Transcript
Chapter Eighteen Topic: Nomenclature Section: 18.2 Difficulty Level: Easy 1. A) B) C) D) E)
Toluene is the common name for: hydroxybenzene aminobenzene methylbenzene ethylbenzene methoxybenzene Ans: C
Topic: Nomenclature Section: 18.2 Difficulty Level: Medium 2. A) B) C) D) E)
Anisole is the common name for: hydroxybenzene aminobenzene methylbenzene ethylbenzene methoxybenzene Ans: E
Topic: Nomenclature Section: 18.2 Difficulty Level: Easy 3. A) B) C) D) E)
Phenol is the common name for: hydroxybenzene aminobenzene methylbenzene ethylbenzene methoxybenzene Ans: A
Topic: Nomenclature Section: 18.2 Difficulty Level: Medium
4. A) B) C) D) E)
o-xylene is the common name for: hydroxybenzene aminobenzene 1,2-dimethylbenzene ethylbenzene 1,3-dimethylbenzene Ans: C
Topic: Nomenclature Section: 18.2 Difficulty Level: Medium 5. What is the IUPAC name for for the following compound? OH
Br
A) B) C) D) E)
5-bromophenol 3-bromophenol 5-bromoaniline 3-bromoaniline 1-bromophenol Ans: B
Topic: Nomenclature Section: 18.2 Difficulty Level: Medium 6. Which of the following is another name for 4-chlorobenzaldehyde? A) B) C) D) E)
o-chlorobenzaldehyde m- chlorobenzaldehyde p-chlorobenzaldehyde styrene 1-chlorobenzaldehyde Ans: C
Topic: Nomenclature Section: 18.2 Difficulty Level: Hard
7. What is the IUPAC name for for the following compound? NH2
Br
NO2
A) B) C) D) E)
5-bromo-4-nitroaniline 5-bromo-p-nitroaniline 1-bromo-2-nitroaniline 3-bromo-4-nitroaniline p-nitro-m-bromoaniline Ans: D
Topic: Nomenclature Section: 18.2 Difficulty Level: Medium 8. What is the correct structure structure for 4-amino-2-chlorophenol? 4-amino-2-chlorophenol? NO2
NO2
Cl
I
OH
OH
Cl
II
OCH3
NH2
Cl
III
NH2
Cl
NH2
Cl
OH
IV
CH
V O
A) B) C) D) E)
I II III IV V Ans: D
Topic: Nomenclature Section: 18.2 Difficulty Level: Medium
9. What is the correct order of the names for the following compound?
I
A) B) C) D) E)
II
I-naphthalene; II-triphenyl; III-biphenyl I-naphthalene; II-phenanthrene; III-biphenyl I-biphenyl; II-anthracene; III-naphthalene I-naphthalene; II-anthracene; III-biphenyl I-biphenyl; IIII- phenanthrene; III-naphthalene Ans: C
Topic: Nomenclature Section: 18.2 Difficulty Level: Medium 10. What is the IUPAC name for for the following compound? NH2
Cl
Cl
A) B) C) D) E)
3,4-dichloroaniline 2,4-dichloroaniline 2,5-dichloroaniline 3,6-dichloroaniline 2,6-dichloroaniline Ans: C
Topic: Nomenclature Section: 18.2 Difficulty Level: Medium
III
11. What is the IUPAC name for for the following compound? OH
A) B) C) D) E)
4-butylphenol 1-sec-butylphenol 4-propylphenol 4-sec-butylphenol 1-isobutylphenol Ans: D
Topic: Nomenclature Section: 18.2 Difficulty Level: Medium 12. What is the IUPAC name for for the following compound? NO2
COH
O
A) B) C) D) E)
6-ethyl-3-nitrobenzoic acid 1-ethyl-4-nitrobenzoic acid 2-ethyl-5-nitrobenzoic acid 2-ethyl-5-nitrobenzaldehyde 4-nitro-3-carboxyethylbenzene Ans: C
Topic: Nomenclature Section: 18.2 Difficulty Level: Medium
13. What is the structure for 1,3-diphenylbutane? Ans:
Topic: Nomenclature Section: 18.2 Difficulty Level: Medium 14. What is the structure for p-aminobenzoic acid (PABA)? Ans:
NH2
COH
O
Topic: Nomenclature Section: 18.2 Difficulty Level: Hard 15. What is the IUPAC name for for the following compound? F
H
O
Ans: 2-ethyl-4-fluoro-5-methylbenzaldehyde
Topic: Nomenclature Section: 18.2 Difficulty Level: Medium
16. What is the IUPAC name for for the following compound? NO2
H3CO
Cl
Ans: 4-chloromethyl-2-nitroanisole
Topic: Nomenclature Section: 18.2 Difficulty Level: Medium 17. What is the IUPAC name for for the following compound?
Ans: Phenanthrene
Topic: Nomenclature Section: 18.2 Difficulty Level: Medium 18. What is the structure of styrene? Ans:
Topic: Nomenclature Section: 18.2 Difficulty Level: Medium
19. What is the structure for 3-isobutyl-5-isopropylaniline? NH2
Ans:
Topic: Nomenclature Section: 18.2 Difficulty Level: Medium 20. What is the structure for 4-amino-2-bromophenol? OH
OH
Br
NH2
I
A) B) C) D) E)
Br
Br
Br
Br
H2N
II
NH2
OCH3
OCH3
OH
III
V
IV NH2
NH2
I II III IV V Ans: B
Topic: Aromaticity, Hückel's Rule, MO theory & Frost circle Section: 18.4 Difficulty Level: Easy 21. Which one of the following statement 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 must have a conjugated system with with p orbital at every vertex D) The compound must satisfy Hückel’s rule –must have (4n + 2)π electrons. E) none of these Ans: B
Topic: Aromaticity, Hückel's Rule, MO theory & Frost circle Section: 18.4 Difficulty Level: Easy 22. What is the main difference between an aromatic and antiaromatic compound? A) B) C) D) E)
Aromatic compounds must be cyclic and planar, but not antiaromatic compounds Aromatic compounds must be monocyclic. Antiaromatic compounds must have a conjugated system system with p orbital at every vertex Aromatic compounds must satisfy satisfy Hückel’s rule. none of these Ans: D
Topic: Aromaticity, Hückel's Rule, MO theory & Frost circle Section: 18.4 Difficulty Level: Easy 23. The number of π electrons present in an antiaromatic compound: A) B) C) D) E)
4n + 2 2n + 2 4n none none of these Ans: C
Topic: Aromaticity, Hückel's Rule, MO theory & Frost circle Section: 18.4 Difficulty Level: Easy 24. The number of π electrons present in an aromatic compound: A) B) C) D) E)
4n + 2 2n + 2 4n none None of these Ans: A
Topic: Aromaticity, Hückel's Rule, MO theory & Frost circle Section: 18.4 Difficulty Level: Easy
25. Using a Frost circle, draw the molecular orbital energy diagram for the cyclopropenyl anion Ans:
and predict if it is aromatic.
∗
ψ
∗
ψ
2
Antibonding MO's
3
Energy
Nonbonding Nonbonding MO's Bonding MO's
ψ1
It is not aromatic. Topic: Aromaticity, Hückel's Rule, MO theory & Frost circle Section: 18.4 Difficulty Level: Medium 26. Using a Frost circle, draw the molecular orbital energy diagram for the cyclopentadienyl
anion Ans:
and predict if it is aromatic.
ψ
∗
ψ
4
∗
Antibonding MO's
5
Energy
Nonbonding MO's ψ
ψ3
2
ψ1
Bonding MO's
It is aromatic. Topic: Aromaticity, Hückel's Rule, MO theory & Frost circle Section: 18.4 Difficulty Level: Medium
27. Using a Frost circle, draw the molecular orbital energy diagram for the tropylium cation cation
and predict if it is aromatic. Ans:
∗
ψ
Energy
∗
ψ
6
∗
Antibonding MO's
7
∗
ψ
4
ψ
ψ
2
ψ3
ψ1
Nonbonding MO's
5
Bonding MO's
It is aromatic. Topic: Aromaticity, Hückel's Rule, MO theory & Frost circle Section: 18.4 Difficulty Level: Medium 28. Using a Frost circle, draw the molecular orbital energy diagram for the
cyclononatetraenyl cation Ans:
and predict if it is aromatic.
ψ
∗
∗
ψ
Energy
Antibonding MO's
∗
ψ
8
9
∗
ψ
6
7
ψ5
ψ4 ψ
ψ3
2
ψ1
It is not aromatic. Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Medium
Nonbonding MO's Bonding MO's
29. Which one of the following compound is is aromatic? S
O
II
I
A) B) C) D) E)
IV
III
I II III IV None of these Ans: D
Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Medium 30. Which one of the following compound is is antiaromatic? H N
N
I
A) B) C) D)
N H
H
H N
H N
N
III
II
I II III IV Ans: B
Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Medium
IV
31. Which one of the following compound is is nonaromatic? H N
N
III
I
A) B) C) D) E)
II
V
IV
I II III IV V Ans: B
Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Hard 32. Which one of the following compound is is aromatic?
I
A) B) C) D)
II
I II III IV Ans: C
Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Medium
III
IV
33. Which one of the following compound is is nonaromatic? O
H
O
H N B
CH3
N
II
I
A) B) C) D)
N
III
H
IV
I II III IV Ans: B
Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Hard 34. Which one of the following compound is is aromatic? O
H
O
H N B
CH3
N
I
A) B) C) D)
N
II
I II III IV Ans: A
Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Hard
III
H
IV
35. Which one of the following compound(s) is antiaromatic? O
H
O
H N B
CH3
N
II
I
A) B) C) D) E)
N
III
H
I II III IV III & IV Ans: E
Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Medium 36. Which one of the following compounds is aromatic? H
B
I
A) B) C) D)
H
O
N
II
III
I II III IV Ans: A
Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Medium
IV
IV
37. Which one of the following compounds is antiaromatic?
S
I
A) B) C) D) E)
O
II
N H
B H
II I
IV
V
I II III IV V Ans: IV
Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Easy 38. Classify the following following compound as aromatic, antiaromatic, or nonaromatic. Explain your choice.
O
Ans: Nonaromatic 3 It is cyclic, planar but not conjugated and one of the carbon atoms is sp hybridized. Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Easy 39. Classify the following following compound as aromatic, antiaromatic, or nonaromatic. Explain your choice.
S
Ans: Nonaromatic 3 It is cyclic, planar, but not conjugated and all the carbon atoms are sp hybridized Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Hard
40. Classify the following following compound as aromatic, antiaromatic, or nonaromatic. Explain your choice.
Ans: Aromatic It is cyclic, planar, conjugated and follows Hückel rule with 5 pairs of π electrons Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: medium 41. Classify the following following compound as aromatic, antiaromatic, or nonaromatic. Explain your choice. O
Ans: Antiaromatic It is cyclic, planar, conjugated but does not follow Hückel’s rule. It has 4 pairs p airs of π electrons Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Hard 42. Classify the following following compound as aromatic, antiaromatic, or nonaromatic. Explain your choice. O
Ans: Aromatic It is cyclic, planar, conjugated and follows Hückel’s rule with 3 pairs of π electrons Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: medium
43. Classify the following following compound as aromatic, antiaromatic, or nonaromatic. Explain your choice. H
N
H
N
Ans: nonaromatic 3 It is cyclic, planar but not conjugated conjuga ted and one of the nitrogen atoms is sp hybridized. Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Hard 44. Classify the following following compound as aromatic, antiaromatic, or nonaromatic. Explain your choice. O
N H
Ans: Antiaromatic It is cyclic, planar, conjugated but does not follow Hückel’s rule with 4 pairs of π electrons Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Hard 45. Classify the following following compound as aromatic, antiaromatic, or nonaromatic. Explain your choice. H N N N
Ans: Aromatic It is cyclic, planar, conjugated and follows Hückel’s rule with 5 pairs of π electrons Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Medium
46. Classify the following following compounds as aromatic, antiaromatic, or nonaromatic. Explain your choice.
O O
I
II
Ans: I. Aromatic It is cyclic, planar, conjugated and follows Hückel’s rule with 3 pairs of π electrons II. Antiaromatic It is cyclic, planar, conjugated but does not follow Hückel’s rule with 4 pairs of π electrons. Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Hard 47. Classify the following following compounds as aromatic, antiaromatic, or nonaromatic. Explain your choice. NH2
O
O N
N H
I
O
O
N H
II III
O
S
IV
Ans: I. Aromatic It is cyclic, planar, conjugated and follows Hückel’s rule with 3 pairs of π electrons II. Antiaromatic It is cyclic, planar, conjugated but does not follow Hückel’s rule with 4 pairs of π electrons. III. Aromatic It is cyclic, planar, conjugated and follows Hückel’s rule with 3 pairs of π electrons IV. Aromatic It is cyclic, planar, conjugated and follows Hückel’s rule with 3 pairs of π electrons
Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Easy
48. Which one of the following compounds is most acidic?
II
I
A) B) C) D) E)
IV
III
I II III IV none of these Ans: A
Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Easy 49. Which one of the following compounds is most acidic? H N
I
A) B) C) D) E)
H N
II
N
I II III I & III II & III Ans: C
Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Medium
N
III
50. Which one of the following compounds is most acidic? Explain your choice.
I
II
Ans: I. The conjugate base of cyclopentadiene is aromatic and is more stable Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Medium 51. Both pyridine and pyrrole are nitrogen containing aromatic heterocyclic compounds. When treated with HCl, only pyridine forms the h ydrochloride salt, where as pyrrole is unreactive. Provide an explanation for this observed reactivity.
N
Pyridine
N H
Pyrrole
Ans: In pyridine, the non bonding electron pair on nitrogen is not part of the aromatic sextet. So it is available for reaction with HCl, without disturbing the aromatic stability. In pyrrole, the non bonding electron pair on nitrogen is part of the aromatic sextet. Being part of the aromatic sextet it is not available for reaction with HCl. If it does react with HCl then it will form a cation c ation that is non aromatic, thus disturbing the aromatic stability. Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Medium
52. Which one of the following compounds will undergo the fastest S N1 reaction? Explain your choice. Br Br
Br
II
I
III
Br
IV
Ans: III The carbocation formed is aromatic and is more stable Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Medium 53. Which one of the following compounds will undergo the fastest S N1 reaction? Explain your choice. Cl
Cl
Cl
I
II
III
Ans: I The carbocation formed is aromatic and is more stable Topic: Reactions at the benzylic position Section: 18.6 Difficulty Level: Medium 54. Provide the reagent(s) necessary to convert toluene to benzoic acid. A) B) C) D) E)
Na2Cr 2O7/H2SO4/H2O 1. NBS, Δ, 2. ΝaΟΗ 1. KMnO4/NaOH/H2O, 2. H3O+ HNO3/H2SO4 + 1. CO2, 2. H3O Ans: A & C
Topic: Reactions at the benzylic position Section: 18.6 Difficulty Level: Medium
55. Provide the product for the following reaction?
Na2Cr 2O7/H2SO4/H2O excess
O
O
O
COH
COH
CH
COH
I
A) B) C) D) E)
II
O
COH
III O
I II III IV V Ans: B
Topic: Reactions at the benzylic position Section: 18.6 Difficulty Level: Hard
CCH3
IV
O
CH
V
O
56. Provide the product for the following reaction? Na2Cr 2O7/H2SO4/H2O excess
COH
COH
CH
CCH3
COH
CH
CCH3
O
I
A) B) C) D) E)
O
O
O
O
II
III
O
IV
O
O
V
O
I II III IV V Ans: B
Topic: Reactions at the benzylic position Section: 18.6 Difficulty Level: Medium 57. Provide the product for the following following reaction? Explain your answer.
excess 1. KMnO4/NaOH/H 2O 2. H3O
+
Ans:
COH
O
There is no hydrogen at the benzylic position with t-butyl group, so it d oes not undergo oxidation.
Topic: Reactions at the benzylic position Section: 18.6 Difficulty Level: Easy 58. Provide the structure of the major product(s) for the following reaction.
Cl2 hν
Cl
Cl
Cl
I
A) B) C) D) E)
II
Cl
I II III IV Both I and II Ans: D
Topic: Reactions at the benzylic position Section: 18.6 Difficulty Level: Medium
III Cl
IV
59. Provide the structure of the major product(s) for the following reaction. CH2 CH2CH3
Br 2 hν CH2CH2CH3
CH2CH2CH2Br
CH2CHBrCH3
CH2CH2CH3
CHBrCH2CH3
Br
I
A) B) C) D) E)
II
Br
I II III IV V Ans: E
Topic: Reactions at the benzylic position Section: 18.6 Difficulty Level: Medium
III
IV
V
60. Provide the structure of the major product(s) for the following reaction. Cl2 hν
Cl
Cl
II
I
Cl
III Cl
Cl
IV
A) B) C) D) E)
V
I II III IV V Ans: E
Topic: Reactions at the benzylic position Section: 18.6 Difficulty Level: Easy 61. Provide the structure of the major product(s) for the following reaction.
NBS Δ
Ans:
Br
Topic: Reactions at the benzylic position Section: 18.6 Difficulty Level: Medium
62. Provide the structure of the major product(s) for the following reaction. NBS Δ
Ans: Br
Topic: Reactions at the benzylic position Section: 18.6 Difficulty Level: Easy 63. Provide the reagents necessary to carry out the following conversion. NC
Ans:
1. NBS/Δ 2. NaCN
Topic: Reactions at the benzylic position Section: 18.6 Difficulty Level: Easy 64. Provide the reagents necessary to carry out the following conversion. O
O
Ans:
1. NBS/Δ O
2.
CH3CONa
Topic: Reactions at the benzylic position Section: 18.6 Difficulty Level: Medium
65. Provide the reagents necessary to carry out the following conversion. OCH3
Ans:
1. NBS/Δ 0 2. CH3OH, 25 C
Topic: Reactions at the benzylic position Section: 18.6 Difficulty Level: Medium 66. Provide the reagents necessary to convert ethylbenzene to styrene. Ans: ethylbenzene
NBS
CH3CH2ONa
styrene
Δ
Topic: Reactions at the benzylic position Section: 18.6 Difficulty Level: Medium 67. Provide the reagents necessary to carry out the following conversion.
Ans:
1. NBS/Δ 2. CH3CH2ONa
Topic: Reactions at the benzylic position Section: 18.6 Difficulty Level: Hard
68. Provide the reagents necessary to carry out the following conversion. O
Ans:
1. NBS/Δ 2. CH3CH2ONa 3. BH3 4. H2O2/NaOH/H2O 5. PCC
Topic: Reactions at the benzylic position Section: 18.6 Difficulty Level: Hard 69. Provide the structure(s) of the intermediate product(s) in the following reaction sequence.
NBS
A
(CH3)3COK
1. BH3
PCC
C
D
2. H2O2/NaOH/H2O
Δ
Ans:
B
O Br
OH
A
B
Topic: Reactions at the benzylic position Section: 18.6 Difficulty Level: Hard
C
H
D
70. Provide the structure(s) of the intermediate product(s) in the following reaction sequence.
NBS
A
(CH3)3COK
H2O/H2SO4
B
C
Na2Cr 2O7/H2SO4/H2O
Δ
Ans:
Br
HO
A
O
C
B
D
Topic: Birch Reduction Section: 18.7 Difficulty Level: Easy 71. Predict the product for the following reaction.
Na, CH3OH NH3
I
A) B) C) D) E)
II
I II III IV V Ans: B
Topic: Birch Reduction Section: 18.7 Difficulty Level: Medium
III
IV
V
D
72. Predict the product for the following reaction. O
Na, CH3OH NH3
A) B) C) D) E)
IV
III
II
I
O
O
O
O
O
V
I II III IV V Ans: A
Topic: Birch Reduction Section: 18.7 Difficulty Level: Medium 73. Predict the product for the following reaction. OCH3
Na, CH3OH NH3 OCH3
I
A) B) C) D) E)
I II III IV V Ans: B
OCH3
OCH3
II
III
OCH3
IV
OCH3
V
Topic: Birch Reduction Section: 18.7 Difficulty Level: Medium 74. Predict the product for the following reaction. Na, CH3OH NH3
Ans:
Topic: Birch Reduction Section: 18.7 Difficulty Level: Medium 75. Predict the product for the following reaction. O
NH2
Na, CH3OH NH3
Ans:
O
NH2
Topic: Birch Reduction Section: 18.7 Difficulty Level: Hard
76. Predict the product for the following reaction. H3 CO
OCH3
Na, CH3OH NH3
Ans:
H3CO
OCH3
Topic: Birch Reduction Section: 18.7 Difficulty Level: Hard 77. Predict the product for the following reaction. O
Na, CH3OH NH3
Ans:
Topic: Synthesis Section: 18.6 Difficulty Level: Hard
O
78. Provide stepwise synthesis for the following O
O
Ans:
Br
CH3CH2ONa
NBS
mCPBA
1. CH3MgBr, ether 2. H2O
Δ
HO
O
PCC
Topic: Synthesis Section: 18.6 & 18.7 Difficulty Level: Hard 79. Provide stepwise synthesis for the following H3CO
Ans:
Br
NBS Δ
Topic: Synthesis Section: 18.6 & 18.7 Difficulty Level: Hard
H3 CO
H3CO
CH3CH2ONa
CH3OH H2SO4
Na, CH3OH NH3
80. Provide stepwise synthesis for the following O
H
Ans:
Br OH
NBS Δ
CH3CH2ONa
1. BH3 2. H2O2/NaOH/H2O
PCC CH2Cl2
O
H
Topic: Spectroscopy Section: 18.8 Difficulty Level: Medium 81. The three isomers of dimethylbenzene are commonly named o—xylene, m—xylene, p—xylene. These three isomers are difficult to distinguish using using 1H NMR, but they can 13 be easily identified using C NMR. 13 Describe how C NMR distinguishes these three isomers. Ans: In the proton decoupled 13C NMR spectra o-xylene will display 4 peaks, pea ks, mxylene will display 5 peaks and p-xylene will display 3 peaks.
Topic: Spectroscopy Section: 18.8 Difficulty Level: Medium
82. Which one of the following compounds would exhibit seven signals in its its spectrum?
I
A) B) C) D) E)
O
O
O
II
C NMR NMR O
O
IV
III
V
I II III IV V Ans: C
Topic: Spectroscopy Section: 18.8 Difficulty Level: Medium 83. Which of the following isomer(s) isomer(s) of tribromoaniline tribromoaniline will show two doublets with 7.5 Hz 1 coupling in HNMR spectrum? NH2
Br Br
I
A) B) C) D) E)
Br
I II III IV II & IV Ans: A
Topic: Spectroscopy Section: 18.8 Difficulty Level: Hard
Br
Br
II
Br
Br
Br
Br
Br
NH2
NH2
NH2
III
Br
IV Br
84. Provide a structure structure for the compound with molecular formula formula C9H9ClO and with the following spectroscopic data. 1 IR: 1680 cm 1 H NMR: 3.5δ (triplet, I=2H), 4.0δ (triplet, I=2H), 7.4δ (triplet, I=2H), 7.6 δ (doublet, I=1H), 7.9δ (triplet, I=2H) Cl Ans: O −
Topic: Spectroscopy Section: 18.8 Difficulty Level: Medium 85. Provide a structure structure for the compound with molecular formula formula C9H12 and with the following spectroscopic data. 1 H NMR: 1.2δ (doublet, I=6H), 3.0δ (septet, I=1H), 7.1δ (singlet, I=5H) Ans:
Topic: Spectroscopy Section: 18.8 Difficulty Level: Hard 86. Provide a structure structure for the compound with molecular formula formula C10H12O2 and with the following spectroscopic data. 1 1 1 IR: 1680 cm , 2750 cm , 2850 cm 1 H NMR: 1.1δ (triplet, I=3H), 3.5δ (quartet, I=2H), 4.5δ (singlet, I=2H), 7.3δ (doublet, I=2H), 7.7δ (doublet, I=2H), 9.9δ (singlet, I=1H) −
Ans:
−
O
H
\
−
O
