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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
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
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
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
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
e) Methoxybenzene
Answer: E
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium
Answer: C
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
a) I
b) II
c) III
d) IV
e) V
Answer: B
Topic: Aromaticity, Hckels Rule
Section: 14.7
Difficulty Level: Medium
42
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
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
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
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
47
a) I
b) II
c) III
d) IV
e) V
Answer: A
Topic: Aromaticity, Hckels Rule
Section: 14.7
Difficulty Level: Medium
a) I
b) II
c) III
d) IV
e) V
Answer: A
Topic: Aromaticity, Hckels Rule
Section: 14.7
Difficulty Level: Medium
a) I
b) II
c) III
d) IV
e) V
Answer: A
Topic: Aromaticity, Hckels Rule
Section: 14.7
Difficulty Level: Medium
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
Answer: O2N
Topic: Nomenclature
Section: 14.2
Difficulty Level: Medium
Br
Answer:
Topic: Nomenclature
Section: 14.2
Difficulty Level: Medium
Answer:
77
Topic: Nomenclature
Section: 14.2
Difficulty Level: Medium
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
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
..
Aromatic
anion
80
B:-
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
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
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.
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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.
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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
Answer:
..N
N
..
Topic: Resonance
Section: 1.8 and 14.9
Difficulty Level: Hard
Answer:
Topic: Resonance
Section: 1.8 and 14.8
Difficulty Level: Hard
201) Draw all significant resonance structures for the cyclopentadienyl anion.
Answer:
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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
.. sp3
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.
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CHO
Cl
Answer:
190.77 CHO
134.82
130.89
129.45
140.91
Cl
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