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What is the IUPAC name of the following compound? 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

E) A) and D)
F) B) and C)

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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.

E) B) and C)
F) None of the above

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What is the IUPAC name of the following compound? 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

E) None of the above
F) B) and D)

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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.

E) A) and B)
F) C) and D)

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Rank the following compounds in order of decreasing acidity, starting with the most acidic. 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

E) A) and C)
F) All of the above

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B

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? <sup> </sup>What is the structure of a compound of molecular formula C<sub>10</sub>H<sub>14</sub>O<sub>2</sub> that shows a strong IR absorption at 3150 ¾2850 cm<sup>-1</sup> and gives the following <sup>1</sup>H 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

E) A) and C)
F) None of the above

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What is the name of the following compound? 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

E) A) and C)
F) A) and D)

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D

What orbitals are used to form the indicated bond? What orbitals are used to form the indicated bond?   A) sp<sup>3</sup> B) sp<sup>2</sup> C) p D) sp<sup>3</sup> and sp<sup>2</sup>


A) sp3
B) sp2
C) p
D) sp3 and sp2

E) A) and B)
F) B) and D)

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Which of the following compounds is aromatic? Which of the following compounds is aromatic?   A) I B) II C) III D) IV


A) I
B) II
C) III
D) IV

E) None of the above
F) All of the above

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How many 13CNMR signals does the following compound exhibit? How many <sup>13</sup>CNMR signals does the following compound exhibit?   A) 4 B) 5 C) 6 D) 8


A) 4
B) 5
C) 6
D) 8

E) A) and B)
F) A) and C)

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What is the correct structure for toluene? What is the correct structure for toluene?   A) I B) II C) III D) IV


A) I
B) II
C) III
D) IV

E) A) and C)
F) A) and B)

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What is the correct structure for aniline? What is the correct structure for aniline?   A) I B) II C) III D) IV


A) I
B) II
C) III
D) IV

E) C) and D)
F) A) and D)

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What is the correct assignment of the number of signals in the 13C NMR spectra of the following disubstituted benzene derivatives? What is the correct assignment of the number of signals in the <sup>13</sup>C 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.

E) A) and C)
F) B) and C)

Correct Answer

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Which of the following ions is aromatic? Which of the following ions is aromatic?   A) I B) II C) III D) IV


A) I
B) II
C) III
D) IV

E) A) and D)
F) B) and C)

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A

What is the correct assignment of the names of the following aromatic heterocycles? 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.

E) C) and D)
F) None of the above

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What is the name of the following compound? 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

E) A) and B)
F) A) and C)

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What is the correct assignment of the names of the following substituted benzenes? 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.

E) B) and D)
F) A) and D)

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Why is the following compound not aromatic? 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.

E) C) and D)
F) All of the above

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Which of the following compounds is aromatic? Which of the following compounds is aromatic?   A) I B) II C) III D) IV


A) I
B) II
C) III
D) IV

E) None of the above
F) C) and D)

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Which of the following compounds is not aromatic? Which of the following compounds is not aromatic?   A) I B) II C) III D) IV


A) I
B) II
C) III
D) IV

E) A) and D)
F) A) and C)

Correct Answer

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