Chapter Fifteen

Topic: Spectroscopy
Section: 15.1
Difficulty Level: Easy

1. Which of the following is not true about electromagnetic radiation?

A) frequency is directly proportional to wavelength
B) frequency is directly proportional to energy
C) frequency is inversely proportional to wavelength
D) wavelength is inversely proportional to energy
E) none of these
Ans: A

Topic: Spectroscopy
Section: 15.1
Difficulty Level: Easy

2. Which of the following electromagnetic radiation has the highest energy?

A) UV
B) X-ray
C) IR
D) microwave
E) visible
Ans: B

Topic: Spectroscopy
Section: 15.1
Difficulty Level: Easy

3. Which of the following electromagnetic radiation has the longest wavelength?

A) UV
B) X-ray
C) IR
D) microwave
E) visible
Ans: D

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

5. Arrange the following electromagnetic radiation in decreasing (highest to lowest) order

of frequency.
microwave -rays visible IR UV
I  III 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: Medium

6. Arrange the following electromagnetic radiation in decreasing (highest to lowest) order

of wavelength.
x-rays radio UV IR visible
I  III 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: E

Topic: Spectroscopy
Section: 15.1
Difficulty Level: Easy
 7. Which of the following information is primarily obtained from infrared spectroscopy?
A) arrangement of carbon and hydrogen atoms in a compound
B) molecular weight of a compound
C) conjugated  system present in a compound
D) functional groups present in a compound
E) all of these
Ans: D

Topic: Infrared Spectroscopy

Section: 15.2
Difficulty Level: Easy

8. 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

9. Which of the following vibrations are observed in IR spectroscopy?

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

Topic: Infrared Spectroscopy

Section: 15.2
Difficulty Level: Easy

10. Which of the following is currently most often 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

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

A) cm-1
B) cm
C) J.s-1
D) mm
E) none of these
Ans: A

Topic: Signal Characteristics

Section: 15.3
Difficulty Level: Easy

12. Which of the following wavenumber 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

Topic: Signal Characteristics

Section: 15.3
Difficulty Level: Easy

13. Which of the following wavenumber corresponds to the fingerprint 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: C

Topic: Signal Characteristics

Section: 15.3
Difficulty Level: Medium
 14. Which of the following statement(s) is(are) true about the frequency of a stretching
vibration according to Hooke’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

Topic: Signal Characteristics

Section: 15.3
Difficulty Level: Easy

15. Rank absorption of the indicated bonds in decreasing (highest to lowest) order of
wavenumber.
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

Topic: Signal Characteristics

Section: 15.3
Difficulty Level: Easy

16. Rank absorption of 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
Topic: Signal Characteristics
Section: 15.3
Difficulty Level: Easy

17. Rank absorption of the indicated bonds in decreasing (highest to lowest) order of
wavenumber.
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

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 O O
O

NH2

II III IV
I
A) I
B) II
C) III
D) IV
E) none of these
Ans: D

Topic: Signal Characteristics

Section: 15.3
Difficulty Level: Medium
 19. Which one of the following compounds will have the lowest wavenumber for carbonyl
absorption?
O O O NH2 O O

O
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: C

Topic: Signal Characteristics

Section: 15.3
Difficulty Level: Medium

20. 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

Topic: Signal Characteristics

Section: 15.3
Difficulty Level: Hard
 21. Which of the following compounds will have the highest wavenumber for carbonyl
absorption?
O O O

O O O
I II III
A) I
B) II
C) III
D) II & III
Ans: C

Topic: Signal Characteristics

Section: 15.3
Difficulty Level: Medium

22. Rank absorption of 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

Topic: Signal Characteristics

Section: 15.3
Difficulty Level: Medium
 23. For the following pair of compounds the expected stretching absorption of the C=O
bond is 1685cm-1 & 1715cm-1 respectively. Explain using both words and structural
drawings.
O O
-1
1685cm 1715cm-1

I II
Ans: Compound I has a conjugated double bond that allows for more single bond
charcter to the carbonyl group. This results in absorption of the carbonyl group at
a lower wavenumber.
O O O

Topic: Signal Characteristics

Section: 15.3
Difficulty Level: Hard
 24. For the following pair of compounds the expected stretching absorption of the C=O
bond is 1685cm-1 & 1655cm-1 respectively. Explain using both words and structural
drawings.
O O
-1
1685cm 1655cm-1

O
I II
Ans: Both compounds I and II have conjugated double bond that allows for single bond
charcter to the carbonyl group. But for compound II the oxygen atom allows for
additional resonance structures, which results in more single bond character for
the carbonyl group. This results in absorption of the carbonyl group at a lower
wavenumber.
O O O

O O
O O

O O
O O

Topic: Signal Characteristics

Section: 15.3
Difficulty Level: Hard

25. The C—O absorption in carboxylic acids appears around 1250cm-1, where as the C—O
absortion in alcohol appears around 1050cm-1. Explain why.
O 1250cm-1
1050cm-1
H H
O O
Ans: The C—O bond in carboxylic acid has a double bond character as indicated by
one of the resonance structures. This results in a stronger C—O bond and thus
higher absorption of around 1250cm-1.

Topic: Signal Characteristics

Section: 15.4
Difficulty Level: Medium
 26. Which of the following statement(s) is(are) true for an IR-active bond?
A) the bond must be symmetrical
B) a vibration must result in a change of bond length
C) a vibration must result in a change of bond angle
D) a vibration must result in a change of bond dipole
E) all of these
Ans: D

Topic: Signal Characteristics

Section: 15.4
Difficulty Level: Medium

27. Which of the following bonds is IR-inactive?

CH3CH2 C C CH2CH3 CH3CH2 C C H

III IV
I II
A) I
B) II
C) III
D) I & IV
E) I & III
Ans: E

Topic: Signal Characteristics

Section: 15.4
Difficulty Level: Medium

28. Which of the following bonds has the weakest absorption?

A) C=C
B) O—H
C) C=O
D) sp3C—H
E) A&D
Ans: A

Topic: Signal Characteristics

Section: 15.4
Difficulty Level: Medium
 29. Which of the following bonds has the strongest absorption?
A) C=N
B) CC
C) C=O
D) sp2C—H
E) C—O
Ans: C

Topic: Signal Characteristics

Section: 15.4
Difficulty Level: Medium

30. 3-Hexyne does not show absorption in the range of 2000-2200 cm—1, whereas 1-hexyne
does. Which of the following explains the reason for this absence of absorption for 3-
hexyne?
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

Topic: Signal Characteristics

Section: 15.4
Difficulty Level: Medium

31. Which of the following alkene groups will produce the strongest signal?

F Cl III Br
I II IV
A) I
B) II
C) III
D) IV
Ans: A

Topic: Signal Characteristics

Section: 15.4
Difficulty Level: Hard
 32. Which of the following alkene groups will produce the stronger signal? Explain why.

F Cl
I II
Ans: Compound I.
The more electronegative fluorine will cause the C=C in compound I to have a
larger dipole moment than the C=C in compound II.

Topic: Signal Characteristics

Section: 15.4
Difficulty Level: Hard

33. Which of the following alkene groups will produce the stronger signal? Explain why.
F

F F
F
I II
Ans: Compound II.
The C=C in compound II will have a larger dipole moment while the C=C in
compound I will not.

Topic: Signal Characteristics

Section: 15.5
Difficulty Level: Medium

34. Diluted alcohols show a _____absorption around 3600cm-1, due to _____.

A) sharp, hydrogen bonding
B) broad, hydrogen bonding
C) sharp, absence of hydrogen bonding
D) broad, absence of hydrogen bonding
Ans: C

Topic: Signal Characteristics

Section: 15.5
Difficulty Level: Medium

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

_____.
A) sharp, hydrogen bonding
B) broad, hydrogen bonding
C) sharp, polarity
D) broad, polarity
Ans: B
Topic: Signal Characteristics
Section: 15.5
Difficulty Level: Medium

36. 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

Topic: Signal Characteristics

Section: 15.5
Difficulty Level: Medium

37. 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

Topic: Signal Characteristics

Section: 15.5
Difficulty Level: Medium

38. 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.
Also, the carboxylic acid will show absorption for carbonyl group that will be
absent in the alcohol.

Topic: Signal Characteristics

Section: 15.5
Difficulty Level: Medium
 39. For each of the following IR spectra determine if it is consistent with the structure of an
alcohol, a ketone, an aldehyde, a carboxylic acid, a primary amine or a secondary
amine.
I.

SDBS: National Institute of Advanced Industrial Science and Technology

II.

SDBS: National Institute of Advanced Industrial Science and Technology

Ans: I: aldehyde
II: alcohol

Topic: Signal Characteristics

Section: 15.5
Difficulty Level: Medium
 40. For each of the following IR spectra determine if it is consistent with the structure of an
alcohol, a ketone, an aldehyde, a carboxylic acid, a primary amine or a secondary
amine.
I.

SDBS: National Institute of Advanced Industrial Science and Technology

II.

Ans: I: secondary amine

II: ketone

Topic: Analyzing an IR spectrum

Section: 15.6
Difficulty Level: Medium
 41. Which of the following compounds will show a broad absorption around 3300 cm-1 and
a sharp absorption 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

Topic: Analyzing an IR spectrum

Section: 15.6
Difficulty Level: Medium

42. Which of the following compounds will show two sharp absorption at 3300 cm-1 and at
2150 cm-1?

C
I N
II III IV
A) I
B) II
C) III
D) IV
E) none of these
Ans: A

Topic: Analyzing an IR spectrum

Section: 15.6
Difficulty Level: Medium
 43. Which of the following compounds will show two absorptions at 2700 cm-1 and at
2800 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

Topic: Analyzing an IR spectrum

Section: 15.6
Difficulty Level: Medium

44. Which of the following compounds will show an 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
 45. Which of the following compounds will have the lowest wavenumber for carbonyl
absorption?
O NH2 O OH O O
O Cl O H

IV V
I II III
A) I
B) II
C) III
D) IV
E) V
Ans: C

Topic: Analyzing an IR spectrum

Section: 15.6
Difficulty Level: Medium

46. Which of the following is true about the IR spectrum of the compound shown below?
O

Cl

A) absorptions at 1720 cm-1 & 2150 cm-1

B) absorptions at 1800 cm-1 & 2150 cm-1
C) absorptions at 1720 cm-1 & 2250 cm-1
D) absorptions at 1800 cm-1 & 2250 cm-1
E) absorptions at 1650 cm-1 & 2150 cm-1
Ans: B

Topic: Analyzing an IR spectrum

Section: 15.6
Difficulty Level: Medium
 47. Which of the following compounds will show absorptions at 1640 cm-1, 2950 cm-1 and
3050 cm-1 on the IR spectrum?
O

O OH
II III IV V
I
A) I
B) II
C) III
D) IV
E) V
Ans: C

Topic: Analyzing an IR spectrum

Section: 15.6
Difficulty Level: Medium

48. 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 OR O

Topic: Analyzing an IR spectrum

Section: 15.6
Difficulty Level: Medium

49. 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 OR (CH3)2CHNH2

Topic: Analyzing an IR spectrum

Section: 15.6
Difficulty Level: Medium

50. 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.
Ans: O O

OR
OH OH
Topic: Analyzing an IR spectrum
Section: 15.6
Difficulty Level: Hard

51. Which of the following compounds will have the highest wavenumber for carbonyl
absorption?
O O
O

O
O
O
O

I II III IV
A) I
B) II
C) III
D) IV
Ans: B

Topic: Analyzing an IR spectrum

Section: 15.6
Difficulty Level: Hard

52. 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
 53. Which one of the following compounds is consistent with the following IR spectrum?

SDBS: National Institute of Advanced Industrial Science and Technology

O OH O H
O OH

II III IV V
I OH OH OH

A) I
B) II
C) III
D) IV
E) V
Ans: D

Topic: Analyzing an IR spectrum

Section: 15.6
Difficulty Level: Medium
 54. 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

N
H
I NH II III IV V
OH HN
2

A) I
B) II
C) III
D) IV
E) V
Ans: B

Topic: Analyzing an IR spectrum

Section: 15.6
Difficulty Level: Medium
 55. Which one of the following compounds is consistent with the following IR spectrum?

SDBS: National Institute of Advanced Industrial Science and Technology

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

Topic: Analyzing an IR spectrum

Section: 15.6
Difficulty Level: Medium
 56. Which one of the following compounds is consistent with the following IR spectrum?

SDBS: National Institute of Advanced Industrial Science and Technology

OH O O O

O H H
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
 57. Which one of the following compounds is consistent with the following IR spectrum?

SDBS: National Institute of Advanced Industrial Science and Technology

OH
OH O O OH

OH OH
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: E

Topic: Analyzing an IR spectrum

Section: 15.6
Difficulty Level: Medium
 58. Which one of the following compounds is consistent with the following IR spectrum?

SDBS: National Institute of Advanced Industrial Science and Technology

NHCH3 NH2 NH2 N(CH3)2
NH2

CH3

CH3
II IV V
I III
CH3
A) I
B) II
C) III
D) IV
E) V
Ans: B

Topic: Analyzing an IR spectrum

Section: 15.6
Difficulty Level: Medium
 59. Which one of the following compounds is consistent with the following IR spectrum?

SDBS: National Institute of Advanced Industrial Science and Technology

OH O O O

O H O
I II III IV V
A) I
B) II
C) III
D) IV
E) V
Ans: E

Topic: Analyzing an IR spectrum

Section: 15.6
Difficulty Level: Medium

60. For the following reaction, which of the following change(s) in the IR spectrum is
consistent with conversion of the reactant to the product?
O H
CN

1. DIBAH

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 absorptions at 2600-2800 cm-1 and 1720
cm-1 should appear.
D) absorption at 2250 cm-1 should disappear, a new absorption around 3400 cm-1 should
appear.
E) none of these
Ans: C

Topic: Analyzing an IR spectrum

Section: 15.6
Difficulty Level: Medium
 61. For the following reaction, which of the following change(s) in the IR spectrum is
consistent with conversion of the reactant to the product?
O

H3O+
HgSO4
A) absorption at 2150 cm-1 should disappear
B) absorption at 3300 cm-1 and 2150cm-1 should disappear
C) absorption at 2250 cm-1 should disappear, a new absorption at 3300 cm-1 should appear
D) absorption at 1650 cm-1 should disappear, a new absorption at 3300 cm-1 should appear
E) 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

62. For the following reaction, which of the following change(s) in the IR spectrum is
consistent with conversion of the reactant to the product?
OH OCH2CH3

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, a new absorption at 3100 cm-1 should appear
D) absorption at 1650 cm-1 should disappear, a new absorption at 3300 cm-1 should appear.
E) none of these
Ans: A

Topic: Analyzing an IR spectrum

Section: 15.6
Difficulty Level: Medium
 63. For the following reaction, which of the following change(s) in the IR spectrum is
consistent with conversion of the reactant to the product?

H
N
+ Br N

A) absorption at 3300-3400 cm-1 should disappear

B) absorption at 3300-3400 cm-1 and 1100 cm-1 should disappear
C) absorption at 1100 cm-1 should disappear, a new absorption at 3100 cm-1 should appear
D) absorption at 1650 cm-1 should disappear, a new absorption at 3300 cm-1 should appear.
E) none of these
Ans: A

Topic: Analyzing an IR spectrum

Section: 15.6
Difficulty Level: Medium

64. For the following reaction, explain how you will use IR spectroscopy to monitor the
progress of the reaction.
H
NH2 N
+ Br
Ans: The two absorptions at 3350cm-1 and at 3450cm-1 for primary amine should
disappear from the product and there should be a single absorption at around
3300cm-1 for the secondary amine.

Topic: Analyzing an IR spectrum

Section: 15.6
Difficulty Level: Hard

65. Predict the product for the following reaction and explain how you will use IR
spectroscopy to monitor the progress of the reaction.
O
H3O+

HO
Ans:

OH
A new absorption for OH at 3200-3600 cm-1 would appear in the product’s IR
spectrum.

Topic: Analyzing an IR spectrum

Section: 15.7
Difficulty Level: Hard
 66. 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. CH3CH2CH2Br
Ans: CH3CH2CH2CCCH2CH2CH3
Absorptions for spC-H around 3300 cm-1 and CC around 2150 cm-1 should
disappear from the product IR spectrum.

Topic: Analyzing an IR spectrum

Section: 15.7
Difficulty Level: Hard

67. 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 in the product IR spectrum.

Topic: Mass Spectrometry

Section: 15.8
Difficulty Level: Easy

68. Mass spectrometry is primarily used to determine:

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

Topic: Mass Spectrometry

Section: 15.8
Difficulty Level: Easy
 69. 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

70. 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

Topic: Mass Spectrometry

Section: 15.8
Difficulty Level: Easy

71. 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

Topic: Mass Spectrometry

Section: 15.8
Difficulty Level: Easy

72. 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

Topic: Mass Spectrometry

Section: 15.8
Difficulty Level: Easy

73. In mass spectrometry using electron impact ionization technique, a beam of high-energy
electrons initially ejects one electron from the compound being studied. This produces a
positively charged ion called the ____________________.
Ans: molecular ion

Topic: Mass Spectrometry

Section: 15.8
Difficulty Level: Easy

74. In mass spectrometry, the tallest peak is assigned an intensity of 100% and is referred to
as the ______________.
Ans: base peak

Topic: Mass Spectrometry

Section: 15.8
Difficulty Level: Easy

75. In mass spectrometry, the cations are separated by their ______________.

Ans: mass to charge ratio

Topic: Analyzing M+ peak

Section: 15.9
Difficulty Level: Easy

76. Which of the following is true about CH3CH3+?

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

Topic: Analyzing M+ peak

Section: 15.9
Difficulty Level: Easy
 77. 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

Topic: Analyzing M+ peak

Section: 15.9
Difficulty Level: Easy

78. 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

Topic: Analyzing M+ peak

Section: 15.9
Difficulty Level: Medium
 79. 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

Topic: Analyzing M+ peak

Section: 15.9
Difficulty Level: Medium

80. Which of the following m/z values corresponds to the base peak for 2-chloro-2-
methylpropane?
A) 15
B) 92
C) 77
D) 47
E) 57
Ans: E

Topic: Analyzing M+ peak

Section: 15.9
Difficulty Level: Medium

81. 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

Topic: Analyzing M+ peak

Section: 15.9
Difficulty Level: Medium
 82. Which of the following is true about the molecular weight and the M+-m/z value for the
following compound?
Cl

NH2

A) odd molecular weight, m/z-115

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

Topic: Analyzing (M+1)+ peak

Section: 15.10
Difficulty Level: Medium

83. Which of the following is true about the (M+1)+ peak on the mass spectrum of a
hydrocarbon?
A) it is always the most abundant peak
B) it is due to the 13C isotope of carbon
C) it has a m/z value lower than the molecular ion
D) it is useful in calculating number of carbon atoms
E) B & D
Ans: E

Topic: Analyzing (M+1)+ peak

Section: 15.10
Difficulty Level: Medium

84. 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) C5H10O
B) C5H8O
C) C5H24
D) C6H12
E) C4H6O2
Ans: B

Topic: Analyzing (M+1)+ peak

Section: 15.10
Difficulty Level: Medium
 85. 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) C4H10O
B) C4H9N
C) C5H12
D) C4H8O
E) none of these
Ans: D

Topic: Analyzing (M+1)+ peak

Section: 15.10
Difficulty Level: Medium

86. 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

87. 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

88. 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
 89. Compounds containing chlorine or bromine usually show a strong _____peak.
A) molecular ion
B) base
C) M+1
D) M+2
E) all of these
Ans: D

Topic: Analyzing (M+2)+ peak

Section: 15.11
Difficulty Level: Medium

90. 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

Topic: Analyzing (M+2)+ peak

Section: 15.11
Difficulty Level: Medium

91. Which of the following will produce (M+2)+ peak one third the intensity of M+ peak?
A) nitrogen
B) chlorine
C) bromine
D) oxygen
E) B&C
Ans: B

Topic: Analyzing (M+2)+ peak

Section: 15.11
Difficulty Level: Medium

92. Presence of bromine produces M+ and (M+2)+ peaks of equal intensity on a mass
spectrum because:
A) 81Br isotope has higher natural abundance than 79Br isotope
B) 79Br and 81Br isotopes have almost equal natural abundance
C) 79Br isotope has higher natural abundance than 81Br isotope
D) none of these
Ans: B

Topic: Analyzing (M+2)+ peak

Section: 15.11
Difficulty Level: Medium

93. 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) C6H6
B) C3H7Cl
C) C6H8
D) C6H9Cl
E) none of these
Ans: B

Topic: Analyzing (M+2)+ peak

Section: 15.11
Difficulty Level: Medium

94. 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) C2H5Br
B) C5H12Cl
C) C8H12
D) C2H7Br
E) none of these
Ans: A

Topic: Analyzing (M+2)+ peak

Section: 15.11
Difficulty Level: Medium

95. For which of the following compounds will the (M+2)+ peak intensity be around one
third the intensity of the molecular ion peak?
A) CH3CH2CH2Br
B) CH3CH2CH2OH
C) CH3CH2CH2Cl
D) CH3CH2CH2NH2
E) none of these
Ans: C

Topic: Analyzing (M+2)+ peak

Section: 15.11
Difficulty Level: Medium
 96. For which of the following compounds will the (M+2)+ peak intensity be equal to the
intensity of the molecular ion peak?
A) CH3CH2CH2Br
B) CH3CH2CH2OH
C) CH3CH2CH2Cl
D) CH3CH2CH2NH2
E) none of these
Ans: A

Topic: Analyzing (M+2)+ peak

Section: 15.11
Difficulty Level: Medium

97. 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 (M+2)+ peak

Section: 15.11
Difficulty Level: Medium

98. Which of the following mass spectra shows the presence of chlorine 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: E

Topic: Analyzing the fragments

Section: 15.12
Difficulty Level: Medium
 99. 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

Topic: Analyzing the fragments

Section: 15.12
Difficulty Level: Medium

100. 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

Topic: Analyzing the fragments

Section: 15.12
Difficulty Level: Medium

101. 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

Topic: Analyzing the fragments

Section: 15.12
Difficulty Level: Medium

102. Which of the following compounds will have a prominent peak at (M-127)?
A) CH3CH2CH2I
B) (CH3CH2)3CCH2Cl
C) (CH3)3CCH2CH2Br
D) (CH3)2CHCH(CH3)2
E) none of these
Ans: A
Topic: Analyzing the fragments
Section: 15.12
Difficulty Level: Medium

103. 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

Topic: Analyzing the fragments

Section: 15.12
Difficulty Level: Medium

104. 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

Topic: Analyzing the fragments

Section: 15.12
Difficulty Level: Medium

105. Which of the following is expected to be the base peak in the mass spectrum of
CH3(CH2)4OH?
A) 88
B) 55
C) 42
D) 31
E) none of these
Ans: C

Topic: Analyzing the fragments

Section: 15.12
Difficulty Level: Medium
 106. 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

Topic: Analyzing the fragments

Section: 15.12
Difficulty Level: Medium

107. 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

Topic: Analyzing the fragments

Section: 15.12
Difficulty Level: Medium

108. Provide the structures of the fragments that result when the molecular ion of 2-
heptanone undergoes fragmentation via McLafferty rearrangement.
H
Ans:
O

Topic: Analyzing the fragments

Section: 15.12
Difficulty Level: Medium

109. Provide the structure of the major fragment that results when the molecular ion of
(CH3)2CHCH2CH2NH2 undergoes fragmentation.
H
Ans:
N
H

Topic: Analyzing the fragments

Section: 15.12
Difficulty Level: Medium
 110. 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

111. 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

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

SDBS: National Institute of Advanced Industrial Science and Technology

A) CH3CH2CH(CH3)2
B) CH3CHOHCH2CH3
C) CH3CH2OCH2CH3
D) CH3CH2NHCH2CH3
E) none of these
Ans: D
Topic: Analyzing the fragments
Section: 15.12
Difficulty Level: Medium

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

SDBS: National Institute of Advanced Industrial Science and Technology

A) CH3CH2CH(CH3)2
B) CH3CHOHCH2CH3
C) CH3CH2OCH2CH3
D) CH3CH2NHCH2CH3
E) none of these
Ans: B

Topic: Analyzing the fragments

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

SDBS: National Institute of Advanced Industrial Science and Technology

A) CH3CH2CH(CH3)2
B) CH3CHOHCH2CH3
C) CH3CH2OCH2CH3
D) CH3CH2NHCH2CH3
E) none of these
Ans: A

Topic: Analyzing the fragments

Section: 15.12
Difficulty Level: Medium

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

SDBS:
A) (CH3CH2CH2)2CH
B) CH3CH2CHOHCH2CH2CH3
C) (CH3CH2CH2)2O
D) (CH3CH2CH2)2NH
E) none of these
Ans: D
Topic: High-resolution mass spectrometry
Section: 15.13
Difficulty Level: Easy

116. High-resolution mass spectrometry is used to determine the _____ of a compound.

A) degree of unsaturation
B) molecular formula
C) molecular weight
D) B&C
E) none of these
Ans: D

Topic: High-resolution mass spectrometry

Section: 15.13
Difficulty Level: Medium

117. 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

Topic: High-resolution mass spectrometry

Section: 15.13
Difficulty Level: Medium

118. 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

Topic: Gas chromatography-mass spectrometry

Section: 15.14
Difficulty Level: Medium
 119. GC-mass spectrometry is used to find the _________ of each compound in a
__________.
A) molecular formula, mixture of alkanes
B) molecular weight, mixture of compounds
C) molecular formula, mixture of compounds
D) B & C
E) none of these
Ans: B

Topic: High-resolution mass spectrometry

Section: 15.15
Difficulty Level: Medium

120. Electrospray ionization is used to obtain mass spectra of proteins because:

A) it allows for faster fragmentation of molecular ion
B) the molecular ion usually does not undergo fragmentation
C) it allows for slow fragmentation of molecular ion
D) none of these
Ans: B

Topic: Hydrogen deficiency index

Section: 15.16
Difficulty Level: Easy

121. Calculate the degree of unsaturation for C9H11N.

A) 4
B) 6
C) 2
D) 5
E) none of these
Ans: D

Topic: Hydrogen deficiency index

Section: 15.16
Difficulty Level: Easy

122. Calculate the degree of unsaturation for C14H14N2O.

A) 4
B) 6
C) 8
D) 10
E) 9
Ans: E

Topic: Hydrogen deficiency index

Section: 15.16
Difficulty Level: Easy

123. Calculate the degree of unsaturation for C11H8ClBrO.

A) 4
B) 6
C) 7
D) 8
E) 10
Ans: C

Topic: Hydrogen deficiency index

Section: 15.16
Difficulty Level: Medium

124. Calculate the degree of unsaturation for C5H5Br2NO.

A) 4
B) 6
C) 2
D) 3
E) 7
Ans: D

Topic: Hydrogen deficiency index

Section: 15.16
Difficulty Level: Medium

125. Which of the following compounds have the same degree of unsaturation?
C5H5Br2NO C6H5Br C8H10BrIO C9H11NO
I II III IV
A) I & II
B) I & III
C) III & IV
D) II & III
E) none of these
Ans: B

Topic: Hydrogen deficiency index

Section: 15.16
Difficulty Level: Medium

126. Propose a possible structure for a compound with molecular formula C6H5Br.
Ans: Br

there are other possible structures.

Topic: Hydrogen deficiency index
Section: 15.16
Difficulty Level: Medium

127. Propose all possible structures for a compound with molecular formula C 4H9N 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: NH
NH2
2
NH2

NH2

Topic: Hydrogen deficiency index

Section: 15.16
Difficulty Level: Medium

128. 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 OR (CH3)2CH2CN

Topic: Hydrogen deficiency index

Section: 15.16
Difficulty Level: Medium

129. Propose a possible structure for a compound with molecular formula C7H12O2 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: O O

Topic: Integrated Spectroscopy

Section: 15.6 & 15.12
Difficulty Level: Medium
130. Following are the IR spectrum and mass spectrum of an unknown compound. Propose a
structure for the unknown compound.

SDBS:
Ans: (CH3CH2CH2)2NH