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17 2018, questions and answers

Organic Chemistry II (The University of Texas at San Antonio)

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Chapter: Chapter 17: Benzene and Aromatic Compounds

Multiple Choice

1. 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.

Ans: D

2. 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.

Ans: B

3. What orbitals are used to form the bond indicated in the following molecule?

A) Csp2  Csp2
B) Csp2  C2p
C) C2p  C2p
D) Csp3  Csp3

Ans: A

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4. 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

Ans: B

5. What is the IUPAC name of the following compound?

A) 2-Nitro-5-carboxychlorobenzene
B) 2-Chloro-4-carboxynitrobenzene
C) 2-Chloro-1-nitro-4-benzoic acid
D) 3-Chloro-4-nitrobenzoic acid

Ans: D

6. 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

Ans: C

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7. What is the IUPAC name of the following compound?

A) 3-Bromo-1-chloro-4-toluene
B) 2-Bromo-4-chlorotoluene
C) 4-Chloro-2-bromo-1-toluene
D) 2-Bromo-4-chloroanisole

Ans: B

8. 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.

Ans: C

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

A) I = Styrene; II = aniline; III = anisole.

B) I = Toluene; II = anisole; III = styrene.
C) I = Styrene; II = anisole; III = phenol.
D) I = Toluene; II = aniline; III = anisole.

Ans: A

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10. How many 13CNMR signals does the following compound exhibit?

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

Ans: C

11. What is the structure of a compound of molecular formula C10H14O2 that shows a strong IR
absorption at 3150  2850 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

Ans: D

12. What is the correct assignment of the number of signals in the 13C NMR spectra of the
following disubstituted benzene derivatives?

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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.

Ans: B

13. 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.

Ans: D

14. 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.

Ans: B

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

A) I = pyridine; II = pyrimidine; III = furan.

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B) I = pyrimidine; II =pyrrole; III = furan.

C) I = pyridine; II = pyrrole; III = furan.
D) I = pyrimidine; II = pyrrole; III = tetrahydrofuran.

Ans: C

16. What is the correct assignment of the names of the following fused aromatic compounds?

A) I = naphthalene; II = anthracene; III = phenanthrene.

B) I = naphthalene; II = phenanthrene; III = anthracene.
C) I = naphthalene; II = phenanthrene; III = benzo[a]pyrene.
D) I = anthracene; II = naphthalene; III = phenanthrene.

Ans: A

17. Which of the following heterocycles is not aromatic?

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

Ans: C

18. Which of the following ions is aromatic?

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

Ans: A

19. Which of the following molecules has the most acidic hydrogen atoms?

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

Ans: C

20. 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

Ans: B

21. Which of the following ions is aromatic?

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

Ans: D

22. Which of the following statements about the molecular orbital (MO) theory is true?
A) When two p orbitals of similar phase overlap side-by-side, a * antibonding molecular
orbital is formed.
B) When two p orbitals of opposite phase overlap side-by-side, a  bonding molecular orbital is
formed.
C) A  bonding molecular orbital is higher in energy than the two atomic p orbitals from which
it is formed.
D) A * antibonding molecular orbital is higher in energy than the two atomic p orbitals from
which it is formed.

Ans: D

23. What orbitals are used to form the indicated bond?

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

Ans: D

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24. What orbitals are used to form the indicated bond?

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

Ans: B

25. What is the name of the following compound?

A) 2,6-dimethylbenzene
B) 5-methyltoluene
C) anisole
D) 1,3-dimethylbenzene

Ans: D

26. What is the name of the following compound?

A) meta-bromophenol
B) para-hydroxybenzene
C) 3-bromoanisole
D) 6-methoxy-2-bromobenzene

Ans: A

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27. What is the correct structure for aniline?

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

Ans: B

28. What is the correct structure for anisole?

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

Ans: C

29. What is the correct structure for toluene?

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

Ans: D

30. What is the correct structure for 1-bromo-2,4-dimethoxybenzene?

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

Ans: C

31. 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

Ans: D

32. How many different proton signals would the following compound show in its 1H NMR
spectrum?

A) 1
B) 3
C) 5
D) 6

Ans: B

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33. What compound is consistent with the following 1H NMR spectrum?

A) phenol
B) anisole
C) 4-bromoanisole
D) 4-bromotoluene

Ans: C

34. What is the correct structure for para-bromotoluene?

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

Ans: A

35. Which of the following compounds is not aromatic?

A) I
B) II

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C) III
D) IV

Ans: B

36. Which of the following compounds is not aromatic?

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

Ans: A

37. Which of the following compounds is aromatic?

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

Ans: D

38. Which of the following compounds is aromatic?

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

Ans: B

39. 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  electron system is not continuous.

Ans: D

40. 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  electron system is not continuous.

Ans: A

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