Aromatic Compounds Chapter 17 Full Test Bank

Organic Chemistry, 4e (Klein)

Chapter 17 Aromatic Compounds

1) Identify the common name for toluene.

A) hydroxybenzene

B) aminobenzene

C) methylbenzene

D) ethylbenzene

E) methoxybenzene

Diff: 2

Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names

2) Identify the common name for anisole.

A) hydroxybenzene

B) aminobenzene

C) methylbenzene

D) ethylbenzene

E) methoxybenzene

Diff: 2

Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names

3) Identify the common name for phenol.

A) hydroxybenzene

B) aminobenzene

C) methylbenzene

D) ethylbenzene

E) methoxybenzene

Diff: 2

Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names

4) Other than an arene, identify the other key functional group found in acetophenone.

A) ether

B) alkene

C) carboxylic acid

D) aldehyde

E) ketone

Diff: 2

Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names

5) Other than an arene, identify the other key functional group found in styrene.

A) ether

B) alkene

C) carboxylic acid

D) aldehyde

E) ketone

Diff: 2

Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names

6) Identify the common name for o-xylene.

A) hydroxybenzene

B) aminobenzene

C) 1,2-dimethylbenzene

D) ethylbenzene

E) 1,3-dimethylbenzene

Diff: 2

Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names

7) Identify the IUPAC name for the following compound.

A) 5-bromophenol

B) 3-bromophenol

C) 5-bromoaniline

D) 3-bromoaniline

E) 1-bromophenol

Diff: 2

Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names

8) Which of the following is another name for 4-chlorobenzaldehyde?

A) o-chlorobenzaldehyde

B) m-chlorobenzaldehyde

C) p-chlorobenzaldehyde

D) m-chlorobenzenecarbaldehyde

E) anisole

Diff: 2

Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names

9) What is the IUPAC name for the following compound?

A) 5-bromo-4-nitroaniline

B) 5-bromo-p-nitroaniline

C) 1-bromo-2-nitroaniline

D) 3-bromo-4-nitroaniline

E) p-nitro-m-bromoaniline

Diff: 2

Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names

10) Identify the correct structure for 4-amino-2-chlorophenol.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names

11) What is the correct order of the names for the following compound?

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

B) I = naphthalene; II = phenanthrene; III = anthracene

C) I = phenanthrene; II = anthracene; III = naphthalene

D) I = phenanthrene; II = naphthalene; III = anthracene

E) I = anthracene; II = phenanthrene; III = naphthalene

Diff: 2

Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names

12) What is the IUPAC name for the following compound?

A) 3,4-dichloroaniline

B) 2,4-dichloroaniline

C) 2,5-dichloroaniline

D) 3,6-dichloroaniline

E) 2,6-dichloroaniline

Diff: 2

Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names

13) What is the IUPAC name for the following compound?

A) 4-butylphenol

B) 1-sec-butylphenol

C) 4-propylphenol

D) 4-sec-butylphenol

E) 1-isobutylphenol

Diff: 2

Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names

14) What is the IUPAC name for the following compound?

A) 6-ethyl-3-nitrobenzoic acid

B) 2-ethyl-5-nitrobenzoic acid

C) 1-ethyl-4-nitrobenzoic acid

D) 2-ethyl-5-nitrobenzaldehyde

E) 4-nitro-3-carboxyethylbenzene

Diff: 2

Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names

15) Identify the structure of 4-amino-2-bromophenol.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names

16) In nomenclature when the benzene ring is treated as a substituent, it is named a(n) ________ group.

A) phenol

B) benzenyl

C) benzyl

D) aryl

E) phenyl

Diff: 1

Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names

17) Identify the structure of acetophenone.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names

18) What is the common name for the following compound?

A) m-toluene

B) p-toluene

C) o-styrene

D) m-xylene

E) o-xylene

Diff: 2

Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names

19) Identify the structure of 1,3-diphenylbutane.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names

20) Identify the structure of p-aminobenzoic acid (PABA).

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names

21) What is the IUPAC name for the following compound?

A) 5-ethyl-4-fluoro-3-methylbenzaldehyde

B) 2-ethyl-4-fluoro-5-methylbenzaldehyde

C) 3-carbaldehyde-4-ethyl-6-fluorotoluene

D) o-ethyl-p-fluoro-m-methylbenzaldehyde

E) 1-ethyl-3-fluoro-4-methyl-6-benzaldehyde

Diff: 2

Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names

22) What is the IUPAC name for the following compound?

A) 3-(chloromethyl)-6-methoxy-2-nitrobenzene

B) 4-methoxy-3-nitro-chlorotoluene

C) p-(chloromethyl)-o-nitroanisole

D) 3-(chloromethyl)-1-nitroanisole

E) 4-(chloromethyl)-2-nitroanisole

Diff: 2

Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names

23) What is the IUPAC name for the following compound?

A) benzene

B) phenanthrene

C) napththalene

D) xylene

E) anthracene

Diff: 2

Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names

24) Identify the structure of styrene.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names

25) Identify the structure of 3-isobutyl-5-isopropylaniline.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names

26) Identify the scientist credited with proposing the structure of benzene.

A) Erich Hückel

B) Victor Grignard

C) Vladimir Markovnikov

D) Robert Woodward

E) August Kekulé

Diff: 1

Learning Objective: 17.3 Describe the structure of benzene, and explain why the structure cannot be shown in a single drawing

27) Which of the following describes the current view of the two Kekulé structures for benzene?

A) they are both correct structures for benzene

B) the two structures are in equilibrium

C) the two are conformational isomers of benzene

D) the true structure of benzene is a resonance hybrid of the two structures

E) the two structures represent constitutional isomers of benzene

Diff: 1

Learning Objective: 17.3 Describe the structure of benzene, and explain why the structure cannot be shown in a single drawing

28) The carbon-carbon bonds in benzene are ________.

A) of equal length and are longer than an isolated double bond

B) of equal length and are midway between a single bond and a double bond

C) of equal length and are shorter than a typical single bond

D) of unequal length and alternate as single and double bonds

E) in fluctuation of length between that of a double bond and a single bond

Diff: 1

Learning Objective: 17.3 Describe the structure of benzene, and explain why the structure cannot be shown in a single drawing

29) The difference between the amount of heat actually released upon the hydrogenation of benzene and that calculated for the hydrogenation of an imaginary cyclohexatriene is called the ________ of benzene.

A) stabilization energy

B) hydrogenation energy

C) Hückel number

D) antibonding MO

E) nonbonding MO

Diff: 1

Learning Objective: 17.4 Explain the cause of stability for benzene, and describe the requirements for this unusual stability

30) Molecular orbitals of equal energy are referred to as ________ orbitals.

A) nonbonding

B) degenerate

C) antibonding

D) hybridized

E) bonding

Diff: 1

Learning Objective: 17.4 Explain the cause of stability for benzene, and describe the requirements for this unusual stability

31) According to the molecular orbital theory, how many molecular orbitals are formed when the six p-orbitals of benzene combine?

A) 6

B) 5

C) 4

D) 3

E) 2

Diff: 2

Learning Objective: 17.4 Explain the cause of stability for benzene, and describe the requirements for this unusual stability

32) According to molecular orbital theory, how many π-bonding molecular orbitals does benzene have?

A) 1

B) 2

C) 3

D) 4

E) 5

Diff: 2

Learning Objective: 17.4 Explain the cause of stability for benzene, and describe the requirements for this unusual stability

33) According to molecular orbital theory, how many π-antibonding molecular orbitals does benzene have?

A) 1

B) 2

C) 3

D) 4

E) 5

Diff: 2

Learning Objective: 17.4 Explain the cause of stability for benzene, and describe the requirements for this unusual stability

34) According to molecular orbital theory, how many non-bonding molecular orbitals does benzene have?

A) 0

B) 1

C) 2

D) 3

E) 4

Diff: 2

Learning Objective: 17.4 Explain the cause of stability for benzene, and describe the requirements for this unusual stability

35) For a compound to be aromatic, it must have a planar cyclic conjugated π system along with a(n) ________ number of electron pairs/π-bonds.

A) even

B) odd

C) whole

D) prime

E) integer

Diff: 1

Learning Objective: 17.4 Explain the cause of stability for benzene, and describe the requirements for this unusual stability

36) Which one of the following statements is not true for a compound to be considered as aromatic?

A) The compound must be cyclic and planar.

B) The compound must be monocyclic.

C) The compound contains a ring comprised of continuously overlapping p orbitals.

D) The compound must satisfy Hückel's rule — must have (4n + 2) π electrons.

E) May contain both E and Z bonds within the ring.

Diff: 1

Learning Objective: 17.4 Explain the cause of stability for benzene, and describe the requirements for this unusual stability

37) What is the main difference between an aromatic and antiaromatic compound?

A) Aromatic compounds must be cyclic and planar, but not antiaromatic compounds.

B) Aromatic compounds must be monocyclic.

C) Antiaromatic compounds must contain a ring comprised of continuously overlapping p orbitals.

D) Aromatic compounds must satisfy Hückel's rule.

E) Antiaromatic compounds tend to be more stable that aromatic compounds.

Diff: 1

Learning Objective: 17.4 Explain the cause of stability for benzene, and describe the requirements for this unusual stability

38) Identify the number of π electrons present in an antiaromatic compound.

A) 4n + 2

B) 2n + 2

C) 4n

D) 3n

E) 2n - 2

Diff: 1

Learning Objective: 17.4 Explain the cause of stability for benzene, and describe the requirements for this unusual stability

39) Identify the number of π electrons present in an aromatic compound.

A) 4n + 2

B) 2n + 2

C) 2n

D) 3n

E) 4n

Diff: 1

Learning Objective: 17.4 Explain the cause of stability for benzene, and describe the requirements for this unusual stability

40) Identify the molecular orbital energy diagram for the cyclopropenyl anion, shown in the box below, and predict if it is aromatic, antiaromatic, or nonaromatic.

A) molecular orbital energy diagram (I); aromatic

B) molecular orbital energy diagram (II); aromatic

C) molecular orbital energy diagram (I); antiaromatic

D) molecular orbital energy diagram (II); antiaromatic

E) molecular orbital energy diagram (I); nonaromatic

Diff: 2

Learning Objective: 17.4 Explain the cause of stability for benzene, and describe the requirements for this unusual stability

41) Identify the molecular orbital energy diagram for the cyclopentadienyl anion, shown in the box below, and predict if it is aromatic, antiaromatic, or nonaromatic.

A) molecular orbital energy diagram (I); aromatic

B) molecular orbital energy diagram (II); aromatic

C) molecular orbital energy diagram (I); antiaromatic

D) molecular orbital energy diagram (II); antiaromatic

E) molecular orbital energy diagram (I); nonaromatic

Diff: 2

Learning Objective: 17.4 Explain the cause of stability for benzene, and describe the requirements for this unusual stability

42) Identify the molecular orbital energy diagram for the tropylium anion, shown in the box below, and predict if it is aromatic, antiaromatic, or nonaromatic.

A) molecular orbital energy diagram (I); aromatic

B) molecular orbital energy diagram (II); aromatic

C) molecular orbital energy diagram (I); antiaromatic

D) molecular orbital energy diagram (II); antiaromatic

E) molecular orbital energy diagram (I); nonaromatic

Diff: 2

Learning Objective: 17.4 Explain the cause of stability for benzene, and describe the requirements for this unusual stability

43) Identify the structure of phenol.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names

44) Identify from the following compounds which one is aromatic.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.5 Identify aromatic compounds other than benzene

45) Identify from the following compounds which one is antiaromatic.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.5 Identify aromatic compounds other than benzene

46) Identify from the following compounds which one is nonaromatic.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.5 Identify aromatic compounds other than benzene

47) Identify from the following compounds which one is aromatic.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.5 Identify aromatic compounds other than benzene

48) Identify from the following compounds which one is nonaromatic.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.5 Identify aromatic compounds other than benzene

49) Identify from the following compounds which one is aromatic.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.5 Identify aromatic compounds other than benzene

50) Identify from the following compounds which one is antiaromatic.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.5 Identify aromatic compounds other than benzene

51) Identify from the following compounds which one is aromatic.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.5 Identify aromatic compounds other than benzene

52) Identify from the following compounds which one is antiaromatic.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.5 Identify aromatic compounds other than benzene

53) Identify which of the following annulenes is not aromatic.

A) [6]-annulene

B) [14]-annulene

C) [16]-annulene

D) [18]-annulene

E) [22]-annulene

Diff: 2

Learning Objective: 17.5 Identify aromatic compounds other than benzene

54) Identify the structure that is not an annulene.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 17.5 Identify aromatic compounds other than benzene

55) Identify the structure that is an annulene.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 17.5 Identify aromatic compounds other than benzene

56) For the following molecules classify them as aromatic, antiaromatic, or nonaromatic.

A) I = aromatic; II = antiaromatic

B) I = nonaromatic; II = aromatic

C) I = antiaromatic; II = nonaromatic

D) I = nonaromatic; II = antiaromatic

E) I = aromatic; II = nonaromatic

Diff: 2

Learning Objective: 17.5 Identify aromatic compounds other than benzene

57) For the following molecules classify them as aromatic, antiaromatic, or nonaromatic.

A) I = aromatic; II = antiaromatic

B) I = nonaromatic; II = aromatic

C) I = antiaromatic; II = nonaromatic

D) I = nonaromatic; II = antiaromatic

E) I = aromatic; II = nonaromatic

Diff: 2

Learning Objective: 17.5 Identify aromatic compounds other than benzene

58) For the following molecules classify them as aromatic, antiaromatic, or nonaromatic.

A) I = aromatic; II = antiaromatic

B) I = nonaromatic; II = aromatic

C) I = antiaromatic; II = nonaromatic

D) I = nonaromatic; II = antiaromatic

E) I = aromatic; II = nonaromatic

Diff: 2

Learning Objective: 17.5 Identify aromatic compounds other than benzene

59) For the following molecules classify them as aromatic, antiaromatic, or nonaromatic.

A) I = aromatic; II = antiaromatic

B) I = nonaromatic; II = aromatic

C) I = antiaromatic; II = aromatic

D) I = nonaromatic; II = antiaromatic

E) I = aromatic; II = nonaromatic

Diff: 2

Learning Objective: 17.5 Identify aromatic compounds other than benzene

60) For the following molecules classify them as aromatic, antiaromatic, or nonaromatic.

A) I = aromatic; II = antiaromatic

B) I = nonaromatic; II = aromatic

C) I = antiaromatic; II = nonaromatic

D) I = aromatic; II = nonaromatic

E) I = nonaromatic; II = antiaromatic

Diff: 2

Learning Objective: 17.5 Identify aromatic compounds other than benzene

61) For the following molecule classify it is as aromatic, antiaromatic, or nonaromatic, and identify the best supporting explanation.

A) nonaromatic; there are only two conjugated double bonds

B) antiaromatic; it only has 2 π bonds

C) aromatic; there are two π bonds and a lone pair on the nitrogen atom

D) nonaromatic; the protonated nitrogen is sp3 hybridized so there is no continuous p orbital system

E) antiaromatic; the compound has 4n π electrons

Diff: 3

Learning Objective: 17.5 Identify aromatic compounds other than benzene

62) For the following molecule classify it is as aromatic, antiaromatic, or nonaromatic, and identify the best supporting explanation.

A) aromatic; cylic conjugated system with Hückel's number of π electrons

B) antiaromatic; it only has 3 π bonds

C) aromatic; there is a p orbital on every atom in the ring

D) antiaromatic; the compound has 4n π electrons when counting the lone pair on the nitrogen atom

E) nonaromatic; the nitrogen is sp3 hybridized to avoid the instability associated antiaromaticity

Diff: 3

Learning Objective: 17.5 Identify aromatic compounds other than benzene

63) For the following molecule classify it is as aromatic, antiaromatic, or nonaromatic, and identify the best supporting explanation.

A) aromatic; cylic conjugated system with Hückel's number of π electrons

B) antiaromatic; it only has 4 π bonds

C) nonaromatic; there is not a continuous system of π electrons due to the NH

D) antiaromatic; the compound has 4n π electrons

E) aromatic; there is a p orbital on every atom in the rings

Diff: 3

Learning Objective: 17.5 Identify aromatic compounds other than benzene

64) For the following molecules classify them as aromatic, antiaromatic, or nonaromatic.

A) I = aromatic; II = antiaromatic

B) I = aromatic; II = aromatic

C) I = antiaromatic; II = nonaromatic

D) I = nonaromatic; II = nonaromatic

E) I = aromatic; II = nonaromatic

Diff: 2

Learning Objective: 17.5 Identify aromatic compounds other than benzene

65) Identify the structure of anisole.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names

66) Identify which of the following compounds is most acidic.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.5 Identify aromatic compounds other than benzene

67) Identify the structure of aniline.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 17.2 Describe how benzene derivatives are named, including the use of common names

68) Identify which of the following compounds is most acidic.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.5 Identify aromatic compounds other than benzene

69) Identify which of the following compounds is most acidic along with the best supporting explanation.

A) (I) is more acidic as the resulting conjugate base is an aromatic anion.

B) (II) is more acidic as the resulting conjugate base is an aromatic anion.

C) (I) is more acidic because the compound has two pi bonds.

D) (II) is more acidic due to the large angle strain in the cyclopropene.

E) (I) is more acidic due to less angle strain in the cyclopentadiene.

Diff: 2

Learning Objective: 17.5 Identify aromatic compounds other than benzene

70) Both pyridine and pyrrole are nitrogen containing aromatic heterocyclic compounds. When treated with HCl, only pyridine forms a hydrochloride salt, whereas pyrrole is unreactive. Which of the following is not a valid explanation for this observed reactivity?

A) The lone pair on pyridine is not part of the aromatic system.

B) The lone pair on pyridine can be protonated without disrupting the aromatic stability.

C) The lone pair on pyrrole is sp3 hybridized and is less prone to protonation.

D) Protonation of pyrrole leads to a nonaromatic cation, which is less stable.

E) The lone pair on pyrrole is involved in making the compound aromatic and thus is less susceptible to protonation.

Diff: 2

Learning Objective: 17.5 Identify aromatic compounds other than benzene

71) The pKa of cyclopentadiene (I) and cycloheptatriene (II) are around 16 and 36 respectively. Which of the following is not a valid explanation for the large difference in the two pKa values?

A) The conjugate base of cyclopentadiene (I) is an aromatic anion.

B) The conjugate base of cycloheptatriene (I) is a nonaromatic anion.

C) If the conjugate base of cycloheptatriene (II) was flat it would be antiaromatic.

D) The conjugate base of cycloheptatriene (II) is less stable due to aromaticity.

E) The conjugate base of cyclopentadiene (I) is more stable due to aromaticity.

Diff: 2

Learning Objective: 17.5 Identify aromatic compounds other than benzene

72) Identify which of the following molecules would undergo the fastest SN1 reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.5 Identify aromatic compounds other than benzene

73) Identify which of the following compounds would undergo the fastest SN1 reaction along with the best supporting explanation.

A) (I) would undergo the fastest SN1 reaction because it would form a stable aromatic carbocation intermediate.

B) (II) would undergo the fastest SN1 reaction because it has less angle strain than the cyclopropene.

C) (III) would undergo the fastest SN1 reaction because it forms a resonance stabilized carbocation intermediate.

D) (I) would undergo the fastest SN1 reaction because it has the greatest amount of angle strain.

E) (III) would undergo the fastest SN1 reaction because it has the no angle strain since it is acyclic.

Diff: 2

Learning Objective: 17.5 Identify aromatic compounds other than benzene

74) Identify the hydrocarbon with the highest total aromatic stabilization energy.

A) phenanthrene

B) benzene

C) naphthalene

D) anthracene

E) cyclopentadiene

Diff: 2

Learning Objective: 17.5 Identify aromatic compounds other than benzene

75) Identify the hydrocarbon with the highest aromatic stabilization energy per ring.

A) phenanthrene

B) benzene

C) naphthalene

D) anthracene

E) cyclopentadiene

Diff: 2

Learning Objective: 17.5 Identify aromatic compounds other than benzene

76) Provide the reagent(s) necessary to convert toluene to benzoic acid.

A) Na2Cr2O7/H2SO4/H2O

B) 1. NBS, Δ; 2. NaOH

C) 1. LiAlH4; 2. H3O+

D) H2, Pd

E) 1. CO2; 2. H3O+

Diff: 2

Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position

77) Identify the expected major product of the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position

78) Identify the expected major product of the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position

79) Identify the expected major product of the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position

80) Identify the expected major product of the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position

81) Identify the expected major product of the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position

82) Identify the expected major product of the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position

83) Identify the expected major product of the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position

84) Identify the expected major product of the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position

85) Identify the reagents, in correct order, expected to accomplish the following transformation.

A) 1. PCC; 2. NaCN

B) 1. KCN; 2. Br2

C) 1. NBS/Δ; 2. NaCN

D) 1. H2SO4/Δ; 2. HCN

E) 1. Na2Cr2O7/H2SO4/H2O; 2. KCN

Diff: 2

Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position

86) Identify the reagents, in correct order, expected to accomplish the following transformation.

A) 1. H2SO4; 2. HBr/ROOR; 3. HOEt

B) 1. NBS/Δ; 2. NaOEt

C) 1. NaOEt; 2. Br2

D) 1. NBS/Δ; 2. NaOH; 3. HOEt

E) 1. Na2Cr2O7/H2SO4/H2O; 2. NaOH; 3. EtBr

Diff: 2

Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position

87) Identify the reagents, in correct order, expected to accomplish the following transformation.

A) 1. H2SO4; 2. HBr/ROOR; 3. CH3OH

B) 1. NBS/Δ; 2. NaOCH3

C) 1. NaOH; 2. CH3OH

D) 1. CH3OH; 2. Br2

E) 1. NBS/Δ; 2. CH3OH, 25°C

Diff: 2

Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position

88) Identify the reagents, in correct order, expected to convert ethylbenzene to styrene.

A) 1. H2SO4; 2. HBr/ROOR; 3. NaOCH2CH3

B) 1. NaOH; 2. Br2

C) 1. TsCl, pyr; 2. t-BuOK

D) 1. NBS/Δ; 2. NaOCH2CH3

E) 1. NBS/Δ; 2. CH3CH2OH, 25°C

Diff: 3

Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position

89) Identify the reagents, in correct order, expected to accomplish the following transformation.

A) 1. NBS/Δ; 2. NaOCH2CH3

B) 1. TsCl, pyr; 2. t-BuOK

C) 1. NBS/Δ; 2. CH3CH2OH, 25°C

D) 1. HBr; 2. t-BuOK

E) 1. H2SO4

Diff: 2

Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position

90) Place the reagents below in the correct order necessary to accomplish the transformation shown in the box.

A) I then II then III then IV then V

B) V then I then II then IV then III

C) I then III then V then II then IV

D) IV then II then IV then III then I

E) V then IV then II then I then III

Diff: 3

Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position

91) Identify the structure of intermediate A expected from the following reaction sequence.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position

92) Identify the structure of intermediate A expected from the following reaction sequence.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position

93) Identify the expected product of the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction

94) Identify the expected major product of the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction

95) Identify the expected major product of the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction

96) Identify the expected major product of the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction

97) Identify the expected major product of the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction

98) Identify the expected major product of the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction

99) Identify the expected major product of the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction

100) Identify the expected major product of the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction

101) Identify the expected major product of the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction

102) Identify the expected major product of the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction

103) Identify the expected major product of the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction

104) Identify the expected major product of the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction

105) Identify the expected major product of the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction

106) Place the reagents below in the correct order necessary to accomplish the transformation shown in the box.

A) I then II then IV then V then III

B) V then III then I then IV then II

C) III Then IV then II then V then I

D) V then II then I then III then IV

E) II then V then I then IV then III

Diff: 3

Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position

107) Place the reagents below in the correct order necessary to accomplish the transformation shown in the box.

A) I then II then IV then III

B) II then IV then III then I

C) I then IV then II then III

D) II then I then III then IV

E) III then I then II then IV

Diff: 3

Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction

108) Place the reagents below in the correct order necessary to accomplish the transformation shown in the box.

A) I then II then IV then III

B) II then IV then III then I

C) I then IV then II then III

D) II then I then III then IV

E) III then I then II then IV

Diff: 3

Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction

109) The three isomers of dimethylbenzene are commonly named o-xylene, m-xylene, p-xylene. These three isomers are difficult to distinguish using 1H NMR, but are readily identified using 13C NMR. Which of the following observations is correct in identifying an isomer of xylene using 13C NMR?

A) In the proton-decoupled 13C NMR spectra o-xylene will display 5 peaks.

B) In the proton-decoupled 13C NMR spectra m-xylene will display 4 peaks.

C) In the proton-decoupled 13C NMR spectra p-xylene will display 3 peaks.

D) In the proton-decoupled 13C NMR spectra p-xylene will display 4 peaks.

E) In the proton-decoupled 13C NMR spectra o-xylene will display 3 peaks.

Diff: 2

Learning Objective: 17.8 Describe the signals produced by aromatic compounds in IR, 1H NMR, and 13C NMR spectroscopy

110) Which one of the following compounds would exhibit seven signals in its 13CNMR spectrum?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.8 Describe the signals produced by aromatic compounds in IR, 1H NMR, and 13C NMR spectroscopy

111) Which of the following isomers of tribromoaniline will show two doublets with 7.5Hz coupling constants in an 1H NMR spectrum?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.8 Describe the signals produced by aromatic compounds in IR, 1H NMR, and 13C NMR spectroscopy

112) Identify the structure with molecular formula C8H9Br that is consistent with the following 1H NMR spectroscopic data.

1H NMR: 2.8 ppm (triplet, I = 2H), 4.65 ppm (triplet, I = 2H), 7.2 ppm (multiplet, I = 5H)

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.8 Describe the signals produced by aromatic compounds in IR, 1H NMR, and 13C NMR spectroscopy

113) Identify the structure with molecular formula C9H9ClO that is consistent with the following spectroscopic data.

IR: 1680 cm-1

1H NMR: 3.5 ppm (triplet, I = 2H), 4.0 ppm (triplet, I = 2H), 7.4 ppm (triplet, I = 2H), 7.6 ppm (triplet, I = 1H), 7.9 ppm (doublet, I = 2H)

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.8 Describe the signals produced by aromatic compounds in IR, 1H NMR, and 13C NMR spectroscopy

114) Identify the structure with molecular formula C9H12 that is consistent with the following spectroscopic data.

1H NMR: 1.2 ppm (doublet, I = 6H), 3.0 ppm (septet, I = 1H), 7.1 ppm (multiplet, I = 5H)

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.8 Describe the signals produced by aromatic compounds in IR, 1H NMR, and 13C NMR spectroscopy

115) Identify the structure with molecular formula C10H12O2 that is consistent with the following spectroscopic data.

IR: 1680 cm-1, 2750 cm-1, 2850 cm-1

1H NMR: 1.1 ppm (triplet, I = 3H), 3.5 ppm (quartet, I = 2H), 4.5 ppm (singlet, I = 2H), 7.3 ppm (doublet, I = 2H), 7.7 ppm (doublet, I = 2H), 9.9 ppm (singlet, I = 1H)

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 17.8 Describe the signals produced by aromatic compounds in IR, 1H NMR, and 13C NMR spectroscopy

116) The following compound shows signals at 190.7, 140.9, 134.8, 130.9 and 129.5 ppm in its broadband decoupled C-13 spectrum. Assign the signals to the indicated carbon atoms in the structure below.

A) I = 109.7; II = 130.9; III = 134.8; IV = 140.9; V = 129.5

B) I = 190.7; II = 134.8; III = 129.5; IV = 130.9; V = 140.9

C) I = 134.8; II = 130.9; III = 129.5; IV = 140.9; V = 190.7

D) I = 129.5; II = 140.9; III = 190.7; IV = 130.9; V = 134.8

E) I = 140.9; II = 129.5; III = 130.9; IV = 134.8; V = 190.7

Diff: 3

Learning Objective: 17.8 Describe the signals produced by aromatic compounds in IR, 1H NMR, and 13C NMR spectroscopy

117) A compound with molecular formula C9H12O displays the following 1H NMR and 13C NMR spectra. Identify the structure consistent with this information.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.8 Describe the signals produced by aromatic compounds in IR, 1H NMR, and 13C NMR spectroscopy

118) A compound with molecular formula C10H14 displays the following IR, 1H NMR, 13C NMR spectra. Identify the structure consistent with this information.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.8 Describe the signals produced by aromatic compounds in IR, 1H NMR, and 13C NMR spectroscopy

119) Identify which of the following compounds is least acidic along with the best supporting explanation.

A) (I) is less acidic as the resulting conjugate base is an antiaromatic anion.

B) (II) is less acidic as the resulting conjugate base is an antiaromatic anion.

C) (I) is less acidic because the compound has two pi bonds.

D) (II) is less acidic due to the large angle strain in the cyclopropene.

E) (I) is less acidic due to less angle strain in the cyclopentadiene.

Diff: 2

Learning Objective: 17.5 Identify aromatic compounds other than benzene

120) Identify the structure of intermediate B expected from the following reaction sequence.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position

121) Identify the structure of intermediate C expected from the following reaction sequence.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position

122) Identify the structure of the product D expected from the following reaction sequence.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position

123) Identify the structure of intermediate B expected from the following reaction sequence.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position

124) Identify the structure of intermediate C expected from the following reaction sequence.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position

125) Identify the structure of the product D expected from the following reaction sequence.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 17.6 Predict the products of reactions that can occur at the benzylic position

126) Identify the expected major product of the following reaction.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 17.7 Draw a mechanism and predict the products of a Birch reduction

127) Place the reagents below in the correct order necessary to accomplish the transformation shown in the box.

A) I then II then III

B) III then II then I

C) I then III then II

D) II then I then III

E) III then I then II

Diff: 3

Learning Objective: 17.8 Describe the signals produced by aromatic compounds in IR, 1H NMR, and 13C NMR spectroscopy

128) The three isomers of dimethylbenzene are commonly named o-xylene, m-xylene, p-xylene. These three isomers are difficult to distinguish using 1H NMR, but are readily identified using 13C NMR. Which of the following observations is correct in identifying an isomer of xylene using 13C NMR?

A) In the proton-decoupled 13C NMR spectra p-xylene will display 5 peaks.

B) In the proton-decoupled 13C NMR spectra m-xylene will display 4 peaks.

C) In the proton-decoupled 13C NMR spectra o-xylene will display 3 peaks.

D) In the proton-decoupled 13C NMR spectra o-xylene will display 4 peaks.

E) In the proton-decoupled 13C NMR spectra p-xylene will display 4 peaks.

Diff: 2

Learning Objective: 17.8 Describe the signals produced by aromatic compounds in IR, 1H NMR, and 13C NMR spectroscopy

129) The three isomers of dimethylbenzene are commonly named o-xylene, m-xylene, p-xylene. These three isomers are difficult to distinguish using 1H NMR, but are readily identified using 13C NMR. Which of the following observations is correct in identifying an isomer of xylene using 13C NMR?

A) In the proton-decoupled 13C NMR spectra m-xylene will display 5 peaks.

B) In the proton-decoupled 13C NMR spectra p-xylene will display 4 peaks.

C) In the proton-decoupled 13C NMR spectra o-xylene will display 3 peaks.

D) In the proton-decoupled 13C NMR spectra m-xylene will display 4 peaks.

E) In the proton-decoupled 13C NMR spectra o-xylene will display 5 peaks.

Diff: 2

Learning Objective: 17.8 Describe the signals produced by aromatic compounds in IR, 1H NMR, and 13C NMR spectroscopy

130) The three isomers of dimethylbenzene are commonly named o-xylene, m-xylene, p-xylene. These three isomers can be readily identified using 13C NMR. How many signals would be expected in the proton-decoupled 3C NMR spectra of p-xylene?

A) 1 peak

B) 2 peaks

C) 3 peaks

D) 4 peaks

E) 5 peaks

Diff: 2

Learning Objective: 17.8 Describe the signals produced by aromatic compounds in IR, 1H NMR, and 13C NMR spectroscopy

131) The three isomers of dimethylbenzene are commonly named o-xylene, m-xylene, p-xylene. These three isomers can be readily identified using 13C NMR. How many signals would be expected in the proton-decoupled 3C NMR spectra of m-xylene?

A) 1 peak

B) 2 peaks

C) 3 peaks

D) 4 peaks

E) 5 peaks

Diff: 2

Learning Objective: 17.8 Describe the signals produced by aromatic compounds in IR, 1H NMR, and 13C NMR spectroscopy

132) The three isomers of dimethylbenzene are commonly named o-xylene, m-xylene, p-xylene. These three isomers can be readily identified using 13C NMR. How many signals would be expected in the proton-decoupled 3C NMR spectra of o-xylene?

A) 1 peak

B) 2 peaks

C) 3 peaks

D) 4 peaks

E) 5 peaks

Diff: 2

Learning Objective: 17.8 Describe the signals produced by aromatic compounds in IR, 1H NMR, and 13C NMR spectroscopy

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