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Chapter Sixteen

Topic: Introduction to NMR


Section: 16.1
Difficulty Level: Easy

1. Which of the following can not be probed 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
Ans: D

Topic: Introduction to NMR


Section: 16.1
Difficulty Level: Easy

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

Topic: Introduction to NMR


Section: 16.1
Difficulty Level: Easy

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

A) UV
B) IR
C) visible
D) γ-rays
E) radio wave
Ans: E

Topic: Introduction to NMR


Section: 16.1
Difficulty Level: Medium
4. _______ 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
Ans: B

Topic: Introduction to NMR


Section: 16.1
Difficulty Level: Medium

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

Topic: Acquiring a 1HNMR spectrum


Section: 16.2
Difficulty Level: Medium

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

Topic: Acquiring a 1HNMR spectrum


Section: 16.2
Difficulty Level: Medium
7. 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
Ans: B

Topic: Acquiring a 1HNMR spectrum


Section: 16.2
Difficulty Level: Easy

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

Topic: Characteristics of a 1HNMR spectrum


Section: 16.3
Difficulty Level: Easy

9. Which of the following is true about the number of signals in a 1H 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
Ans: C

Topic: Characteristics of a 1HNMR spectrum


Section: 16.3
Difficulty Level: Easy
10. Which of the following is true about the location of signals in a 1H 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 protons
D) it indicates the electronic environment of absorbing protons
E) it indicates the number of protons in the signal
Ans: D

Topic: Characteristics of a 1HNMR spectrum


Section: 16.3
Difficulty Level: Easy

11. Which of the following is true about the area under each signal in a 1H 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 protons
D) it indicates the electronic environment of absorbing protons
E) it indicates the number of protons in the signal
Ans: E

Topic: Characteristics of a 1HNMR spectrum


Section: 16.3
Difficulty Level: Easy

12. Which of the following is true about the shape of the signal in a 1H 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 protons
D) it indicates the electronic environment of absorbing protons
E) it indicates the number of protons in the signal
Ans: A

Topic: Number of signals


Section: 16.4
Difficulty Level: Medium
13. Which of the following type of protons are chemically non equivalent?

A) homotopic
B) enantiotopic
C) diastereotopic
D) A&B
E) B&C
Ans: C

Topic: Number of signals


Section: 16.4
Difficulty Level: Medium

14. Which of the following type of protons are chemically equivalent?

A) homotopic
B) enantiotopic
C) diastereotopic
D) A&B
E) B&C
Ans: D

Topic: Number of signals


Section: 16.4
Difficulty Level: Easy

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


Ha Hb

A) homotopic
B) enantiotopic
C) diastereotopic
D) mesotopic
E) none of these
Ans: A

Topic: Number of signals


Section: 16.4
Difficulty Level: Easy
16. Protons Ha and Hb in the following compound are _________.
Ha Hb

A) homotopic
B) enantiotopic
C) diastereotopic
D) mesotopic
E) none of these
Ans: B

Topic: Number of signals


Section: 16.4
Difficulty Level: Medium

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


Ha

Hb

A) homotopic
B) enantiotopic
C) diastereotopic
D) mesotopic
E) none of these
Ans: C

Topic: Number of signals


Section: 16.4
Difficulty Level: Medium
18. Protons Ha and Hb in the following compound are _________.
Br H

Hb
Ha

A) homotopic
B) enantiotopic
C) diastereotopic
D) mesotopic
E) none of these
Ans: C

Topic: Number of signals


Section: 16.4
Difficulty Level: Medium

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


OH

Ha
Hb
A) homotopic
B) enantiotopic
C) diastereotopic
D) mesotopic
E) none of these
Ans: C

Topic: Number of signals


Section: 16.4
Difficulty Level: Medium
20. Protons Ha and Hb in the following compound are _________.
Ha

Hb

A) homotopic
B) enantiotopic
C) diastereotopic
D) mesotopic
E) none of these
Ans: C

Topic: Number of signals


Section: 16.4
Difficulty Level: Easy

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

Topic: Number of signals


Section: 16.4
Difficulty Level: Easy

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

Topic: Number of signals


Section: 16.4
Difficulty Level: Easy
23. How many signals would you expect to find in the 1H NMR spectrum of
(CH3)2CHCH2CH2CH3?
A) 1
B) 2
C) 3
D) 4
E) 5
Ans: E

Topic: Number of signals


Section: 16.4
Difficulty Level: Medium

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

Topic: Number of signals


Section: 16.4
Difficulty Level: Medium

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

Topic: Number of signals


Section: 16.4
Difficulty Level: Medium
26. How many signals would you expect to find in the 1H NMR spectrum of the following
compound?

O
A) 4
B) 5
C) 6
D) 7
E) 8
Ans: B

Topic: Number of signals


Section: 16.4
Difficulty Level: Medium

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

Topic: Number of signals


Section: 16.4
Difficulty Level: Medium

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

Topic: Number of signals


Section: 16.4
Difficulty Level: Medium

30. How many signals would you expect to find in the 1H NMR spectrum of the following
compound?

O O

Ans: 3

Topic: Chemical shift


Section: 16.5
Difficulty Level: Medium

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

Topic: Chemical shift


Section: 16.5
Difficulty Level: Easy

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

Topic: Chemical shift


Section: 16.5
Difficulty Level: Medium

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

Topic: Chemical shift


Section: 16.5
Difficulty Level: Hard
35. Which of the indicated protons in the following compound would appear most upfield in
the 1H NMR spectrum?
O II O IV

O F

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

Topic: Chemical shift


Section: 16.5
Difficulty Level: Easy

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

Topic: Chemical shift


Section: 16.5
Difficulty Level: Easy
37. Which of the following is a correct prediction of the chemical shifts for the signals in
the 1H NMR spectrum for the following compound?
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
Ans: D

Topic: Chemical shift


Section: 16.5
Difficulty Level: Medium

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

Topic: Chemical shift


Section: 16.5
Difficulty Level: Medium
39. 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 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
Ans: B

Topic: Chemical shift


Section: 16.5
Difficulty Level: Hard

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

Topic: Chemical shift


Section: 16.5
Difficulty Level: Hard
41. Predict the chemical shifts for the signals in the 1H NMR spectrum for the following
compound?
O O

O
Ans: O 4.2 ppm O 1.4 ppm

1.9 ppm 2.7 ppm 2.2 ppm 0.9 ppm

Topic: Chemical shift


Section: 16.5
Difficulty Level: Medium

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

Topic: Chemical shift


Section: 16.5
Difficulty Level: Medium

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

A) I-3H, II-9H, III-2H


B) I-2H, II-9H, III-3H
C) I-4H, II-6H, III-4H
D) none of these
Ans: A

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

A) I-6H, II-3H, III-2H


B) I-5H, II-4H, III-2H
C) I-6H, II-4H, III-1H
D) none of these
Ans: C

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

SDBS: National Institute of Advanced Industrial Science and Technology

Ans: I-3H, II-2H, III-3H, IV-2H

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

Ans: sextet singlet


O

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

60. Presence of which of the following protons is confirmed by D2O exchange?

A) OH
B) NH2
C) CH
D) A&B
E) none of these
Ans: D

Topic: 1H NMR spectrum


Section: 16.8
Difficulty Level: Medium
61. Determine the multiplicity and predict the chemical shifts of each signal in the expected
1
H NMR spectrum of the following compound.
I III O

II IV
Ans: 0.9 ppm 3.9 ppm
triplet triplet O

sextet singlet
1.7 ppm 2.4 ppm

Topic: 1H NMR spectrum


Section: 16.8
Difficulty Level: Medium

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

Topic: 1H NMR spectrum


Section: 16.8
Difficulty Level: Medium
63. Determine the multiplicity and predict the chemical shifts of each signal in the expected
1
H NMR spectrum of the following compound.
O

O O
Ans: doublet singlet
1.9 ppm
4.4 ppm

O
triplet O
singlet 5.7 ppm
5.2 ppm

Topic: 1H NMR spectroscopy to distinguish between compounds


Section: 16.9
Difficulty Level: Medium

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

Topic: 1H NMR spectroscopy to distinguish between compounds


Section: 16.9
Difficulty Level: Medium
65. 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 three signals.


Compound I: a triplet, a quartet and a singlet
Compound II: a singlet, a triplet and a quintet

Topic: 1H NMR spectroscopy to distinguish between compounds


Section: 16.9
Difficulty Level: Medium

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.

Topic: 1H NMR spectroscopy to distinguish between compounds


Section: 16.9
Difficulty Level: Medium

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

Topic: Analyzing a 1H NMR spectrum


Section: 16.10
Difficulty Level: Medium
69. Which of the following structures is consistent with this 1H NMR spectrum?

1 1

SDBS: National Institute of Advanced Industrial Science and Technology

O O O

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

Topic: Analyzing a 1H NMR spectrum


Section: 16.10
Difficulty Level: Medium
70. A compound with a molecular formula C9H10O2 has the following 1H NMR spectrum.
Which of the following structures is consistent with this spectrum?

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

Topic: Analyzing a 1H NMR spectrum


Section: 16.10
Difficulty Level: Medium
71. A compound with a molecular formula C5H10O has the following 1H NMR spectrum.
Propose a structure for this compound.

10 8 6 4 2 0
PPM

Ans:
H

Topic: Analyzing a 1H NMR spectrum


Section: 16.10
Difficulty Level: Medium

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

Topic: Analyzing a 1H NMR spectrum


Section: 16.10
Difficulty Level: Medium
73. Propose a structure for a compound with molecular formula C8H14O3 that fits the
following spectroscopic data.
IR:1820cm-1, 1760cm-1
1
H NMR: 1.0δ (triplet, I=6), 1.6δ (sextet, I=4), 2.2δ (triplet, I=4)
O O
Ans:

Topic: Analyzing a 1H NMR spectrum


Section: 16.10
Difficulty Level: Medium

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:

Topic: Analyzing a 1H NMR spectrum


Section: 16.10
Difficulty Level: Medium
75. A compound with a molecular formula C8H16O has the following 1H NMR spectrum.
Provide a structure that is consistent with this spectrum?
6

2 2 2

2 1 0
PPM

Ans: O

Topic: Analyzing a 1H NMR spectrum


Section: 16.10
Difficulty Level: Medium
76. A compound with a molecular formula C10H12O2 has the following HNMR 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

II III IV
O
I

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

Topic: 13C NMR spectroscopy


Section: 16.11 & 16.12
Difficulty Level: Easy
77. How many signals would you expect to find in the 13C NMR spectrum of the following
compound?
O

A) 6
B) 7
C) 8
D) 9
E) none of these
Ans: B

Topic: 13C NMR spectroscopy


Section: 16.11 & 16.12
Difficulty Level: Easy

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

Topic: 13C NMR spectroscopy


Section: 16.11 & 16.12
Difficulty Level: Medium
79. How many signals would you expect to find in the 13C NMR spectrum of the following
compound?

A) 6
B) 7
C) 8
D) 9
E) none of these
Ans: D

Topic: 13C NMR spectroscopy


Section: 16.11 & 16.12
Difficulty Level: Medium

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

Topic: 13C NMR spectroscopy


Section: 16.11 & 16.12
Difficulty Level: Easy
81. Which of the following carbon atoms will display the signal most downfield in the 13C
NMR spectrum?
O F
C N
C C C C
C
I III V
II IV
A) I
B) II
C) III
D) IV
E) none of these
Ans: B

Topic: 13C NMR spectroscopy


Section: 16.11 & 16.12
Difficulty Level: Medium

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

Topic: 13C NMR spectroscopy


Section: 16.11 & 16.12
Difficulty Level: Medium
83. Which of the following compounds will display five signals in the 13C NMR spectrum?
Br Br
Br

Br Br

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

Topic: 13C NMR spectroscopy


Section: 16.11 & 16.12
Difficulty Level: Medium

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

Topic: 13C NMR spectroscopy


Section: 16.11 & 16.12
Difficulty Level: Hard
85. Which of the following compounds is consistent with the following 13C NMR spectrum?

200 180 160 140 120 100 80 60 40 20 0


PPM

O O
O O

I II III IV

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

Topic: 13C NMR spectroscopy


Section: 16.11 & 16.12
Difficulty Level: Hard
86. Which of the following compounds is consistent with the following 13C NMR spectrum?

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

Topic: 13C NMR spectroscopy


Section: 16.11 & 16.12
Difficulty Level: Hard
87. Which of the following compounds is consistent with the following 13C NMR spectrum?

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

Topic: 13C NMR spectroscopy


Section: 16.11 & 16.12
Difficulty Level: Hard
88. Which of the following compounds is consistent with the following 13C NMR spectrum?

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

Topic: DEPT 13C NMR spectroscopy


Section: 16.13
Difficulty Level: Easy

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

Topic: DEPT 13C NMR spectroscopy


Section: 16.13
Difficulty Level: Easy
90. Which of the following displays a negative signal in the DEPT-135 13C NMR
spectroscopy?
A) CH3
B) CH2
C) CH
D) C
E) none of these
Ans: B

Topic: DEPT 13C NMR spectroscopy


Section: 16.13
Difficulty Level: Easy

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

Topic: DEPT 13C NMR spectroscopy


Section: 16.13
Difficulty Level: Medium

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

Topic: DEPT 13C NMR spectroscopy


Section: 16.13
Difficulty Level: Medium
DEPT-90

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

Topic: DEPT 13C NMR spectroscopy


Section: 16.13
Difficulty Level: Hard

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.

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


PPM
Three spectra above: courtesy of SDBS: National Institute of Advanced Industrial Science and Technology
O
Ans:

Topic: Integrated Spectroscopy


Section: 15.6, 16.10, 16.12
6

Difficulty Level: Medium


3
96. A compound with molecular formula C7H14O2 displays the following IR, 1HNMR and
13
CNMR spectrum.
1 Propose a structure
2 for2 this compound.

180 160 140 120 100 80 60 40 20 0


PPM
Three spectra above: courtesy of SDBS: National Institute of Advanced Industrial Science and Technology
Ans: O

Topic: Integrated Spectroscopy


Section: 15.6, 16.10, 16.12
Difficulty Level: Hard
97. A compound with molecular formula C5H7NO2 displays the following IR, 1HNMR and
13
CNMR spectrum. Propose a structure for this compound.

SDBS: National Institute of Advanced Industrial Science and Technology

SDBS: National Institute of Advanced Industrial Science and Technology

SDBS: National Institute of Advanced Industrial Science and Technology


Ans: O
N
C
O

Topic: Integrated Spectroscopy


Section: 15.6, 16.10, 16.12
Difficulty Level: Medium

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:

Topic: Integrated Spectroscopy


Section: 15.6, 16.10, 16.12
Difficulty Level: Medium

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

Topic: Integrated Spectroscopy


Section: 15.6, 16.10, 16.12
Difficulty Level: Hard

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

Topic: Integrated Spectroscopy


Section: 15.6, 16.10, 16.12
Difficulty Level: Hard

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

Topic: Integrated Spectroscopy


Section: 15.6, 16.10, 16.12
Difficulty Level: Hard

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

Topic: Integrated Spectroscopy


Section: 15.6, 16.10, 16.12 & 16.13
DEPT-90

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

Topic: Integrated Spectroscopy


DEPT-90

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

Topic: Integrated Spectroscopy


DEPT-90

DEPT-135 Section: 15.6, 16.10, 16.12 & 16.13


Difficulty Level: Hard

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

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