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W Aroma 1 All PDF
W Aroma 1 All PDF
Name___________________________________
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
2) Why does benzene undergo a substitution reaction with Br2 while cyclohexene undergoes an addition reaction.
3) What is suggested by the fact that benzene's molar heat of hydrogenation is 36 kcal less than three times the
molar heat of hydrogenation of cyclohexene?
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
5) In the molecular orbital representation of benzene, how many π molecular orbitals are present? 5)
A) 8 B) 1 C) 2 D) 6 E) 4
6) How many distinct nodal planes which are perpendicular to the molecular plane are present in the 6)
π4 * orbital of benzene?
A) 0 B) 1 C) 2 D) 4 E) 5
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
7) Provide a diagram which depicts the relative energies of the π molecular orbitals of 7)
benzene. Show which molecular orbitals are filled in benzene's ground state.
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
9) Show how the participating p orbitals interact to form the highest energy π molecular orbital of benzene.
10) List the criteria which compounds must meet in order to be considered aromatic.
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MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
16) Provide the major resonance structures of the ion which results when the most acidic hydrogen of
cyclopentadiene is lost.
17) Explain the relative acidities of cyclohexene (pKa of 46) and cyclopentadiene (pKa of 16).
18) Why would the reaction below proceed at an extremely slow rate if at all?
19) When cycloheptatriene is deprotonated, an anion with seven resonance forms of equal energy can be drawn.
Given this fact, explain why cycloheptatriene is only slightly more acidic than propene.
20) 3-Chlorocyclopropene is solvolyzed in methanol at a much higher rate than is chlorocyclopropane. Offer an
explanation.
21) Classify 1,3,5-heptatriene as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.
22) Classify cyclopentadienyl cation as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.
23) Classify cyclopropenyl cation as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network
24) Classify cycloheptatrienyl cation as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.
25) Classify naphthalene as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.
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26) Classify pyridine as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.
27) Classify the compound below as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.
28) Classify the compound below as aromatic antiaromatic, or nonaromatic. Assume planarity of the π network.
29) Classify the compound below as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.
30) Classify cycloheptatriene as aromatic antiaromatic, or nonaromatic. Assume planarity of the π network.
31) Classify cyclopentadiene as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.
33) Why are researchers interested in the properties of large polynuclear aromatic hydrocrobons?
34) Provide the structure of the major organic product which results when phenanthrene is treated with Br2 in
carbon tetrachloride.
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36) Provide an acceptable name for the compound below.
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
46) Which of the following compounds has the lowest boiling point? 46)
A) 1,2,4-tirchlorobenzene
B) p-dichlorobenzene
C) 1,2,3-trichlorobenzene
D) o-dichlorobenzene
E) m-dichlorobenzene
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47) Which of the following compound has the highest melting point? 47)
A) toluene
B) p-dichlorobenzene
C) o-dichlorobenzene
D) benzene
E) m-dichlorobenzene
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
48) The IR spectrum of m-xylene contains stretches which are characteristic of most aromatic 48)
hydrocarbons. List the peaks (in cm-1) associated with the aromatic CC stretch and the
aromatic CH stretch.
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
49) In the proton NMR, in what region of the spectrum does one typically observe hydrogens bound to 49)
the aromatic ring?
A) 1.0-1.5 ppm
B) 2.0-3.0 ppm
C) 4.5-5.5 ppm
D) 7.0-8.0 ppm
E) 9.0-10.0 ppm
50) In the carbon NMR, in what region of the spectrum does one typically observe carbons which are 50)
part of the aromatic ring?
A) -10-0 ppm
B) 40-60 ppm
C) 80-100 ppm
D) 120-150 ppm
E) 200-220 ppm
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
51) How might one distinguish the isomers of trimethylbenzene by noise-decoupled 13C 51)
NMR?
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
52) Which of the following compounds has the most signals in the noise-decoupled 13C NMR 52)
spectrum?
A) o-dibromobenzene
B) m-dibromobenzene
C) 1,2,3,4-tetrabromobenzene
D) 1,3,5-tribromobenzene
E) p-dibromobenzene
53) In the mass spectrum of isobutylbenzene, the base peak occurs at m/z: 53)
A) 119 B) 105 C) 133 D) 91 E) 134
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
54) Describe the benzenoid band which appears in the UV-visible spectrum of most aromatic hydrocarbons.
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MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
55) In the UV-visible spectra of the following compounds, in which does lambda max appear at the 55)
highest wavelength?
A) isopropylbenzene
B) 1-phenylpropene
C) 3-phenylpropene
D) benzene
E) n-octylbenzene
57) Which of the following is another accepted name for methyl phenyl ketone? 57)
A) cresol
B) anisole
C) acetophenone
D) cresone
E) benzophenone
58) Which of the following undergoes SN2 reaction with sodium methoxide most rapidly? 58)
A) PhCH2CH2 Br
B) PhCH2Br
C) PhCH2CH2 CH2 Br
D) Ph3CBr
E) PhBr
59) Which of the following undergoes solvolysis in methanol most rapidly? 59)
A) Ph3CBr
B) PhCH2CH2 Br
C) PhCH2CH2 CH2 Br
D) PhCH2Br
E) PhBr
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
61) When cyclohexene is treated with KMnO4 , H2 O, the syn-1,2-diol is produced. What 61)
reaction occurs when benzene is similarly treated?
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MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
63) Classify pyrrole as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π 63)
network.
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
65) __________ is similar to furan, with a sulfur atom in place of the oxygen. 65)
ESSAY. Write your answer in the space provided or on a separate sheet of paper.
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
68) Which of the following is also an acceptable name for 3-nitrophenol? 68)
A) m-nitrophenol
B) p-nitrophenol
C) hydroquinone
D) 3-cresol
E) o-nitrophenol
69) Which of the following is also an acceptable name for 1,3,5-trimethylbenzene? 69)
A) 1,3,5-xylene
B) styrene
C) cumene
D) cymene
E) mesitylene
70) Which of the following is the same as the tropylium ion? 70)
A) cyclopropenyl anion
B) cyclopentadienyl cation
C) cyclopentadienyl anion
D) cycloheptatrienyl anion
E) cycloheptatrienyl cation
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SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
71) Classify the compound below as aromatic, antiaromatic, or nonaromatic. Assume 71)
planarity of the π network.
72) Classify the compound below as aromatic, antiaromatic, or nonaromatic. Assume 72)
planarity of the π network.
73) Classify the compound below as aromatic, antiaromatic, or nonaromatic. Assume 73)
planarity of the π network.
74) Classify the compound below as aromatic, antiaromatic, or nonaromatic. Assume 74)
planarity of the π network.
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75) Classify the compound below as aromatic, antiaromatic, or nonaromatic. Assume 75)
planarity of the π network.
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
81) What is the bond order of the carbon-carbon bonds in benzene? 81)
A) 0.5 B) 2 C) 1 D) 3 E) 1.5
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
82) Describe the occupied p molecular orbitals in the gound state of cyclobutadiene. 82)
83) What compound results when cyclooctatetraene is treated with excess potassium metal? 83)
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
84) Nitrogen's lone pair electrons occupy what type of orbital in pyridine? 84)
A) p B) s C) sp D) sp2 E) sp3
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SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
91) What is the major difference between an antiaromatic and aromatic compound? 91)
A) Aromatic compounds cannot have a charged atom in the structure
B) Antiaromatic compounds can assume a chair-like structure while aromatic compounds are
nearly flat
C) Antiaromatic compounds have at least one sp3 hybridized atom in the ring
D) Only aromatic compounds follow Huckle's rule.
E) The structure must be cyclic for aromatic but not antiaromatic compounds?
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92) Which of the following structures is aromatic? 92)
A)
B)
C)
D)
E)
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93) Which of the following structures, if flat, would be classified as antiaromatic? 93)
A)
B)
C)
D)
E)
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94) Which of the labeled H atoms (1 -5) in the following molecule would be predicted to be the most 94)
acidic?
A) 2 B) 3 C) 4 D) 1 E) 5
95) Rank the following in order of increasing pKa (from lowest to highest pKa) 95)
A) 1 < 2 < 3 B) 2 < 1 < 3 C) 3 < 2 < 1 D) 2 < 3 < 1 E) 3 < 1 < 2
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Answer Key
Testname: AROMA_1_ALL
1) E
2) Addition of Br2 to benzene is highly unfavorable because it would result in a nonaromatic product.
3) This suggests that the type of π bonding in benzene lends special stability to the molecule.
4) annulenes
5) D
6) C
7)
8) C
9) All adjacent interactions are antibonding.
22) antiaromatic
23) aromatic
24) aromatic
25) aromatic
26) aromatic
27) aromatic
28) aromatic
29) aromatic
30) nonaromatic
31) nonaromatic
32) Pyrrole is a much weaker base than pyridine. When pyrrole is protonated, the system's aromaticity is destroyed.
33) These compounds are formed to some extent in nearly all combustion reactions of organic compounds and are known
to be potent carcinogens.
34)
41)
42)
43)
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Answer Key
Testname: AROMA_1_ALL
44)
45)
46) B
47) B
48) CC: around 1600 cm-1
CH: just above 3000 cm-1 (usually around 3030 cm-1 )
49) D
50) D
51) 1,3,5-trimethylbenzene: 3 signals
1,2,4-trimethylbenzene: 9 signals
1,2,3-trimethylbenzene: 6 signals
52) B
53) D
54) Band centered at 254 nm; 3-6 small, sharp peaks; weak molar absorptivity.
55) B
56) A
57) C
58) B
59) A
60) A
61) No reaction takes place.
62) D
63) aromatic
64)
65) Thiophene
66)
76) 1,3,5-trinitrobenzene
77)
78)
79)
86)
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Answer Key
Testname: AROMA_1_ALL
87)
88)
89)
90)
91) D
92) E
93) E
94) D
95) B
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