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IR Orgo Worksheet
IR Orgo Worksheet
Topic: Spectroscopy
Section: 15.1
Difficulty Level: Easy
1.
A)
B)
C)
D)
E)
Topic: Spectroscopy
Section: 15.1
Difficulty Level: Easy
2.
A)
B)
C)
D)
E)
Topic: Spectroscopy
Section: 15.1
Difficulty Level: Easy
3.
A)
B)
C)
D)
E)
Topic: Spectroscopy
Section: 15.1
Difficulty Level: Easy
4.
A)
B)
C)
D)
E)
Topic: Spectroscopy
Section: 15.1
Difficulty Level: Medium
5. Arrange the following electromagnetic radiation in decreasing (highest to lowest) order
of frequency.
-rays
visible
microwave
IR
UV
III
I
IV
V
A) V>III>IV>II>I
B) II>V>III>IV>I
C) I>IV>III>V>II
D) V>II>IV>III>I
E) II>IV>V>III>I
Ans: B
Topic: Spectroscopy
Section: 15.1
Difficulty Level: Easy
6.
A)
B)
C)
D)
E)
14. Rank the indicated bonds in decreasing (highest to lowest) order of wavenumber.
H
II
A)
B)
C)
D)
E)
III
III>II>I
I>II>III
II>I>III
III>I>II
none of these
Ans: B
II
H
N
A)
B)
C)
D)
E)
III>II>I
I>II>III
II>I>III
III>I>II
none of these
Ans: D
III
16. Rank the indicated bonds in decreasing (highest to lowest) order of wavenumber.
O
II
III
H
N
A)
B)
C)
D)
E)
III>II>I
I>II>III
II>I>III
III>I>II
none of these
Ans: D
A)
B)
C)
D)
E)
II
III
IV
I
II
III
IV
V
Ans: D
18. Which one of the following compounds will have the lowest wavenumber for carbonyl
absorption?
O
NH2
II
A)
B)
C)
D)
E)
IV
III
I
II
III
IV
V
Ans: C
A)
B)
C)
D)
E)
I
II
III
IV
V
Ans: C
II
III
IV
20. Which of the following compounds will have the highest wavenumber for carbonyl
absorption?
O
A)
B)
C)
D)
II
III
I
II
III
II & III
Ans: C
I
C
N
II
A)
B)
C)
D)
E)
III
IV
I>V>II>IV>III
IV>II>I>V>III
II>I>V>III>IV
IV>I>V>II>III
IV>II>V>I>III
Ans: E
CH3CH2
CH2CH3
CH3CH2
III
I
A)
B)
C)
D)
E)
I
II
III
I & IV
I & III
Ans: E
II
C=C
OH
C=O
sp3CH
A&D
Ans: A
C=N
CC
C=O
sp2CH
CO
Ans: C
IV
26. 3-hexyne does not show absorption in the range of 2000-2200 cm1, whereas 1-hexyne
does. Which of the following explains the reason for this absence of absorption for 3hexyne?
A)
B)
C)
D)
E)
it is a symmetrical compound
there is no change in bond dipole
there is no bond dipole
it is an unsymmetrical compound
A, B & C
Ans: E
A)
B)
C)
D)
II
Cl
III
Br
IV
I
II
III
IV
Ans: A
dimer
polymer
trimer
tetramer
Ans: A
symmetric stretching
asymmetric stretching
both symmetric and asymmetric stretching
hydrogen bonding
Ans: C
32. How can you distinguish between cyclohexanol and cyclohexanecarboxylic acid using
IR spectroscopy?
O
OH
OH
Cyclohexanol
Cyclohexanecarboxylic acid
Ans: The OH absorption for the carboxylic acid is much broader than the alcoholic OH
and it will also show absorption for carbonyl group.
Topic: Analyzing an IR spectrum
Section: 15.6
Difficulty Level: Medium
33. Which of the following compounds will show a broad absorption around 3300 cm-1 and
at 1650 cm-1?
O
OH
A)
B)
C)
D)
E)
II
I
II
III
IV
V
Ans: D
III
OH
OH
IV
34. Which of the following compounds will show a sharp absorption at 3300 cm-1 and at
2150 cm-1?
C
A)
B)
C)
D)
E)
II
III
IV
I
II
III
IV
none of these
Ans: A
NH2
A)
B)
C)
D)
E)
III
II
IV
I
II
III
IV
none of these
Ans: D
A)
B)
C)
D)
E)
I
II
III
IV
none of these
Ans: D
II
N
H
III
IV
A)
B)
C)
D)
E)
Cl
II
NH2
III
OH
IV
I
II
III
IV
V
Ans: C
Cl
A)
B)
C)
D)
E)
39. Which of the following compounds will show absorptions at 1640 cm-1, 2950 cm-1 and
3050 cm-1 on the IR spectrum?
O
A)
B)
C)
D)
E)
II
III
IV
OH
I
II
III
IV
V
Ans: C
42. A compound with molecular formula C4H8O2, shows absorptions at 2200-3600 cm-1
(broad), 1720 cm-1 and at 1200 cm-1 on the IR spectrum. Propose a possible structure for
this compound.
O
Ans:
OH
O
O
O
O
O
III
II
A)
B)
C)
D)
IV
I
II
III
IV
Ans: B
OH
A)
B)
C)
D)
E)
I
II
III
IV
V
Ans: D
II
NH2
III
IV
Cl
I OH
A)
B)
C)
D)
E)
OH
OH
II
I
II
III
IV
V
Ans: D
III
IV
OH
OH
46. Which one of the following compounds is consistent with the following IR spectrum?
O
O
NH2
N
N
H
I NH
2
A)
B)
C)
D)
E)
II
I
II
III
IV
V
Ans: B
III
IV
OH
HN
47. Which one of the following compounds is consistent with the following IR spectrum?
A)
B)
C)
D)
E)
OH
II
I
II
III
IV
V
Ans: A
OH
C
N
III
O
HO
IV
48. Which one of the following compounds is consistent with the following IR spectrum?
OH
A)
B)
C)
D)
E)
II
I
II
III
IV
V
Ans: D
III
IV
49. Which one of the following compounds is consistent with the following IR spectrum?
OH
A)
B)
C)
D)
E)
II
I
II
III
IV
V
Ans: E
OH
OH
OH
III
IV
OH
50. Which one of the following compounds is consistent with the following IR spectrum?
NH2
NHCH3
NH2
N(CH3)2
CH3
II
IV
III
CH3
A)
B)
C)
D)
E)
I
II
III
IV
V
Ans: B
CH3
51. For the following reaction, which of the following is consistent with the IR spectrum of
the product?
O
CN
1. DIBAH
2. 3
H3O+
A)
B)
C)
D)
E)
53. For the following reaction, which of the following is consistent with the IR spectrum of
the product?
OCH2CH3
OH
1. NaH
2. CH3CH2Br
A)
B)
C)
D)
E)
1. NaNH2
2. CH3CH2Br
Ans: CH3CH2CH2CCCH2CH3
Absorptions for spC-H around 3300 cm-1 and CC around 2150 cm-1 should
disappear from the product IR.
Topic: Analyzing an IR spectrum
Section: 15.7
Difficulty Level: Hard
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
Topic: Mass Spectrometry
Section: 15.8
Difficulty Level: Easy
56.
A)
B)
C)
D)
E)
Which of the following is not true about the molecular ion in mass spectrometry?
The molecular ion is produced by loss of one electron from the molecule.
The mass of the molecular ion is equivalent to the mass of the molecule.
The ion is produced by a loss of pair of electrons from the molecule.
The molecular ion is often unstable and can undergo fragmentation.
none of these
Ans: C
Which of the following is always true about the base peak in a mass spectrum?
peak corresponding to molecular ion
peak corresponding to the most abundant ion
peak corresponding to lowest m/z
A&C
none of these
Ans: B
Section: 15.8
Difficulty Level: Easy
60.
A)
B)
C)
D)
E)
61.
A)
B)
C)
D)
E)
62. Which of the m/z values corresponds to the base peak in the following mass spectrum?
A)
B)
C)
D)
E)
45
44
29
15
none of these
Ans: C
A)
B)
C)
D)
E)
45
44
29
15
none of these
Ans: B
64. Which of the m/z values correspond to the molecular ion for the following compound?
OH
A)
B)
C)
D)
E)
18
82
100
102
103
Ans: D
65. Which of the following compounds will have odd m/z value for the molecular ion?
O
Br
N
A)
B)
C)
D)
E)
III
II
IV
Br
I
II
III
IV
none of these
Ans: B
66. Which of the following is true about the molecular weight and the M+ -m/z value for the
following compound?
Cl
NH2
A)
B)
C)
D)
E)
67. Which of the following is true about the (M+1)+ peak on the mass spectrum of a
hydrocarbon?
A)
B)
C)
D)
E)
68. Which molecular formula is consistent with the following mass spectrum data?
M+ at m/z= 84, relative height=10.0%
(M+1)+ at m/z= 85, relative height=0.56%
A)
B)
C)
D)
E)
C5H10O
C5H8O
C5H24
C6H12
C4H6O2
Ans: B
69. Which molecular formula is consistent with the following mass spectrum data?
M+ at m/z= 72, relative height=73.0%
(M+1)+ at m/z= 73, relative height=3.3%
A)
B)
C)
D)
E)
C4H10O
C4H9N
C5H12
C4H8O
none of these
Ans: D
70. Provide a molecular formula that is consistent with the following mass spectrum data.
M+ at m/z= 73, relative height=86.1%
(M+1)+ at m/z= 74, relative height=3.2%
Ans: C3H7NO
Topic: Analyzing (M+1)+ peak
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%
(M+1)+ at m/z= 137, relative height=6.2%
Ans: C9H12O
72. Provide a molecular formula that is consistent with the following mass spectrum data.
M+ at m/z= 167, relative height=50.0%
(M+1)+ at m/z= 168, relative height=4.4%
Ans: C8H9NO3
Topic: Analyzing (M+2)+ peak
Section: 15.11
Difficulty Level: Medium
molecular ion
base
M+1
M+2
all of these
Ans: D
74. Which of the following will produce M+ and (M+2)+ peaks of equal intensity?
A)
B)
C)
D)
E)
nitrogen
chlorine
bromine
oxygen
B&C
Ans: C
75. Presence of bromine produces M+ and (M+2)+ peaks of equal intensity on a mass
spectrum because:
A)
B)
C)
D)
76. Which molecular formula is consistent with the following mass spectrum data?
M+ at m/z= 78, relative height=23.5%
(M+1)+ at m/z= 79, relative height=0.78%
(M+2)+ at m/z= 80, relative height=7.5%
A)
B)
C)
D)
E)
C6H6
C3H7Cl
C6H8
C6H9Cl
none of these
Ans: B
77. Which molecular formula is consistent with the following mass spectrum data?
M+ at m/z= 108, relative height=61.5%
(M+1)+ at m/z= 109, relative height=1.5%
(M+2)+ at m/z= 110, relative height=61.3%
A)
B)
C)
D)
E)
C2H5Br
C5H12Cl
C8H12
C2H7Br
none of these
Ans: A
78. For which of the following compounds will the (M+2)+ peak intensity be around 25%
of the intensity of the molecular ion peak?
A)
B)
C)
D)
E)
CH3CH2CH2Br
CH3CH2CH2OH
CH3CH2CH2Cl
CH3CH2CH2NH2
none of these
Ans: C
79. Which of the following mass spectra shows the presence of bromine in a compound?
III
II
IV
Four spectra above: courtesy of SDBS: National Institute of Advanced Industrial Science and Technology
A)
B)
C)
D)
E)
I
II
III
IV
none of these
Ans: A
2-methylheptane
1-heptanol
heptanamine
heptanal
none of these
Ans: B
2-methylheptane
1-heptanol
heptanamine
1-chloroheptane
none of these
Ans: A
(M-15)
(M-18)
(M-29)
(M-16)
none of these
Ans: D
83. Which of the following compounds will have a prominent peak at (M-127)?
A)
B)
C)
D)
E)
CH3CH2CH2I
(CH3CH2)3CCH2Cl
(CH3)3CCH2CH2Br
(CH3)2CHCH(CH3)2
none of these
Ans: A
CH3CH2CH2CH2CH2CH3
(CH3CH2)2CHCH3
(CH3)3CCH2CH3
(CH3)2CHCH(CH3)2
none of these
Ans: D
114
57
42
29
none of these
Ans: B
86. Which of the following is expected to be the base peak in the mass spectrum of
CH3(CH2)4OH?
A)
B)
C)
D)
E)
88
55
42
31
none of these
Ans: C
73
55
43
31
59
Ans: E
15
28
30
45
none of these
Ans: C
89. Provide the structures of the fragments that result when the molecular ion of 2heptanone undergoes fragmentation via McLafferty rearrangement.
H
Ans:
H
N
H
O
H
CH3CH2CH2CH2CH
pentanal
A)
B)
C)
D)
E)
29
41
44
58
86
Ans: C
A)
B)
C)
D)
E)
CH3CH2CH(CH3)2
CH3CHOHCH2CH3
CH3CH2OCH2CH3
CH3CH2NHCH2CH3
none of these
Ans: D
94. Which one of the following compounds is consistent with the mass spectrum below?
A)
B)
C)
D)
E)
CH3CH2CH(CH3)2
CH3CHOHCH2CH3
CH3CH2OCH2CH3
CH3CH2NHCH2CH3
none of these
Ans: B
A)
B)
C)
D)
E)
CH3CH2CH(CH3)2
CH3CHOHCH2CH3
CH3CH2OCH2CH3
CH3CH2NHCH2CH3
none of these
Ans: A
degree of unsaturation
molecular formula
molecular weight
B&C
none of these
Ans: B
Cl
II
II
4
6
2
5
none of these
Ans: D
4
6
8
10
9
Ans: E
4
6
7
8
10
Ans: C
4
6
2
3
7
Ans: D
105. Which of the following compounds have the same degree of unsaturation?
C5H5Br2NO
C6H5Br
C8H10BrIO
C9H11NO
A)
B)
C)
D)
E)
II
I
I & II
I & III
III & IV
II & III
none of these
Ans: B
III
IV
Br
109. Propose a possible structure for a compound with molecular formula C5H8O2 that shows
absorption at 1720 cm-1 and no absorption in the range of 1500-1700 cm-1 or 2600-2800
cm-1 in its IR spectrum.
Ans: