Klein 3e CH 15 Testbank FINAL

Klein, Organic Chemistry 3e
Chapter 15
1. NMR is an abbreviation for ____________ ____________ __________.
Answer: nuclear magnetic resonance

Learning Objective: 15.1 Describe the interaction between electromagnetic radiation
and atomic nuclei in a magnetic field that makes NMR spectroscopy possible
Difficulty: Easy
2. List the most common nuclei that are used in NMR.
Answer: 1H and 13C

Difficulty: Easy
3. Identify the nuclei that cannot be analyzed by NMR.

15
A. N
14
B. C
19
C. F
31
D. P
1
E. H
Answer: B
Difficulty: Easy
4. Which of the following nuclei cannot be analyzed by an NMR spectrometer?
A. nucleus with odd number of protons & odd number of neutrons

B. nucleus with odd number of protons &even number of neutrons
C. nucleus with even number of protons & odd number of neutrons
D. nucleus with even number of protons & even number of neutrons
E. none of these
Answer: D
Difficulty: Easy
5. How many nuclear spin states are possible for the 1H nucleus?
A. 1
B. 2
C. 4
D. 5
E. none of these
Answer: B
Difficulty: Easy
6. Which of the following electromagnetic radiation is used in NMR spectroscopy?
A. UV
B. IR
C. visible
D. γ-rays
E. radio wave
Answer: E
Difficulty: Easy
7. _______ protons experience a net magnetic field strength that is smaller than the
applied magnetic field.
A. Deshielded
B. Shielded
C. Paramagnetic
D. Diamagnetic
E. none of these
Answer: B
Difficulty: Medium
8. _______ protons experience a net magnetic field strength that is higher than the
_____ protons.
A. Deshielded, shielded
B. Shielded, deshielded
C. Paramagnetic, diamagnetic
D. Shielded, diamagnetic
E. none of these
Answer: A
Difficulty: Medium
9. Which of the following is true about the relationship between the energy gap (∆E)
between the spin states for a 1H nucleus and the strength of the external
magnetic field?
A. they are inversely proportional

B. they are directly proportional
C. there is no relationship
D. the magnetic field is slightly less
E. none of these
Answer: B
Learning Objective: 15.2 Describe how NMR spectrometers work and the process of
preparing a sample for NMR spectral analysis
Difficulty: Medium
10. The strength of the magnetic field is a determining factor for the range of
_______that must be used for NMR spectrometer.
A. temperature
B. frequencies
C. tesla
D. spin states
D. none of these
Answer: B
Difficulty: Medium
11. Which of the following is not a common solvent used for acquiring a 1H NMR
spectrum?
A. CDCl3
B. CCl4
C. CD3CN
D. CH3OH
E. D2O
Answer: D
Difficulty: Easy
1
12. Which of the following is true about the number of signals in a H NMR
spectrum?
A. it indicates the number of neighboring protons

B. it indicates the electronic environment of neighboring protons
C. it indicates the number of different kinds of protons
D. it indicates the electronic environment of absorbing protons
E. it indicates the number of protons in the signal
Answer: C
Learning Objective: 15.3 State the significance of the number of signals, along with their
locations, areas, and shapes, in am NMR spectrum
Difficulty: Easy
1
13. Which of the following is true about the location of signals in a H NMR
spectrum?

C. it indicates the number of different protons
Answer: D
Difficulty: Easy
14. Which of the following is true about the area under each signal in a 1H NMR
spectrum?

E. it indicates the relative number of protons in the signal
Answer: E
Difficulty: Easy
15. Which of the following is true about the shape (multiplicity) of the signal in a 1H
NMR spectrum?

Answer: A
Difficulty: Easy
16. In an NMR spectrometer, the receiver coil records a complex signal, called a
________________, which is converted into a spectrum via a mathematical
technique called a ____________________.
Answer: free induction decay (FID), Fourier transform (FT)

Difficulty: Easy
17. Which of the following type(s) of protons are chemically non-equivalent?
A. homotopic
B. enantiotopic
C. diastereotopic
D. A&B
E. B&C
Answer: C
Learning Objective: 15.4 Describe chemical equivalence and a procedure for
determining whether two protons are homotopic, enantiotopic, or not chemically
equivalent
Difficulty: Medium
18. Which of the following type(s) of protons are chemically equivalent?
A. homotopic
B. enantiotopic
C. diastereotopic
D. A&B
E. B&C
Answer: D
equivalent
Difficulty: Easy
19. Protons Ha and Hb in the following compound are _________.
Ha Hb
A. homotopic
B. enantiotopic
C. diastereotopic
D. mesotopic
E. none of these
Answer: A
equivalent
Difficulty: Easy

Ha Hb
A. homotopic
B. enantiotopic
C. diastereotopic
D. mesotopic
E. none of these
Answer: B
equivalent
Difficulty: Medium
Ha
Hb
A. homotopic
B. enantiotopic
C. diastereotopic
D. mesotopic
E. none of these
Answer: C
equivalent
Difficulty: Medium

Br H
Hb
Ha
A. homotopic
B. enantiotopic
C. diastereotopic
D. mesotopic
E. none of these
Answer: C
equivalent
Difficulty: Medium
OH
Ha
Hb
A. homotopic
B. enantiotopic
C. diastereotopic
D. mesotopic
E. none of these
Answer: C
equivalent
Difficulty: Medium

Ha
Hb
A. homotopic
B. enantiotopic
C. diastereotopic
D. mesotopic
E. none of these
Answer: C
equivalent
Difficulty: Medium
NH2
Ha
Hb
A. homotopic
B. enantiotopic
C. diastereotopic
D. mesotopic
E. none of these
Answer: C
equivalent
Difficulty: Medium

Ha Hb
O O
A. homotopic
B. enantiotopic
C. diastereotopic
D. mesotopic
E. none of these
Answer: A
equivalent
Difficulty: Medium
27. How many signals would you expect in the 1H NMR spectrum of CH3OCH2CH3?
A. 1
B. 2
C. 3
D. 4
E. 5
Answer: C
equivalent
Difficulty: Medium
1
28. How many signals would you expect in the H NMR spectrum of
CH3OCH2CH2OCH3?
A. 1
B. 2
C. 3
D. 4
E. 5
Answer: B
equivalent
Difficulty: Medium
1
(CH3)2CHCH2CH2CH3?
A. 1
B. 2
C. 3
D. 4
E. 5
Answer: E
equivalent
Difficulty: Medium
1
HOCH2CH2CH2CH2OH?
A. 1
B. 2
C. 3
D. 4
E. 5
Answer: C
equivalent
Difficulty: Medium
31. How many signals would you expect in the 1H NMR spectrum of the following
compound?
A. 4
B. 5
C. 6
D. 7
E. 8
Answer: D
equivalent
Difficulty: Medium
compound?
O
A. 4
B. 5
C. 6
D. 7
E. 8
Answer: B
equivalent
Difficulty: Medium
compound?
O OH
A. 4
B. 5
C. 6
D. 7
E. 9
Answer: D
equivalent
Difficulty: Medium
compound?
O
O
Answer: 4
equivalent
Difficulty: Medium
compound?
O O
Cl
Answer: 6
equivalent
Difficulty: Medium
compound?
O O
Answer: 3
equivalent
Difficulty: Medium
37. The 1H NMR spectrum of bromoethane shows a signal at 3.5 ppm when the
spectrum is recorded using a 60 MHz spectrometer. Where do you expect to see
the signal if a 300 MHz instrument is used instead?
A. 3.5 ppm
B. 7.5 ppm
C. 6.8 ppm
D. 5.8 ppm
E. none of these
Answer: A
Learning Objective: 15.5 Define chemical shift, inductive effect, and anisotropic effect,
and describe the signals produced by methyl, methylene, and methine groups
Difficulty: Medium
38. ______is used as a reference for recording NMR spectra and is assigned a
chemical shift value of zero.
Answer: Tetramethylsilane (TMS)/ (CH3)4Si

Difficulty: Easy
39. Which of the indicated protons in the following compound would appear most
downfield in the 1H NMR spectrum?
III
OH
I
II IV
A. I
B. II
C. III
D. IV
Answer: D
Difficulty: Medium
upfield in the 1H NMR spectrum?
III
OH
I
II IV
A. I
B. II
C. III
D. IV
Answer: A
Difficulty: Medium
downfield in the 1H NMR spectrum?
I II III
IV
H H H H
C C C CH3
H F
V
A. I
B. II
C. III
D. IV
E. V
Answer: E
Difficulty: Hard
upfield in the 1H NMR spectrum?
II IV
O O
O F
I III
A. I
B. II
C. III
D. IV
E. I & III
Answer: A
Difficulty: Hard
43. Which of the following is the best prediction of the chemical shifts for the signals
in the 1H NMR spectrum for the following compound?
I
O
HO
II III
A. I = 3.7 ppm, II = 2.7 ppm, III = 1.9 ppm

B. I = 3.7 ppm, II = 2.2 ppm, III = 1.9 ppm
C. I = 3.9 ppm, II = 2.7 ppm, III = 1.9 ppm
D. I = 3.9 ppm, II = 2.2 ppm, III = 2.4 ppm
E. none of these
Answer: C
Difficulty: Medium
II
O
O
I III IV
A. I = 3.9 ppm, II = 4.2 ppm, III = 2.2 ppm, IV = 3.4 ppm

B. I = 3.4 ppm, II = 2.2 ppm, III = 2.2 ppm, IV = 3.4 ppm
C. I = 3.4 ppm, II = 2.2 ppm, III = 4.2 ppm, IV = 3.4 ppm
D. I = 3.4 ppm, II = 4.2 ppm, III = 4.2 ppm, IV = 3.4 ppm
E. none of these
Answer: D
Difficulty: Medium
I III
O
II IV
A. I = 0.9 ppm, II = 1.8 ppm, III = 4.2 ppm, IV = 1.9 ppm

B. I = 0.9 ppm, II = 1.2 ppm, III = 3.7 ppm, IV = 1.9 ppm
C. I = 0.9 ppm, II = 1.7 ppm, III = 3.4 ppm, IV = 2.4 ppm
D. I = 0.9 ppm, II = 1.7 ppm, III = 3.4 ppm, IV = 1.9 ppm
E. none of these
Answer: A
Difficulty: Medium
I O O III
O
II
IV
A. I=0.9 ppm, II=2.7 ppm, III=1.2 ppm, IV=0.9 ppm

B. I=1.1 ppm, II=3.2 ppm, III=1.4 ppm, IV=0.9 ppm
C. I=0.9 ppm, II=1.7 ppm, III=1.2 ppm, IV=1.1 ppm
D. I=0.9 ppm, II=1.9 ppm, III=3.4 ppm, IV=0.9 ppm
E. none of these
Answer: B
Difficulty: Medium
47. Predict the chemical shifts for the signals in the 1H NMR spectrum for the
following compound.
II IV
O
O
O O
III
I
Answer:
4.4 ppm 1.9 ppm
O
O
O O
5.7 ppm
5.2 ppm
Difficulty: Hard
48. Predict the chemical shifts for the signals in the 1H NMR spectrum for the
following compound.
O O
O
Answer:
3.9 ppm 1.4 ppm

O O
1.9 ppm 2.7 ppm 2.2 ppm 0.9 ppm
Difficulty: Hard
49. Aromatic protons produce signals in the range of 7 – 8 ppm, due to the
_________effect of  electrons
A. diamagnetic anisotropy
B. paramagnetic anisotropy
C. diamagnetic isotropy
D. paramagnetic isotropy
E. none of these
Answer: A
Difficulty: Medium
50. Which of the following protons appear most upfield in the 1H NMR spectrum?
II III
H H
IV
I H
A. I
B. II
C. III
D. IV
E. none of these
Answer: D
Difficulty: Medium
51. A compound with molecular formula C 8H14 has the following 1H NMR spectrum.
Which of the following is the correct number of protons giving rise to each signal?
II
I
III
8 7 6 5 4 3 2 1 0
PPM
A. I – 3H, II – 9H, III – 2H

B. I – 2H, II – 9H, III – 3H
C. I – 4H, II – 6H, III – 4H
D. I – 3H, II – 6H, III – 2H
Answer: A
Learning Objective: 15.6 Define integration, and explain what it indicates
Difficulty: Medium
52. A compound with molecular formula C 6H11N has the following 1H NMR spectrum.
Which of the following is the correct number of protons giving rise to each signal?
II
III
8 7 6 5 4 3 2 1 0
PPM
A. I – 6H, II – 3H, III – 2H

B. I – 5H, II – 4H, III – 2H
C. I – 6H, II – 4H, III – 1H
D. I – 1H, II – 4H, III – 6H
Answer: C
Difficulty: Medium
53. A compound with molecular formula C8H10O has the following 1H NMR spectrum.
Which of the following is the correct number of protons giving rise to each signal.
III
II
IV
SDBS: National Institute of Advanced Industrial Science and Technology
Answer: I – 3H, II – 2H, III – 3H, IV – 2H

Difficulty: Medium
54. Draw a structure, with a formula of C 4H10O, which has an integration of 6H, 2H,
1H, and 1H.
Answer: (CH3)2CHCH2OH
Difficulty: Medium
55. Draw a structure, with a formula of C5H13N, which has an integration of 9H, 3H,
1H.
Answer: (CH3)3CNHCH3
Difficulty: Medium
56. Draw a structure, with a formula of C4H9Br, which has an integration of 3H, 2H,
2H, and 2H.
Answer: CH3CH2CH2CH2Br
Difficulty: Medium
57. Which of the following compounds gives a 1H NMR spectrum consisting of only a
singlet?
A. 1,1-dichloropropane
B. 1,3-dichloropropane
C. 1,2-dichloropropane
D. 2,2-dichloropropane
E. 1-chloropropane
Answer: D
Learning Objective: 15.7 Describe spin-spin splitting and multiplicity
Difficulty: Medium
58. How many 1H NMR signals does 2-chloro-3-methyl-2-butene exhibit?
A. 1
B. 2
C. 3
D. 4
E. 5
Answer: C
Difficulty: Medium
59. Which of the following compounds displays two triplets and a singlet in its 1H
NMR spectrum?
A. CH3CH(OCH3)2
B. CH3OCH2CH2OCH3
C. CH3OCH2CH(OH)CH3
D. CH3OCH2CH2CH2CH2OCH3
E. CH3CH2OCH2CH3
Answer: D
Difficulty: Medium
60. Which of the following compounds will display only two singlets in its 1H NMR
spectrum?
O O O O O O O
O O O
I II III IV V
A. I
B. II
C. III
D. IV
E. V
Answer: B
Difficulty: Medium
61. Which of the following compounds will display only three singlets in its 1H NMR
spectrum?
O O O O O O O
O
O
O
I II III IV V
A. I
B. II
C. III
D. IV
E. V
Answer: A
Difficulty: Medium
62. Which of the following compounds will display a singlet, a triplet and a quartet in
its 1H NMR spectrum?
A. 2-chloro-4-methylpentane
B. 3-chloro-2-methylpentane
C. 3-chloropentane
D. 1-chloro-2,2-dimethylbutane
E. 3-chloro-3-methylpentane
Answer: E
Difficulty: Medium
63. Determine the multiplicity of each signal in the expected 1H NMR spectrum of the
following compound.
O
Answer:
doublet septet quartet

triplet
O
Difficulty: Hard
following compound.
N
H
Answer:
sextet singlet
O
N
H singlet
triplet triplet
singlet

Difficulty: Hard
following compound.
O
Answer:
multiplet doublet
O
singlet
doublet O

Difficulty: Hard
following compound.
O
H
O
Answer:
doublet
O sextet singlet
H
singlet
O
singlet doublet

Difficulty: Hard
following compound.
HO O NH2
Answer:
triplet singlet
O
singlet
HO O NH2
singlet triplet

Difficulty: Hard
68. Predict the multiplicity of each signal in the expected 1H NMR spectrum of 2,3-
dimethyl-2-pentanol.
Answer:
singlet
OH quintet
singlet triplet
doublet sextet

Difficulty: Hard
following compound.
Answer:
doublet doublet
septet
singlet
O doublet

Difficulty: Hard
70. The coupling constant (J) for bromoethane is 7 Hz when the 1H NMR spectrum is
acquired at 250 MHz. What is the coupling constant between these protons when
the spectrum is acquired at 500 MHz?
A. 3.5 Hz
B. 7 Hz
C. 14 Hz
D. 21 Hz
E. 1 Hz
Answer: B
Difficulty: Hard
71. Which of the following is the maximum multiplicity observed for H c protons in the
following compound? Assume that Jcd and Jcb values are different.
H c
N
a b d
A. 5
B. 6
C. 8
D. 12
E. none of these
Answer: B
Difficulty: Hard
72. Which of the following is the maximum multiplicity observed for H b protons in the
following compound? Assume that Jab and Jbc values are different.
b O
a c d
A. 9
B. 12
C. 21
D. 24
E. none of these
Answer: A
Difficulty: Medium
73. Which of the following Jab values is consistent with the following structure?
Hb Ha
O
Hc O
A. 1.2 Hz
B. 6.5 Hz
C. 17 Hz
D. 20 Hz
E. 11 Hz
Answer: B
Difficulty: Hard
74. Which of the following Jac values is consistent with the following structure?
Hb Ha
O
Hc O
A. 1.2 Hz
B. 6.5 Hz
C. 17 Hz
D. 20 Hz
E. 11 Hz
Answer: C
Difficulty: Hard
75. Which of the following Jbc values is consistent with the following structure?
Hb Ha
O
Hc O
A. 1.2 Hz
B. 6.5 Hz
C. 14 Hz
D. 20 Hz
E. none of these
Answer: A
Difficulty: Hard
76. Presence of which of the following protons is confirmed by D 2O exchange?
A. OH
B. NH2
C. CH
D. A&B
E. none of these
Answer: D
Difficulty: Medium
77. The 1H NMR spectrum of 1-propanol displays a singlet for the OH proton instead
of a triplet. Explain why.
Answer: A rapid exchange of the OH proton between 1-propanol molecules does not
allow for splitting of the signal.
Difficulty: Medium
78. The 1H NMR spectrum of ethanamine (CH3CH2NH2) displays a singlet for the NH2
protons instead of a triplet. Explain why.
Answer: A rapid exchange of the NH 2 protons between ethanamine molecules does not
allow for splitting of the signal.
Difficulty: Hard
79. The 1H NMR spectrum of an alcohol displays a singlet for the OH protons in the
range of 2 – 5 ppm. Explain how you can confirm the signal for the OH protons.
Answer: Acquire the 1H NMR spectrum for the alcohol. Then add D 2O to the sample
and re-aquire the 1H NMR spectrum. The absence of the OH absorption because of D 2O
exchange will confirm the signal.
Difficulty: Hard
80. Determine the multiplicity and predict the chemical shifts of each signal in the
expected 1H NMR spectrum of the following compound.
I III
O
II IV
Answer:
0.9 ppm 4.2 ppm

triplet triplet
O
sextet singlet
1.7 ppm 1.9 ppm
Learning Objective: 15.8 Draw the expected 1H NMR spectrum of a compound

Difficulty: Medium
O O
Answer:
septet sextet
2.7 ppm 1.4 ppm
O O
doublet O
1.1 ppm
triplet triplet
2.2 ppm 0.9 ppm

Difficulty: Medium
O
O
O O
Answer:
doublet singlet
4.4 ppm 1.9 ppm
O
O
O O
triplet
singlet
5.2 ppm 5.7 ppm
Difficulty: Medium
83. How would you use 1H NMR spectroscopy to distinguish between the following
compounds?
O O O
H H
O II
I
A. I = 3 and II = 2 signals
B. I = 4 and II = 3 signals
C. I = 5 and II = 3 signals
D. I = 5 and II = 4 signals
E. I = 3 and II = 4 signales
Answer: B
Learning Objective: 15.9 Distinguish between compounds using 1H NMR spectroscopy
Difficulty: Medium
compounds?
O O
O O
I II
Answer: Both compounds will have three signals. The chemical shift would be higher
for the singlet in Compound I.
Compound I: a triplet, a quartet and a singlet
Compound II: a singlet, a triplet and a quintet

Difficulty: Medium
compounds?
O O
O O
I II
Answer: Both compounds will have five signals.

Compound I: a doublet, a septet, two triplets and a sextet.
Compound II: two doublets, a multiplet, a quartet and a triplet.

Difficulty: Medium
compounds?
O
O
O
I II O
Answer: Both compounds will have five signals. The H a proton in compound I will
appear more downfield than the Ha proton in compound II.
O
O
O
I
a II O
a
Learning Objective: 15.10 Describe the steps in the analysis of a 1H NMR spectrum
Difficulty: Medium
87. A compound with a molecular formula C9H12 has the following 1H NMR spectrum.
Which of the following structures is consistent with this spectrum?
9
7 6 5 4 3 2 1 0
PPM
I II III IV
A. I
B. II
C. III
D. IV
E. none of these
Answer: C
Difficulty: Medium
88. Which of the following structures is consistent with this 1H NMR spectrum?
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1 1
O O O
I II III IV
A. I
B. II
C. III
D. IV
E. none of these
Answer: B
Difficulty: Medium
89. A compound with a molecular formula C 9H10O2 has the following 1H NMR
spectrum. Which of the following structures is consistent with this spectrum?
12 10 8 6 4 2 0
PPM
O O
OH O OH
O H O
I
II III IV
A. I
B. II
C. III
D. IV
E. none of these
Answer: B
Difficulty: Medium
90. A compound with a molecular formula C8H15ClO3 has the following 1H NMR
spectrum. The IR spectrum shows a strong absorption at 1800 cm -1. Which of the
following structures is consistent with this spectrum?
6
2 2
4 3 2 1 0
PPM
O O O O
O O O O
Cl Cl Cl Cl
O O O O
III IV
I II
A. I
B. II
C. III
D. IV
E. none of these
Answer: D
Difficulty: Medium
91. A compound with a molecular formula C 5H11NO has the following 1H NMR
spectrum. The IR spectrum shows an absorption at around 3400 cm -1. Which of
the following structures is consistent with this spectrum?
3 3
2 2
1
exchanges with D2O
9 8 7 6 5 4 3 2 1 0
PPM
O O O O
N N N N
H H H H
I II III IV
A. I
B. II
C. III
D. IV
E. none of these
Answer: B
Difficulty: Medium
92. A compound with a molecular formula of C 5H10O has the following 1H NMR
spectrum. Propose a structure for this compound.
10 8 6 4 2 0
PPM
Answer:
O
Difficulty: Medium
93. Propose a structure for a compound, with molecular formula C5H11Cl, that fits the
following spectroscopic data:
1
H NMR: 0.9  (triplet, 3H), 1.3  (sextet, 2H), 1.5  (quartet, 2H), 1.6  (doublet, 3H),
3.6  (sextet, 1H)
Answer:
Cl
Difficulty: Medium
94. Propose a structure for a compound, with molecular formula C8H14O3, that fits the
IR: 1820cm-1, 1760cm-1

1
H NMR: 1.0  (triplet, 6H), 1.6  (sextet, 4H), 2.2  (triplet, 4H)
Answer:
O O
Difficulty: Medium
95. Propose a structure for a compound, with molecular formula C10H12O, that fits the
IR: 1680 cm-1

1
H NMR: 1.0  (triplet, 3H), 1.5  (sextet, 2H), 2.6  (triplet, 2H), 7.4  (triplet, 2H), 7.5 
(triplet, 1H), 7.9  (doublet, 2H)
Answer:
Difficulty: Medium
96. A compound with a molecular formula of C 8H16O has the following 1H NMR
spectrum. Provide a structure that is consistent with this spectrum.
2 2 2
2 1 0
PPM
Answer:
O
Difficulty: Medium
97. A compound with a molecular formula of C 10H12O2 has the following 1H NMR
spectrum. Which of the following structures is consistent with this spectrum?
3
2 2 2 2
1
11 10 9 8 7 6 5 4 3 2 1 0
PPM
O
O O O
CH O COH COH
I II III IV
A. I
B. II
C. III
D. IV
E. none of these
Answer: C
Difficulty: Medium
98. The broadband decoupling in 13C NMR suppresses ________ splitting.

12
A. C-13C
12
B. C-1H
13
C. C-13C
13
D. C-1H
E. none of these
Answer: D
Learning Objective: 15.11 Describe how signal averaging and broadband decoupling
are important in 13C NMR spectroscopy
Section: 15.11
Difficulty: Easy
99. The off-resonance decoupling in 13C NMR allows for ________ splitting.
12
A. C-13C
12
B. C-1H
13
C. C-13C
13
D. C-1H
E. none of these
Answer: D
Difficulty: Easy
13
100. Identify the splitting pattern for a CH 3 in an off-resonance decoupled C NMR
spectrum.
A. no peak
B. singlet
C. doublet
D. triplet
E. quartet
Answer: E
Difficulty: Easy
13
101. Identify the splitting pattern for a CH 2 in an off-resonance decoupled C NMR
spectrum.
A. no peak
B. singlet
C. doublet
D. triplet
E. quartet
Answer: D
Difficulty: Easy
13
102. Identify the splitting pattern for a CH in an off-resonance decoupled C NMR
spectrum.
A. no peak
B. singlet
C. doublet
D. triplet
E. quartet
Answer: C
Difficulty: Easy
103. Identify the splitting pattern for a C in a carbonyl group in an off-resonance

decoupled 13C NMR spectrum.
A. no peak
B. singlet
C. doublet
D. triplet
E. quartet
Answer: B
Difficulty: Easy
13
104. How many signals would you expect to find in the C NMR spectrum of the
following compound?
A. 6
B. 7
C. 8
D. 9
E. 10
Answer: B
Learning Objective: 15.12 Explain what is revealed by the number of signals and their
general location in a 13C NMR spectrum
Difficulty: Easy
13
following compound?
O O
A. 2
B. 3
C. 4
D. 5
E. 6
Answer: C
Difficulty: Medium
13
following compound?
A. 6
B. 7
C. 8
D. 9
E. 10
Answer: D
Difficulty: Medium
13
following compounds?
Cl
O
I II CH CH
2 3
A. I – 5, II – 8
B. I – 3, II – 6
C. I – 4, II – 8
D. I – 5, II – 6
E. I – 3, II – 3
Answer: D
Difficulty: Easy
108. Which of the following carbon atoms will display the signal most downfield in the
13
C NMR spectrum?
O F
C N C C
C C C
I II III IV V
A. I
B. II
C. III
D. IV
E. V
Answer: B
Difficulty: Medium
13
109. Which of the following compounds will display four signals in its C NMR
spectrum?
A. 2,6-dimethylheptane
B. 2,4-dimethylheptane
C. 3,5-dimethylheptane
D. 4,4-dimethylheptane
E. 3,4-dimethylheptane
Answer: A
Difficulty: Medium
13
110. Which of the following compounds will display five signals in its C NMR
spectrum?
Br Br Br Br Br
Br Br
Br Br
Br
I II III IV V
A. I
B. II
C. III
D. IV
E. V
Answer: A
Difficulty: Medium
111. Which of the following 13C NMR chemical shifts corresponds to C a in the following
compound?
a
O
A. 100 – 150 ppm

B. 200 – 220 ppm
C. 60 – 90 ppm
D. 45 – 60 ppm
E. 45 – 80 ppm
Answer: A
Difficulty: Medium
112. Which of the following compounds is consistent with the 13C NMR spectrum shown
below?
200 180 160 140 120 100 80 60 40 20 0

PPM
O O O
O O
I II III IV IV
A. I
B. II
C. III
D. IV
E. V
Answer: A
Difficulty: Hard
below?
80 70 60 50 40 30 20 10 0
PPM
OH HO OH
OH
I II III IV V OH
A. I
B. II
C. III
D. IV
E. V
Answer: D
Difficulty: Hard
below?
60 50 40 30 20 10 0
PPM
Cl
Cl Cl Cl Cl
I II III IV V
A. I
B. II
C. III
D. IV
E. V
Answer: C
Difficulty: Hard
13
115. Which of the following compounds is consistent with the following C NMR
spectrum?
80 70 60 50 40 30 20 10 0
PPM
OH OH OH
HO
I II III IV OH V
A. I
B. II
C. III
D. IV
E. V
Answer: C
Difficulty: Hard
116. Which of the following displays a signal in the DEPT-90 13C NMR spectroscopy?
A. CH3
B. CH2
C. CH
D. C
E. none of these
Answer: C
Learning Objective: 15.13 Describe what can be learned from DEPT C NMR
spectroscopy
Difficulty: Easy
13
117. Which of the following displays a negative signal in the DEPT-135 C NMR
spectroscopy?
A. CH3
B. CH2
C. CH
D. C
E. none of these
Answer: B
spectroscopy
Difficulty: Easy
13
118. Which of the following does not display a signal in the DEPT-135 C NMR
spectroscopy?
A. CH3
B. CH2
C. CH
D. C
E. none of these
Answer: D
spectroscopy
Difficulty: Easy
119. Which of the following does not display a signal in the DEPT-90, but displays a
positive signal in DEPT-135 13C NMR spectroscopy?
A. CH3
B. CH2
C. CH
D. C
E. none of these
Answer: A
spectroscopy
Difficulty: Easy
120. Which of the following compounds will not display a carbonyl carbon signal in the
DEPT-90 and DEPT-135 13C NMR spectroscopy?
O O O
H O N
I II III H
A. I
B. II
C. III
D. II and III
E. I and II
Answer: D
spectroscopy
Difficulty: Medium
121. A compound, with molecular formula C 5H10Br2, displays the following 13C NMR
along with the DEPT-90 and DEPT-135 13C NMR spectra. What is the structure
for this compound?
DEPT-90
DEPT-135
Broadband decoupled
Answer: BrCH2CH2CH2CH2CH2Br
spectroscopy
Difficulty: Hard
122. A compound, with molecular formula C 7H7Br, displays the following 13C NMR along
with the DEPT-90 and DEPT-135 13C NMR spectra. What is the structure for this
compound?
DEPT-90
DEPT-135
Broadband decoupled
Answer:
Br
spectroscopy
Difficulty: Hard
123. A compound, with molecular formula C 4H9Br, displays the following 1H NMR and
13
C NMR spectra. Propose a structure for this compound.
3 2 1 0
PPM
40 35 30 25 20 15 10 5 0
PPM
Answer:
Br
Learning Objective: Integrated Spectroscopy
Difficulty: Medium
124. Which of the following compounds, with molecular formula C 9H18O2, is consistent
with the 1H NMR and 13C NMR spectra shown below?
180 160 140 120 100 80 60 40 20 0
PPM
O O O O
O O O O
I II III IV
A. I
B. II
C. III
D. IV
E. None of these
Answer: A
Difficulty: Medium
125. Which of the following compounds, with molecular formula C 9H12O, is consistent
with the 1H NMR and 13C NMR spectra shown below?
3
2 2 2 2
1
exchanges with D2O
7 6 5 4 3 2 1 0
PPM
160 140 120 100 80 60 40 20 0

PPM
O
HO
O HO
I II III IV
A. I
B. II
C. III
D. IV
E. None of these
Answer: C
Difficulty: Medium
126. A compound, with molecular formula C 11H14O, displays the following IR, 1H NMR
and 13C NMR spectra. Propose a structure for this compound.
220 200 180 160 140 120 100 80 60 40 20 0

PPM
Answer:
O

Difficulty: Hard
127. A compound, with molecular formula C 7H14O2, displays the following IR, 1H NMR
1 2 2
180 160 140 120 100 80 60 40 20 0
PPM
Answer:

Difficulty: Medium
128. A compound, with molecular formula C5H7NO2, displays the following IR, 1H NMR

Answer:
O
N
C
O

Difficulty: Hard
IR: 1720 cm-1

1
H NMR: 1.1  (doublet, 6H), 2.1  (singlet, 3H), 2.7  (septet, 1H)
13
C NMR: 15, 22, 45, 210
Answer:
O
Difficulty: Medium
130. Propose a structure for a compound, with molecular formula C8H19N, that fits the
IR: 3400 cm-1

1
H NMR: 0.9  (triplet, 6H), 1.1  (singlet, 1H, exchanges with D2O), 1.3  (sextet, 4H),
1.4  (quintet, 4H), 2.6  (triplet, 4H)
13
C NMR: 13.7, 20.5, 30.4, 49.2
Answer:
N
H
Difficulty: Medium
131. Propose a structure for a compound, with molecular formula C5H12O2, that fits the
IR: 1200 cm-1

1
H NMR: 1.4  (singlet, 6H), 3.2  (singlet, 6H)
13
C NMR: 28, 45, 100
Answer:
O O
Difficulty: Hard
IR: 3400 cm-1(broad), 3250 cm-1(sharp), 2150 cm-1

1
H NMR: 1.0  (triplet, 3H), 1.5  (singlet, 3H), 1.6  (quartet, 2H), 2.0  (singlet, 1H), 2.5
 (singlet, 1H)
13
C NMR: 4.1, 26, 35, 67.6, 69.4
Answer:
OH

Difficulty: Hard
133. Propose a structure for a compound, with molecular formula C 8H15ClO3, that fits
the following spectroscopic data:
IR: 1780 cm-1, 1150 cm-1

1
H NMR: 1.1  (triplet, 6H), 1.9  (quartet, 2H), 2.8  (triplet, 2H), 3.4  (quartet, 4H), 4.2
 (triplet, 1H)
13
C NMR: 15, 31, 38, 57, 100, 173
Answer:
O
O
Cl
O

Difficulty: Hard
134. A compound with molecular formula C 3H6O2 displays the following IR, 1H NMR and
13
DEPT-90
DEPT-135
Answer:
OH
Difficulty: Medium
135. A compound with molecular formula C6H12O displays the following IR, 1H NMR
DEPT-90
DEPT-135
Broadband decoupled
Answer:
O

Difficulty: Medium
136. A compound with molecular formula C 6H4Cl2O displays the following IR, 1H NMR
DEPT-90
DEPT-135
Broadband decoupled
Answer:
Cl
OH
Cl

Difficulty: Medium
137. A compound with molecular formula C10H14 displays the following IR, 1H NMR, 13C
NMR spectra. Propose a structure for this compound.
SDBS
Answer:

Difficulty: Medium
138. A compound with molecular formula C 8H11N displays the following IR, 1H NMR,
13
SDBS
140 120 100 80 60 40 20 0

PPM
Answer:
NH2

Difficulty: Medium
139. A compound with molecular formula C8H14O3 displays the following IR, 1H NMR,
13
SDBS
180 160 140 120 100 80 60 40 20 0

PPM
Answer:
O O
O
Difficulty: Medium
140. A compound with molecular formula C 7H14O2 displays the following IR, 1H NMR,
13
SDBS
180 160 140 120 100 80 60 40 20 0
PPM
Answer:

Difficulty: Hard
141. An unknown compound displays the following IR, 1H NMR, 13

C NMR and.mass
spectra. Propose a structure for this compound.
SDBS
Answer:
N
H
Difficulty: Hard

Klein 3e CH 15 Testbank FINAL

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Klein, Organic Chemistry 3e

1. NMR is an abbreviation for ____________ ____________ __________.

Answer: nuclear magnetic resonance

2. List the most common nuclei that are used in NMR.

Answer: 1H and 13C

3. Identify the nuclei that cannot be analyzed by NMR.

4. Which of the following nuclei cannot be analyzed by an NMR spectrometer?

A. nucleus with odd number of protons & odd number of neutrons

6. Which of the following electromagnetic radiation is used in NMR spectroscopy?

A. they are inversely proportional

A. it indicates the number of neighboring protons

A. it indicates the number of neighboring protons

A. it indicates the number of neighboring protons

A. it indicates the number of neighboring protons

Answer: free induction decay (FID), Fourier transform (FT)

17. Which of the following type(s) of protons are chemically non-equivalent?

18. Which of the following type(s) of protons are chemically equivalent?

19. Protons Ha and Hb in the following compound are _________.

20. Protons Ha and Hb in the following compound are _________.

21. Protons Ha and Hb in the following compound are _________.

22. Protons Ha and Hb in the following compound are _________.

23. Protons Ha and Hb in the following compound are _________.

24. Protons Ha and Hb in the following compound are _________.

25. Protons Ha and Hb in the following compound are _________.

26. Protons Ha and Hb in the following compound are _________.

Answer: Tetramethylsilane (TMS)/ (CH3)4Si

A. I = 3.7 ppm, II = 2.7 ppm, III = 1.9 ppm

A. I = 3.9 ppm, II = 4.2 ppm, III = 2.2 ppm, IV = 3.4 ppm

A. I = 0.9 ppm, II = 1.8 ppm, III = 4.2 ppm, IV = 1.9 ppm

A. I=0.9 ppm, II=2.7 ppm, III=1.2 ppm, IV=0.9 ppm

3.9 ppm 1.4 ppm

1.9 ppm 2.7 ppm 2.2 ppm 0.9 ppm

A. I – 3H, II – 9H, III – 2H

A. I – 6H, II – 3H, III – 2H

SDBS: National Institute of Advanced Industrial Science and Technology

Answer: I – 3H, II – 2H, III – 3H, IV – 2H

58. How many 1H NMR signals does 2-chloro-3-methyl-2-butene exhibit?

doublet septet quartet

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity

Learning Objective: 15.7 Describe spin-spin splitting and multiplicity

76. Presence of which of the following protons is confirmed by D 2O exchange?

0.9 ppm 4.2 ppm

Learning Objective: 15.8 Draw the expected 1H NMR spectrum of a compound

Learning Objective: 15.8 Draw the expected 1H NMR spectrum of a compound

Learning Objective: 15.9 Distinguish between compounds using 1H NMR spectroscopy

Answer: Both compounds will have five signals.

Learning Objective: 15.9 Distinguish between compounds using 1H NMR spectroscopy

SDBS: National Institute of Advanced Industrial Science and Technology

IR: 1820cm-1, 1760cm-1

IR: 1680 cm-1

98. The broadband decoupling in 13C NMR suppresses ________ splitting.

103. Identify the splitting pattern for a C in a carbonyl group in an off-resonance

A. 100 – 150 ppm

200 180 160 140 120 100 80 60 40 20 0

160 140 120 100 80 60 40 20 0

220 200 180 160 140 120 100 80 60 40 20 0

Learning Objective: Integrated Spectroscopy

Learning Objective: Integrated Spectroscopy

1. NMR is an abbreviation for __ .