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Deck 17: Benzene and Aromatic Compounds
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Question
What is the IUPAC name of the following compound?
A)3,6-Dichloroaniline
B)2,5-Dichloroaniline
C)2,5-Dichloroaminobenzene
D)2,5-Dichloroanisole
A)3,6-Dichloroaniline
B)2,5-Dichloroaniline
C)2,5-Dichloroaminobenzene
D)2,5-Dichloroanisole
Question
What is the structure of a compound of molecular formula C10H14O2 that shows a strong IR absorption at 3150 ¾2850 cm-1 and gives the following 1H NMR absorptions: 1.4 (triplet, 6H); 4.0 (quartet, 4H); and 6.8 (singlet, 4H) ppm?
A)I
B)II
C)III
D)IV
A)I
B)II
C)III
D)IV
Question
What is the correct assignment of the number of signals in the 13C NMR spectra of the following disubstituted benzene derivatives?
A)I = 3 signals; II = 3 signals; III = 2 signals.
B)I = 3 signals; II = 4 signals; III = 2 signals.
C)I = 6 signals; II = 6 signals; III = 6 signals.
D)I = 3 signals; II = 4 signals; III = 3 signals.
A)I = 3 signals; II = 3 signals; III = 2 signals.
B)I = 3 signals; II = 4 signals; III = 2 signals.
C)I = 6 signals; II = 6 signals; III = 6 signals.
D)I = 3 signals; II = 4 signals; III = 3 signals.
Question
What orbitals are used to form the indicated bond?
A)sp3
B)sp2
C)p
D)sp3 and sp2
A)sp3
B)sp2
C)p
D)sp3 and sp2
Question
Which of the following ions is aromatic?
A)Only I and II
B)Only II and III
C)Only III and IV
D)Only II and IV
A)Only I and II
B)Only II and III
C)Only III and IV
D)Only II and IV
Question
Question
Question
What is the name of the following compound?
A)Meta-bromophenol
B)Para-hydroxybenzene
C)3-bromoanisole
D)6-methoxy-2-bromobenzene
A)Meta-bromophenol
B)Para-hydroxybenzene
C)3-bromoanisole
D)6-methoxy-2-bromobenzene
Question
How many 13CNMR signals does the following compound exhibit?
A)4
B)5
C)6
D)8
A)4
B)5
C)6
D)8
Question
What is the correct assignment of the names of the following aromatic heterocycles?
A)I = pyridine; II = pyrimidine; III = furan.
B)I = pyrimidine; II =pyrrole; III = furan.
C)I = pyridine; II = pyrrole; III = furan.
D)I = pyrimidine; II = pyrrole; III = tetrahydrofuran.
A)I = pyridine; II = pyrimidine; III = furan.
B)I = pyrimidine; II =pyrrole; III = furan.
C)I = pyridine; II = pyrrole; III = furan.
D)I = pyrimidine; II = pyrrole; III = tetrahydrofuran.
Question
What is the name of the following compound?
A)2,6-Dimethylbenzene
B)5-Methyltoluene
C)Anisole
D)1,3-Dimethylbenzene
A)2,6-Dimethylbenzene
B)5-Methyltoluene
C)Anisole
D)1,3-Dimethylbenzene
Question
Which of the following ions is aromatic?
A)I
B)II
C)III
D)IV
A)I
B)II
C)III
D)IV
Question
Rank the following compounds in order of decreasing acidity, starting with the most acidic. 
A)I > II > III
B)III > II > I
C)III > I > II
D)I > III > II
A)I > II > III
B)III > II > I
C)III > I > II
D)I > III > II
Question
Question
What is the IUPAC name of the following compound?
A)1-Chloro-4-ethyl-3-propylbenzene
B)1-Chloro-4-ethyl-5-propylbenzene
C)4-Chloro-1-ethyl-2-propylbenzene
D)4-Chloro-2-propyltoluene
A)1-Chloro-4-ethyl-3-propylbenzene
B)1-Chloro-4-ethyl-5-propylbenzene
C)4-Chloro-1-ethyl-2-propylbenzene
D)4-Chloro-2-propyltoluene
Question
Question
What is the correct assignment of the names of the following substituted benzenes?
A)I = Phenol; II = anisole; III = toluene.
B)I = Benzaldehyde; II = phenol; III = anisole.
C)I = Benzaldehyde; II = phenol; III = toluene.
D)I = Phenol; II = anisole; III = styrene.
A)I = Phenol; II = anisole; III = toluene.
B)I = Benzaldehyde; II = phenol; III = anisole.
C)I = Benzaldehyde; II = phenol; III = toluene.
D)I = Phenol; II = anisole; III = styrene.
Question
What orbitals are used to form the indicated bond?
A)sp3
B)sp2
C)p
D)sp3 and sp2
A)sp3
B)sp2
C)p
D)sp3 and sp2
Question
Which of the following molecules has the most acidic hydrogen atoms?
A)I
B)II
C)III
D)IV
A)I
B)II
C)III
D)IV
Question
Which of the following heterocycles is not aromatic?
A)I
B)II
C)III
D)IV
A)I
B)II
C)III
D)IV
Question
What is the correct structure for aniline?
A)I
B)II
C)III
D)IV
A)I
B)II
C)III
D)IV
Question
What is the correct structure for toluene?
A)I
B)II
C)III
D)IV
A)I
B)II
C)III
D)IV
Question
Which of the following compounds is not aromatic?
A)I
B)II
C)III
D)IV
A)I
B)II
C)III
D)IV
Question
Which of the following compounds is not aromatic?
A)I
B)II
C)III
D)IV
A)I
B)II
C)III
D)IV
Question
Question
Which of the following compounds is aromatic?
A)I
B)II
C)III
D)IV
A)I
B)II
C)III
D)IV
Question
Why is the following compound not aromatic?
A)It has 4n pi electrons.
B)It is not cyclic.
C)It has 4n+2 pi electrons.
D)The p electron system is not continuous.
A)It has 4n pi electrons.
B)It is not cyclic.
C)It has 4n+2 pi electrons.
D)The p electron system is not continuous.
Question
What is the correct structure for anisole?
A)I
B)II
C)III
D)IV
A)I
B)II
C)III
D)IV
Question
Why is the following compound not aromatic?
A)It has 4n electrons.
B)It is not cyclic.
C)It has 4n+2 electrons.
D)The p electron system is not continuous.
A)It has 4n electrons.
B)It is not cyclic.
C)It has 4n+2 electrons.
D)The p electron system is not continuous.
Question
What is the correct structure for 1-bromo-2,4-dimethoxybenzene?
A)I
B)II
C)III
D)IV
A)I
B)II
C)III
D)IV
Question
Which of the following compounds is aromatic?
A)I
B)II
C)III
D)IV
A)I
B)II
C)III
D)IV
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Deck 17: Benzene and Aromatic Compounds
1
What is the IUPAC name of the following compound?
A)3,6-Dichloroaniline
B)2,5-Dichloroaniline
C)2,5-Dichloroaminobenzene
D)2,5-Dichloroanisole
A)3,6-Dichloroaniline
B)2,5-Dichloroaniline
C)2,5-Dichloroaminobenzene
D)2,5-Dichloroanisole
2,5-Dichloroaniline
2
What is the structure of a compound of molecular formula C10H14O2 that shows a strong IR absorption at 3150 ¾2850 cm-1 and gives the following 1H NMR absorptions: 1.4 (triplet, 6H); 4.0 (quartet, 4H); and 6.8 (singlet, 4H) ppm?
A)I
B)II
C)III
D)IV
A)I
B)II
C)III
D)IV
IV
3
What is the correct assignment of the number of signals in the 13C NMR spectra of the following disubstituted benzene derivatives?
A)I = 3 signals; II = 3 signals; III = 2 signals.
B)I = 3 signals; II = 4 signals; III = 2 signals.
C)I = 6 signals; II = 6 signals; III = 6 signals.
D)I = 3 signals; II = 4 signals; III = 3 signals.
A)I = 3 signals; II = 3 signals; III = 2 signals.
B)I = 3 signals; II = 4 signals; III = 2 signals.
C)I = 6 signals; II = 6 signals; III = 6 signals.
D)I = 3 signals; II = 4 signals; III = 3 signals.
I = 3 signals; II = 4 signals; III = 2 signals.
4
What orbitals are used to form the indicated bond?
A)sp3
B)sp2
C)p
D)sp3 and sp2
A)sp3
B)sp2
C)p
D)sp3 and sp2
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5
Which of the following ions is aromatic?
A)Only I and II
B)Only II and III
C)Only III and IV
D)Only II and IV
A)Only I and II
B)Only II and III
C)Only III and IV
D)Only II and IV
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6
Which of the following statements about the structure of benzene is not true?
A)Benzene is planar.
B)Benzene has three short double bonds alternating with three longer single bonds.
C)The electrons in the pi bonds are delocalized around the ring.
D)Benzene has six pi electrons.
A)Benzene is planar.
B)Benzene has three short double bonds alternating with three longer single bonds.
C)The electrons in the pi bonds are delocalized around the ring.
D)Benzene has six pi electrons.
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7
Which of the following statements about benzene is true?
A)Benzene is a saturated hydrocarbon.
B)Benzene undergoes addition reactions.
C)Benzene has five degrees of unsaturation.
D)Benzene undergoes substitution reactions.
A)Benzene is a saturated hydrocarbon.
B)Benzene undergoes addition reactions.
C)Benzene has five degrees of unsaturation.
D)Benzene undergoes substitution reactions.
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8
What is the name of the following compound?
A)Meta-bromophenol
B)Para-hydroxybenzene
C)3-bromoanisole
D)6-methoxy-2-bromobenzene
A)Meta-bromophenol
B)Para-hydroxybenzene
C)3-bromoanisole
D)6-methoxy-2-bromobenzene
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9
How many 13CNMR signals does the following compound exhibit?
A)4
B)5
C)6
D)8
A)4
B)5
C)6
D)8
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10
What is the correct assignment of the names of the following aromatic heterocycles?
A)I = pyridine; II = pyrimidine; III = furan.
B)I = pyrimidine; II =pyrrole; III = furan.
C)I = pyridine; II = pyrrole; III = furan.
D)I = pyrimidine; II = pyrrole; III = tetrahydrofuran.
A)I = pyridine; II = pyrimidine; III = furan.
B)I = pyrimidine; II =pyrrole; III = furan.
C)I = pyridine; II = pyrrole; III = furan.
D)I = pyrimidine; II = pyrrole; III = tetrahydrofuran.
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11
What is the name of the following compound?
A)2,6-Dimethylbenzene
B)5-Methyltoluene
C)Anisole
D)1,3-Dimethylbenzene
A)2,6-Dimethylbenzene
B)5-Methyltoluene
C)Anisole
D)1,3-Dimethylbenzene
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12
Which of the following ions is aromatic?
A)I
B)II
C)III
D)IV
A)I
B)II
C)III
D)IV
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13
Rank the following compounds in order of decreasing acidity, starting with the most acidic.
A)I > II > III
B)III > II > I
C)III > I > II
D)I > III > II
A)I > II > III
B)III > II > I
C)III > I > II
D)I > III > II
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14
Which of the following is not one of the Hückel's criteria for aromaticity?
A)The molecule must be cyclic.
B)The molecule must be planar.
C)The molecule must be completely conjugated.
D)The molecule must have 4n pi electrons.
A)The molecule must be cyclic.
B)The molecule must be planar.
C)The molecule must be completely conjugated.
D)The molecule must have 4n pi electrons.
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15
What is the IUPAC name of the following compound?
A)1-Chloro-4-ethyl-3-propylbenzene
B)1-Chloro-4-ethyl-5-propylbenzene
C)4-Chloro-1-ethyl-2-propylbenzene
D)4-Chloro-2-propyltoluene
A)1-Chloro-4-ethyl-3-propylbenzene
B)1-Chloro-4-ethyl-5-propylbenzene
C)4-Chloro-1-ethyl-2-propylbenzene
D)4-Chloro-2-propyltoluene
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16
Which of the following is not a criterion for antiaromaticity?
A)The molecule must be cyclic.
B)The molecule must have (4n + 2) pi electrons.
C)The molecule must be planar.
D)The molecule must be completely conjugated.
A)The molecule must be cyclic.
B)The molecule must have (4n + 2) pi electrons.
C)The molecule must be planar.
D)The molecule must be completely conjugated.
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17
What is the correct assignment of the names of the following substituted benzenes?
A)I = Phenol; II = anisole; III = toluene.
B)I = Benzaldehyde; II = phenol; III = anisole.
C)I = Benzaldehyde; II = phenol; III = toluene.
D)I = Phenol; II = anisole; III = styrene.
A)I = Phenol; II = anisole; III = toluene.
B)I = Benzaldehyde; II = phenol; III = anisole.
C)I = Benzaldehyde; II = phenol; III = toluene.
D)I = Phenol; II = anisole; III = styrene.
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18
What orbitals are used to form the indicated bond?
A)sp3
B)sp2
C)p
D)sp3 and sp2
A)sp3
B)sp2
C)p
D)sp3 and sp2
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19
Which of the following molecules has the most acidic hydrogen atoms?
A)I
B)II
C)III
D)IV
A)I
B)II
C)III
D)IV
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20
Which of the following heterocycles is not aromatic?
A)I
B)II
C)III
D)IV
A)I
B)II
C)III
D)IV
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21
What is the correct structure for aniline?
A)I
B)II
C)III
D)IV
A)I
B)II
C)III
D)IV
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22
What is the correct structure for toluene?
A)I
B)II
C)III
D)IV
A)I
B)II
C)III
D)IV
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23
Which of the following compounds is not aromatic?
A)I
B)II
C)III
D)IV
A)I
B)II
C)III
D)IV
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24
Which of the following compounds is not aromatic?
A)I
B)II
C)III
D)IV
A)I
B)II
C)III
D)IV
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25
Where do the protons in benzene appear in the 1H NMR spectrum?
A)Around 1600 cm-1
B)Around 120 ppm
C)Around 0 ppm
D)Around 7 ppm
A)Around 1600 cm-1
B)Around 120 ppm
C)Around 0 ppm
D)Around 7 ppm
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26
Which of the following compounds is aromatic?
A)I
B)II
C)III
D)IV
A)I
B)II
C)III
D)IV
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27
Why is the following compound not aromatic?
A)It has 4n pi electrons.
B)It is not cyclic.
C)It has 4n+2 pi electrons.
D)The p electron system is not continuous.
A)It has 4n pi electrons.
B)It is not cyclic.
C)It has 4n+2 pi electrons.
D)The p electron system is not continuous.
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28
What is the correct structure for anisole?
A)I
B)II
C)III
D)IV
A)I
B)II
C)III
D)IV
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29
Why is the following compound not aromatic?
A)It has 4n electrons.
B)It is not cyclic.
C)It has 4n+2 electrons.
D)The p electron system is not continuous.
A)It has 4n electrons.
B)It is not cyclic.
C)It has 4n+2 electrons.
D)The p electron system is not continuous.
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30
What is the correct structure for 1-bromo-2,4-dimethoxybenzene?
A)I
B)II
C)III
D)IV
A)I
B)II
C)III
D)IV
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31
Which of the following compounds is aromatic?
A)I
B)II
C)III
D)IV
A)I
B)II
C)III
D)IV
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