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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
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 the following compound?
OH
Br
A) B) C) D) E)
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
Br NO2
A) B) C) D) E)
Topic: Nomenclature Section: 18.2 Difficulty Level: Medium 8. What is the correct structure for 4-amino-2-chlorophenol?
NO2 NO2 OH NH2 NH2
Cl
Cl
Cl
Cl OH CH
Cl
OH
II
OCH3
III NH2 IV
A) B) C) D) E)
I II III IV V Ans: D
9. What is the correct order of the names for the following compound?
A) B) C) D) E)
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; II- phenanthrene; III-naphthalene Ans: C
II
III
Topic: Nomenclature Section: 18.2 Difficulty Level: Medium 10. What is the IUPAC name for the following compound?
NH2 Cl
A) B) C) D) E)
Cl
A) B) C) D) E)
Topic: Nomenclature Section: 18.2 Difficulty Level: Medium 12. What is the IUPAC name for the following compound?
NO2
COH O
A) B) C) D) E)
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 the following compound?
F
Cl
Ans: 4-chloromethyl-2-nitroanisole Topic: Nomenclature Section: 18.2 Difficulty Level: Medium 17. What is the IUPAC name 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 20. What is the structure for 4-amino-2-bromophenol?
OH OH Br OH Br OCH3 OCH3 Br
NH2
H2N
Br
Br
II NH2
III
IV
V
NH2
NH2
A) B) C) D) E)
I II III IV V Ans: B
Topic: Aromaticity, Hckel'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 p orbital at every vertex D) The compound must satisfy Hckels rule must have (4n + 2) electrons. E) none of these Ans: B
Topic: Aromaticity, Hckel'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 with p orbital at every vertex Aromatic compounds must satisfy Hckels rule. none of these Ans: D
Topic: Aromaticity, Hckel's Rule, MO theory & Frost circle Section: 18.4 Difficulty Level: Easy 23. The number of electrons present in an antiaromatic compound: A) B) C) D) E) 4n + 2 2n + 2 4n none none of these Ans: C
Topic: Aromaticity, Hckel's Rule, MO theory & Frost circle Section: 18.4 Difficulty Level: Easy 24. The number of electrons present in an aromatic compound: A) B) C) D) E) 4n + 2 2n + 2 4n none None of these Ans: A
Topic: Aromaticity, Hckel'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.
Energy
1
It is not aromatic.
Topic: Aromaticity, Hckel'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:
Energy
3
1
It is aromatic. Topic: Aromaticity, Hckel'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
6 Energy
4
7 1
5
It is aromatic. Topic: Aromaticity, Hckel'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
and
predict if it is aromatic.
4
2 1
5 3
It is not aromatic. Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Medium
II
A) B) C) D) E)
III
IV
Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Medium 30. Which one of the following compound is antiaromatic?
H N H N H H N
N H
A) B) C) D)
I II III IV Ans: B
II
III
IV
Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Medium
A) B) C) D) E)
I II III IV V Ans: B
II
III
IV
Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Hard 32. Which one of the following compound is aromatic?
II
III
IV
A) B) C) D)
I II III IV Ans: C
Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Medium
O
H
O
II
III
IV
A) B) C) D)
I II III IV Ans: B
Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Hard 34. Which one of the following compound is aromatic?
H N
B CH3
O
H
O
II
III
IV
A) B) C) D)
I II III IV Ans: A
Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Hard
O
H
O
II
III
IV
A) B) C) D) E)
Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Medium 36. Which one of the following compounds is aromatic?
H B O H N
II
III
IV
A) B) C) D)
I II III IV Ans: A
Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Medium
A) B) C) D) E)
I II III IV V Ans: IV
II
N H
B H
III
IV
Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Easy 38. Classify the following compound as aromatic, antiaromatic, or nonaromatic. Explain your choice.
Ans: Nonaromatic It is cyclic, planar but not conjugated and one of the carbon atoms is sp3 hybridized. Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Easy 39. Classify the following compound as aromatic, antiaromatic, or nonaromatic. Explain your choice.
Ans: Nonaromatic It is cyclic, planar, but not conjugated and all the carbon atoms are sp3 hybridized Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Hard
40. Classify the following compound as aromatic, antiaromatic, or nonaromatic. Explain your choice.
Ans: Aromatic It is cyclic, planar, conjugated and follows Hckel rule with 5 pairs of electrons Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: medium 41. Classify the following compound as aromatic, antiaromatic, or nonaromatic. Explain your choice.
O
Ans: Antiaromatic It is cyclic, planar, conjugated but does not follow Hckels rule. It has 4 pairs of electrons Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Hard 42. Classify the following compound as aromatic, antiaromatic, or nonaromatic. Explain your choice.
O
Ans: Aromatic It is cyclic, planar, conjugated and follows Hckels rule with 3 pairs of electrons Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: medium
43. Classify the following compound as aromatic, antiaromatic, or nonaromatic. Explain your choice.
H N H
Ans: nonaromatic It is cyclic, planar but not conjugated and one of the nitrogen atoms is sp3 hybridized. Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Hard 44. Classify the following compound as aromatic, antiaromatic, or nonaromatic. Explain your choice.
O
N H
Ans: Antiaromatic It is cyclic, planar, conjugated but does not follow Hckels rule with 4 pairs of electrons Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Hard 45. Classify the following compound as aromatic, antiaromatic, or nonaromatic. Explain your choice.
H N N N
Ans: Aromatic It is cyclic, planar, conjugated and follows Hckels rule with 5 pairs of electrons Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Medium
46. Classify the following compounds as aromatic, antiaromatic, or nonaromatic. Explain your choice.
O O
Ans: I. Aromatic It is cyclic, planar, conjugated and follows Hckels rule with 3 pairs of electrons II. Antiaromatic It is cyclic, planar, conjugated but does not follow Hckels rule with 4 pairs of electrons. Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Hard 47. Classify the following compounds as aromatic, antiaromatic, or nonaromatic. Explain your choice.
NH2 O N O
II
N H
N H
II
Ans: I. Aromatic It is cyclic, planar, conjugated and follows Hckels rule with 3 pairs of electrons II. Antiaromatic It is cyclic, planar, conjugated but does not follow Hckels rule with 4 pairs of electrons. III. Aromatic It is cyclic, planar, conjugated and follows Hckels rule with 3 pairs of electrons IV. Aromatic It is cyclic, planar, conjugated and follows Hckels rule with 3 pairs of electrons Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Easy
III
IV
A) B) C) D) E)
II
III
IV
Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Easy 49. Which one of the following compounds is most acidic?
H N H N
A) B) C) D) E)
II
III
Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Medium
50. Which one of the following compounds is most acidic? Explain your choice.
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 hydrochloride salt, where as pyrrole is unreactive. Provide an explanation for this observed reactivity.
II
N H
Pyridine
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 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 SN1 reaction? Explain your choice.
Br Br Br Br
II
III
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 SN1 reaction? Explain your choice.
Cl Cl Cl
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) Na2Cr2O7/H2SO4/H2O 1. NBS, , 2. a 1. KMnO4/NaOH/H2O, 2. H3O+ HNO3/H2SO4 1. CO2, 2. H3O+ Ans: A & C
II
III
Topic: Reactions at the benzylic position Section: 18.6 Difficulty Level: Medium
O COH
O COH
O CH
COH
COH
CCH3
CH
II O
III O
IV
A) B) C) D) E)
I II III IV V Ans: B
Topic: Reactions at the benzylic position Section: 18.6 Difficulty Level: Hard
COH O
CH
CCH3
A) B) C) D) E)
I II III IV V Ans: B
II
III
IV
Topic: Reactions at the benzylic position Section: 18.6 Difficulty Level: Medium 57. Provide the product for the following reaction? Explain your answer.
Ans:
COH O
There is no hydrogen at the benzylic position with t-butyl group, so it does 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 h
Cl Cl
Cl
A) B) C) D) E)
II Cl
III Cl
IV
Topic: Reactions at the benzylic position Section: 18.6 Difficulty Level: Medium
59. Provide the structure of the major product(s) for the following reaction.
CH2CH2CH3
Br2 h
CH2CH2CH2Br CH2CH2CH3 CH2CHBrCH3 CH2CH2CH3 Br CHBrCH2CH3
II Br
III
IV
A) B) C) D) E)
I II III IV V Ans: E
Topic: Reactions at the benzylic position Section: 18.6 Difficulty Level: Medium
60. Provide the structure of the major product(s) for the following reaction.
Cl2 h
Cl
Cl
II
Cl Cl
III
Cl
IV
A) B) C) D) E)
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
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
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/ 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
Ans:
1. NBS/
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:
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
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/ 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. 2. 3. 4. 5.
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
(CH3)3COK
1. BH3 2. H2O2/NaOH/H2O
PCC
Ans:
Br OH
Topic: Reactions at the benzylic position Section: 18.6 Difficulty Level: Hard
70. Provide the structure(s) of the intermediate product(s) in the following reaction sequence.
NBS
(CH3)3COK
H2O/H2SO4
Na2Cr2O7/H2SO4/H2O
Ans:
Br
HO
Topic: Birch Reduction Section: 18.7 Difficulty Level: Easy 71. Predict the product for the following reaction.
II
III
IV
A) B) C) D) E)
I II III IV V Ans: B
A) B) C) D) E)
I II III IV V Ans: A
II
III
IV
Topic: Birch Reduction Section: 18.7 Difficulty Level: Medium 73. Predict the product for the following reaction.
OCH3
A) B) C) D) E)
I II III IV V Ans: B
II
III
IV
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
Ans:
NH2
Ans:
H3CO
OCH3
Topic: Birch Reduction Section: 18.7 Difficulty Level: Hard 77. Predict the product for the following reaction.
O
Ans:
Ans:
O Br
NBS
CH3CH2ONa
mCPBA
HO
PCC
Topic: Synthesis Section: 18.6 & 18.7 Difficulty Level: Hard 79. Provide stepwise synthesis for the following
H3CO
Ans:
NBS
Br
H3CO
H3CO
CH3CH2ONa
CH3OH H2SO4
Ans:
Br OH
NBS
O
CH3CH2ONa
1. BH3 2. H2O2/NaOH/H2O
PCC CH2Cl2
Topic: Spectroscopy Section: 18.8 Difficulty Level: Medium 81. The three isomers of dimethylbenzene are commonly named oxylene, mxylene, pxylene. These three isomers are difficult to distinguish using 1H NMR, but they can be easily identified using 13C NMR. Describe how 13C NMR distinguishes these three isomers. Ans: In the proton decoupled 13C NMR spectra o-xylene will display 4 peaks, 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 13C NMR spectrum?
O O O O O
II
III
IV
A) B) C) D) E)
I II III IV V Ans: C
Topic: Spectroscopy Section: 18.8 Difficulty Level: Medium 83. Which of the following isomer(s) of tribromoaniline will show two doublets with 7.5 Hz coupling in 1HNMR spectrum?
NH2 Br Br NH2 Br NH2 Br NH2 Br
Br
Br
Br
Br
Br
II
Br
III Br
IV
A) B) C) D) E)
84. Provide a structure for the compound with molecular formula C9H9ClO and with the following spectroscopic data. IR: 1680 cm1 1 H NMR: 3.5 (triplet, I=2H), 4.0 (triplet, I=2H), 7.4 (triplet, I=2H), 7.6 (doublet, I=1H), 7.9 (triplet, I=2H) Cl Ans: O
Topic: Spectroscopy Section: 18.8 Difficulty Level: Medium 85. Provide a structure for the compound with molecular formula C9H12 and with the following spectroscopic data. 1 H NMR: 1.2 (doublet, I=6H), 3.0 (septet, I=1H), 7.1 (singlet, I=5H) Ans:
Topic: Spectroscopy Section: 18.8 Difficulty Level: Hard 86. Provide a structure for the compound with molecular formula C10H12O2 and with the following spectroscopic data. IR: 1680 cm1, 2750 cm1, 2850 cm1 1 H NMR: 1.1 (triplet, I=3H), 3.5 (quartet, I=2H), 4.5 (singlet, I=2H), 7.3 (doublet, I=2H), 7.7 (doublet, I=2H), 9.9 (singlet, I=1H) Ans:
O