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Chapter Fifteen

Topic: Spectroscopy
Section: 15.1
Difficulty Level: Easy
1.
A)
B)
C)
D)
E)

Which of the following is not true about electromagnetic radiation?


frequency is directly proportional to wavelength
frequency is directly proportional to energy
frequency is inversely proportional to wavelength
wavelength is inversely proportional to energy
none of these
Ans: A

Topic: Spectroscopy
Section: 15.1
Difficulty Level: Easy
2.
A)
B)
C)
D)
E)

Which of the following electromagnetic radiation has the highest energy?


UV
X-ray
IR
microwave
visible
Ans: B

Topic: Spectroscopy
Section: 15.1
Difficulty Level: Easy
3.
A)
B)
C)
D)
E)

Which of the following electromagnetic radiation has the longest wavelength?


UV
X-ray
IR
microwave
visible
Ans: D

Topic: Spectroscopy
Section: 15.1
Difficulty Level: Easy

4.
A)
B)
C)
D)
E)

Which of the following electromagnetic radiation has the highest frequency?


UV
X-ray
IR
microwave
visible
Ans: B

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)

Which of the following information is primarily obtained from infrared spectroscopy?


arrangement of carbon and hydrogen atoms in a compound
molecular weight of a compound
conjugated system present in a compound
functional groups present in a compound
all of these
Ans: D

Topic: Infrared Spectroscopy


Section: 15.2
Difficulty Level: Easy

7. Absorption of _______radiation results in vibrational excitation of the bonds in a


compound.
A) UV
B) Microwave
C) IR
D) Visible
E) x-ray
Ans: C
Topic: Infrared Spectroscopy
Section: 15.2
Difficulty Level: Easy
8.
A)
B)
C)
D)
E)

Which of the following vibrations are observed in IR spectroscopy?


stetching
rotational
bending
A&B
A&C
Ans: E

Topic: Infrared Spectroscopy


Section: 15.2
Difficulty Level: Easy
9. Which of the following is currently used to indicate the location of a signal on an IR
spectrum?
A) wavelength
B) wavenumber
C) frequency
D) A & B
E) all of these
Ans: B
Topic: Infrared Spectroscopy
Section: 15.2
Difficulty Level: Easy
10.
A)
B)
C)
D)
E)

Which of the following are units for wavenumber in IR spectroscopy?


cm1
cm
J.s1
mm
none of these
Ans: A

Topic: Signal Characteristics


Section: 15.3
Difficulty Level: Easy
11.
A)
B)
C)
D)
E)

Which of the following corresponds to the functional group region on an IR spectrum?


1500-4000cm1
400-4000cm1
400-1500cm1
1500-2500cm1
none of these
Ans: A

Topic: Signal Characteristics


Section: 15.3
Difficulty Level: Easy
12.
A)
B)
C)
D)
E)

Which of the following corresponds to the fingerprint region on an IR spectrum?


1500-4000cm1
400-4000cm1
400-1500cm1
1500-2500cm1
none of these
Ans: C

Topic: Signal Characteristics


Section: 15.3
Difficulty Level: Medium
13. Which of the following statement(s) is(are) true about the frequency of a stretching
vibration according to Hooks 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
Topic: Signal Characteristics
Section: 15.3
Difficulty Level: Easy

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

Topic: Signal Characteristics


Section: 15.3
Difficulty Level: Easy
15. Rank the indicated bonds in decreasing (highest to lowest) order of wavenumber.
H

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

Topic: Signal Characteristics


Section: 15.3
Difficulty Level: Easy

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

Topic: Signal Characteristics


Section: 15.3
Difficulty Level: Medium
17. Which one of the following compounds will have the lowest wavenumber for carbonyl
absorption?

A)
B)
C)
D)
E)

II

III

IV

I
II
III
IV
V
Ans: D

Topic: Signal Characteristics


Section: 15.3
Difficulty Level: Medium

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

Topic: Signal Characteristics


Section: 15.3
Difficulty Level: Medium
19. Which one of the following compounds will have the highest wavenumber for C=C
absorption?

A)
B)
C)
D)
E)

I
II
III
IV
V
Ans: C

II

Topic: Signal Characteristics


Section: 15.3
Difficulty Level: Hard

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

Topic: Signal Characteristics


Section: 15.3
Difficulty Level: Medium
21. Arrange the indicated bonds in decreasing (highest to lowest) order of wavenumber.
O

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

Topic: Signal Characteristics


Section: 15.4
Difficulty Level: Medium
22. Which of the following statement(s) is(are) true for an IR-active bond?
A)
B)
C)
D)
E)

the bond must be symmetrical


it must change bond length
it must change bond angle
it must change bond dipole
all of these
Ans: D

Topic: Signal Characteristics


Section: 15.4
Difficulty Level: Medium

23. Which of the following bonds is IR inactive?

CH3CH2

CH2CH3

CH3CH2

III
I

A)
B)
C)
D)
E)

I
II
III
I & IV
I & III
Ans: E

II

Topic: Signal Characteristics


Section: 15.4
Difficulty Level: Medium
24. Which of the following bonds would produce the weakest absorption?
A)
B)
C)
D)
E)

C=C
OH
C=O
sp3CH
A&D
Ans: A

Topic: Signal Characteristics


Section: 15.4
Difficulty Level: Medium
25. Which of the following bonds would produce the strongest absorption?
A)
B)
C)
D)
E)

C=N
CC
C=O
sp2CH
CO
Ans: C

Topic: Signal Characteristics


Section: 15.4
Difficulty Level: Medium

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

Topic: Signal Characteristics


Section: 15.4
Difficulty Level: Medium
27. Which of the following alkene groups will produce the strongest signal?

A)
B)
C)
D)

II

Cl

III

Br

IV

I
II
III
IV
Ans: A

Topic: Signal Characteristics


Section: 15.5
Difficulty Level: Medium
28. Diluted alcohols show a _____absorption around 3600cm-1, due to _____.
A)
B)
C)
D)

sharp, hydrogen bonding


broad, hydrogen bonding
sharp, absence of hydrogen bonding
broad, absence of hydrogen bonding
Ans: C

Topic: Signal Characteristics


Section: 15.5
Difficulty Level: Medium

29. Concentrated alcohols show a _____absorption in the region of 3200-3600cm-1, due to


_____.
A)
B)
C)
D)

sharp, hydrogen bonding


broad, hydrogen bonding
sharp, polarity
broad, polarity
Ans: B

Topic: Signal Characteristics


Section: 15.5
Difficulty Level: Medium
30. Carboxylic acids show a very broad absorption for the OH compared to alcohols,
because they can form a ______.
A)
B)
C)
D)

dimer
polymer
trimer
tetramer
Ans: A

Topic: Signal Characteristics


Section: 15.5
Difficulty Level: Medium
31. Primary amines show two medium absorption bands around 3400 cm-1, due to _______.
A)
B)
C)
D)

symmetric stretching
asymmetric stretching
both symmetric and asymmetric stretching
hydrogen bonding
Ans: C

Topic: Signal Characteristics


Section: 15.5
Difficulty Level: Medium

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

Topic: Analyzing an IR spectrum


Section: 15.6
Difficulty Level: Medium

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

Topic: Analyzing an IR spectrum


Section: 15.6
Difficulty Level: Medium
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

NH2

A)
B)
C)
D)
E)

III

II

IV

I
II
III
IV
none of these
Ans: D

Topic: Analyzing an IR spectrum


Section: 15.6
Difficulty Level: Medium
36. Which of the following compounds will show absorption at 2250 cm-1?
N
NH2

A)
B)
C)
D)
E)

I
II
III
IV
none of these
Ans: D

II

N
H

III

IV

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

A)
B)
C)
D)
E)

Cl

II

NH2

III

OH

IV

I
II
III
IV
V
Ans: C

Topic: Analyzing an IR spectrum


Section: 15.6
Difficulty Level: Medium
38. Which of the following is true about the IR spectrum of the following compound?
O

Cl

A)
B)
C)
D)
E)

absorptions at 1720 cm-1 & 2150 cm-1


absorptions at 1800 cm-1 & 2150 cm-1
absorptions at 1720 cm-1 & 2250 cm-1
absorptions at 1800 cm-1 & 2250 cm-1
absorptions at 1650 cm-1 & 2150 cm-1
Ans: B

Topic: Analyzing an IR spectrum


Section: 15.6
Difficulty Level: Medium

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

Topic: Analyzing an IR spectrum


Section: 15.6
Difficulty Level: Medium
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

Topic: Analyzing an IR spectrum


Section: 15.6
Difficulty Level: Medium
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
Topic: Analyzing an IR spectrum
Section: 15.6
Difficulty Level: Medium

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

Topic: Analyzing an IR spectrum


Section: 15.6
Difficulty Level: Hard
43. Which of the following compounds will have highest wavenumber for carbonyl
absorption?
O

O
O
O

O
O

III

II

A)
B)
C)
D)

IV

I
II
III
IV
Ans: B

Topic: Analyzing an IR spectrum


Section: 15.6
Difficulty Level: Hard
44. Which of the following compounds will have two absorptions at 1820 cm-1 and
1740cm-1?
O

OH

A)
B)
C)
D)
E)

I
II
III
IV
V
Ans: D

II

NH2

III

IV

Cl

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?

SDBS: National Institute of Advanced Industrial Science and Technology


O

I OH

A)
B)
C)
D)
E)

OH

OH

II

I
II
III
IV
V
Ans: D

Topic: Analyzing an IR spectrum


Section: 15.6
Difficulty Level: Medium

III

IV

OH

OH

46. Which one of the following compounds is consistent with the following IR spectrum?

SDBS: National Institute of Advanced Industrial Science and Technology


O

O
O

NH2
N

N
H

I NH
2

A)
B)
C)
D)
E)

II

I
II
III
IV
V
Ans: B

Topic: Analyzing an IR spectrum


Section: 15.6
Difficulty Level: Medium

III

IV

OH

HN

47. Which one of the following compounds is consistent with the following IR spectrum?

SDBS: National Institute of Advanced Industrial Science and Technology


OH

A)
B)
C)
D)
E)

OH

II

I
II
III
IV
V
Ans: A

Topic: Analyzing an IR spectrum


Section: 15.6
Difficulty Level: Medium

OH
C
N

III

O
HO

IV

48. Which one of the following compounds is consistent with the following IR spectrum?

SDBS: National Institute of Advanced Industrial Science and Technology

OH

A)
B)
C)
D)
E)

II

I
II
III
IV
V
Ans: D

Topic: Analyzing an IR spectrum


Section: 15.6
Difficulty Level: Medium

III

IV

49. Which one of the following compounds is consistent with the following IR spectrum?

SDBS: National Institute of Advanced Industrial Science and Technology

OH

A)
B)
C)
D)
E)

II

I
II
III
IV
V
Ans: E

Topic: Analyzing an IR spectrum


Section: 15.6
Difficulty Level: Medium

OH

OH

OH

III

IV

OH

50. Which one of the following compounds is consistent with the following IR spectrum?

SDBS: National Institute of Advanced Industrial Science and Technology


NH2

NH2

NHCH3

NH2

N(CH3)2

CH3

II

IV

III
CH3

A)
B)
C)
D)
E)

I
II
III
IV
V
Ans: B

Topic: Analyzing an IR spectrum


Section: 15.6
Difficulty Level: Medium

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

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
Topic: Analyzing an IR spectrum
Section: 15.6
Difficulty Level: Medium
52. For the following reaction, which of the following is consistent with the IR spectrum of
the product?
O

H3O+

A)
B)
C)
D)
E)

absorption at 2150 cm-1 should disappear


absorption at 3300 cm-1 and 2150cm-1 should disappear
absorption at 2250 cm-1 should disappear, new absorption at 3300 cm-1 should appear
absorption at 1650 cm-1 should disappear and absorption at 3300 cm-1 should appear
absorption at 3300 cm-1 and 2150cm-1 should disappear, a new absorption at 1720 cm-1
should appear
Ans: E

Topic: Analyzing an IR spectrum


Section: 15.6
Difficulty Level: Medium

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)

absorption at 3200-3600 cm-1 should disappear


absorption at 3200-3600 cm-1 and 1100 cm-1 should disappear
absorption at 1100 cm-1 should disappear and absorption at 3100 cm-1 should appear
absorption at 1650 cm-1 should disappear and absorption at 3300 cm-1 should appear.
none of these
Ans: A

Topic: Analyzing an IR spectrum


Section: 15.7
Difficulty Level: Hard
54. Predict the product for the following reaction and explain how you will use IR
spectroscopy to monitor the progress of the reaction.
1-pentyne

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)

Mass spectrometry is primarily used to determine:


molecular formula of a compound
molecular weight of a compound
conjugation in a compound
A&B
A&C
Ans: D

Topic: Mass Spectrometry


Section: 15.8
Difficulty Level: Easy
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
Topic: Mass Spectrometry
Section: 15.8
Difficulty Level: Easy
58.
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

Topic: Mass Spectrometry


Section: 15.8
Difficulty Level: Easy
59.
A)
B)
C)
D)
E)

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

Topic: Mass Spectrometry

Section: 15.8
Difficulty Level: Easy
60.
A)
B)
C)
D)
E)

The separation of ions in the mass spectrometer is done by their ______.


electrons to protons ratio
mass to neutrons ratio
protons to neutrons ratio
mass to charge ratio
none of these
Ans: D

Topic: Analyzing M+ peak


Section: 15.9
Difficulty Level: Easy

61.
A)
B)
C)
D)
E)

Which of the following is true about CH3CH3+ ?


it is the parent ion of ethane
it is a molecular ion of ethane with m/z =30
it is a fragment of propane
A&B
none of these
Ans: D

Topic: Analyzing M+ peak


Section: 15.9
Difficulty Level: Easy

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

Topic: Analyzing M+ peak


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)
B)
C)
D)
E)

45
44
29
15
none of these
Ans: B

Topic: Analyzing M+ peak


Section: 15.9
Difficulty Level: Medium

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

Topic: Analyzing M+ peak


Section: 15.9
Difficulty Level: Medium

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

Topic: Analyzing M+ peak


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

A)
B)
C)
D)
E)

odd molecular weight, m/z-115


odd molecular weight, m/z-121
even molecular weight, m/z-96
even molecular weight, m/z-132
none of these
Ans: B

Topic: Analyzing (M+1)+ peak


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?

A)
B)
C)
D)
E)

it is the most abundant peak


it is due to the 13C isotope of carbon
it has a m/z value lower than the molecular ion
it is useful in calculating number of carbon atoms
B&D
Ans: E

Topic: Analyzing (M+1)+ peak


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%
(M+1)+ at m/z= 85, relative height=0.56%

A)
B)
C)
D)
E)

C5H10O
C5H8O
C5H24
C6H12
C4H6O2
Ans: B

Topic: Analyzing (M+1)+ peak


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%
(M+1)+ at m/z= 73, relative height=3.3%

A)
B)
C)
D)
E)

C4H10O
C4H9N
C5H12
C4H8O
none of these
Ans: D

Topic: Analyzing (M+1)+ peak


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%
(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

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%
(M+1)+ at m/z= 168, relative height=4.4%

Ans: C8H9NO3
Topic: Analyzing (M+2)+ peak
Section: 15.11
Difficulty Level: Medium

73. Compounds containing chlorine or bromine usually show a strong _____peak.


A)
B)
C)
D)
E)

molecular ion
base
M+1
M+2
all of these
Ans: D

Topic: Analyzing (M+2)+ peak


Section: 15.11
Difficulty Level: Medium

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

Topic: Analyzing (M+2)+ peak


Section: 15.11
Difficulty Level: Medium

75. Presence of bromine produces M+ and (M+2)+ peaks of equal intensity on a mass
spectrum because:

A)
B)
C)
D)

81Br isotope has higher natural abundance than 79Br isotope


79Br and 81Br isotopes have almost equal natural abundance
79Br isotope has higher natural abundance than 81Br isotope
none of these
Ans: B

Topic: Analyzing (M+2)+ peak


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%
(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

Topic: Analyzing (M+2)+ peak


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%
(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

Topic: Analyzing (M+2)+ peak


Section: 15.11
Difficulty Level: Medium

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

Topic: Analyzing (M+2)+ peak


Section: 15.11
Difficulty Level: Medium

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

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)
B)
C)
D)
E)

2-methylheptane
1-heptanol
heptanamine
heptanal
none of these
Ans: B

Topic: Analyzing the fragments


Section: 15.12
Difficulty Level: Medium
81. Which of the following compounds will produce a prominent (M-15) peak in the mass
spectrum?
A)
B)
C)
D)
E)

2-methylheptane
1-heptanol
heptanamine
1-chloroheptane
none of these
Ans: A

Topic: Analyzing the fragments


Section: 15.12
Difficulty Level: Medium
82. Which of the following is not a prominent peak in the mass spectrum of 2-methyl-2pentanol?
A)
B)
C)
D)
E)

(M-15)
(M-18)
(M-29)
(M-16)
none of these
Ans: D

Topic: Analyzing the fragments


Section: 15.12
Difficulty Level: Medium

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

Topic: Analyzing the fragments


Section: 15.12
Difficulty Level: Medium
84. Which of the following compounds will have a base peak at m/z=43?
A)
B)
C)
D)
E)

CH3CH2CH2CH2CH2CH3
(CH3CH2)2CHCH3
(CH3)3CCH2CH3
(CH3)2CHCH(CH3)2
none of these
Ans: D

Topic: Analyzing the fragments


Section: 15.12
Difficulty Level: Medium
85. Which of the following is the base peak in the mass spectrum of 2,2,4-trimethylpentane?
A)
B)
C)
D)
E)

114
57
42
29
none of these
Ans: B

Topic: Analyzing the fragments


Section: 15.12
Difficulty Level: Medium

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

Topic: Analyzing the fragments


Section: 15.12
Difficulty Level: Medium
87. Which of the following is expected to be the base peak in the mass spectrum of 2methyl-2-butanol?
A)
B)
C)
D)
E)

73
55
43
31
59
Ans: E

Topic: Analyzing the fragments


Section: 15.12
Difficulty Level: Medium
88. Which of the following is expected to be the base peak in the mass spectrum of
CH3CH2NH2?
A)
B)
C)
D)
E)

15
28
30
45
none of these
Ans: C

Topic: Analyzing the fragments


Section: 15.12
Difficulty Level: Medium

89. Provide the structures of the fragments that result when the molecular ion of 2heptanone undergoes fragmentation via McLafferty rearrangement.
H

Ans:

Topic: Analyzing the fragments


Section: 15.12
Difficulty Level: Medium
90. Provide the structure of the major fragment that results when the molecular ion of
(CH3)2CHCH2CH2NH2 undergoes fragmentation.
Ans:

H
N
H

Topic: Analyzing the fragments


Section: 15.12
Difficulty Level: Medium
91. Provide the structure of the major fragment that results when the molecular ion of
CH3CH2CH2CH2OH undergoes fragmentation via alpha cleavage.
Ans:

O
H

Topic: Analyzing the fragments


Section: 15.12
Difficulty Level: Medium
92. Which of the following is expected to be the base peak in the mass spectrum of
pentanal?
O

CH3CH2CH2CH2CH
pentanal

A)
B)
C)
D)
E)

29
41
44
58
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?

SDBS: National Institute of Advanced Industrial Science and Technology

A)
B)
C)
D)
E)

CH3CH2CH(CH3)2
CH3CHOHCH2CH3
CH3CH2OCH2CH3
CH3CH2NHCH2CH3
none of these
Ans: D

Topic: Analyzing the fragments


Section: 15.12
Difficulty Level: Medium

94. Which one of the following compounds is consistent with the mass spectrum below?

SDBS: National Institute of Advanced Industrial Science and Technology

A)
B)
C)
D)
E)

CH3CH2CH(CH3)2
CH3CHOHCH2CH3
CH3CH2OCH2CH3
CH3CH2NHCH2CH3
none of these
Ans: B

Topic: Analyzing the fragments


Section: 15.12
Difficulty Level: Medium
95. Which one of the following compounds is consistent with the mass spectrum below?

SDBS: National Institute of Advanced Industrial Science and Technology

A)
B)
C)
D)
E)

CH3CH2CH(CH3)2
CH3CHOHCH2CH3
CH3CH2OCH2CH3
CH3CH2NHCH2CH3
none of these
Ans: A

Topic: High-resolution mass spectrometry


Section: 15.13
Difficulty Level: Easy
96. High-resolution mass spectrometry is used to determine the _____ of a compound.
A)
B)
C)
D)
E)

degree of unsaturation
molecular formula
molecular weight
B&C
none of these
Ans: B

Topic: High-resolution mass spectrometry


Section: 15.13
Difficulty Level: Medium
97. How will you distinguish between the following compounds using high-resolution mass
spectrometry?
O

Cl

II

Ans: Compound I: m/z at 102.0678


Compound II: m/z at 102.0235
Topic: High-resolution mass spectrometry
Section: 15.13
Difficulty Level: Medium
98. How will you distinguish between the following compounds using high-resolution mass
spectrometry?
OH

II

Ans: Compound I: m/z at 98.0729


Compound II: m/z at 98.1092
Topic: Gas chromatography-mass spectrometry
Section: 15.14
Difficulty Level: Medium

99. GC-mass spectrometry is used to find the _________ of each compound in a


__________.
A)
B)
C)
D)
E)

molecular formula, mixture of alkanes


molecular weight, mixture of compounds
molecular formula, mixture of compounds
B&C
none of these
Ans: B

Topic: High-resolution mass spectrometry


Section: 15.15
Difficulty Level: Medium
100. Electrospray ionization is used to obtain mass spectra of proteins because:
A)
B)
C)
D)

it allows for faster fragmentation of molecular ion


the molecular ion usually does not undergo fragmentation
it allows for slow fragmentation of molecular ion
none of these
Ans: B

Topic: Hydrogen deficiency index


Section: 15.16
Difficulty Level: Easy
101. Calculate the degree of unsaturation for C9H11N.
A)
B)
C)
D)
E)

4
6
2
5
none of these
Ans: D

Topic: Hydrogen deficiency index


Section: 15.16
Difficulty Level: Easy

102. Calculate the degree of unsaturation for C14H14N2O.


A)
B)
C)
D)
E)

4
6
8
10
9
Ans: E

Topic: Hydrogen deficiency index


Section: 15.16
Difficulty Level: Easy
103. Calculate the degree of unsaturation for C11H8ClBrO.
A)
B)
C)
D)
E)

4
6
7
8
10
Ans: C

Topic: Hydrogen deficiency index


Section: 15.16
Difficulty Level: Medium
104. Calculate the degree of unsaturation for C5H5Br2NO.
A)
B)
C)
D)
E)

4
6
2
3
7
Ans: D

Topic: Hydrogen deficiency index


Section: 15.16
Difficulty Level: Medium

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

Topic: Hydrogen deficiency index


Section: 15.16
Difficulty Level: Medium
106. Propose a possible structure for a compound with molecular formula C6H5Br
Ans:

Br

Topic: Hydrogen deficiency index


Section: 15.16
Difficulty Level: Medium
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 16001800 cm-1 in its IR spectrum.
NH2
Ans:
NH2

Topic: Hydrogen deficiency index


Section: 15.16
Difficulty Level: Medium
108. Propose possible structure(s) for a compound with molecular formula C4H7N that shows
absorption at 2250 cm-1 in its IR spectrum.
Ans: CH3CH2CH2CN
Topic: Hydrogen deficiency index
Section: 15.16
Difficulty Level: Medium

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:

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