Chapter 14 Test Bank Chem 200 PDF

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
Br
NH 2
a) m-bromoaniline
b) o-bromoaniline
c) p-bromoaniline
d) o-bromobenzyl amine
e) 3-bromophenyl amine
Answer: A

Section: 14.2
1
OCH3
O2N
a) o-nitroanisole
b) m-nitroanisole
c) p-nitroanisole
d) p-nitrotoluene
e) 4-nitrophenol
Answer: C

Section: 14.2
Br
CH 3
a) 3-bromobenzene
b) 4-bromobenzene
c) m-bromobenzene
d) o-bromotoluene
e) Bromomethylbenzene
Answer: D

Section: 14.2
5) Which of the following is NOT 2-bromo-5-nitrobenzoic acid?
2
Br Br O
NO2
HO OH HO
NO2 O2N
O O Br
I II III
HO O
Br
Br
HO
O NO2 NO2
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: D

Section: 14.2
6) Toluene is the name commonly assigned to:
a) Hydroxybenzene
b) Aminobenzene
c) Methylbenzene
d) Ethylbenzene
e) Methoxybenzene
Answer: C

Section: 14.2
7) Anisole is the name commonly assigned to:
a) Hydroxybenzene
b) Aminobenzene
c) Methylbenzene
d) Ethylbenzene
3
e) Methoxybenzene
Answer: E

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

Section: 14.2
9) Aniline is the name commonly assigned to:
a) Hydroxybenzene
b) Aminobenzene
c) Methylbenzene
d) Ethylbenzene
e) Methoxybenzene
Answer: B

Section: 14.2
10) Xylene is the name commonly assigned to:
a) Hydroxybenzene
b) Aminobenzene
c) Dimethylbenzene
d) Ethylbenzene
e) Methoxybenzene
4
Answer: C

Section: 14.2
11) Cumene is the name commonly assigned to:
a) Hydroxybenzene
b) Aminobenzene
c) Ethylbenzene
d) Isopropylbenzene
e) Isobutylbenzene
Answer: D

Section: 14.2
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

Section: 14.2
13) 2-Bromo-4-nitroaniline is:
5
Br Br
NH2
Br NO2
NO2
NH2 NO2 H2N
I II III
OCH3 Br
Br H3CO
NO2 NO2
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 14.2
Br Br
NH2
Br NO2
NO2
NH2 NO2 H2N
I II III
OCH3 Br
Br H3CO
NO2 NO2
IV V
a) I
b) II
c) III
d) IV
e) V
6
Answer: B

Section: 14.2
Br Br
NH2
Br NO2
NO2
NH2 NO2 H2N
I II III
OCH3 Br
Br H3CO
NO2 NO2
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 14.2
16) m-chlorobenzenesulfonic acid is:
7
Cl
Cl SO 3HCl
SO3 H
Cl SO 3H HOOC
I II III
HO3 S HOOC
Cl Cl
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: D

Section: 14.2
Br Br
NH2
Br NO2
NO2
NH2 NO2 H2N
I II III
OCH3 Br
Br H3CO
NO2 NO2
IV V
a) I
b) II
c) III
d) IV
e) V
8
Answer: A

Section: 14.2
18) 4-Amino-2-chlorophenol is:

Cl Cl
OH O
Cl O
NH2 NO2 H2N
I II III
OH OH
Cl Cl
NH2 NO2
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: D

Section: 14.2
19) 3-bromo-4-nitroacetophenone is:

Br O O O
Br Br
H H
O2 N O 2N O 2N
I II III
O O
O 2N O 2N
H
Br
Br
IV V
9
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 14.2
20) 4-Chloro-3-nitro-benzaldehyde is:

Cl Cl
OH O
Cl O
NH2 NO2 H2N
I II III
OH OH
Cl Cl
NH2 NO2
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 14.2
21) 4-Amino-2-chlorobenzaldehyde is:
10
Cl Cl
OH O
Cl O
NH2 NO2 H2N
I II III
OH OH
Cl Cl
NH2 NO2
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

Section: 14.2
22) 4-Amino-2-bromoanisole is:

Br Br
OCH3 Br
H3CO O
NH2 NO2 H2N
I II III
OCH3 OCH3
Br Br
NH2 NO2
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: D

11
Section: 14.2
23) 4-Bromomethyl-2-nitroanisole is:
Br Br
OCH3 Br
H3CO O
NH2 NO2 H2N
I II III
OCH3 OCH3
Br Br
NH2 NO2
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 14.2
24) 3-chloro-4-nitrobenzoic acid is:

Cl O O O
Cl Cl
H OH
O2 N O 2N O 2N
I II III
O O
O 2N O 2N
H
Cl
Cl
IV V
a) I
12
b) II
c) III
d) IV
e) V
Answer: B

Section: 14.2
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

Section: 14.2
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

Section: 14.2 and 14.3
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.
Answer: C

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

Section: 14.3
29) Which of these is the single best representation for naphthalene?
I II III
IV V
a) I
b) II
c) III
d) IV
e) V
14
Answer: A

Section: 14.8
30) How many dichloronaphthalenes are possible?
a) 7
b) 8
c) 9
d) 10
e) 12
Answer: D

Difficulty Level: Hard
31) How many monochloronaphthalenes are possible?
a) 2
b) 3
c) 4
d) 5
e) 6
Answer: A

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

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

34) Which dibromobenzene can, in theory, yield three mononitro derivatives?
a) o-Dibromobenzene
b) m-Dibromobenzene
c) p-Dibromobenzene
d) All of these choices.
Answer: B

Section: 14.3
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.
Answer: C

36) How many different dibromophenols are possible?
a) 8
b) 7
c) 6
d) 5
e) 4
Answer: C

37) How many different dichloronitrobenzenes are possible?
a) 8
b) 7
c) 6
d) 5
e) 4
Answer: C

38) How many different dihydroxybromobenzenes are possible?
17
a) 8
b) 7
c) 6
d) 5
e) 4
Answer: C

39) Which is the only one of these reagents which will react with benzene under the specified
conditions?
a) Cl2, FeCl3, heat

b) H2, 25°C
c) Br2/CCl4, 25°C, dark
d) KMnO4/H2O, 25°C
e) H3O+, heat
Answer: A
Topic: Chemical Tests and Reactions

Section: 14.3
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
Answer: B

Section: 14.3
18
between benzene and cyclohexene?
a) NaOH in H2O
b) Br2 in CCl4
c) AgNO3 in C2H5OH
d) NaHSO3 in H2O
Answer: B

Section: 14.3
between ethylbenzene and vinylcyclohexane?
a) H2CrO4
b) LAH
c) NaBH4, H2O
d) KMnO4, OH−, H2O
e) Two of these choices.
Answer: D

Section: 14.3
between ethylbenzene and vinylcyclohexane?
a) H2CrO4
b) LAH
c) NaBH4, H2O
d) O3/Zn, H+
Answer: D

Section: 14.3
19
between naphthalene and 2,4,6-decatriene?
a) NaOH in H2O
b) KMnO4, OH−, H2O
c) NaBH4, H2O
d) H2CrO4
Answer: B

Section: 14.3
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
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.
3 4 5 6
2 7
1 8
10 9
a) 1, 2
b) 1, 4
c) 3, 4
d) 7, 8
20
e) 9, 10
Answer: E

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

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

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
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

Section: 14.6
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

Section: 14.6
52) Which cyclization(s) should occur with a decrease in pi-electron energy?
22
I CH2 CH CH CH2 + H2
II CH2 CH CH2 + H2
III CH2 CH CH2 + H2
IV CH2 CH CH2 + H2
a) I
b) II
c) III
d) IV
Answer: B

Section: 14.7
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
Answer: B

Section: 14.7
54) Which cyclization(s) should occur with an increase in pi-electron energy?
a) I
b) II
c) III
d) IV
Answer: D

Section: 14.7
55) Which cyclization(s) should occur with an increase in pi-electron energy?
24
a) I
b) II
c) III
d) IV
Answer: A

Section: 14.7
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

Section: 14.7
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

58) In the molecular orbital model of benzene, how many π-bonding molecular orbitals are
there?
a) 6
b) 5
c) 4
d) 3
e) 2
Answer: D

59) In the molecular orbital model of benzene, how many π-antibonding molecular orbitals are
there?
a) 6
b) 5
c) 4
d) 3
e) 2
Answer: D

26
60) In the molecular orbital model of benzene, how many pairs of degenerate π-molecular
orbitals are there?
a) 6
b) 5
c) 4
d) 3
e) 2
Answer: E

61) In the molecular orbital model of benzene, how many pairs of degenerate π-bonding
molecular orbitals are there?
a) 1
b) 2
c) 3
d) 4
e) 5
Answer: A

62) In the molecular orbital model of benzene, how many pairs of degenerate π-antibonding
a) 1
b) 2
c) 3
d) 4
e) 5
Answer: A

27
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

64) In the molecular orbital model of the cyclopentadienyl cation, how many π-bonding
a) 6
b) 5
c) 4
d) 3
e) 2
Answer: D

65) In the molecular orbital model of the cyclopentadienyl cation, how many π-antibonding
a) 6
b) 5
c) 4
d) 3
e) 2
Answer: E
28
66) In the molecular orbital model of the cyclopentadienyl cation, how many pairs of degenerate
π-molecular orbitals are there?
a) 6
b) 5
c) 4
d) 3
e) 2
Answer: E

π-bonding molecular orbitals are there?
a) 1
b) 2
c) 3
d) 4
e) 5
Answer: A

π-antibonding molecular orbitals are there?
a) 1
b) 2
c) 3
d) 4
e) 5
29
Answer: A

69) In the molecular orbital model of the cyclopentadienyl cation, how many non-bonding
a) 1
b) 2
c) 3
d) 4
e) 0
Answer: E

70) In the molecular orbital model of cyclobutadiene, how many π-bonding molecular orbitals
are there?
a) 1
b) 2
c) 3
d) 4
e) 5
Answer: A

71) In the molecular orbital model of cyclobutadiene, how many π-antibonding molecular
orbitals are there?
a) 5
b) 4
c) 3
d) 2
30
e) 1
Answer: E

72) In the molecular orbital model of cyclobutadiene, how many pairs of degenerate π-molecular
orbitals are there?
a) 0
b) 1
c) 2
d) 3
e) 4
Answer: A

73) In the molecular orbital model of the cyclobutadiene, how many pairs of degenerate π-
bonding molecular orbitals are there?
a) 1
b) 2
c) 3
d) 4
e) 0
Answer: E

74) In the molecular orbital model of cyclobutadiene, how many pairs of degenerate π-
antibonding molecular orbitals are there?
a) 1
b) 2
31
c) 3
d) 4
e) 0
Answer: E

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

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

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

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

79) In the molecular orbital model of cycloheptadienyl cation, how many pi-electrons are in
a) 6
b) 5
c) 4
d) 3
e) 2
Answer: A

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

81) In the molecular orbital model of 1,3-cyclobutadiene, how many electrons are in non-
a) 6
b) 5
c) 4
d) 3
e) 2
Answer: E

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.
Answer: D

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

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

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

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.
Answer: D

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

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

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
90) Which of the following statements regarding the cycloheptatrienyl radical is correct?
a) It is aromatic.
c) It obeys Hückel's rule.
Answer: B

Section: 14.7
91) Which of the following statements regarding the cyclopentadienyl cation is correct?
a) It is aromatic.
c) It obeys Hückel’s rule.
Answer: B

Section: 14.7
37
92) Which of the following statements regarding the cyclopropenyl anion is correct?
a) It is aromatic.
Answer: B

Section: 14.7
93) Which of the following statements regarding the cyclopropenyl radical is correct?
a) It is aromatic.
Answer: B

Section: 14.7
94) Which of the following statements regarding the cycloheptatrienyl anion is correct?
a) It is aromatic.
Answer: B

Section: 14.7
38
95) Of Hückel’s 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) π electrons.
d) The Hückel number of electrons must be completely delocalized.
e) None. All of these rules must apply in every case.
Answer: B
Topic: Aromaticity, Hückel’s Rule

Section: 14.7
96) Which of the following would you expect to be aromatic?
H
H
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: E
Topic: Aromaticity, Huckel’s Rule

Section: 14.7
H
H 2+
I II III IV V
a) I
b) II
39
c) III
d) IV
e) V
Answer: E

Section: 14.7
H H
I II III IV
a) I
b) II
c) III
d) IV
Answer: B

Section: 14.7
99) Which of the following would you expect to show aromatic character?
a) I
b) II
c) III
d) IV
40
Answer: B

Section: 14.7
I II III IV
a) I
b) II
c) III
d) IV
Answer: A

Section: 14.7
a) I
b) II
c) III
d) IV
Answer: A

Section: 14.7
41
a) I
b) II
c) III
d) IV
Answer: A

Section: 14.7
103) Which of the following structures would be aromatic?
a) I
b) II
c) III
d) IV
e) V
Answer: B

Section: 14.7
42
H H
I II III IV
a) I
b) II
c) III
d) IV
Answer: C

Section: 14.7
a) I
b) II
c) III
d) IV
Answer: C

Section: 14.7
106) On the basis of molecular orbital theory and Hückel’s rule, which molecules and/or ions
should be aromatic?
43
H H H
H
I II III IV V
N
H H H 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

Section: 14.7
should be antiaromatic?
H H H
H
I II III IV V
N
H H H 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

Section: 14.7
should be non-aromatic?
H H H
H
I II III IV V
N
H H H 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

Section: 14.7
109) On the basis of molecular orbital theory and Hückel’s rule, which of these compounds
should be aromatic?
45
H H
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: E

Section: 14.7
should be aromatic?
a) I
b) II
c) III
d) IV
e) V
Answer: E

Section: 14.7
should be aromatic?
46
a) I
b) II
c) III
d) IV
e) V
Answer: E

Section: 14.7
112) Which of these is an aromatic molecule?
N O B
N S
CH3 CH3
H O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 14.7
47
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 14.7
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 14.7
48
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 14.7
116) Which of these is not an aromatic molecule?
a) I
b) II
c) III
d) IV
e) V
Answer: D

Section: 14.7
49
117) Of the following C-10 compounds, which is expected to possess the greatest resonance
(delocalization) energy?
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

118) Which of the following would you expect to be antiaromatic?
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

119) Which of these would you expect to have significant resonance stabilization energy?
50
N
H N
I II III
a) I
b) II
c) III
Answer: D

I II III
a) I
b) II
c) III
Answer: D

51
a) I
b) II
c) III
Answer: D

I II III
a) I
b) II
c) III
Answer: D

52
CH
I II III
a) I
b) II
c) III
Answer: D

124) Which compound would you NOT expect to be aromatic?
S N O B
N
H R
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: E

53
a) I
b) II
c) III
d) IV
e) V
Answer: E

S N O
N
H
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: E

127) Which of these species is aromatic?
54
O O
N O N O S
H H
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B

128) In which case is the indicated unshared pair of electrons NOT a contributor to the π
aromatic system?
N O
N
H H
I II III IV
a) I
b) II
c) III
d) IV
Answer: B

129) In which case is the indicated unshared pair of electrons NOT a contributor to the π
aromatic system?
55
S
O
N
H
I II III IV
a) I
b) II
c) III
d) IV
Answer: B

O O
N O N O S
H H
IV V
I II III
a) I
b) II
c) III
d) IV
e) V
Answer: B

56
O
O O
N N O S
H H
IV V
I II III
a) I
b) II
c) III
d) IV
e) V
Answer: B


O
O O
N S N O S
H H
IV V
I II III
a) I
b) II
c) III
d) IV
e) V
Answer: B

57
O O
N N O N O S
H H H
IV V
I II III
a) I
b) II
c) III
d) IV
e) V
Answer: B


NH2
O O
N
N S N O N O
H H H
III IV V
I II
a) I
b) II
c) III
d) IV
e) V
Answer: E

58
O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C

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

59
O
I II IV V
III
a) I
b) II
c) III
d) IV
e) V
Answer: C

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

60
O
N O B
N S
CH3
CH3 H O
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: A

Section: 14.7
should be aromatic?
H H
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: E

Section: 14.7
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
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

Section: 14.7
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

Section: 14.7
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

Section: 14.7
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
a) 1
b) 2
c) 3
d) 4
63
e) 5
Answer: C
Topic: Spectroscopy
Section: 14.11
a) 1
b) 2
c) 3
d) 4
e) 5
Answer: E
Topic: Spectroscopy
Section: 14.11
a) 2
b) 3
c) 4
d) 5
e) 6
Answer: E
Topic: Spectroscopy
64
Section: 14.11
CHO
Cl
a) 2
b) 3
c) 4
d) 5
e) 6
Answer: D
Topic: Spectroscopy
Section: 14.11
a) 3
b) 4
c) 5
d) 6
e) 7
Answer: E
Topic: Spectroscopy
Section: 14.11
65
a) 2
b) 3
c) 4
d) 5
e) 6
Answer: B
Topic: Spectroscopy
Section: 14.11
a) 4
b) 5
c) 6
d) 7
e) 8
Answer: E
Topic: Spectroscopy
Section: 14.11
66
a) 4
b) 5
c) 6
d) 7
e) 8
Answer: A
Topic: Spectroscopy
Section: 14.11
a) 4
b) 5
c) 6
d) 7
e) 8
Answer: E
Topic: Spectroscopy
Section: 14.11
a) 4
67
b) 5
c) 6
d) 7
e) 8
Answer: B
Topic: Spectroscopy
Section: 14.11
a) 5
b) 6
c) 7
d) 8
e) 9
Answer: E
Topic: Spectroscopy
Section: 14.11
a) 4
b) 5
c) 6
d) 7
e) 8
68
Answer: E
Topic: Spectroscopy
Section: 14.11
158) Which of these compounds absorbs at the longest wavelength in the UV-visible region?
I II III IV V
a) I
b) II
c) III
d) IV
e) V
Answer: B
Topic: Spectroscopy
Section: 14.11
159) A compound has the formula C8H9Br. Its 1H NMR spectrum consists of:
doublet, δ 2.0
quartet, δ 5.15
multiplet, δ 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
I II III
Br
Br
IV V
a) I
b) II
69
c) III
d) IV
e) V
Answer: D
Topic: Spectroscopy
Section: 14.11
160) Which of the following substances, formula C8H9Br, might exhibit the following 1H NMR
spectrum?
triplet, δ 2.8
triplet, δ 4.65
multiplet, δ 7.2
Br Br
Br
I II III
Br
Br
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C
Topic: Spectroscopy
Section: 14.11
spectrum?
triplet, δ 1.2
quartet, δ 2.45
multiplet, δ 7.4
70
Br Br
Br
I II III
Br
Br
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: A
Topic: Spectroscopy
Section: 14.11
spectrum?
singlet, δ 2.45
singlet, δ 2.5
multiplet, δ 7.35
Br Br
Br
I II III
Br
Br
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: E
71
Topic: Spectroscopy
Section: 14.11
163) Which of the following substances, C8H9Cl, would exhibit five signals in its 13C NMR
spectrum?
Cl
Cl Cl
I II III
Cl
Cl
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: C
Topic: Spectroscopy
Section: 14.11
164) Which of the following substances, C9H10O, would exhibit seven signals in its 13C NMR
spectrum?
O
O
O
I II III
HO
O
IV V
a) I
b) II
72
c) III
d) IV
e) V
Answer: A
Topic: Spectroscopy
Section: 14.11
165) For which of the following substances, C9H10O, would the aromatic multiplet, in its 1H
NMR spectrum, consist of two doublets?
O
O
O
I II III
HO
O
IV V
a) I
b) II
c) III
d) IV
e) V
Answer: A
Topic: Spectroscopy
Section: 14.11
166) In the 1H NMR spectra of which of the following substances, C9H10O, would you expect to
see two singlets in the range of δ 2.0-2.5 ppm?
73
O
O
O
I II III
HO
O
IV V
a) I and III
b) I, II, and III
c) IV
d) V
e) All of these substances would exhibit two singlets δ 2.0-2.5 ppm in their 1H NMR spectra.
Answer: B
Topic: Spectroscopy
Section: 14.11
167) Which isomer of C7H7Cl exhibits strong IR absorbances at 690 and 750 cm1?
CH3 CH3 CH3 CH2Cl

Cl
Cl
Cl
I II III IV
a) I
b) II
c) III
d) IV
e) II and IV
Answer: E
Topic: Spectroscopy
Section: 14.11
168) Which reagent(s)/technique would serve to distinguish between azulene and

bicyclo[5.3.0]decane?
74
a) Br2, CCl4
c) NMR Spectroscopy
d) UV Spectroscopy
Answer: E
Topic: Chemical and Spectroscopic Analysis

Section: 13.9, 14.7 and 14.11
169) Which reagent(s)/technique would serve to distinguish between azulene and

bicyclo[5.3.0]decane?
a) Br2, CCl4
c) NMR Spectroscopy
d) NaBH4, H2O
Answer: C
Topic: Chemical and Spectroscopic Analysis

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
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

Section: 14.10
172) Cagelike molecules with the geometry of a truncated icosahedron are called ___.
Answer: fullerenes

Section: 14.8
173) Monocyclic compounds with alternating single and double bonds are called ___.
Answer: annulenes

Section: 14.7
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

Section: 14.5
175) Molecular orbitals of equal energy are referred to as ___ orbitals.
Answer: degenerate

Section: 14.6
76
176) When a benzene ring is used as a substituent, it is called a ___ group.
Answer: phenyl
Topic: Nomenclature
Section: 14.2
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
178) Draw the structure corresponding to the following name:

3-bromo 5-phenylaniline
NH2
Br
Answer:
Topic: Nomenclature
Section: 14.2
179) Draw the structure corresponding to the following name: 3-nitro-4-iodoanisole
O2N O
Answer: I
77
Topic: Nomenclature
Section: 14.2
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
181) Draw the structure corresponding to the following name: 2-hydroxy-4-(3-

methylcyclopentyl)benzoic acid
HO
HO2C
Answer:
Topic: Nomenclature
Section: 14.2
Question type: fill-in-the-blank
182) Hückel’s Rule requires ___ π electrons for an aromatic compound.
Answer: 4n+2
Topic: Hückel’s rule

Section: 14.7
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 Æ C6H12 ΔHo = -120 kJ/mol

C6H6 + 3H2 Æ C6H12 ΔHo = -208 kJ/mol
Answer: The resonance stabilization energy of benzene is the difference between the theoretical
and observed ΔHo values.
Hydrogenation of three double bonds should release 3 times the energy released when one
double bond is hydrogenated. Thus, the theoretical ΔHo 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
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
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
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

Section: 14.7
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 π-electrons, that is antiaromatic.
B:−
..
H
H H Aromatic
anion
80
H H
H
B:-

Section: 14.7
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
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
H H Aromatic
anion

Section: 14.7
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
H H
H
+ Ph3C+ + Ph3CH
Answer: This reaction readily proceeds because the product, cycloheptatrienyl cation, is aromatic
and much more stable than even the triphenyl substituted carbocation.

Section: 14.7
191) Pyrrole is not particularly basic, because the lone pair on the nitrogen is ___.
Answer: part of the aromatic system

Section: 14.9
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
2 H
sp
pyridinium chloride pyridinium chloride
.. p
H
N H + HCl X N + Cl−
H
pyrrole not aromatic

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 π 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.

Section: 14.9
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 H
N N
1 equivalent HCl
N N

Section: 14.9
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 H
N N
pyrrole pyrrolidine
Answer:
83
sp2 sp3
NH 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.

Section: 14.9
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
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
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 Hückel 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 7-
membered 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
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 1 1 1
2 2 2 2
longer
3 3 3 3
I II III IV
Topic: Resonance, Bond Lengths, Bond Order

Section: 14.7
Question type: Molecular Drawing
199) Draw all significant resonance structures for pyridine, C6H5N
Answer: ..N N
..
Topic: Resonance
200) Draw all significant resonance structures for azulene, C10H8
Answer:
Topic: Resonance
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
2 .. sp
O .. sp O
.. sp3
Furan: sp2 hybridized Tetrahydrofuran: sp3 hybridized

one electron pair in p orbital: both electron pairs
part of aromatic pi sextet 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
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 δ
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
88

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Course Title: Solomons 11e

Question type: Multiple choice

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

Topic: Nomenclature and Isomerism

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

Topic: Nomenclature and Isomerism

Topic: Nomenclature and Isomerism

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

Topic: Nomenclature and Isomerism

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

Topic: Nomenclature and Isomerism

6) Toluene is the name commonly assigned to:

Topic: Nomenclature and Isomerism

7) Anisole is the name commonly assigned to:

Topic: Nomenclature and Isomerism

8) Phenol is the name commonly assigned to:

Topic: Nomenclature and Isomerism

9) Aniline is the name commonly assigned to:

Topic: Nomenclature and Isomerism

10) Xylene is the name commonly assigned to:

Topic: Nomenclature and Isomerism

11) Cumene is the name commonly assigned to:

Topic: Nomenclature and Isomerism

Topic: Nomenclature and Isomerism

13) 2-Bromo-4-nitroaniline is:

Topic: Nomenclature and Isomerism

14) 2-Bromo-5-nitroaniline is:

Topic: Nomenclature and Isomerism

15) 2-Bromo-4-nitroaniline is:

Topic: Nomenclature and Isomerism

16) m-chlorobenzenesulfonic acid is:

Topic: Nomenclature and Isomerism

17) 4-Bromo-2-nitroaniline is:

Topic: Nomenclature and Isomerism

18) 4-Amino-2-chlorophenol is:

Topic: Nomenclature and Isomerism

19) 3-bromo-4-nitroacetophenone is:

Topic: Nomenclature and Isomerism

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

Topic: Nomenclature and Isomerism

21) 4-Amino-2-chlorobenzaldehyde is:

Topic: Nomenclature and Isomerism

22) 4-Amino-2-bromoanisole is:

Topic: Nomenclature and Isomerism

23) 4-Bromomethyl-2-nitroanisole is:

Topic: Nomenclature and Isomerism

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

Topic: Nomenclature and Isomerism

Topic: Nomenclature and Isomerism

26) Which dichlorobenzene might theoretically yield three mononitro products?

Topic: Nomenclature and Isomerism

27) Which dibromobenzene can yield only one mononitro derivative?

Topic: Nomenclature and Isomerism

Topic: Nomenclature and Isomerism

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

Topic: Nomenclature and Isomerism

30) How many dichloronaphthalenes are possible?

Topic: Nomenclature and Isomerism

31) How many monochloronaphthalenes are possible?

Topic: Nomenclature and Isomerism

32) The complete name for the following compound is:

Topic: Nomenclature and Isomerism