Chapter 15 Test Bank Benzene And Aromatic Compounds

Organic Chemistry, 6e (Smith)

Chapter 15 Benzene and Aromatic Compounds

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.

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.

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

A) Csp2¾Csp2

B) Csp2¾ C2p

C) C2p¾C2p

D) Csp3¾Csp3

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

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

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

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

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

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

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

A) 4

B) 5

C) 6

D) 8

11) 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

12) 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

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.

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.

15) 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

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

17) Which of the following heterocycles is not aromatic?

A) I

B) II

C) III

D) IV

18) Which of the following ions is aromatic?

A) I

B) II

C) III

D) IV

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

A) I

B) II

C) III

D) IV

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

21) 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

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 p* antibonding molecular orbital is formed.

B) When two p orbitals of opposite phase overlap side-by-side, a p bonding molecular orbital is formed.

C) A p bonding molecular orbital is higher in energy than the two atomic p orbitals from which it is formed.

D) A p* antibonding molecular orbital is higher in energy than the two atomic p orbitals from which it is formed.

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

A) sp3

B) sp2

C) p

D) sp3 and sp2

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

A) sp3

B) sp2

C) p

D) sp3 and sp2

25) What is the name of the following compound?

A) 2,6-Dimethylbenzene

B) 5-Methyltoluene

C) Anisole

D) 1,3-Dimethylbenzene

26) What is the name of the following compound?

A) Meta-bromophenol

B) Para-hydroxybenzene

C) 3-bromoanisole

D) 6-methoxy-2-bromobenzene

27) What is the correct structure for aniline?

A) I

B) II

C) III

D) IV

28) What is the correct structure for anisole?

A) I

B) II

C) III

D) IV

29) What is the correct structure for toluene?

A) I

B) II

C) III

D) IV

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

A) I

B) II

C) III

D) IV

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

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

A) 1

B) 3

C) 5

D) 6

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

A) Phenol

B) Anisole

C) 4-bromoanisole

D) 4-bromotoluene

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

A) I

B) II

C) III

D) IV

35) Which of the following compounds is not aromatic?

A) I

B) II

C) III

D) IV

36) Which of the following compounds is not aromatic?

A) I

B) II

C) III

D) IV

37) Which of the following compounds is aromatic?

A) I

B) II

C) III

D) IV

38) Which of the following compounds is aromatic?

A) I

B) II

C) III

D) IV

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 pi electron system is not continuous.

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 pi electron system is not continuous.

41) What is the hybridization of the indicated N atom in the following compound?

A) p

B) sp

C) sp2

D) sp3

42) What is the hybridization of the indicated N atom in the following compound?

A) p

B) sp

C) sp2

D) sp3

43) In what type of orbital does the lone pair on the indicated N atom reside?

A) p

B) sp

C) sp2

D) sp3

44) In what type of orbital does the lone pair on the indicated N atom reside?

A) p

B) sp

C) sp2

D) sp3

45) What is the IUPAC name of the following compound?

A) o-nitroanisole

B) m-nitroanisole

C) p-nitroanisole

D) 2-nitroaniline

46) What is the IUPAC name of the following compound?

A) o-nitroaniline

B) m-nitroaniline

C) p-nitroaniline

D) 4-nitroanilsole

47) What is the IUPAC name of the following compound?

A) o-nitrotoluene

B) m-nitrotoluene

C) p-nitrotoluene

D) 3-nitroanisole