Solomons Ch.14 Aromatic Compounds Test Bank Answers - Organic Chemistry 13e | Test Bank by Solomons by Graham Solomons. DOCX document preview.
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:
a) m-chlorophenol
b) o-chlorophenol
c) p-chlorophenol
d) o-chlorobenzyl alcohol
e) 2-chlorophenyl alcohol
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Easy
2) The correct name for the compound shown below is:
a) m-bromoaniline
b) o-bromoaniline
c) p-bromoaniline
d) o-bromobenzyl amine
e) 3-bromophenyl amine
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Easy
3) The correct name for the compound shown below is:
a) o-nitroanisole
b) m-nitroanisole
c) p-nitroanisole
d) p-nitrotoluene
e) 4-nitrophenol
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Easy
4) The correct name for the compound shown below is:
a) 3-bromobenzene
b) 4-bromobenzene
c) m-bromobenzene
d) o-bromotoluene
e) bromomethylbenzene
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Easy
5) Which of the following is NOT 2-bromo-5-nitrobenzoic acid?
a) I
b) II
c) III
d) IV
e) V
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
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
e) Methoxybenzene
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
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
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
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
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium
12) The correct name for the compound shown below is:
a) 3,4-Dibromoaniline
b) 2,4-Dibromoaniline
c) 2,5-Dibromoaniline
d) 3,6-Dibromoaniline
e) 2,6-Dibromoaniline
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium
13) 2-Bromo-4-nitroaniline is:
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium
14) 2-Bromo-5-nitroaniline is:
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium
15) 2-Bromo-4-nitroaniline is:
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium
16) m-Chlorobenzenesulfonic acid is:
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium
17) 4-Bromo-2-nitroaniline is:
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium
18) 4-Amino-2-chlorophenol is:
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium
19) 3-Bromo-4-nitroacetophenone is:
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium
20) 4-Chloro-3-nitro-benzaldehyde is:
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium
21) 4-Amino-2-chlorobenzaldehyde is:
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium
22) 4-Amino-2-bromoanisole is:
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium
23) 4-Bromomethyl-2-nitroanisole is:
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium
24) 3-Chloro-4-nitrobenzoic acid is:
a) I
b) II
c) III
d) IV
e) V
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.
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.
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
c) p-Dibromobenzene
d) More than one of these choices.
e) None of these choices.
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?
a) 1
b) 2
c) 3
d) 4
e) 5
Topic: Nomenclature and Isomerism
Section: 14.3
Difficulty Level: Medium
29) Which of these is the single best representation for naphthalene?
a) I
b) II
c) III
d) IV
e) V
Topic: Nomenclature and Isomerism
Section: 14.11
Difficulty Level: Medium
30) How many dichloronaphthalenes are possible?
a) 7
b) 8
c) 9
d) 10
e) 12
Topic: Nomenclature and Isomerism
Section: 14,11
Difficulty Level: Hard
31) How many monochloronaphthalenes are possible?
a) 2
b) 3
c) 4
d) 5
e) 6
Topic: Nomenclature and Isomerism
Section: 14.11
Difficulty Level: Hard
32) The complete name for the following compound is:
a) sec-Hexylbenzene
b) 2-Phenylhexane
c) (R)-2-Phenylhexane
d) (S)-2-Phenylhexane
e) Butylmethylphenylmethane
Topic: Nomenclature and Isomerism
Section: 5.7 and 14.2
Difficulty Level: Hard
33) The complete name for the following compound is:
a) sec-Hexylbenzene
b) 2-Phenylhexane
c) (R)-2-Phenylhexane
d) (S)-2-Phenylhexane
e) Butylmethylphenylmethane
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.
Topic: Nomenclature and Isomerism
Section: 14.3
Difficulty Level: Hard
35) Which dihydroxybenzene can yield only one mononitro derivative?
a) o-Dihydroxybenzene
b) m-Dihydroxybenzene
c) p-Dihydroxybenzene
d) More than one of these choices.
e) None of these choices.
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
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
Topic: Nomenclature and Isomerism
Section: 14.2 and 14.3
Difficulty Level: Hard
38) How many different dihydroxybromobenzenes are possible?
a) 8
b) 7
c) 6
d) 5
e) 4
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
b) H2, 25 °C
c) Br2/CCl4, 25 °C, dark
d) KMnO4/H2O, 25 °C
e) H3O+, heat
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
c) AgNO3 in C2H5OH
d) NaHSO3 in H2O
e) None of these choices.
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 between benzene and cyclohexene?
a) NaOH in H2O
b) Br2
c) AgNO3 in C2H5OH
d) NaHSO3 in H2O
e) None of these choices.
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 naphthalene and 2,4,6-decatriene?
a) NaOH in H2O
b) KMnO4, OH–, H2O
c) NaBH4, H2O
d) H2CrO4
e) None of these choices.
Topic: Chemical Tests and Reactions
Section: 14.3
Difficulty Level: Medium
43) 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.
Topic: Explanations and Predictions
Section: 14.5
Difficulty Level: Medium
44) 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.
a) 1, 2
b) 1, 4
c) 3, 4
d) 7, 8
e) 9, 10
Topic: Explanations and Predictions
Section: 14.3 and 14.5
Difficulty Level: Medium
45) 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.
Topic: Explanations and Predictions
Section: 14.5 and 14.7
Difficulty Level: Medium
46) 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.
Topic: Explanations and Predictions
Section: 14.5 and 14.7
Difficulty Level: Medium
47) 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
d) 4
e) 5
Topic: Molecular Orbital Theory
Section: 14.6
Difficulty Level: Medium
48) 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
Topic: Molecular Orbital Theory
Section: 14.6
Difficulty Level: Medium
49) 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
Topic: Molecular Orbital Theory
Section: 14.6
Difficulty Level: Medium
50) Which cyclization(s) should occur with a decrease in pi-electron energy?
a) I
b) II
c) III
d) IV
e) All of these choices.
Topic: Molecular Orbital Theory
Section: 14.7
Difficulty Level: Medium
51) Which cyclization(s) should occur with a decrease in pi-electron energy?
a) I
b) II
c) III
d) IV
e) All of these choices.
Topic: Molecular Orbital Theory
Section: 14.7
Difficulty Level: Medium
52) 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.
Topic: Molecular Orbital Theory
Section: 14.7
Difficulty Level: Medium
53) 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.
Topic: Molecular Orbital Theory
Section: 14.7
Difficulty Level: Medium
54) 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
Topic: Molecular Orbital Theory
Section: 14.7
Difficulty Level: Medium
55) In the molecular orbital model of benzene, the six p orbitals combine to form how many molecular orbitals?
a) 6
b) 5
c) 4
d) 3
e) 2
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
56) 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
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
57) 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
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
58) 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
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
59) 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
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
60) In the molecular orbital model of benzene, how many pairs of degenerate π-antibonding molecular orbitals are there?
a) 1
b) 2
c) 3
d) 4
e) 5
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
61) 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
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
62) In the molecular orbital model of the cyclopentadienyl cation, how many π-bonding molecular orbitals are there?
a) 6
b) 5
c) 4
d) 3
e) 2
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
63) In the molecular orbital model of the cyclopentadienyl cation, how many π-antibonding molecular orbitals are there?
a) 6
b) 5
c) 4
d) 3
e) 2
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 pairs of degenerate π-molecular orbitals are there?
a) 6
b) 5
c) 4
d) 3
e) 2
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 pairs of degenerate π-bonding molecular orbitals are there?
a) 1
b) 2
c) 3
d) 4
e) 5
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 π-antibonding molecular orbitals are there?
a) 1
b) 2
c) 3
d) 4
e) 5
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 non-bonding molecular orbitals are there?
a) 1
b) 2
c) 3
d) 4
e) 0
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
68) 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
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
69) In the molecular orbital model of cyclobutadiene, how many π-antibonding molecular orbitals are there?
a) 5
b) 4
c) 3
d) 2
e) 1
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
70) 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
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
71) 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
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 π-antibonding molecular orbitals are there?
a) 1
b) 2
c) 3
d) 4
e) 0
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
73) 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
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
74) 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
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
75) In the molecular orbital model of cyclopentadienyl anion, how many pi electrons are delocalized about the ring?
a) 2
b) 3
c) 4
d) 5
e) 6
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
76) 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
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
77) In the molecular orbital model of cycloheptatrienyl cation, how many pi electrons are in bonding molecular orbitals?
a) 6
b) 5
c) 4
d) 3
e) 2
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
78) In the molecular orbital model of cycloheptatrienyl cation, how many pi electrons are delocalized about the ring?
a) 6
b) 5
c) 4
d) 3
e) 2
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
79) In the molecular orbital model of 1,3-cyclobutadiene, how many electrons are in non-bonding molecular orbitals?
a) 6
b) 5
c) 4
d) 3
e) 2
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
80) 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.
Topic: Molecular Orbital Theory
Section: 14.6 and 14.7
Difficulty Level: Medium
81) 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.
Topic: Bonding and Resonance
Section: 14.4 and 14.6
Difficulty Level: Easy
82) 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.
Topic: Bonding and Resonance
Section: 14.4 and 14.6
Difficulty Level: Easy
83) 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.
Topic: Bonding and Resonance
Section: 14.4 and 14.6
Difficulty Level: Easy
84) We now know that the two Kekulé 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.
Topic: Bonding and Resonance
Section: 14.4 and 14.6
Difficulty Level: Easy
85) 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
Topic: Nomenclature, Bonding and Resonance
Section: 14.4 and 14.6
Difficulty Level: Medium
86) 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
Topic: Nomenclature, Bonding and Resonance
Section: 14.4 and 14.6
Difficulty Level: Hard
87) Which of the following statements regarding the cyclopentadienyl radical is correct?
a) It is aromatic.
b) It is not aromatic.
c) It obeys Hückel's rule.
d) It undergoes reactions characteristic of benzene.
e) It has a closed shell of 6 pi electrons.
Topic: Aromatic/ Antiaromatic/ Nonaromatic
Section: 14.7
Difficulty Level: Medium
88) Which of the following statements regarding the cycloheptatrienyl radical is correct?
a) It is aromatic.
b) It is not aromatic.
c) It obeys Hückel's rule.
d) It undergoes reactions characteristic of benzene.
e) It has a closed shell of 6 pi electrons.
Topic: Aromatic/ Antiaromatic/ Nonaromatic
Section: 14.7
Difficulty Level: Medium
89) Which of the following statements regarding the cyclopentadienyl cation is correct?
a) It is aromatic.
b) It is not aromatic.
c) It obeys Hückel’s rule.
d) It undergoes reactions characteristic of benzene.
e) It has a closed shell of 6 pi electrons.
Topic: Aromatic/ Antiaromatic/ Nonaromatic
Section: 14.7
Difficulty Level: Medium
90) Which of the following statements regarding the cyclopropenyl anion is correct?
a) It is aromatic.
b) It is not aromatic.
c) It obeys Hückel’s rule.
d) It undergoes reactions characteristic of benzene.
e) It has a closed shell of 6 pi electrons.
Topic: Aromatic/ Antiaromatic/ Nonaromatic
Section: 14.7
Difficulty Level: Medium
91) Which of the following statements regarding the cyclopropenyl radical is correct?
a) It is aromatic.
b) It is not aromatic.
c) It obeys Hückel’s rule.
d) It undergoes reactions characteristic of benzene.
e) It has a closed shell of 6 pi electrons.
Topic: Aromatic/ Antiaromatic/ Nonaromatic
Section: 14.7
Difficulty Level: Medium
92) Which of the following statements regarding the cycloheptatrienyl anion is correct?
a) It is aromatic.
b) It is antiaromatic.
c) It obeys Hückel’s rule.
d) It undergoes reactions characteristic of benzene.
e) It has a closed shell of 6 pi electrons.
Topic: Aromatic/ Antiaromatic/ Nonaromatic
Section: 14.7
Difficulty Level: Medium
93) 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) electrons.
d) The Hückel number of electrons must be completely delocalized.
e) None. All of these rules must apply in every case.
Topic: Aromaticity, Hückel’s Rule
Section: 14.7
Difficulty Level: Easy
94) Which of the following would you expect to be aromatic?
a) I
b) II
c) III
d) IV
e) V
Topic: Aromaticity, Huckel’s Rule
Section: 14.7
Difficulty Level: Medium
95) Which of the following would you expect to be aromatic?
a) I
b) II
c) III
d) IV
e) V
Topic: Aromaticity, Hückel’s Rule
Section: 14.7
Difficulty Level: Medium
96) Which of the following would you expect to be aromatic?
a) I
b) II
c) III
d) IV
e) None of these choices.
Topic: Aromaticity, Hückel’s Rule
Section: 14.7
Difficulty Level: Medium
97) Which of the following would you expect to be aromatic?
a) I
b) II
c) III
d) IV
e) All of these choices.
Topic: Aromaticity, Hückel’s Rule
Section: 14.7
Difficulty Level: Medium
98) Which of the following would you expect to be aromatic?
a) I
b) II
c) III
d) IV
e) All of these choices.
Topic: Aromaticity, Hückel’s Rule
Section: 14.7
Difficulty Level: Medium
99) Which of the following structures would be aromatic?
a) I
b) II
c) III
d) IV
e) V
Topic: Aromaticity, Hückel’s Rule
Section: 14.7
Difficulty Level: Medium
100) Which of the following would you expect to be aromatic?
a) I
b) II
c) III
d) IV
e) None of these choices.
Topic: Aromaticity, Hückel’s 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) None of these choices.
Topic: Aromaticity, Hückel’s Rule
Section: 14.7
Difficulty Level: Medium
102) On the basis of molecular orbital theory and Hückel’s rule, which molecules and/or ions should be aromatic?
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
Topic: Aromaticity, Hückel’s Rule
Section: 14.7
Difficulty Level: Medium
103) On the basis of molecular orbital theory and Hückel’s rule, which molecules and/or ions should be antiaromatic?
a) I and V
b) I, II and V
c) III and VIII
d) IV, VII and IX
e) IV, VI, VII and IX
Topic: Aromaticity, Hückel’s Rule
Section: 14.7
Difficulty Level: Medium
104) On the basis of molecular orbital theory and Hückel’s rule, which molecules and/or ions should be non-aromatic?
a) I and V
b) I and II
c) III and VIII
d) IV, VII and IX
e) IV, VI, VII and IX
Topic: Aromaticity, Hückel’s Rule
Section: 14.7
Difficulty Level: Medium
105) On the basis of molecular orbital theory and Hückel’s rule, which of these compounds should be aromatic?
a) I
b) II
c) III
d) IV
e) V
Topic: Aromaticity, Hückel’s Rule
Section: 14.7
Difficulty Level: Medium
106) Which of these is an aromatic molecule?
a) I
b) II
c) III
d) IV
e) V
Topic: Aromaticity, Hückel’s Rule
Section: 14.7
Difficulty Level: Medium
107) Which of these is an aromatic molecule?
a) I
b) II
c) III
d) IV
e) V
Topic: Aromaticity, Hückel’s Rule
Section: 14.7
Difficulty Level: Medium
108) Which of these is an aromatic molecule?
a) I
b) II
c) III
d) IV
e) V
Topic: Aromaticity, Hückel’s Rule
Section: 14.7
Difficulty Level: Medium
109) Which of these is an aromatic molecule?
a) I
b) II
c) III
d) IV
e) V
Topic: Aromaticity, Hückel’s Rule
Section: 14.7
Difficulty Level: Medium
110) Of the following C-10 compounds, which is expected to possess the greatest resonance (delocalization) energy?
a) I
b) II
c) III
d) IV
e) V
Topic: Aromaticity, Hückel’s Rule
Section: 14.11
Difficulty Level: Medium
111) Which of the following would you expect to be antiaromatic?
a) I
b) II
c) III
d) IV
e) V
Topic: Aromaticity, Hückel’s Rule
Section: 14.11
Difficulty Level: Medium
112) Which of these would you expect to have significant resonance stabilization energy?
a) I
b) II
c) III
d) All of these choices.
e) None of these choices.
Topic: Aromaticity, Huckel’s Rule
Section: 14.12
Difficulty Level: Medium
113) Which of these would you expect to have significant resonance stabilization energy?
a) I
b) II
c) III
d) All of these choices.
e) None of these choices.
Topic: Aromaticity, Hückel’s Rule
Section: 14.12
Difficulty Level: Medium
114) Which of these would you expect to have significant resonance stabilization energy?
a) I
b) II
c) III
d) All of these choices.
e) None of these choices.
Topic: Aromaticity, Hückel’s Rule
Section: 14.12
Difficulty Level: Medium
115) Which of these would you expect to have significant resonance stabilization energy?
a) I
b) II
c) III
d) All of these choices.
e) None of these choices.
Topic: Aromaticity, Hückel’s Rule
Section: 14.12
Difficulty Level: Medium
116) Which of these would you expect to have significant resonance stabilization energy?
a) I
b) II
c) III
d) All of these choices.
e) None of these choices.
Topic: Aromaticity, Hückel’s Rule
Section: 14.12
Difficulty Level: Medium
117) Which compound would you NOT expect to be aromatic?
a) I
b) II
c) III
d) IV
e) V
Topic: Aromaticity, Huckel’s Rule
Section: 14.12
Difficulty Level: Medium
118) Which compound would you NOT expect to be aromatic?
a) I
b) II
c) III
d) IV
e) V
Topic: Aromaticity, Huckel’s Rule
Section: 14.12
Difficulty Level: Medium
119) Which compound would you NOT expect to be aromatic?
a) I
b) II
c) III
d) IV
e) V
Topic: Aromaticity, Hückel’s Rule
Section: 14.12
Difficulty Level: Medium
120) Which of these species is aromatic?
a) I
b) II
c) III
d) IV
e) V
Topic: Aromaticity, Huckel’s Rule
Section: 14.12
Difficulty Level: Medium
121) In which case is the indicated unshared pair of electrons NOT a contributor to the aromatic system?
a) I
b) II
c) III
d) IV
e) None of these choices.
Topic: Aromaticity, Hückel’s Rule
Section: 14.12
Difficulty Level: Medium
122) In which case does an unshared pair of electrons NOT contribute to the aromatic system?
a) I
b) II
c) III
d) IV
e) None of these choices.
Topic: Aromaticity, Hückel’s Rule
Section: 14.12
Difficulty Level: Medium
123) Which of the following would you expect to be antiaromatic?
a) I
b) II
c) III
d) IV
e) V
Topic: Aromaticity, Hückel’s Rule
Section: 14.11
Difficulty Level: Hard
124) Which of the following would you expect to be antiaromatic?
a) I
b) II
c) III
d) IV
e) V
Topic: Aromaticity, Hückel’s Rule
Section: 14.11
Difficulty Level: Hard
125) Which of the following would you expect to be antiaromatic?
a) I
b) II
c) III
d) IV
e) V
Topic: Aromaticity, Hückel’s Rule
Section: 14.11
Difficulty Level: Hard
126) Which annulene would you NOT expect to be aromatic?
a) [6]Annulene
b) [14]Annulene
c) [16]Annulene
d) [18]Annulene
e) [22]Annulene
Topic: Aromaticity, Hückel’s Rule
Section: 14.11
Difficulty Level: Hard
127) How many equivalent resonance structures can be written for the cyclopentadienyl anion?
a) 3
b) 4
c) 5
d) 6
e) 7
Topic: Resonance Forms
Section: 14.7
Difficulty Level: Medium
128) How many equivalent resonance structures can be written for the cycloheptatrienyl cation?
a) 3
b) 4
c) 5
d) 6
e) 7
Topic: Resonance Forms
Section: 14.7
Difficulty Level: Medium
129) How many equivalent resonance structures can be written for the cyclopropenyl cation?
a) 1
b) 2
c) 3
d) 4
e) 5
Topic: Resonance Forms
Section: 14.7
Difficulty Level: Medium
130) How many equivalent resonance structures can be written for the cyclobutadienyl dication?
a) 1
b) 2
c) 3
d) 4
e) No equivalent resonance forms can be drawn.
Topic: Resonance Forms
Section: 14.7
Difficulty Level: Medium
131) How many resonances would be expected in the broadband proton-decoupled 13C spectrum of:
a) 1
b) 2
c) 3
d) 4
e) 5
Topic: Spectroscopy
Section: 14.14
Difficulty Level: Medium
132) How many resonances would be expected in the broadband proton-decoupled 13C spectrum of:
a) 1
b) 2
c) 3
d) 4
e) 5
Topic: Spectroscopy
Section: 14.14
Difficulty Level: Medium
133) How many resonances would be expected in the broadband proton-decoupled 13C spectrum of:
a) 1
b) 2
c) 3
d) 4
e) 5
Topic: Spectroscopy
Section: 14.14
Difficulty Level: Medium
134) How many resonances would be expected in the broadband proton-decoupled 13C spectrum of:
a) 2
b) 3
c) 4
d) 5
e) 6
Topic: Spectroscopy
Section: 14.14
Difficulty Level: Medium
135) How many resonances would be expected in the broadband proton-decoupled 13C spectrum of:
a) 2
b) 3
c) 4
d) 5
e) 6
Topic: Spectroscopy
Section: 14.14
Difficulty Level: Medium
136) How many resonances would be expected in the broadband proton-decoupled 13C spectrum of:
a) 3
b) 4
c) 5
d) 6
e) 7
Topic: Spectroscopy
Section: 14.14
Difficulty Level: Medium
137) How many resonances would be expected in the broadband proton-decoupled 13C spectrum of:
a) 2
b) 3
c) 4
d) 5
e) 6
Topic: Spectroscopy
Section: 14.14
Difficulty Level: Medium
138) How many resonances would be expected in the broadband proton-decoupled 13C spectrum of:
a) 4
b) 5
c) 6
d) 7
e) 8
Topic: Spectroscopy
Section: 14.14
Difficulty Level: Medium
139) How many resonances would be expected in the broadband proton-decoupled 13C spectrum of:
a) 4
b) 5
c) 6
d) 7
e) 8
Topic: Spectroscopy
Section: 14.14
Difficulty Level: Medium
140) How many resonances would be expected in the broadband proton-decoupled 13C spectrum of:
a) 4
b) 5
c) 6
d) 7
e) 8
Topic: Spectroscopy
Section: 14.14
Difficulty Level: Medium
141) How many resonances would be expected in the broadband proton-decoupled 13C spectrum of:
a) 4
b) 5
c) 6
d) 7
e) 8
Topic: Spectroscopy
Section: 14.14
Difficulty Level: Medium
142) How many resonances would be expected in the broadband proton-decoupled 13C spectrum of:
a) 5
b) 6
c) 7
d) 8
e) 9
Topic: Spectroscopy
Section: 14.14
Difficulty Level: Medium
143) How many resonances would be expected in the broadband proton-decoupled 13C spectrum of:
a) 4
b) 5
c) 6
d) 7
e) 8
Topic: Spectroscopy
Section: 14.14
Difficulty Level: Medium
144) Which of these compounds absorbs at the longest wavelength in the UV-visible region?
a) I
b) II
c) III
d) IV
e) V
Topic: Spectroscopy
Section: 14.14
Difficulty Level: Medium
145) 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?
a) I
b) II
c) III
d) IV
e) V
Topic: Spectroscopy
Section: 14.14
Difficulty Level: Medium
146) Which of the following substances, formula C8H9Br, might exhibit the following 1H NMR spectrum?
triplet, 2.8
triplet, 4.65
multiplet, 7.2
a) I
b) II
c) III
d) IV
e) V
Topic: Spectroscopy
Section: 14.14
Difficulty Level: Medium
147) Which of the following substances, formula C8H9Br, might exhibit the following 1H NMR spectrum?
triplet, 1.2
quartet, 2.45
multiplet, 7.4
a) I
b) II
c) III
d) IV
e) V
Topic: Spectroscopy
Section: 14.14
Difficulty Level: Medium
148) Which of the following substances, formula C8H9Br, might exhibit the following 1H NMR spectrum?
singlet, 2.45
singlet, 2.5
multiplet, 7.35
a) I
b) II
c) III
d) IV
e) V
Topic: Spectroscopy
Section: 14.14
Difficulty Level: Medium
149) Which of the following substances, C8H9Cl, would exhibit five signals in its 13C NMR spectrum?
a) I
b) II
c) III
d) IV
e) V
Topic: Spectroscopy
Section: 14.14
Difficulty Level: Medium
150) Which of the following substances, C9H10O, would exhibit seven signals in its 13C NMR spectrum?
a) I
b) II
c) III
d) IV
e) V
Topic: Spectroscopy
Section: 14.14
Difficulty Level: Medium
151) For which of the following substances, C9H10O, would the aromatic multiplet, in its 1H NMR spectrum, consist of two doublets?
a) I
b) II
c) III
d) IV
e) V
Topic: Spectroscopy
Section: 14.14
Difficulty Level: Medium
152) 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?
a) I and III
b) I, II, III, and V
c) IV
d) V
e) All of these substances would exhibit two singlets 2.0-2.5 ppm in their 1H NMR spectra.
Topic: Spectroscopy
Section: 14.14
Difficulty Level: Medium
153) Which isomer of C7H7Cl exhibits strong IR absorbances at 690 and 750 cm–1?
a) I
b) II
c) III
d) IV
e) II and IV
Topic: Spectroscopy
Section: 14.14
Difficulty Level: Hard
154) 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) UV Spectroscopy
e) Two of these choices.
Topic: Chemical and Spectroscopic Analysis
Section: 14.14
Difficulty Level: Medium
155) 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.
Topic: Chemical and Spectroscopic Analysis
Section: 14.14
Difficulty Level: Medium
Question type: fill-in-the-blank
156) 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.
Topic: General Concepts
Section: 14.1
Difficulty Level: Easy
157) Humans do not have the biochemical ability to synthesize the benzene ring. Therefore, two amino acids, ___ and ___, are essential to the human diet.
Topic: General Concepts
Section: 14.13
Difficulty Level: Easy
158) Cagelike molecules with the geometry of a truncated icosahedron are called ___.
Topic: General Concepts
Section: 14.11
Difficulty Level: Easy
159) Monocyclic compounds with alternating single and double bonds are called ___.
Topic: General Concepts
Section: 14.7
Difficulty Level: Easy
160) The difference between the amount of heat actually released upon hydrogenation of benzene and that calculated on the basis of the Kekulé structure is called the ___ of benzene.
Topic: General Concepts
Section: 14.5
Difficulty Level: Easy
161) Molecular orbitals of equal energy are referred to as ___ orbitals.
Topic: General Concepts
Section: 14.6
Difficulty Level: Medium
162) When a benzene ring is used as a substituent, it is called a ___ group.
Topic: Nomenclature
Section: 14.2
Difficulty Level: Easy
Question type: Molecular Drawing
163) Draw the structure corresponding to the following name: 2-bromo-5-nitrophenol
Topic: Nomenclature
Section: 14.2
Difficulty Level: Medium
164) Draw the structure corresponding to the following name:
3-bromo-5-phenylaniline
Topic: Nomenclature
Section: 14.2
Difficulty Level: Medium
165) Draw the structure corresponding to the following name: 3-nitro-4-iodoanisole
Topic: Nomenclature
Section: 14.2
Difficulty Level: Medium
Question type: Essay
166) Give the IUPAC name for the following substance:
Topic: Nomenclature
Section: 14.2
Difficulty Level: Hard
167) Draw the structure corresponding to the following name: 2-hydroxy-4-(3-methylcyclopentyl)benzoic acid
Topic: Nomenclature
Section: 14.2
Difficulty Level: Hard
Question type: fill-in-the-blank
168) Hückel’s Rule requires ___ electrons for an aromatic compound.
Topic: Hückel’s rule
Section: 14.7
Difficulty Level: Easy
Question type: Essay
169) The heats of hydrogenation for cyclohexene and benzene are given below. Calculate the resonance stabilization energy of benzene.
C6H10 + H2 🡪 C6H12 Ho = -120 kJ/mol
C6H6 + 3H2 🡪 C6H12 Ho = -208 kJ/mol
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
170) 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?
Topic: Aromaticity, Molecular Orbital Theory
Section: 14.7
Difficulty Level: Medium
171) 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.
Topic: Aromaticity, Molecular Orbital Theory
Section: 14.7
Difficulty Level: Hard
172) Benzene, while unusually unreactive with electrophiles, will react under certain conditions. However, when it does react, it does so by ___ rather than by addition.
Topic: Aromaticity, Reactivity
Section: 14.3
Difficulty Level: Easy
173) Explain briefly why cyclopentadiene readily reacts with strong bases.
Topic: Aromaticity, Reactivity
Section: 14.7
Difficulty Level: Medium
174) Cycloheptatriene is found to readily undergo a hydride transfer with triphenylmethyl arbocation to generate the cycloheptatrienyl cation and triphenylmethane. Explain why this transformation is facile.
Topic: Aromaticity, Reactivity
Section: 14.7
Difficulty Level: Medium
175) Pyrrole is not particularly basic, because the lone pair on the nitrogen is ___.
Topic: Aromaticity, Reactivity
Section: 14.12
Difficulty Level: Medium
176) 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.
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 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: 14.12
Difficulty Level: Medium
177) Predict the product of the reaction of one equivalent of hydrochloric acid with the organic compound shown:
Topic: Aromaticity, Reactivity
Section: 14.12
Difficulty Level: Medium
178) Briefly explain why the aromatic hydrocarbon shown possesses a significant dipole moment. Use diagrams as needed to illustrate/clarify your 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
179) Briefly explain why the aromatic hydrocarbon shown possesses a significant dipole moment. Use diagrams as needed to illustrate/clarify your 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: 14.11
Difficulty Level: Hard
180) Briefly explain why the aromatic hydrocarbon azulene, C10H8, possesses a significant dipole moment. Use diagrams as needed to illustrate/clarify your answer.
Topic: Aromaticity
Section: 14.7
Difficulty Level: Hard
181) 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.
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.
Topic: Resonance, Bond Lengths, Bond Order
Section: 14.7
Difficulty Level: Medium
Question type: Molecular Drawing
182) Draw all significant resonance structures for pyridine, C6H5N
Topic: Resonance
Section: 14.12
Difficulty Level: Hard
183) Draw all significant resonance structures for azulene, C10H8
Topic: Resonance
Section: 1.8 and 14.8
Difficulty Level: Hard
184) Draw all significant resonance structures for the cyclopentadienyl anion.
Topic: Resonance
Section: 14.11
Difficulty Level: Hard
185) 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.
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 sp2 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: 14.11
Difficulty Level: Hard
186) The correct carbon assignment of the broadband decoupled 13C NMR signals for p-chlorobenzaldehyde is?
a) I
b) II
c) III
d) IV
e) V
Topic: Spectroscopy and Resonance Theory
Section: 14.14
Difficulty Level: Medium
187) The correct name for the compound shown below is?
a) 2-bromo-5-nitrobenzoic acid
b) 2-bromo-6 nitrobenzoic acid
c) 6-bromo-3-nitrobenzoic acid
d) 6-bromo-2-nitrobenzoic acid
e) 5-bromo-2-nitrobenzoic acid
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Easy
188) The correct name for the compound shown below is?
a) 2-bromo-5-nitrobenzoic acid
b) 2-bromo-6 nitrobenzoic acid
c) 6-bromo-3-nitrobenzoic acid
d) 6-bromo-2-nitrobenzoic acid
e) 5-bromo-2-nitrobenzoic acid
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Easy
189) The correct name for the compound shown below is?
a) 4-bromo-2-nitroaniline
b) 2-bromo-5-nitroaniline
c) 3-bromo-4-nitroaniline
d) 2-bromo-4-nitroanisole
e) 2-bromo-5-nitroanisole
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium
190) The correct name for the compound shown below is?
a) 4-bromo-2-nitroaniline
b) 2-bromo-5-nitroaniline
c) 3-bromo-4-nitroaniline
d) 2-bromo-4-nitroanisole
e) 2-bromo-5-nitroanisole
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium
191) The correct name for the compound shown below is?
a) 4-bromo-2-nitroaniline
b) 2-bromo-5-nitroaniline
c) 3-bromo-4-nitroaniline
d) 2-bromo-4-nitroanisole
e) 2-bromo-5-nitroanisole
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium
192) The correct name for the compound shown below is?
a) 4-bromo-2-nitroaniline
b) 2-bromo-5-nitroaniline
c) 3-bromo-4-nitroaniline
d) 2-bromo-4-nitroanisole
e) 2-bromo-5-nitroanisole
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium
193) The correct name for the compound shown below is?
a) 4-bromo-2-nitroaniline
b) 2-bromo-5-nitroaniline
c) 3-bromo-4-nitroaniline
d) 2-bromo-4-nitroanisole
e) 2-bromo-5-nitroanisole
Topic: Nomenclature and Isomerism
Section: 14.2
Difficulty Level: Medium