

e) 9, 10
Answer: E
Topic: Explanations and Predictions
Section: 14.3 and 14.5
Difficulty Level: Medium

47) Which of the following statements about cyclooctatetraene is NOT true?


a) The compound rapidly decolorizes Br2/CCl4 solutions.
b) The compound rapidly decolorizes aqueous solutions of KMnO4.
c) The compound readily adds hydrogen.
d) The compound is nonplanar.
e) The compound is comparable to benzene in stability.
Answer: E
Topic: Explanations and Predictions
Section: 14.5 and 14.7
Difficulty Level: Medium

48) Cyclopentadiene is unusually acidic for a hydrocarbon. An explanation for this is the
following statement.
a) The carbon atoms of cyclopentadiene are all sp2-hybridized.
b) Cyclopentadiene is aromatic.
c) Removal of a proton from cyclopentadiene yields an aromatic anion.
d) Removal of a hydrogen atom from cyclopentadiene yields a highly stable free radical.
e) Removal of a hydride ion from cyclopentadiene produces an aromatic cation.
Answer: C
Topic: Explanations and Predictions
Section: 14.5 and 14.7
Difficulty Level: Medium

49) Consider the molecular orbital model of benzene. In the ground state how many molecular
orbitals are filled with electrons?
a) 1
b) 2
c) 3
21

d) 4
e) 5
Answer: C
Topic: Molecular Orbital Theory
Section: 14.6
Difficulty Level: Medium

50) In the molecular orbital model of benzene, how many pi-electrons are delocalized about the
ring?
a) 2
b) 3
c) 4
d) 5
e) 6
Answer: E
Topic: Molecular Orbital Theory
Section: 14.6
Difficulty Level: Medium

51) In the molecular orbital model of benzene, how many pi-electrons are in bonding molecular
orbitals?
a) 6
b) 5
c) 4
d) 3
e) 2
Answer: A
Topic: Molecular Orbital Theory
Section: 14.6
Difficulty Level: Medium

52) Which cyclization(s) should occur with a decrease in pi-electron energy?

22

CH2

CH

CH

II

CH2

CH

CH2

III CH2

CH

CH2

IV CH2

CH

CH2

CH2

+ H2

+ H2

+ H2

+ H2

a) I
b) II
c) III
d) IV
e) All of these choices.
Answer: B
Topic: Molecular Orbital Theory
Section: 14.7
Difficulty Level: Medium

53) Which cyclization(s) should occur with a decrease in pi-electron energy?


I

H2

II

H2

III

H2

IV

H2

23

a) I
b) II
c) III
d) IV
e) All of these choices.
Answer: B
Topic: Molecular Orbital Theory
Section: 14.7
Difficulty Level: Medium

54) Which cyclization(s) should occur with an increase in pi-electron energy?

a) I
b) II
c) III
d) IV
e) All of these choices.
Answer: D
Topic: Molecular Orbital Theory
Section: 14.7
Difficulty Level: Medium

55) Which cyclization(s) should occur with an increase in pi-electron energy?


24

a) I
b) II
c) III
d) IV
e) All of these choices.
Answer: A
Topic: Molecular Orbital Theory
Section: 14.7
Difficulty Level: Medium

56) Application of the polygon-and-circle technique reveals that single electrons occupy each of
the two nonbonding orbitals in the molecular orbital diagram of:
a) Cyclobutadiene
b) Benzene
c) Cyclopropenyl cation
d) Cyclopentadienyl anion
e) Cycloheptatrienyl cation
Answer: A
Topic: Molecular Orbital Theory
Section: 14.7
Difficulty Level: Medium

57) In the molecular orbital model of benzene, the six p-orbitals combine to form how many
25

molecular orbitals?
a) 6
b) 5
c) 4
d) 3
e) 2
Answer: A
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
58) In the molecular orbital model of benzene, how many -bonding molecular orbitals are
there?
a) 6
b) 5
c) 4
d) 3
e) 2
Answer: D
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
59) In the molecular orbital model of benzene, how many -antibonding molecular orbitals are
there?
a) 6
b) 5
c) 4
d) 3
e) 2
Answer: D
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium

26

60) In the molecular orbital model of benzene, how many pairs of degenerate -molecular
orbitals are there?
a) 6
b) 5
c) 4
d) 3
e) 2
Answer: E
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
61) In the molecular orbital model of benzene, how many pairs of degenerate -bonding
molecular orbitals are there?
a) 1
b) 2
c) 3
d) 4
e) 5
Answer: A
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
62) In the molecular orbital model of benzene, how many pairs of degenerate -antibonding
molecular orbitals are there?
a) 1
b) 2
c) 3
d) 4
e) 5
Answer: A
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
27

Difficulty Level: Medium

63) In the molecular orbital model of benzene, how many non-bonding molecular orbitals are
there?
a) 1
b) 2
c) 3
d) 4
e) 0
Answer: E
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
64) In the molecular orbital model of the cyclopentadienyl cation, how many -bonding
molecular orbitals are there?
a) 6
b) 5
c) 4
d) 3
e) 2
Answer: D
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
65) In the molecular orbital model of the cyclopentadienyl cation, how many -antibonding
molecular orbitals are there?
a) 6
b) 5
c) 4
d) 3
e) 2
Answer: E

28

Topic: Molecular Orbital Theory


Section: 14.6 and 14.7
Difficulty Level: Medium

66) In the molecular orbital model of the cyclopentadienyl cation, how many pairs of degenerate
-molecular orbitals are there?
a) 6
b) 5
c) 4
d) 3
e) 2
Answer: E
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium

67) In the molecular orbital model of the cyclopentadienyl cation, how many pairs of degenerate
-bonding molecular orbitals are there?
a) 1
b) 2
c) 3
d) 4
e) 5
Answer: A
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium

68) In the molecular orbital model of the cyclopentadienyl cation, how many pairs of degenerate
-antibonding molecular orbitals are there?
a) 1
b) 2
c) 3
d) 4
e) 5

29

Answer: A
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium

69) In the molecular orbital model of the cyclopentadienyl cation, how many non-bonding
molecular orbitals are there?
a) 1
b) 2
c) 3
d) 4
e) 0
Answer: E
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
70) In the molecular orbital model of cyclobutadiene, how many -bonding molecular orbitals
are there?
a) 1
b) 2
c) 3
d) 4
e) 5
Answer: A
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
71) In the molecular orbital model of cyclobutadiene, how many -antibonding molecular
orbitals are there?
a) 5
b) 4
c) 3
d) 2
30

e) 1
Answer: E
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
72) In the molecular orbital model of cyclobutadiene, how many pairs of degenerate -molecular
orbitals are there?
a) 0
b) 1
c) 2
d) 3
e) 4
Answer: A
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
73) In the molecular orbital model of the cyclobutadiene, how many pairs of degenerate bonding molecular orbitals are there?
a) 1
b) 2
c) 3
d) 4
e) 0
Answer: E
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
74) In the molecular orbital model of cyclobutadiene, how many pairs of degenerate antibonding molecular orbitals are there?
a) 1
b) 2
31

c) 3
d) 4
e) 0
Answer: E
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium

75) In the molecular orbital model of cyclobutadiene, how many non-bonding molecular orbitals
are there?
a) 1
b) 2
c) 3
d) 4
e) 0
Answer: B
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium

76) Consider the molecular orbital model of cyclopentadienyl anion. In the ground state how
many molecular orbitals are filled with electrons?
a) 1
b) 2
c) 3
d) 4
e) 5
Answer: C
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium

77) In the molecular orbital model of cyclopentadienyl anion, how many pi-electrons are
delocalized about the ring?

32

a) 2
b) 3
c) 4
d) 5
e) 6
Answer: E
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium

78) In the molecular orbital model of cyclopentadienyl anion, how many pi-electrons are in
bonding molecular orbitals?
a) 6
b) 5
c) 4
d) 3
e) 2
Answer: A
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium

79) In the molecular orbital model of cycloheptadienyl cation, how many pi-electrons are in
bonding molecular orbitals?
a) 6
b) 5
c) 4
d) 3
e) 2
Answer: A
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium

80) In the molecular orbital model of cycloheptadienyl cation, how many pi-electrons are
33

delocalized about the ring?


a) 6
b) 5
c) 4
d) 3
e) 2
Answer: A
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium

81) In the molecular orbital model of 1,3-cyclobutadiene, how many electrons are in nonbonding molecular orbitals?
a) 6
b) 5
c) 4
d) 3
e) 2
Answer: E
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium

82) In the molecular orbital model of which of the following substance(s) are non-bonding
orbitals found?
a) 1,3-Cyclobutadiene
b) Cyclopentadienyl anion
c) 1,3,5,7-Cyclooctatetraene
d) Two of these choices.
e) All of these choices.
Answer: D
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium

34

83) Which of the following is NOT true of benzene?


a) Benzene tends to undergo substitution rather than addition reactions, even though it has a high
index of hydrogen deficiency.
b) All of the hydrogen atoms of benzene are equivalent.
c) The carbon-carbon bonds of benzene are alternately short and long around the ring.
d) Only one o-dichlorobenzene has ever been found.
e) Benzene is more stable than the hypothetical compound 1,3,5-cyclohexatriene.
Answer: C
Topic: Bonding and Resonance
Section: 14.4 and 14.6
Difficulty Level: Easy

84) Which of the following is true of benzene?


a) Benzene tends to undergo addition rather than substitution reactions.
b) All of the hydrogen atoms of benzene are equivalent.
c) The carbon-carbon bonds of benzene are alternately short and long around the ring.
d) The benzene ring is a distorted hexagon.
e) Benzene has the stability expected for cyclohexatriene.
Answer: B
Topic: Bonding and Resonance
Section: 14.4 and 14.6
Difficulty Level: Easy

85) The carbon-carbon bonds in benzene are:


a) of equal length and are shorter than the double bond of ethene.
b) of equal length and are intermediate between a double bond and a single bond.
c) of unequal length and are alternately short and long around the ring.
d) due only to p-orbital overlap.
e) of equal length and intermediate between the carbon-carbon bond lengths in ethene and
ethyne.
Answer: B
Topic: Bonding and Resonance
Section: 14.4 and 14.6
Difficulty Level: Easy
35

86) We now know that the two Kekule structures for benzene are related in the following way:
a) They are each equally correct as a structure for benzene.
b) Benzene is sometimes one structure and sometimes the other.
c) The two structures are in a state of rapid equilibrium.
d) Neither of the two structures adequately describes benzene; benzene is a resonance hybrid of
the two.
e) None of these choices.
Answer: D
Topic: Bonding and Resonance
Section: 14.4 and 14.6
Difficulty Level: Easy

87) In which of the following compounds would the shortest carbon-carbon bond(s) be found?
a) Toluene
b) 2-Ethylcyclopentene
c) 4-Methyl-1,3-cyclohexadiene
d) 3-Methyl-1-hexyne
e) 3-Methyl-1,3-hexadiene
Answer: D
Topic: Nomenclature, Bonding and Resonance
Section: 14.4 and 14.6
Difficulty Level: Medium

88) In which of the following compounds would the longest carbon-carbon bond(s) be found?
a) 2-Bromobenzaldehyde
b) Vinylbenzene
c) 1,3,5-Heptatriene
d) 2,4,6-Octatriene
e) 2-Ethylbenzoic acid
Answer: D
Topic: Nomenclature, Bonding and Resonance
Section: 14.4 and 14.6
Difficulty Level: Hard
36

89) Which of the following statements regarding the cyclopentadienyl radical is correct?
a) It is aromatic.
b) It is not aromatic.
c) It obeys Huckel's rule.
d) It undergoes reactions characteristic of benzene.
e) It has a closed shell of 6 pi-electrons.
Answer: B
Topic: Aromatic/ Antiaromatic/ Nonaromatic
Section: 14.7
Difficulty Level: Medium

90) Which of the following statements regarding the cycloheptatrienyl radical is correct?
a) It is aromatic.
b) It is not aromatic.
c) It obeys Hckel's rule.
d) It undergoes reactions characteristic of benzene.
e) It has a closed shell of 6 pi-electrons.
Answer: B
Topic: Aromatic/ Antiaromatic/ Nonaromatic
Section: 14.7
Difficulty Level: Medium

91) Which of the following statements regarding the cyclopentadienyl cation is correct?
a) It is aromatic.
b) It is not aromatic.
c) It obeys Hckels rule.
d) It undergoes reactions characteristic of benzene.
e) It has a closed shell of 6 pi-electrons.
Answer: B
Topic: Aromatic/ Antiaromatic/ Nonaromatic
Section: 14.7
Difficulty Level: Medium

37

92) Which of the following statements regarding the cyclopropenyl anion is correct?
a) It is aromatic.
b) It is not aromatic.
c) It obeys Hckels rule.
d) It undergoes reactions characteristic of benzene.
e) It has a closed shell of 6 pi-electrons.
Answer: B
Topic: Aromatic/ Antiaromatic/ Nonaromatic
Section: 14.7
Difficulty Level: Medium

93) Which of the following statements regarding the cyclopropenyl radical is correct?
a) It is aromatic.
b) It is not aromatic.
c) It obeys Hckels rule.
d) It undergoes reactions characteristic of benzene.
e) It has a closed shell of 6 pi-electrons.
Answer: B
Topic: Aromatic/ Antiaromatic/ Nonaromatic
Section: 14.7
Difficulty Level: Medium

94) Which of the following statements regarding the cycloheptatrienyl anion is correct?
a) It is aromatic.
b) It is not aromatic.
c) It obeys Hckels rule.
d) It undergoes reactions characteristic of benzene.
e) It has a closed shell of 6 pi-electrons.
Answer: B
Topic: Aromatic/ Antiaromatic/ Nonaromatic
Section: 14.7
Difficulty Level: Medium

38

95) Of Hckels requirements for aromatic character, only this one is waived in the case of
certain compounds considered to be aromatic.
a) The ring system must be planar.
b) The system must be monocyclic.
c) There must be (4n + 2) electrons.
d) The Hckel number of electrons must be completely delocalized.
e) None. All of these rules must apply in every case.
Answer: B
Topic: Aromaticity, Hckels Rule
Section: 14.7
Difficulty Level: Easy

96) Which of the following would you expect to be aromatic?


H
H

II

III

IV

a) I
b) II
c) III
d) IV
e) V
Answer: E
Topic: Aromaticity, Huckels Rule
Section: 14.7
Difficulty Level: Medium

97) Which of the following would you expect to be aromatic?


H
H

II

III

IV

2+
V

a) I
b) II
39

c) III
d) IV
e) V
Answer: E
Topic: Aromaticity, Hckels Rule
Section: 14.7
Difficulty Level: Medium

98) Which of the following would you expect to be aromatic?

H H

II

III

IV

a) I
b) II
c) III
d) IV
e) None of these choices.
Answer: B
Topic: Aromaticity, Hckels Rule
Section: 14.7
Difficulty Level: Medium

99) Which of the following would you expect to show aromatic character?

a) I
b) II
c) III
d) IV
e) None of these choices.
40

Answer: B
Topic: Aromaticity, Hckels Rule
Section: 14.7
Difficulty Level: Medium

100) Which of the following would you expect to be aromatic?

II

III

IV

a) I
b) II
c) III
d) IV
e) All of these choices.
Answer: A
Topic: Aromaticity, Hckels Rule
Section: 14.7
Difficulty Level: Medium

101) Which of the following would you expect to be aromatic?

a) I
b) II
c) III
d) IV
e) All of these choices.
Answer: A
Topic: Aromaticity, Hckels Rule
Section: 14.7
Difficulty Level: Medium
41

102) Which of the following would you expect to be aromatic?

a) I
b) II
c) III
d) IV
e) All of these choices.
Answer: A
Topic: Aromaticity, Hckels Rule
Section: 14.7
Difficulty Level: Medium

103) Which of the following structures would be aromatic?

a) I
b) II
c) III
d) IV
e) V
Answer: B
Topic: Aromaticity, Hckels Rule
Section: 14.7
Difficulty Level: Medium

42

104) Which of the following would you expect to be aromatic?

H H

II

III

IV

a) I
b) II
c) III
d) IV
e) None of these choices.
Answer: C
Topic: Aromaticity, Hckels Rule
Section: 14.7
Difficulty Level: Medium

105) Which of the following would you expect to be aromatic?

a) I
b) II
c) III
d) IV
e) None of these choices.
Answer: C
Topic: Aromaticity, Hckels Rule
Section: 14.7
Difficulty Level: Medium

106) On the basis of molecular orbital theory and Hckels rule, which molecules and/or ions
should be aromatic?
43

H H

II

III

IV

N
H

VI

VII

VIII

IX

a) I and V
b) III and VIII
c) IV, VII and IX
d) IV, VI, VII and IX
e) All of the structures, I-IX
Answer: D
Topic: Aromaticity, Hckels Rule
Section: 14.7
Difficulty Level: Medium

107) On the basis of molecular orbital theory and Hckels rule, which molecules and/or ions
should be antiaromatic?

H H

II

III

IV

N
H

VI

VII

VIII

IX

a) I and V
b) I, II and V
c) III and VIII
44

d) IV, VII and IX


e) IV, VI, VII and IX
Answer: B
Topic: Aromaticity, Hckels Rule
Section: 14.7
Difficulty Level: Medium

108) On the basis of molecular orbital theory and Hckels rule, which molecules and/or ions
should be non-aromatic?

H H

II

III

IV

N
H

VI

VII

VIII

IX

a) I and V
b) I and II
c) III and VIII
d) IV, VII and IX
e) IV, VI, VII and IX
Answer: C
Topic: Aromaticity, Hckels Rule
Section: 14.7
Difficulty Level: Medium

109) On the basis of molecular orbital theory and Hckels rule, which of these compounds
should be aromatic?

45

H H

II

III

IV

a) I
b) II
c) III
d) IV
e) V
Answer: E
Topic: Aromaticity, Hckels Rule
Section: 14.7
Difficulty Level: Medium

110) On the basis of molecular orbital theory and Hckels rule, which of these compounds
should be aromatic?

a) I
b) II
c) III
d) IV
e) V
Answer: E
Topic: Aromaticity, Hckels Rule
Section: 14.7
Difficulty Level: Medium

111) On the basis of molecular orbital theory and Hckels rule, which of these compounds
should be aromatic?

46

a) I
b) II
c) III
d) IV
e) V
Answer: E
Topic: Aromaticity, Hckels Rule
Section: 14.7
Difficulty Level: Medium

112) Which of these is an aromatic molecule?

CH3

B
CH3

II

III

IV

a) I
b) II
c) III
d) IV
e) V
Answer: A
Topic: Aromaticity, Hckels Rule
Section: 14.7
Difficulty Level: Medium

113) Which of these is an aromatic molecule?

47

a) I
b) II
c) III
d) IV
e) V
Answer: A
Topic: Aromaticity, Hckels Rule
Section: 14.7
Difficulty Level: Medium

114) Which of these is an aromatic molecule?

a) I
b) II
c) III
d) IV
e) V
Answer: A
Topic: Aromaticity, Hckels Rule
Section: 14.7
Difficulty Level: Medium

115) Which of these is an aromatic molecule?


48

a) I
b) II
c) III
d) IV
e) V
Answer: A
Topic: Aromaticity, Hckels Rule
Section: 14.7
Difficulty Level: Medium

116) Which of these is not an aromatic molecule?

a) I
b) II
c) III
d) IV
e) V
Answer: D
Topic: Aromaticity, Hckels Rule
Section: 14.7
Difficulty Level: Medium

49

117) Of the following C-10 compounds, which is expected to possess the greatest resonance
(delocalization) energy?

II

III

IV

a) I
b) II
c) III
d) IV
e) V
Answer: C
Topic: Aromaticity, Hckels Rule
Section: 14.7 and 14.8
Difficulty Level: Medium

118) Which of the following would you expect to be antiaromatic?

II

III

IV

a) I
b) II
c) III
d) IV
e) V
Answer: C
Topic: Aromaticity, Hckels Rule
Section: 14.7 and 14.8
Difficulty Level: Medium

119) Which of these would you expect to have significant resonance stabilization energy?
50

N
H

II

III

a) I
b) II
c) III
d) All of these choices.
e) None of these choices.
Answer: D
Topic: Aromaticity, Huckels Rule
Section: 14.7 and 14.9
Difficulty Level: Medium

120) Which of these would you expect to have significant resonance stabilization energy?

O
N

II

III

a) I
b) II
c) III
d) All of these choices.
e) None of these choices.
Answer: D
Topic: Aromaticity, Hckels Rule
Section: 14.7 and 14.9
Difficulty Level: Medium

121) Which of these would you expect to have significant resonance stabilization energy?

51

a) I
b) II
c) III
d) All of these choices.
e) None of these choices.
Answer: D
Topic: Aromaticity, Hckels Rule
Section: 14.7 and 14.9
Difficulty Level: Medium

122) Which of these would you expect to have significant resonance stabilization energy?

S
N

II

III

a) I
b) II
c) III
d) All of these choices.
e) None of these choices.
Answer: D
Topic: Aromaticity, Hckels Rule
Section: 14.7 and 14.9
Difficulty Level: Medium

123) Which of these would you expect to have significant resonance stabilization energy?

52

CH
N

II

III

a) I
b) II
c) III
d) All of these choices.
e) None of these choices.
Answer: D
Topic: Aromaticity, Hckels Rule
Section: 14.7 and 14.9
Difficulty Level: Medium

124) Which compound would you NOT expect to be aromatic?

II

III

B
R

IV

a) I
b) II
c) III
d) IV
e) V
Answer: E
Topic: Aromaticity, Huckels Rule
Section: 14.7 and 14.9
Difficulty Level: Medium

125) Which compound would you NOT expect to be aromatic?

53

a) I
b) II
c) III
d) IV
e) V
Answer: E
Topic: Aromaticity, Huckels Rule
Section: 14.7 and 14.9
Difficulty Level: Medium

126) Which compound would you NOT expect to be aromatic?

II

III

IV

a) I
b) II
c) III
d) IV
e) V
Answer: E
Topic: Aromaticity, Hckels Rule
Section: 14.7 and 14.9
Difficulty Level: Medium

127) Which of these species is aromatic?

54

N
H

N
H

II

III

IV

a) I
b) II
c) III
d) IV
e) V
Answer: B
Topic: Aromaticity, Huckels Rule
Section: 14.7 and 14.9
Difficulty Level: Medium
128) In which case is the indicated unshared pair of electrons NOT a contributor to the
aromatic system?

N
H

II

III

IV

a) I
b) II
c) III
d) IV
e) None of these choices.
Answer: B
Topic: Aromaticity, Hckels Rule
Section: 14.7 and 14.9
Difficulty Level: Medium
129) In which case is the indicated unshared pair of electrons NOT a contributor to the
aromatic system?

55

N
I

II

III

IV

a) I
b) II
c) III
d) IV
e) None of these choices.
Answer: B
Topic: Aromaticity, Hckels Rule
Section: 14.7 and 14.9
Difficulty Level: Medium

130) Which of these species is aromatic?


O
O

IV

N
H

N
H

II

III

a) I
b) II
c) III
d) IV
e) V
Answer: B
Topic: Aromaticity, Hckels Rule
Section: 14.7 and 14.9
Difficulty Level: Hard

131) Which of these species is aromatic?

56

N
H

N
H

IV

III

II

a) I
b) II
c) III
d) IV
e) V
Answer: B
Topic: Aromaticity, Hckels Rule
Section: 14.7 and 14.9
Difficulty Level: Hard

132) Which of these species is aromatic?


O
O

IV

N
H

N
H

II

III

a) I
b) II
c) III
d) IV
e) V
Answer: B
Topic: Aromaticity, Hckels Rule
Section: 14.7 and 14.9
Difficulty Level: Hard

133) Which of these species is aromatic?


57

N
H

N
H

II

N
H

IV

III

a) I
b) II
c) III
d) IV
e) V
Answer: B
Topic: Aromaticity, Hckels Rule
Section: 14.7 and 14.9
Difficulty Level: Hard

134) Which of these species is aromatic?


NH2
O

O
N

N
H

N
H

II

III

N
H

IV

a) I
b) II
c) III
d) IV
e) V
Answer: E
Topic: Aromaticity, Hckels Rule
Section: 14.7 and 14.9
Difficulty Level: Hard

135) Which of the following would you expect to be antiaromatic?

58

III

II

IV

a) I
b) II
c) III
d) IV
e) V
Answer: C
Topic: Aromaticity, Hckels Rule
Section: 14.7 and 14.8
Difficulty Level: Hard

136) Which of the following would you expect to be antiaromatic?


O

II

IV

III

a) I
b) II
c) III
d) IV
e) V
Answer: C
Topic: Aromaticity, Hckels Rule
Section: 14.7 and 14.8
Difficulty Level: Hard

137) Which of the following would you expect to be antiaromatic?

59

II

III

IV

a) I
b) II
c) III
d) IV
e) V
Answer: C
Topic: Aromaticity, Hckels Rule
Section: 14.7 and 14.8
Difficulty Level: Hard

138) Which annulene would you NOT expect to be aromatic?


a) [6]-Annulene
b) [14]-Annulene
c) [16]-Annulene
d) [18]-Annulene
e) [22]-Annulene
Answer: C
Topic: Aromaticity, Hckels Rule
Section: 14.7 and 14.8
Difficulty Level: Hard

139) Which of these is an aromatic molecule?

60

CH3

CH3

II

III

IV

a) I
b) II
c) III
d) IV
e) V
Answer: A
Topic: Aromaticity, Hckels Rule
Section: 14.7
Difficulty Level: Hard

140) On the basis of molecular orbital theory and Hckels rule, which of these compounds
should be aromatic?

H H

II

III

IV

a) I
b) II
c) III
d) IV
e) V
Answer: E
Topic: Aromaticity, Hckels Rule
Section: 14.7
Difficulty Level: Hard

61

141) How many equivalent resonance structures can be written for the cyclopentadienyl anion?
a) 3
b) 4
c) 5
d) 6
e) 7
Answer: C
Topic: Resonance Forms
Section: 14.7
Difficulty Level: Medium

142) How many equivalent resonance structures can be written for the cycloheptatrienyl cation?
a) 3
b) 4
c) 5
d) 6
e) 7
Answer: E
Topic: Resonance Forms
Section: 14.7
Difficulty Level: Medium

143) How many equivalent resonance structures can be written for the cyclopropenyl cation?
a) 1
b) 2
c) 3
d) 4
e) 5
Answer: C
Topic: Resonance Forms
Section: 14.7
Difficulty Level: Medium

144) How many equivalent resonance structures can be written for the cyclobutadienyl dication?
62

a) 1
b) 2
c) 3
d) 4
e) No equivalent resonance forms can be drawn.
Answer: D
Topic: Resonance Forms
Section: 14.7
Difficulty Level: Medium

145) How many resonances would be expected in the broad-band decoupled C-13 spectra of:

a) 1
b) 2
c) 3
d) 4
e) 5
Answer: D
Topic: Spectroscopy
Section: 14.11
Difficulty Level: Medium

146) How many resonances would be expected in the broad-band decoupled C-13 spectra of:

a) 1
b) 2
c) 3
d) 4
63

e) 5
Answer: C
Topic: Spectroscopy
Section: 14.11
Difficulty Level: Medium

147) How many resonances would be expected in the broad-band decoupled C-13 spectra of:

a) 1
b) 2
c) 3
d) 4
e) 5
Answer: E
Topic: Spectroscopy
Section: 14.11
Difficulty Level: Medium

148) How many resonances would be expected in the broad-band decoupled C-13 spectra of:

a) 2
b) 3
c) 4
d) 5
e) 6
Answer: E
Topic: Spectroscopy
64

Section: 14.11
Difficulty Level: Medium

149) How many resonances would be expected in the broad-band decoupled C-13 spectra of:
CHO

Cl

a) 2
b) 3
c) 4
d) 5
e) 6
Answer: D
Topic: Spectroscopy
Section: 14.11
Difficulty Level: Medium

150) How many resonances would be expected in the broad-band decoupled C-13 spectra of:

a) 3
b) 4
c) 5
d) 6
e) 7
Answer: E
Topic: Spectroscopy
Section: 14.11
Difficulty Level: Medium
65

151) How many resonances would be expected in the broad-band decoupled C-13 spectra of:

a) 2
b) 3
c) 4
d) 5
e) 6
Answer: B
Topic: Spectroscopy
Section: 14.11
Difficulty Level: Medium

152) How many resonances would be expected in the broad-band decoupled C-13 spectra of:

a) 4
b) 5
c) 6
d) 7
e) 8
Answer: E
Topic: Spectroscopy
Section: 14.11
Difficulty Level: Medium

153) How many resonances would be expected in the broad-band decoupled C-13 spectra of:
66

a) 4
b) 5
c) 6
d) 7
e) 8
Answer: A
Topic: Spectroscopy
Section: 14.11
Difficulty Level: Medium

154) How many resonances would be expected in the broad-band decoupled C-13 spectra of:

a) 4
b) 5
c) 6
d) 7
e) 8
Answer: E
Topic: Spectroscopy
Section: 14.11
Difficulty Level: Medium

155) How many resonances would be expected in the broad-band decoupled C-13 spectra of:

a) 4
67

b) 5
c) 6
d) 7
e) 8
Answer: B
Topic: Spectroscopy
Section: 14.11
Difficulty Level: Medium

156) How many resonances would be expected in the broad-band decoupled C-13 spectra of:

a) 5
b) 6
c) 7
d) 8
e) 9
Answer: E
Topic: Spectroscopy
Section: 14.11
Difficulty Level: Medium

157) How many resonances would be expected in the broad-band decoupled C-13 spectra of:

a) 4
b) 5
c) 6
d) 7
e) 8
68

Answer: E
Topic: Spectroscopy
Section: 14.11
Difficulty Level: Medium

158) Which of these compounds absorbs at the longest wavelength in the UV-visible region?

II

III

IV

a) I
b) II
c) III
d) IV
e) V
Answer: B
Topic: Spectroscopy
Section: 14.11
Difficulty Level: Medium
159) A compound has the formula C8H9Br. Its 1H NMR spectrum consists of:
doublet, 2.0
quartet, 5.15
multiplet, 7.35
The IR spectrum shows two peaks in the 680-840 cm-1 region; one is between 690 and 710 cm-1
and the other is between 730 and 770 cm-1. Which is a possible structure for the compound?
Br

Br

Br

II

III

Br

Br

IV

a) I
b) II
69

c) III
d) IV
e) V
Answer: D
Topic: Spectroscopy
Section: 14.11
Difficulty Level: Medium
160) Which of the following substances, formula C8H9Br, might exhibit the following 1H NMR
spectrum?
triplet, 2.8
triplet, 4.65
multiplet, 7.2
Br

Br

Br

II

III

Br

Br

IV

a) I
b) II
c) III
d) IV
e) V
Answer: C
Topic: Spectroscopy
Section: 14.11
Difficulty Level: Medium
161) Which of the following substances, formula C8H9Br, might exhibit the following 1H NMR
spectrum?
triplet, 1.2
quartet, 2.45
multiplet, 7.4

70

Br

Br

Br

II

III

Br

Br

IV
a) I
b) II
c) III
d) IV
e) V
Answer: A
Topic: Spectroscopy
Section: 14.11
Difficulty Level: Medium

162) Which of the following substances, formula C8H9Br, might exhibit the following 1H NMR
spectrum?
singlet, 2.45
singlet, 2.5
multiplet, 7.35
Br

Br

Br

II

III

Br

Br

IV

a) I
b) II
c) III
d) IV
e) V
Answer: E
71

Topic: Spectroscopy
Section: 14.11
Difficulty Level: Medium
163) Which of the following substances, C8H9Cl, would exhibit five signals in its 13C NMR
spectrum?
Cl
Cl

Cl

III

II
Cl

Cl

IV

a) I
b) II
c) III
d) IV
e) V
Answer: C
Topic: Spectroscopy
Section: 14.11
Difficulty Level: Medium
164) Which of the following substances, C9H10O, would exhibit seven signals in its 13C NMR
spectrum?
O
O

II

III

HO

IV

a) I
b) II

72

c) III
d) IV
e) V
Answer: A
Topic: Spectroscopy
Section: 14.11
Difficulty Level: Medium
165) For which of the following substances, C9H10O, would the aromatic multiplet, in its 1H
NMR spectrum, consist of two doublets?
O
O

II

III

HO

IV

a) I
b) II
c) III
d) IV
e) V
Answer: A
Topic: Spectroscopy
Section: 14.11
Difficulty Level: Medium
166) In the 1H NMR spectra of which of the following substances, C9H10O, would you expect to
see two singlets in the range of 2.0-2.5 ppm?

73

O
O
O

II

III

HO

IV

a) I and III
b) I, II, and III
c) IV
d) V
e) All of these substances would exhibit two singlets 2.0-2.5 ppm in their 1H NMR spectra.
Answer: B
Topic: Spectroscopy
Section: 14.11
Difficulty Level: Medium
167) Which isomer of C7H7Cl exhibits strong IR absorbances at 690 and 750 cm1?
CH3

CH3

CH3

CH2Cl

Cl
Cl
Cl

I
a) I
b) II
c) III
d) IV
e) II and IV

II

III

IV

Answer: E
Topic: Spectroscopy
Section: 14.11
Difficulty Level: Hard

168) Which reagent(s)/technique would serve to distinguish between azulene and


bicyclo[5.3.0]decane?
74

a) Br2, CCl4
b) KMnO4, OH, H2O
c) NMR Spectroscopy
d) UV Spectroscopy
e) Two of these choices.
Answer: E
Topic: Chemical and Spectroscopic Analysis
Section: 13.9, 14.7 and 14.11
Difficulty Level: Medium

169) Which reagent(s)/technique would serve to distinguish between azulene and


bicyclo[5.3.0]decane?

a) Br2, CCl4
b) KMnO4, OH, H2O
c) NMR Spectroscopy
d) NaBH4, H2O
e) Two of these choices.
Answer: C
Topic: Chemical and Spectroscopic Analysis
Section: 14.7 and 14.11
Difficulty Level: Medium

Question type: fill-in-the-blank

170) A compound that reacts like an alkane, alkene, alkyne, or one of their derivatives, is called
an ___ compound, while one that reacts like benzene is called an ___ compound.
Answer: aliphatic, aromatic
Topic: General Concepts
Section: 14.1
Difficulty Level: Easy
75

171) Humans do not have the biochemical ability to synthesize the benzene ring. Therefore, two
amino acids, ___ and ___, are essential to the human diet.
Answer: tryptophan, phenylalanine
Topic: General Concepts
Section: 14.10
Difficulty Level: Easy

172) Cagelike molecules with the geometry of a truncated icosahedron are called ___.
Answer: fullerenes
Topic: General Concepts
Section: 14.8
Difficulty Level: Easy

173) Monocyclic compounds with alternating single and double bonds are called ___.
Answer: annulenes
Topic: General Concepts
Section: 14.7
Difficulty Level: Easy

174) The difference between the amount of heat actually released upon hydrogenation of
benzene and that calculated on the basis of the Kekule structure is called the ___ of benzene.
Answer: resonance energy
Topic: General Concepts
Section: 14.5
Difficulty Level: Easy

175) Molecular orbitals of equal energy are referred to as ___ orbitals.


Answer: degenerate
Topic: General Concepts
Section: 14.6
76

Difficulty Level: Medium

176) When a benzene ring is used as a substituent, it is called a ___ group.


Answer: phenyl
Topic: Nomenclature
Section: 14.2
Difficulty Level: Easy

Question type: Molecular Drawing

177) Draw the structure corresponding to the following name: 2-bromo-5-nitrophenol


OH
Br

Answer: O2N
Topic: Nomenclature
Section: 14.2
Difficulty Level: Medium

178) Draw the structure corresponding to the following name:


3-bromo 5-phenylaniline
NH2

Br

Answer:
Topic: Nomenclature
Section: 14.2
Difficulty Level: Medium

179) Draw the structure corresponding to the following name: 3-nitro-4-iodoanisole


O2N

Answer:

77

Topic: Nomenclature
Section: 14.2
Difficulty Level: Medium

Question type: Essay

180) Give the IUPAC name for the following substance:


OH
O

Answer: 2-methyl-4-(3-methylbutyl)benzoic acid


Topic: Nomenclature
Section: 14.2
Difficulty Level: Hard

181) Draw the structure corresponding to the following name: 2-hydroxy-4-(3methylcyclopentyl)benzoic acid
HO

Answer:

HO2C

Topic: Nomenclature
Section: 14.2
Difficulty Level: Hard

Question type: fill-in-the-blank


182) Hckels Rule requires ___ electrons for an aromatic compound.
Answer: 4n+2
Topic: Hckels rule
Section: 14.7
Difficulty Level: Easy

Question type: Essay


78

183) The heats of hydrogenation for cyclohexene and benzene are given below. Calculate the
resonance stabilization energy of benzene.
C6H10 + H2 C6H12
C6H6 + 3H2 C6H12

Ho = -120 kJ/mol
Ho = -208 kJ/mol

Answer: The resonance stabilization energy of benzene is the difference between the theoretical
and observed Ho values.
Hydrogenation of three double bonds should release 3 times the energy released when one
double bond is hydrogenated. Thus, the theoretical Ho for benzene can be calculated as [3x (120)] kJ/mol = -360 kJ/mol
Therefore,
Resonance stabilization energy of benzene = (-208) (-360) kJ/mol
= 152 kJ/mol
Topic: Aromaticity, Resonance Stabilization Energy
Section: 14.5
Difficulty Level: Medium

184) Use the polygon-in-circle method to draw an MO diagram showing the pi-electron
distribution pattern in the cyclopentadienyl anion. How is this diagram useful in explaining the
aromatic properties of this anion?
Answer: The following MO diagram can be generated using the polygon-in-circle method. The
six pi electrons of the cyclopentadienyl anion in the bonding molecular orbitals form a closed
bonding shell, accounting for its aromatic properties.

Antibonding MO
Bonding MO
6 pi electrons
"closed bonding shell"
Topic: Aromaticity, Molecular Orbital Theory
Section: 14.7
Difficulty Level: Medium

185) Use the polygon-in-circle method to draw an MO diagram showing the pi-electron
distribution pattern in the cyclopentadienyl cation. How is this diagram useful in explaining the
antiaromatic properties of this anion?

79

Answer: This MO diagram can be generated using the polygon-in-circle method. The 4 pi
electrons of the cyclopentadienyl cation in the bonding molecular orbitals form a bonding shell
which lacks 2 pi electrons from being closed, accounting for its antiaromatic properties.
Topic: Aromaticity, Molecular Orbital T heory
Section: 14.7
Difficulty Level: Medium

186) Use the polygon-in-circle method to draw an MO diagram showing the pi-electron
distribution pattern in the cycloheptatrienyl cation. How is this diagram useful in explaining the
antiaromatic properties of this anion?

Answer: This MO diagram can be generated using the polygon-in-circle method. The six pi
electrons of the cycloheptatrienyl cation in the bonding molecular orbitals form a closed bonding
shell, accounting for its aromatic properties
Topic: Aromaticity, Molecular Orbital Theory
Section: 14.7
Difficulty Level: Medium

187) The pka of cyclopentadiene is found to be 16 while, by contrast, that of cycloheptatriene is


found to be 36. Explain the large difference found in the two pka values.

..

Answer: The 20 order of magnitude difference in acidity of cyclopentadiene compared with


cycloheptatriene lies in the fact that the conjugate base of cyclopentadiene is the aromatic
cyclopentadienyl anion, a very stable conjugate base species. However, in the case of
cycloheptatriene, removal of a proton produces the cyclohe[tatrienyl anion, a cyclic, conjugated,
planar system with 8 -electrons, that is antiaromatic.
B:
H

Aromatic
anion

80

B:-

Topic: Aromaticity, Molecular Orbital Theory


Section: 14.7
Difficulty Level: Hard

188) Benzene, while unusually unreactive with electrophiles, will react under certain conditions.
However, when it does react, it does so by ___ rather than by addition.
Answer: substitution
Topic: Aromaticity, Reactivity
Section: 14.3
Difficulty Level: Easy

189) Explain briefly why cyclopentadiene readily reacts with strong bases.

..

Answer: The acidity of a substance can be often be correlated with the stability of its conjugate
base: substances that have exceptionally stable conjugate bases tend to be strong acids. The
conjugate base of cyclopentadiene, formed during reaction with a base, is exceptionally stable,
by virtue of being an aromatic anion (6 pi electrons, planar ring), thus accounting for the
readiness with which cyclopentadiene reacts with bases.
B:
H

Aromatic
anion

Topic: Aromaticity, Reactivity


Section: 14.7
Difficulty Level: Medium

190) Cyclohepatriene is found to readily undergo a hydride transfer with triphenylmethyl


arbocation to generate the cycloheptatrienyl cation and triphenylmethane. Explain why this
transformation is facile.

81

Ph3C+

Ph3CH

Answer: This reaction readily proceeds because the product, cycloheptatrienyl cation, is aromatic
and much more stable than even the triphenyl substituted carbocation.
Topic: Aromaticity, Reactivity
Section: 14.7
Difficulty Level: Medium

191) Pyrrole is not particularly basic, because the lone pair on the nitrogen is ___.
Answer: part of the aromatic system
Topic: Aromaticity, Reactivity
Section: 14.9
Difficulty Level: Medium

192) The Lewis structures of both pyridine and pyrrole have an electron pair on the nitrogen
atom, suggesting that both substances might possess basic properties. However, only pyridine
reacts readily with HCl to form pyridinium chloride, while pyrrole is rather unreactive. Explain
clearly, using relevant diagrams to illustrate/clarify your answer.
Answer:
+ HCl
N

..

N+
Cl
H

sp
pyridinium chloride

pyridinium chloride

.. p
N H

+ HCl

H
N + Cl
H

not aromatic
pyrrole
electron pair:
part of aromatic pi sextet
Both pyridine and pyrrole are known to exhibit aromatic properties; the nitrogen atom must
therefore be sp2 hybridized in both cases.
In the pyridine molecule, this places the electron pair in an sp2 hybrid orbital, and not involved in
the aromatic sextet needed for aromatic stability; the electron pair is thus available for

82

reacting with HCl, forming pyridinium chloride, while preserving aromatic stability.
By contrast, the electron pair in pyrrole must be placed in the p orbital, since all three sp2 orbitals
are used in sigma bonds with neighboring atoms. This allows the electron pair to contribute to
aromatic stability by becoming part of the aromatic sextet. Thus, the electron pair on nitrogen is
not available for reacting with HCl, because doing so would destroy the aromaticity of the
ring.
Topic: Aromaticity, Reactivity
Section: 14.9
Difficulty Level: Medium

193) Predict the product of the reaction of one equivalent of hydrochloric acid with the organic
compound shown:
H
N

1 equivalent HCl

Answer:
H
N

H
N

1 equivalent HCl

Topic: Aromaticity, Reactivity


Section: 14.9
Difficulty Level: Medium

194) Consider the nitrogen atom in the molecules of pyrrole and pyrrolidine. Bearing in mind
that pyrrole exhibits aromatic properties, compare the hybridization of nitrogen in both species,
explaining why it must be different, although at first glance, it may appear identical.
H
N

pyrrole

H
N

pyrrolidine

Answer:

83

sp2
NH

sp3
NH

In pyrrole, the conjugated unsaturated ring system forces the nitrogen to be trigonal planar, that
is sp2 hybridized, with the lone pair electrons in an unhybridized p-orbital. This allows for
overlap with the conjugate system accounting for the aromatic character. The nitrogen in
pyrrolidine, on the other hand, is closer to tetrahedral, and as a result sp3 hybridized, and the lone
pair electrons reside in an sp3 hybrid orbital.
Topic: Aromaticity, Reactivity
Section: 14.9
Difficulty Level: Medium

195) Briefly explain why the aromatic hydrocarbon shown possesses a significant dipole
moment. Use diagrams as needed to illustrate/clarify your answer.

Answer:

+
=

The stable, low energy resonance contributor shown creates an aromatic system in both rings.
This separation of charge creates the significant dipole observed.
Topic: Aromaticity
Section: 14.7
Difficulty Level: Hard

196) Briefly explain why the aromatic hydrocarbon shown possesses a significant dipole
moment. Use diagrams as needed to illustrate/clarify your answer.

84

Answer:

The stable, low energy resonance contributor shown creates an aromatic system in both rings.
This separation of charge creates the significant dipole observed.
Topic: Aromaticity
Section: 14.7 and 14.8
Difficulty Level: Hard

197) Briefly explain why the aromatic hydrocarbon azulene, C10H8, possesses a significant
dipole moment. Use diagrams as needed to illustrate/clarify your answer.
Answer: Azulene has the bicyclic structure shown below. Since the non-polar resonance
hybrid meets the Hckel rule for aromaticity, it accounts for the observed aromatic properties of
azulene. However, closer scrutiny suggests that a shift in electron density, in which the 7membered ring is electron deficient and the 5-membered ring is electron-rich would be
especially stable: each ring is now independently aromatic, an aromatic cycloheptatrienyl cation
fused with an aromatic cyclopentadienyl anion. Thus, the most stable pi-electron distribution
would suggest a polar structure for azulene, accounting for this substance having a significant
dipole moment.

non-polar

polar

Topic: Aromaticity
Section: 14.7
Difficulty Level: Hard

198) Although all bond lengths in benzene are identical, that is not always true for all aromatic
compounds. In naphthalene, for instance, the C1-C2 bond is shorter than the C2-C3 bond.
Explain, using resonance theory.
85

Answer: The major resonance structures for naphthalene are drawn below. The observed bond
lengths reflect the contribution of each structure to the overall resonance hybrid:
The C1-C2 bond: two double bonds (I and II), and one single bond (III)
The C2-C3 bond: one double bond (III), and two single bonds (I and II)
Overall: C1-C2 bond is more double-bond-like, thus shorter.

shorter
1

II

III

longer

IV

Topic: Resonance, Bond Lengths, Bond Order


Section: 14.7
Difficulty Level: Medium

Question type: Molecular Drawing

199) Draw all significant resonance structures for pyridine, C6H5N

Answer:

..N

N
..

Topic: Resonance
Section: 1.8 and 14.9
Difficulty Level: Hard

200) Draw all significant resonance structures for azulene, C10H8

Answer:
Topic: Resonance
Section: 1.8 and 14.8
Difficulty Level: Hard

201) Draw all significant resonance structures for the cyclopentadienyl anion.
Answer:
86

202) Consider the oxygen atom in the molecules of furan and tetrahydrofuran. Bearing in mind
that furan exhibits aromatic properties, compare the hybridization of oxygen in both species,
explaining why it must be different, although at first glance, it may appear identical.
..
..
O.
O..
.

Furan

THF

Answer:
.. p

3
.. sp

2
O .. sp

Furan: sp2 hybridized


one electron pair in p orbital:
part of aromatic pi sextet

.. sp3

Tetrahydrofuran: sp3 hybridized


both electron pairs
in sp3 orbitals

Oxygen has 2 lone electron pairs in both species and, at first glance, it might appear that the
hybridization patterns are identical. In THF, the oxygen atom is sp3 hybridized and both pairs
can be placed in sp3 hybrid orbitals. In furan, there are two possibilities that must be considered:
i) the oxygen may be sp3 hybridized, with both electron pairs sp3 hybrid orbitals, as in THF, or,
ii) oxygen may be sp2 hybridized, with one electron pair in an sp3 hybrid orbital, the other in a p
orbital. In the latter case, the electrons in the p orbital can then become part of an aromatic
sextet, allowing the molecule to gain aromatic stability. Since furan is known to exhibit markedly
aromatic properties, the oxygen must be sp2 hybridized.
Topic: Resonance
Section: 1.8 and 14.8
Difficulty Level: Hard

203) The compound illustrated below is found to have the following signals in its broadband
decoupled C-13 spectra:
190.77, 140.91, 134.82, 130.89 and 129.45
Using resonance theory, assign the C-13 peaks to the appropriate carbons.

87

CHO

Cl

Answer:
190.77 CHO
134.82
130.89
129.45
140.91
Cl

Topic: Spectroscopy and Resonance Theory


Section: 14.11
Difficulty Level: Medium

88