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ch16 Ques 2013 PDF
ch16 Ques 2013 PDF
2. How many nuclear spin states are possible for the 1H nucleus?
A) 1
B) 2
C) 4
D) 5
E) none of these
Ans: B
A) UV
B) IR
C) visible
D) γ-rays
E) radio wave
Ans: E
5. _______ protons experience a net magnetic field strength that is higher than the applied
magnetic field.
A) deshielded
B) shielded
C) paramagnetic
D) diamagnetic
E) none of these
Ans: A
6. Which of the following is true about the relationship between the energy gap (ΔE)
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
Ans: B
8. 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
Ans: D
9. Which of the following is true about the number of signals in a 1H NMR spectrum?
11. Which of the following is true about the area under each signal in a 1H NMR spectrum?
12. Which of the following is true about the shape of the signal in a 1H NMR spectrum?
A) homotopic
B) enantiotopic
C) diastereotopic
D) A&B
E) B&C
Ans: C
A) homotopic
B) enantiotopic
C) diastereotopic
D) A&B
E) B&C
Ans: D
A) homotopic
B) enantiotopic
C) diastereotopic
D) mesotopic
E) none of these
Ans: A
A) homotopic
B) enantiotopic
C) diastereotopic
D) mesotopic
E) none of these
Ans: B
Hb
A) homotopic
B) enantiotopic
C) diastereotopic
D) mesotopic
E) none of these
Ans: C
Hb
Ha
A) homotopic
B) enantiotopic
C) diastereotopic
D) mesotopic
E) none of these
Ans: C
Ha
Hb
A) homotopic
B) enantiotopic
C) diastereotopic
D) mesotopic
E) none of these
Ans: C
Hb
A) homotopic
B) enantiotopic
C) diastereotopic
D) mesotopic
E) none of these
Ans: C
21. How many signals would you expect to find in the 1H NMR spectrum of
CH3OCH2CH3?
A) 1
B) 2
C) 3
D) 4
E) 5
Ans: C
22. How many signals would you expect to find in the 1H NMR spectrum of
CH3OCH2CH2OCH3?
A) 1
B) 2
C) 3
D) 4
E) 5
Ans: B
24. How many signals would you expect to find in the 1H NMR spectrum of
HOCH2CH2CH2CH2OH?
A) 1
B) 2
C) 3
D) 4
E) 5
Ans: C
25. How many signals would you expect to find in the 1H NMR spectrum of the following
compound?
A) 4
B) 5
C) 6
D) 7
E) 8
Ans: D
O
A) 4
B) 5
C) 6
D) 7
E) 8
Ans: B
27. How many signals would you expect to find in the 1H NMR spectrum of the following
compound?
O OH
A) 4
B) 5
C) 6
D) 7
E) 9
Ans: D
28. How many signals would you expect to find in the 1H NMR spectrum of the following
compound?
O
Ans: 4
Topic: Number of signals
Section: 16.4
Difficulty Level: Medium
29. How many signals would you expect to find in the 1H NMR spectrum of the following
compound?
O O
Cl
Ans: 6
30. How many signals would you expect to find in the 1H NMR spectrum of the following
compound?
O O
Ans: 3
31. The 1H NMR spectrum of bromoethane shows a signal at 3.5ppm 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
Ans: A
32. ______is used as a reference for recording NMR spectroscopy and is assigned a
chemical shift value of zero.
Ans: Tetramethylsilane (TMS)/ (CH3)4Si
Topic: Chemical shift
Section: 16.5
Difficulty Level: Easy
33. 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
Ans: D
34. Which of the indicated protons in the following compound would appear most
downfield in the 1H NMR spectrum?
I II III
H H H IV
H
C C C CH3
H F
H
A) I
B) II
C) III
D) IV
E) V
Ans: E
O F
I III
A) I
B) II
C) III
D) IV
E) I & III
Ans: A
36. Which of the following is a correct 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
Ans: C
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
Ans: D
38. Which of the following is a correct prediction of the chemical shifts for the signals in
the 1H NMR spectrum for the following compound?
I III O
II IV
A) I=0.9 ppm, II=1.7 ppm, III=3.9 ppm, IV=2.4 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
Ans: A
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
Ans: B
40. Predict the chemical shifts for the signals in the 1H NMR spectrum for the following
compound.
II IV
O O
III
I
Ans: 4.4 ppm 1.9 ppm
O
5.7 ppm O
5.2 ppm
O
Ans: O 4.2 ppm O 1.4 ppm
42. Aromatic protons produce signal in the range of 7-8 ppm, due to the _________effect of
π electrons
A) diamagnetic anisotropy
B) paramagnetic anisotropy
C) diamagnetic isotropy
D) paramagnetic isotropy
E) none of these
Ans: A
43. 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
Ans: D
Topic: Integration
Section: 16.6
Difficulty Level: Medium
44. A compound with molecular formula C8H14 has the following 1H NMR spectrum.
Which of the following is the correct number of protons giving rise to each signal?
I
I
I
III
8 7 6 5 4 3 2 1 0
PPM
Topic: Integration
Section: 16.6
Difficulty Level: Medium
45. A compound with molecular formula C6H11N 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
Topic: Integration
Section: 16.6
Difficulty Level: Medium
46. 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
Topic: Multiplicity
Section: 16.7
Difficulty Level: Medium
47. Which of the following four 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) none of these
Ans: D
Topic: Multiplicity
Section: 16.7
Difficulty Level: Medium
48. How many 1H NMR signals will 2-chloro-3-methyl-2-butene exhibit?
A) 1
B) 2
C) 3
D) 4
E) none of these
Ans: C
Topic: Multiplicity
Section: 16.7
Difficulty Level: Medium
49. Which of the following compounds will display two triplets and a singlet in the
1
H NMR spectrum?
A) CH3CH(OCH3)2
B) CH3OCH2CH2OCH3
C) CH3OCH2CH(OH)CH3
D) CH3OCH2CH2CH2CH2OCH3
E) none of these
Ans: D
Topic: Multiplicity
Section: 16.7
Difficulty Level: Hard
50. Which of the following compounds will display a singlet, a triplet and a quartet in the
1
H 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
Ans: E
Topic: Multiplicity
Section: 16.7
Difficulty Level: Medium
51. Determine the multiplicity of each signal in the expected 1H NMR spectrum of the
following compound.
O
Ans: doublet septet quartet
triplet
O
Topic: Multiplicity
Section: 16.7
Difficulty Level: Easy
52. Determine the multiplicity of each signal in the expected 1H NMR spectrum of the
following compound.
O
N
H
N
H singlet
triplet
triplet singlet
Topic: Multiplicity
Section: 16.7
Difficulty Level: Medium
53. Determine the multiplicity of each signal in the expected 1H NMR spectrum of the
following compound.
O
O
Ans: multiplet doublet
singlet
doublet
O
Topic: Multiplicity
Section: 16.7
Difficulty Level: Medium
54. Determine the multiplicity of each signal in the expected 1H NMR spectrum of the
following compound.
O
O
Ans: doublet
O singlet
sextet
H
singlet
O
singlet doublet
Topic: Multiplicity
Section: 16.7
Difficulty Level: Medium
55. Determine the multiplicity of each signal in the expected 1H NMR spectrum of the
following compound.
O
HO O NH2
Ans: triplet singlet
O
singlet
HO O NH2
singlet
triplet
Topic: Multiplicity
Section: 16.7
Difficulty Level: Hard
56. Determine the multiplicity of each signal in the expected 1H NMR spectrum of 2,3-
dimethyl-2-pentanol.
Ans: singlet
OH quintet
singlet
triplet
sextet
doublet
Topic: Multiplicity
Section: 16.7
Difficulty Level: Medium
57. 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) none of these
Ans: B
Topic: Multiplicity
Section: 16.7
Difficulty Level: Hard
58. Which of the following is the maximum multiplicity observed for Hc protons in the
following compound? Assume that Jcd and Jcb values are different.
H c
N
a d
b
A) 5
B) 6
C) 8
D) 12
E) none of these
Ans: D
Topic: Multiplicity
Section: 16.7
Difficulty Level: Hard
59. Which of the following is the maximum multiplicity observed for Hb protons in the
following compound? Assume that Jab and Jbc values are different.
a
b O
a d
c
A) 9
B) 12
C) 21
D) 24
E) none of these
Ans: C
Topic: Multiplicity
Section: 16.7
Difficulty Level: Hard
A) OH
B) NH2
C) CH
D) A&B
E) none of these
Ans: D
II IV
Ans: 0.9 ppm 3.9 ppm
triplet triplet O
sextet singlet
1.7 ppm 2.4 ppm
62. Determine the multiplicity and predict the chemical shifts of each signal in the expected
1
H NMR spectrum of the following compound.
O O
Ans: sextet
septet
1.4 ppm
3.2 ppm O O
doublet O
1.1 ppm
triplet triplet
2.7 ppm 0.9 ppm
O O
Ans: doublet singlet
1.9 ppm
4.4 ppm
O
triplet O
singlet 5.7 ppm
5.2 ppm
64. How would you use 1H NMR spectroscopy to distinguish between the following two
compounds?
O O O
H H
O II
I
A) I=3 & II=2 signals
B) I=4 & II=3 signals
C) I=5 & II=3 signals
D) none of these
Ans: B
66. How would you use 1H NMR spectroscopy to distinguish between the following two
compounds?
O O
O O
I II
Ans: Both compounds will have five signals.
Compound I: a doublet, a septet, two triplets and a sextet.
Compound II: a doublet, a multiplet, a quartet and a triplet.
67. How would you use 1H NMR spectroscopy to distinguish between the following two
compounds?
O
O
O
I II O
Ans: Both compounds will have five signals. The Ha proton in compound I will appear
more downfield than the Ha proton in compound II.
O
O
O
I a O
a
II
Topic: Analyzing a 1H NMR spectrum
Section: 16.10
Difficulty Level: Medium
68. A compound with a molecular formula C9H12 has the following 1H NMR spectrum.
Which of the following structures is consistent with this spectrum?
7 6 5 4 3 2 1 0
PPM
II III IV
I
A) I
B) II
C) III
D) IV
E) none of these
Ans: C
1 1
O O O
I II III IV
A) I
B) II
C) III
D) IV
E) none of these
Ans: B
12 10 8 6 4 2 0
PPM
H OH O
O O
IV
II III
I
A) I
B) II
C) III
D) IV
E) none of these
Ans: B
10 8 6 4 2 0
PPM
Ans:
H
72. Propose a structure for a compound with molecular formula C5H11Cl, that fits the
following spectroscopic data:
1
H NMR: 0.9δ (triplet, I=3), 1.3δ (sextet, I=2), 1.5δ (quartet, I=2), 1.6δ (doublet, I=3),
3.6δ (sextet, I=1)
Ans: Cl
74. Propose a structure for a compound with molecular formula C10H12O that fits the
following spectroscopic data.
IR:1680cm-1
1
H NMR: 1.0δ (triplet, I=3), 1.5δ (sextet, I=2), 2.6δ (triplet, I=4), 7.4δ (triplet, I=2),
7.5δ (triplet, I=1), 7.9δ (doublet, I=2)
O
Ans:
2 2 2
2 1 0
PPM
Ans: O
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
II III IV
O
I
A) I
B) II
C) III
D) IV
E) none of these
Ans: C
A) 6
B) 7
C) 8
D) 9
E) none of these
Ans: B
78. How many signals would you expect to find in the 13C NMR spectrum of the following
compound?
O O
A) 2
B) 3
C) 4
D) 5
E) none of these
Ans: C
A) 6
B) 7
C) 8
D) 9
E) none of these
Ans: D
80. How many signals would you expect to find in the 13C NMR spectrum of the following
compounds?
Cl
I II CH2CH3
A) I-5, II-8
B) I-3, II-6
C) I-4, II-8
D) I-5, II-6
E) none of these
Ans: D
82. Which of the following compounds will display four signals in the 13C NMR spectrum?
A) 2,6-dimethylheptane
B) 2,4-dimethylheptane
C) 3,5-dimethylheptane
D) 4,4-dimethylheptane
E) none of these
Ans: A
Br Br
Br Br
II III IV
I Br
A) I
B) II
C) III
D) IV
E) none of these
Ans: A
84. Which of the following 13C NMR chemical shifts corresponds to Ca in the following
compound?
a
O
A) 120 ppm
B) 145 ppm
C) 159 ppm
D) 200 ppm
E) none of these
Ans: C
O O
O O
I II III IV
A) I
B) II
C) III
D) IV
E) none of these
Ans: A
80 70 60 50 40 30 20 10 0
PPM
OH OH
HO
I II IV
III OH
A) I
B) II
C) III
D) IV
E) none of these
Ans: D
60 50 40 30 20 10 0
PPM
Cl
Cl
Cl
I II III
A) I
B) II
C) III
D) none of these
Ans: C
80 70 60 50 40 30 20 10 0
PPM
OH OH
HO
I II III IV
OH
A) I
B) II
C) III
D) IV
E) none of these
Ans: C
89. Which of the following display a signal in the DEPT-90 13C NMR spectroscopy?
A) CH3
B) CH2
C) CH
D) C
E) none of these
Ans: C
91. Which of the following does not display a signal in the DEPT-135 13C NMR
spectroscopy?
A) CH3
B) CH2
C) CH
D) C
E) none of these
Ans: D
92. 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 & III
E) none of these
Ans: D
DEPT-90
DEPT-135
DEPT-135
93. A compound with molecular formula C5H10Br2 displays the following 13C NMR along
with the DEPT-90 and DEPT-135 13CNMR spectrum. What is the structure for this
Broadband decoupled
compound?
Broadband decoupled
Ans: BrCH2CH2CH2CH2CH2Br
94. A compound with molecular formula C7H7Br displays the following 13C NMR along
with the DEPT-90 and DEPT-135 13CNMR spectrum. What is the structure for this
compound?
Ans:
Br
Topic: Integrated Spectroscopy
Section: 15.6, 16.10, 16.12
Difficulty Level: Medium
95. A compound with molecular formula C11H14O displays the following IR, 1HNMR and
13
CNMR spectrum. Propose a structure for this compound.
98. Propose a structure for a compound with molecular formula C5H10O that fits the
following spectroscopic data.
IR:1720cm-1
1
H NMR: 1.1δ (doublet, I=6), 2.1δ (singet, I=3), 2.7δ (septet, I=1)
13
C NMR: 15, 22, 45, 210
Ans:
99. Propose a structure for a compound with molecular formula C8H19N that fits the
following spectroscopic data.
IR: 3400cm-1
1
H NMR: 0.9δ (triplet, I=6), 1.1δ (singlet, I=1, exchanges with D2O), 1.3δ (sextet, I=4),
1.4δ (quintet, I=4), 2.6δ (triplet, I=4)
13
C NMR: 13.7, 20.5, 30.4, 49.2
Ans:
N
H
100. Propose a structure for a compound with molecular formula C5H12O2 that fits the
following spectroscopic data.
IR: 1200cm-1
1
H NMR: 1.4δ (singlet, I=6), 3.2δ (singlet, I=6)
13
C NMR: 28, 45, 100
Ans:
O O
101. Propose a structure for a compound with molecular formula C6H10O that fits the
following spectroscopic data.
IR: 3400 cm-1(broad), 3250 cm-1(sharp), 2150 cm-1
1
H NMR: 1.0δ (triplet, I=3), 1.5δ (singlet, I=3), 1.6δ (quartet, I=2), 2.5δ (singlet, I=1),
3.4δ (singlet, I=1)
13
C NMR: 5, 26, 35, 67, 69
Ans: OH
102. Propose a structure for a compound with molecular formula C8H15ClO3 that fits the
following spectroscopic data.
IR: 1780 cm-1, 1150 cm-1
1
H NMR: 1.1δ (triplet, I=6), 1.9δ (quartet, I=2), 2.8δ (triplet, I=2), 3.4δ (quartet, I=4),
4.2δ (triplet, I=1)
13
C NMR: 15, 31, 38, 57, 100, 173
Ans: O
O
Cl
DEPT-135
Difficulty Level: Medium
103. A compound with molecular formula C3H6O2 displays the following IR, 1HNMR and
13
CNMR spectrum. Propose a structure for this compound.
Broadband decoupled
Ans: O
OH
DEPT-135
Section: 15.6, 16.10, 16.12 & 16.13
Difficulty Level: Medium
Broadband decoupled
104. A compound with molecular formula C6H12O displays the following IR, 1HNMR and
13
CNMR spectrum. 1Propose a structure for this compound.
Ans:
O
105. A compound with molecular formula C6H4Cl2O displays the following IR, 1HNMR and
Broadband decoupled 13
CNMR spectrum. Propose a structure for this compound.
Cl
Ans:
OH
Cl