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ch15 Ques 2013 PDF
ch15 Ques 2013 PDF
Topic: Spectroscopy
Section: 15.1
Difficulty Level: Easy
Topic: Spectroscopy
Section: 15.1
Difficulty Level: Easy
Topic: Spectroscopy
Section: 15.1
Difficulty Level: Easy
Topic: Spectroscopy
Section: 15.1
Difficulty Level: Easy
4. Which of the following electromagnetic radiation has the highest frequency?
A) UV
B) X-ray
C) IR
D) microwave
E) visible
Ans: B
Topic: Spectroscopy
Section: 15.1
Difficulty Level: Medium
Topic: Spectroscopy
Section: 15.1
Difficulty Level: Easy
11. Which of the following corresponds to the functional group region on an IR spectrum?
A) 1500-4000cm—1
B) 400-4000cm—1
C) 400-1500cm—1
D) 1500-2500cm—1
E) none of these
Ans: A
13. Which of the following statement(s) is(are) true about the frequency of a stretching
vibration according to Hook’s law?
A) it is directly proportional to strength of the bond & the reduced mass
B) it is inversely proportional to strength of the bond & the reduced mass
C) it is directly proportional to strength of the bond
D) it is inversely proportional to the reduced mass
E) C & D
Ans: E
H H II
H
I
III
A) III>II>I
B) I>II>III
C) II>I>III
D) III>I>II
E) none of these
Ans: B
15. Rank the indicated bonds in decreasing (highest to lowest) order of wavenumber.
H II
H H
N O
I III
H
A) III>II>I
B) I>II>III
C) II>I>III
D) III>I>II
E) none of these
Ans: D
O
III
II
H
N
I
A) III>II>I
B) I>II>III
C) II>I>III
D) III>I>II
E) none of these
Ans: D
17. Which one of the following compounds will have the lowest wavenumber for carbonyl
absorption?
O O O O
O
II III IV V
I
A) I
B) II
C) III
D) IV
E) V
Ans: D
O
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: C
19. Which one of the following compounds will have the highest wavenumber for C=C
absorption?
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: C
O O O
I II III
A) I
B) II
C) III
D) II & III
Ans: C
21. Arrange the indicated bonds in decreasing (highest to lowest) order of wavenumber.
O
O
I V
C O
N
III
H
II
IV
A) I>V>II>IV>III
B) IV>II>I>V>III
C) II>I>V>III>IV
D) IV>I>V>II>III
E) IV>II>V>I>III
Ans: E
22. Which of the following statement(s) is(are) true for an IR-active bond?
24. Which of the following bonds would produce the weakest absorption?
A) C=C
B) O—H
C) C=O
D) sp3C—H
E) A&D
Ans: A
25. Which of the following bonds would produce the strongest absorption?
A) C=N
B) C≡C
C) C=O
D) sp2C—H
E) C—O
Ans: C
A) it is a symmetrical compound
B) there is no change in bond dipole
C) there is no bond dipole
D) it is an unsymmetrical compound
E) A, B & C
Ans: E
27. Which of the following alkene groups will produce the strongest signal?
F Cl Br
I II III IV
A) I
B) II
C) III
D) IV
Ans: A
30. Carboxylic acids show a very broad absorption for the OH compared to alcohols,
because they can form a ______.
A) dimer
B) polymer
C) trimer
D) tetramer
Ans: A
31. Primary amines show two medium absorption bands around 3400 cm-1, due to _______.
A) symmetric stretching
B) asymmetric stretching
C) both symmetric and asymmetric stretching
D) hydrogen bonding
Ans: C
OH
OH
33. Which of the following compounds will show a broad absorption around 3300 cm-1 and
at 1650 cm-1?
O
OH
O O OH
OH
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: D
C
I N
II III IV
A) I
B) II
C) III
D) IV
E) none of these
Ans: A
35. Which of the following compounds will show two absorptions at 2600 cm-1 and at
2700 cm-1 along with the carbonyl absorption?
O O O O
O NH2 H
I II III IV
A) I
B) II
C) III
D) IV
E) none of these
Ans: D
36. Which of the following compounds will show absorption at 2250 cm-1?
N
NH2 N C
H N
I II III IV
A) I
B) II
C) III
D) IV
E) none of these
Ans: D
Topic: Analyzing an IR spectrum
Section: 15.6
Difficulty Level: Medium
37. Which of the following compounds will have the lowest wavenumber for carbonyl
absorption?
O Cl O H O NH2 O OH O O
IV V
I II III
A) I
B) II
C) III
D) IV
E) V
Ans: C
38. Which of the following is true about the IR spectrum of the following compound?
O
Cl
O OH
II III IV V
I
A) I
B) II
C) III
D) IV
E) V
Ans: C
40. A compound with molecular formula C6H10O, shows absorptions at 1720 cm-1 and at
2980 cm-1 on the IR spectrum. Propose a possible structure for this compound.
Ans:
O
41. A compound with molecular formula C3H9N, shows absorptions at 3400 cm-1 (two),
2980 cm-1 and at 1100 cm-1 on the IR spectrum. Propose a possible structure for this
compound.
Ans: CH3CH2CH2NH2
Ans: O
OH
43. Which of the following compounds will have highest wavenumber for carbonyl
absorption?
O O
O
O O
O
I II III IV
A) I
B) II
C) III
D) IV
Ans: B
44. Which of the following compounds will have two absorptions at 1820 cm-1 and
1740cm-1?
O O O O O O
OH NH2 O O Cl
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: D
Topic: Analyzing an IR spectrum
Section: 15.6
Difficulty Level: Medium
45. Which one of the following compounds is consistent with the following IR spectrum?
O OH O H
O OH
I OH II III IV V
OH OH
A) I
B) II
C) III
D) IV
E) V
Ans: D
O O
O NH2
N N
N
H
II III IV V
I NH OH HN
2
A) I
B) II
C) III
D) IV
E) V
Ans: B
OH
OH OH O
C HO C
I II N III IV N
A) I
B) II
C) III
D) IV
E) V
Ans: A
OH O O O
O H H
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: D
OH
OH O O OH
OH OH
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: E
CH3
CH3
II III IV V
I
CH3
A) I
B) II
C) III
D) IV
E) V
Ans: B
1. DIBAH
+
2. Η3Ο
A) absorption at 2250 cm-1 should disappear
B) absorption at 3200-3400 cm-1 and 1720cm-1 should appear
C) absorption at 2250 cm-1 should disappear, new absorption at 2600-2800 cm-1 and 1720
cm-1 should appear.
D) absorption at 2250 cm-1 should disappear and absorption around 3400 cm-1 should
appear.
E) none of these
Ans: C
52. For the following reaction, which of the following is consistent with the IR spectrum of
the product?
O
H3O+
1. NaH
2. CH3CH2Br
A) absorption at 3200-3600 cm-1 should disappear
B) absorption at 3200-3600 cm-1 and 1100 cm-1 should disappear
C) absorption at 1100 cm-1 should disappear and absorption at 3100 cm-1 should appear
D) absorption at 1650 cm-1 should disappear and absorption at 3300 cm-1 should appear.
E) none of these
Ans: A
54. Predict the product for the following reaction and explain how you will use IR
spectroscopy to monitor the progress of the reaction.
1. NaNH2
1-pentyne
2. CH3CH2Br
Ans: CH3CH2CH2C≡CCH2CH3
Absorptions for spC-H around 3300 cm-1 and C≡C around 2150 cm-1 should
disappear from the product IR.
55. Predict the product for the following reaction and explain how you will use IR
spectroscopy to monitor the progress of the reaction.
O
1. CH3CH2MgBr
2. H2O
Ans: HO
Absorptions for C=O around 1720 cm-1 would disappear and a new absorption for
OH at 3200-3600 cm-1 would appear from the product IR
57. Which of the following is initially produced when a compound is bombarded with high
energy electrons?
A) anion
B) free radical
C) radical cation
D) cation
E) none of these
Ans: C
58. Which of the following is not true about the molecular ion in mass spectrometry?
A) The molecular ion is produced by loss of one electron from the molecule.
B) The mass of the molecular ion is equivalent to the mass of the molecule.
C) The ion is produced by a loss of pair of electrons from the molecule.
D) The molecular ion is often unstable and can undergo fragmentation.
E) none of these
Ans: C
59. Which of the following is always true about the base peak in a mass spectrum?
A) peak corresponding to molecular ion
B) peak corresponding to the most abundant ion
C) peak corresponding to lowest m/z
D) A&C
E) none of these
Ans: B
60. The separation of ions in the mass spectrometer is done by their ______.
A) electrons to protons ratio
B) mass to neutrons ratio
C) protons to neutrons ratio
D) mass to charge ratio
E) none of these
Ans: D
Section: 15.9
Difficulty Level: Easy
Section: 15.9
Difficulty Level: Easy
62. Which of the m/z values corresponds to the base peak in the following mass spectrum?
A) 45
B) 44
C) 29
D) 15
E) none of these
Ans: C
Section: 15.9
Difficulty Level: Easy
63. Which of the m/z values correspond to the molecular ion peak in the following mass
spectrum?
A) 45
B) 44
C) 29
D) 15
E) none of these
Ans: B
Section: 15.9
Difficulty Level: Medium
64. Which of the m/z values correspond to the molecular ion for the following compound?
OH
A) 18
B) 82
C) 100
D) 102
E) 103
Ans: D
Section: 15.9
Difficulty Level: Medium
65. Which of the following compounds will have odd m/z value for the molecular ion?
O O Br
N
H H N N
I II III IV
Br
A) I
B) II
C) III
D) IV
E) none of these
Ans: B
Section: 15.9
Difficulty Level: Medium
66. Which of the following is true about the molecular weight and the M+ -m/z value for the
•
following compound?
Cl
NH2
Section: 15.10
Difficulty Level: Medium
67. Which of the following is true about the (M+1)+ peak on the mass spectrum of a
•
hydrocarbon?
Section: 15.10
Difficulty Level: Medium
68. Which molecular formula is consistent with the following mass spectrum data?
M+ at m/z= 84, relative height=10.0%
•
A) C5H10O
B) C5H8O
C) C5H24
D) C6H12
E) C4H6O2
Ans: B
Section: 15.10
Difficulty Level: Medium
69. Which molecular formula is consistent with the following mass spectrum data?
M+ at m/z= 72, relative height=73.0%
•
A) C4H10O
B) C4H9N
C) C5H12
D) C4H8O
E) none of these
Ans: D
Section: 15.10
Difficulty Level: Medium
70. Provide a molecular formula that is consistent with the following mass spectrum data.
M+ at m/z= 73, relative height=86.1%
•
Ans: C3H7NO
Section: 15.10
Difficulty Level: Hard
71. Provide a molecular formula that is consistent with the following mass spectrum data.
M+ at m/z= 136, relative height=65.6%
•
Ans: C9H12O
Topic: Analyzing (M+1)+ peak
•
Section: 15.10
Difficulty Level: Hard
72. Provide a molecular formula that is consistent with the following mass spectrum data.
M+ at m/z= 167, relative height=50.0%
•
Ans: C8H9NO3
Section: 15.11
Difficulty Level: Medium
A) molecular ion
B) base
C) M+1
D) M+2
E) all of these
Ans: D
Section: 15.11
Difficulty Level: Medium
74. Which of the following will produce M+ and (M+2)+ peaks of equal intensity?
• •
A) nitrogen
B) chlorine
C) bromine
D) oxygen
E) B&C
Ans: C
Section: 15.11
Difficulty Level: Medium
75. Presence of bromine produces M+ and (M+2)+ peaks of equal intensity on a mass
• •
spectrum because:
Section: 15.11
Difficulty Level: Medium
76. Which molecular formula is consistent with the following mass spectrum data?
M+ at m/z= 78, relative height=23.5%
•
A) C6H6
B) C3H7Cl
C) C6H8
D) C6H9Cl
E) none of these
Ans: B
Section: 15.11
Difficulty Level: Medium
77. Which molecular formula is consistent with the following mass spectrum data?
M+ at m/z= 108, relative height=61.5%
•
A) C2H5Br
B) C5H12Cl
C) C8H12
D) C2H7Br
E) none of these
Ans: A
Section: 15.11
Difficulty Level: Medium
78. For which of the following compounds will the (M+2)+ peak intensity be around 25%
•
A) CH3CH2CH2Br
B) CH3CH2CH2OH
C) CH3CH2CH2Cl
D) CH3CH2CH2NH2
E) none of these
Ans: C
Section: 15.11
Difficulty Level: Medium
79. Which of the following mass spectra shows the presence of bromine in a compound?
I II
III IV
Four spectra above: courtesy of SDBS: National Institute of Advanced Industrial Science and Technology
A) I
B) II
C) III
D) IV
E) none of these
Ans: A
Topic: Analyzing the fragments
Section: 15.12
Difficulty Level: Medium
80. Which of the following compounds will produce a prominent (M-18) peak in the mass
spectrum?
A) 2-methylheptane
B) 1-heptanol
C) heptanamine
D) heptanal
E) none of these
Ans: B
81. Which of the following compounds will produce a prominent (M-15) peak in the mass
spectrum?
A) 2-methylheptane
B) 1-heptanol
C) heptanamine
D) 1-chloroheptane
E) none of these
Ans: A
82. Which of the following is not a prominent peak in the mass spectrum of 2-methyl-2-
pentanol?
A) (M-15)
B) (M-18)
C) (M-29)
D) (M-16)
E) none of these
Ans: D
A) CH3CH2CH2I
B) (CH3CH2)3CCH2Cl
C) (CH3)3CCH2CH2Br
D) (CH3)2CHCH(CH3)2
E) none of these
Ans: A
84. Which of the following compounds will have a base peak at m/z=43?
A) CH3CH2CH2CH2CH2CH3
B) (CH3CH2)2CHCH3
C) (CH3)3CCH2CH3
D) (CH3)2CHCH(CH3)2
E) none of these
Ans: D
85. Which of the following is the base peak in the mass spectrum of 2,2,4-trimethylpentane?
A) 114
B) 57
C) 42
D) 29
E) none of these
Ans: B
A) 88
B) 55
C) 42
D) 31
E) none of these
Ans: C
87. Which of the following is expected to be the base peak in the mass spectrum of 2-
methyl-2-butanol?
A) 73
B) 55
C) 43
D) 31
E) 59
Ans: E
88. Which of the following is expected to be the base peak in the mass spectrum of
CH3CH2NH2?
A) 15
B) 28
C) 30
D) 45
E) none of these
Ans: C
90. Provide the structure of the major fragment that results when the molecular ion of
(CH3)2CHCH2CH2NH2 undergoes fragmentation.
H
Ans:
N
H
91. Provide the structure of the major fragment that results when the molecular ion of
CH3CH2CH2CH2OH undergoes fragmentation via alpha cleavage.
Ans: O
H
92. Which of the following is expected to be the base peak in the mass spectrum of
pentanal?
O
CH3CH2CH2CH2CH
pentanal
A) 29
B) 41
C) 44
D) 58
E) 86
Ans: C
Topic: Analyzing the fragments
Section: 15.12
Difficulty Level: Medium
93. Which one of the following compounds is consistent with the mass spectrum below?
95. Which one of the following compounds is consistent with the mass spectrum below?
A) degree of unsaturation
B) molecular formula
C) molecular weight
D) B&C
E) none of these
Ans: B
97. How will you distinguish between the following compounds using high-resolution mass
spectrometry?
O Cl
O
I II
Ans: Compound I: m/z at 102.0678
Compound II: m/z at 102.0235
98. How will you distinguish between the following compounds using high-resolution mass
spectrometry?
OH
I II
Ans: Compound I: m/z at 98.0729
Compound II: m/z at 98.1092
A) 4
B) 6
C) 2
D) 5
E) none of these
Ans: D
A) 4
B) 6
C) 8
D) 10
E) 9
Ans: E
A) 4
B) 6
C) 7
D) 8
E) 10
Ans: C
A) 4
B) 6
C) 2
D) 3
E) 7
Ans: D
106. Propose a possible structure for a compound with molecular formula C6H5Br
Ans: Br
107. Propose all possible structures for a compound with molecular formula C4H9N that
shows two medium absorptions at 3400 cm-1 and no absorption in the range of 1600-
1800 cm-1 in its IR spectrum.
Ans: NH2
NH2
108. Propose possible structure(s) for a compound with molecular formula C4H7N that shows
absorption at 2250 cm-1 in its IR spectrum.
Ans: CH3CH2CH2C≡N
Ans: O O