Question 1: Choose the correct answer or answer

1. Which one of the following pieces of information can be obtained from an infra-red
spectrum?
A. The molecular mass
B. The presence of C=O bonds
C. The number of O-H bonds
D. The number of types of protons in the molecule
2. To check that a secondary alcohol has been completely oxidized to a ketone you can...
A. Check that the IR spectrum has absorptions at 3500cm-1 and 1650cm-1
B. Check that the IR spectrum has no absorption around 3500cm-1
C. Check that the IR spectrum has no absorption around 1650cm-1
D. Check that the IR spectrum no absorptions at 3500cm-1 and 1650cm-1
3. Which one of the following compound exhibits an absorption band in the region from 2100-
2300 cm-1 in the IR spectrum? C
O O
O
O
O NH2

OH
B C D
A
4. Unit of wavenumber is cm-1
A. True
B. False
5. Degeneracy of bands in IR from several absorptions of the same frequency leads to increase
the number of fundamental vibration
A. True
B. False
6. Which two isomers of C3H6Br2 have three signals (other than the TMS peak) in their 1H
NMR spectrum? (in the same pairs) B

7. Nuclei having either the number of neutrons as odd have _______ spin.
A. Integral spin
B. Half integral spin
C. Zero spin
D. Positive spin
8. Distortionless Enhancement by Polarization Transfer is a technique used in
A. 13CNMR
B. 1HNMR
C. IR
D. UV
9. What do you expect to observe in the 1H NMR spectrum of chloroethane CH3CH2Cl?
A. A triplet and a quartet.
B. A doublet and a triplet.

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 C. Two doublets.
D. A doublet and a quartet.
10. All proton in 1H-NMR are shielded relative to proton of trimethylsilane
A. True
B. False
11. Number of signals of compound 1 in 1HNMR and 13C-NMR are equal.
A. True
B. False
12. Which carbon is the most deshielded carbon in 13C-NMR for compound 2?
A. C1
B. C2
C. C3
D. C4
13. A compound of molecular formula C8H9Cl give the following integrated HNMR Spectrum.
How many proton rise to each signal? From the right in the spectrum

A. 3, 2, 4 H
B. 4, 2, 3 H
C. 3, 2, 4 H
D. 2, 3, 4 H

14. How many signals do you expect to see in the 1H NMR spectra of 1-bromopropane
CH3CH2CH2Br and 2-bromopropane (CH3)2CHBr?
A. 1-Bromopropane: 2; 2-bromopropane: 3.
B. 1-Bromopropane: 2; 2-bromopropane: 2.
Bromopropane 3; 2-bromopropane: 2.
C. 1-Bromopropane:
D. 1-Bromopropane: 3; 2-bromopropane: 3.
E. None of the above
15. If a proton nucleus in 1H-NMR experiences a lower magnetic field strength, it needs a
lower frequency to achieve resonance
A. True
B. False
16. The carbon atom bonded to the hydrogen(s) under consideration are described as
A. alpha carbons
B. alpha subistuent
C. beta carbons
D. delta carbon
E. none of the above
17. ……………………..magnetization vector along the direction of the static magnetic field
reaches thermodynamic equilibrium with its surroundings
A. Spin - lattice relaxation
B. Spin - Spin relaxation
C. Magnetization
D. Gyro-magnetic ratio

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 E. Spin number
18. Which of the following compounds contains one or more protons that could undergo
exchange with protons in water?
A. (CH3)2O
B. CH3OH
C. (CH3)3N
D. CH3Br
E. None of above
19. Vicinal coupling is
A. Coupling between 1H nuclei in an alkane.
B. Coupling between 1H nuclei in an alkene
C. Coupling between 1H nuclei attached to adjacent C atoms
D. Coupling between 1H nuclei attached to the same C atom
E. None of the above
20. Which of hydrogens a-d in the following molecule gives a triplet signal in a normal 1H NMR
spectrum?
A. Hydrogen A
B. Hydrogen B
C. Hydrogen C
D. Hydrogen D
E.
21. H, 13C, 19F are spin active nuclei in NMR.
1

A. True
B. False
22. Which hydrogen of 1-chloropent-2-ene shows the largest chemical (downfield) shift in its
NMR spectrum?
A. the H on C1
B. the H on either C2 or C3
C. the H on C4
D. the H on C5

23. Which of the following statements regarding NMR spectroscopy is wrong?

A. NMR signals towards the left of the spectral chart correspond to larger chemical shifts
B. Chemical shifts are larger when the frequencies of the radiation which induces the
nuclear transitions are higher.
C. Chemical shifts are larger when shielding effects are greater.
D. A hydrogen signal splits into n+1 peaks by spin-spin coupling when the number of
equivalent hydrogen atoms on adjacent atom(s) is n, and no other neighboring atoms are
involved.
24. The region of an infra-red spectrum which is most useful for the purpose of identification
of the compound is 650-1350 cm-1.
A. Thumbprint region
B. Handprint region
C. Footprint region
D. Fingerprint region

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25. In the IR spectrum of a compound X, there is a strong absorption at 1718 cm–1 in addition
to bands at 2978 and 2940 cm–1 and bands below 1500 cm–1. The 1H NMR spectrum
contains two signals: a quartet and a triplet with relative integrals of 2: 3. Of the following
compounds, which is X most likely to be?
A. CH3CH2OCH2CH3
B. CH3CH2COCH2CH3
C. CH3CH2CO2H
D. CH3CH2OH

26. Which is the correct sequence of wavenumbers associated with the stretching of the
following bonds?
A. C–Cl > C=O > C≡C
B. C=O < C–Cl < C≡C
C. C–Cl < C=O < C≡C
D. C≡C > C–Cl > C=O
27. Where would you find the absorption due to the stretch of the nitrogen-hydrogen bond of an
amine?
A. 400-1450 cm-1
B. 3200-3500 cm-1
C. 2700-3000 cm-1
D. 1650-1950 cm-1
28. Which of the following statements in the context of 1H NMR spectroscopy is true?
A. Aromatic C-H chemical shift (δ) values are greater than simple alkenes C-H chemical
shift values because of the aromatic ring current.
B. Aromatic C-H chemical shift (δ) values are smaller than simple alkenes C-H chemical
shift values because of the aromatic ring current.
C. Aromatic C-H signals are always multiplets
D. Aromatic C-H signals are always singlets
29. Tetramethylsilane is inert and produces a single peak at δ=10 ppm.
A. True
B. False
30. Hydrogen bond in IR spectroscopy
A. Increase the frequency of X-H
B. Increase the energy of X-H
C. Increase the broadness of X-H
D. None
31. The frequency of carbonyl group in 1-cycloalkanone increases when the ring size decreases
due to
A. Increasing bond angle
B. Increasing the P character in the double bond in carbonyl group
C. Increasing the S character in the double bond in carbonyl group
D. Decreasing the bond strength of the double bond in carbonyl group
32. The conjugation in spectroscopy
A. Increase the frequency
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 B. Decrease the frequency
C. Increase the broadness
D. Decrease the broadness

33. Which molecular vibration is depicted as shown?

A. Asymmetric stretch
B. Symmetric stretch
C. Asymmetric in-plane bend
D. Symmetric in-plane bend
34. Concentration of solutions can affect
A. Intermolecular hydrogen bond
B. Intramolecular hydrogen bond
C. Both of them
D. None of them
35. What is the order of the following carbonyl compounds in decreasing wave number?
A. III, II, I, IV
O NH O O
B. I, II, III, IV 2

Cl O O
C. IV, I, III,II butanone methyl butyrate
butanoyl chloride pentanamide
D. I, IV, III, II I II III IV
36. The mid-infrared is
A. 14000-4000 cm-1
B. 4000-400 cm-1
C. 400-10 cm-1
D. All of the above
37. Which technique can differentiate between two isomers?
A. IR
B. HNMR
C. UV
D. None
38. The IR spectrum of a certain compound has an absorption band in the region from 3200-
3500 cm-1 as a doublet band (two head) and has an absorption band in the region from 1700-
1800 cm-1. To what functional class must this compound belong?
A. Ketone
B. Alkyne
C. Alcohol
D. Amide
39. Central carbon in Neopentane can be detected by
A. Ordinary broadband-decoupled spectrum
B. DEPT-90
C. DEPT-135
D. DEPT-45
40. In broadband decoupling, all are correct except
A. All C-H coupling is suppressed
B. All split signals become singlet
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 C. Signal intensity increases
D. Leads to more time required to obtain spectrum
41. Compound A has less wave number of carbonyl group than
compound B due to conjugation
A. True
B. False
42. Identify the compound associated with the following spectrum

1690

A B C D E
43. Which of the following statements accurately describes the molecular vibrations of IR
spectroscopy?
A. Triple bonds have lower stretching frequencies than corresponding double bonds, which
in turn have lower frequencies than single bonds.
B. Bonds to hydrogen have higher stretching frequencies than those to heavier atoms
C. Stretching frequencies appear mostly in the fingerprint region.
D. Stretching frequencies are lower than corresponding bending frequencies.
44. Which type of encircled bond C-H has the highest chemical shift?
A. (A)
B. (B)
C. (C)
D. (D)
45. NMR spectroscopy observes
A. Electronic transitions in a molecule
B. Bond vibration frequencies in a molecule
C. Chemical environment of the hydrogen and carbon atoms in a compound.
D. Fragments in the molecule and measures their mass.
46. Which of the following compounds have two signal, both are identical in multiplicity? C

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 A B C D
Br
Br O
Br
O
Br Br Cl
47. The multiplicity pattern of encircled group compound 4 in HNMR spectrum is
A. Singlet
B. Doublet
C. Triplet
D. quartet
48. The first signal in HNMR spectrum of compound 3 contains
A. One proton
B. Two proton
C. Three proton
D. Six proton

49. The amount of energy available in radio frequency radiation is sufficient for which of the
following?
A. Excite an atom
B. Vibrate an atom
C. Vibrate a molecule
D. Affect the nuclear spin of an atom
50. In which compounds, all protons are equivalent?
A. A
B. B
C. C
D. All of the above
51. The difference between the absorption position of a particular proton and the absorption
position of the reference proton
A. Coupling constant
B. Spin constant
C. Spin-spin coupling
D. Chemical shift
52. The splitting pattern for a signal of certain hydrogen is found by counting the number of
hydrogen atoms on adjacent atoms and adding 1 provided it is equivalent to this hydrogen
A. True
B. False
53. How many compound has a singlet signal in 1H NMR?
A. 1 H CH3
B. 2 H
C. 3 H H3C CH3
D. 4 H CH3
54. Which of the following is the least likely to occur?
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 A. 1H with 1H
B. 1H with 13C
C. 13C with 13C
D. All are the same
55. Which is correct about the number of signals in the following compounds in CNMR?
A. All have different number A
B. B & C is equal but A is different B C
O
C. A & C is equal but B is different O
D. A & B is equal but C is different O
O O O
E. All have the same number
56. The terms up field in NMR refers to
A. The low energy of the signals
B. The high energy of the signals.
57. Chemical shift allows a chemist to obtain the idea of how many atoms per different types
atoms are found in the compound.
A. True
B. False
58. Which of the following signals equals 2.5 ppm from a 1H NMR spectra from a 400 MHz
spectrometer. Convert to δ units
A. CHCl3 1450 Hz
B. CH3Cl 600 Hz
C. CH3OH 2100 Hz
D. CH2Cl2 1000 Hz H H
H H
H H
59. The encircled protons H
O
A. Alpha proton is more shielded than beta proton O
B. Beta proton is more shielded than alpha proton
C. Alpha and beta proton are equal
60. If a signal in 13 CNMR is above 160 ppm, it means that the drug might be
A. Alcohol
B. Ketone
C. Amine
D. Alkane
61. The number of signals of any organic compounds in CNMR are ………………as in HNMR
A. The same
B. The half
C. The double
D. None of the above
62. Which is the correct arrangement of these compounds according the wave number of double
bond?
A. D > C > B > A
B. A > B > C > D
C. A > D > C > B A B C D
D. B > C > D > A
63. For a Compound A C5H11Br, Broadband-decoupled 13C NMR: 22, 28, 34 and43
, DEPT-90: 28, DEPT-135: positive peak at 22 and 28, negative peak at 34 and 43. D

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 Br Br

Br Br

B C D
A

64. Which of the following are considered to be the lowest form of Electromagnetic radiation?
A. IR radiation
B. Micro waves
C. UV radiation
D. Radio waves
65. Which instrument can differentiate between the following carbonyl compounds?
A. IR
B. 1HNMR
C. 13CNMR
D. All of the above
66. The following spectra is for the accompanying compound. What are the peak that conforms
to encircled bond in the spectrum?

A. A
B. B
C. C A C
D. D B
B

67. Which molecular vibration is depicted as shown?

A. Scissor in-plane bend
B. Rock in-plane bend
C. Twist in-plane bend
D. Wag in-plane bend
68. In which region of the infrared spectrum would you expect to find a peak characteristic of
a triple bond stretch?
A. 4000 - 3000cm-1
B. 2500 - 2000cm-1
C. 2000 - 1500cm-1
D. 1500 - 750cm-1
69. Which of the following information can NOT be obtained from the CNMR?
A. How many different types of carbon of molecules?
B. What types of carbon of molecules?
C. How many carbons of each type (equivalent carbon)?
D. None of the above
70. Which statement is incorrect about CO2?
A. CO2 has two stretching modes of vibration.
B. CO2 has two bending modes of vibration.
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 C. The IR spectrum of CO2 shows four modes of vibration.
D. CO2 is a nonlinear.

71. The IR spectrum of methanol (CH3OH) shows strong absorptions at 3340 (broad), 2945, 2833
and 1030 cm–1. Which band is assigned to the O–H stretch?
A. 1030 cm–1
B. 2945 cm–1
C. 3340 cm–1
D. 2833 cm–1
72. All hydrogen atoms
A. Have the same resonance frequency
B. Resonate at different frequencies depending on their environment.
C. Are attached to carbon
D. Resonate at about the same frequency as its attached carbon
73. Which of the following compounds would be expected to show spin-spin splitting in their 1H
NMR spectra? C
A. (CH3)3C-O-CH3
B. Br-CH2CH2-Br
C. Br-CH2CH2CH2-Br

D.
74. Which type of encircled bond C-H has the highest wavenumber?
A. (A)
B. (B)
C. (C)
D. (D)

75. NMR spectroscopy indicates the chemical nature of the_____ and spatial positions of_____
A. Electrons, Protons
B. Neutrons, electrons
C. Nuclei, electrons
D. Nuclei, neighboring nuclei
76. Chemical shift of certain carbon are affected by
A. Nearby electronegative atoms
B. Hybridization of carbon atoms
C. A and B
D. None
77. Broadness of peaks in IR spectrum appears in
A. Gas state
B. Solid state
C. Non- H-bonding liquid

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 D. H-bonding liquid
E. B and D H
H
H H
78. Which encircled bond has the H C Cl
H C Br
HC I HC F
highest wavenumber? D H
H
H H
A B C D

79. The difference in wave number between types of C-H bond depends on difference in
A. Electronegativity
B. Number of double bond
C. SP character
D. Bond angle
80. Vinyl C-H stretch occurs at 3000-3100 cm-1
A. True
B. False
81. Based on the absorption spectrum, what is the likely name of the compound below? B

82. FT-IR is used mostly for

A. Functional group analysis of organic molecules
B. Classification of types and number of protons in organic molecules
C. Heavy metal analysis
D. Molecular weight determination
83. Based on the absorption spectrum, what is the likely name of the compound below?
A. Methane
B. Methanol
C. Formaldehyde
D. D. Acetone

84. Which is the correct order of increasing wave number of the stretching vibrations of

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 (1) C-H (alkane), (2) O-H (alcohol), (3) C=O (ketone), and (4) C≡C (alkyne)?
A. (4) < (3) < (2) < (1)
B. (3) < (4) < (1) < (2)
C. (3) < (4) < (2) < (1)
D. (4) < (3) < (1) < (2)
85. Overtone of bending region in benzene appears at 1667-2000 cm-1
A. True
B. False
86. A shift to higher wavenumber for an absorption in a spectrum corresponds to:
A. A shift to lower frequency.
B. A loss of intensity.
C. A shift to lower energy.
D. A shift to lower wavelength.
87. In the absence of an external magnetic field, magnetic nuclear spins of atoms (protons) are
oriented
A. Parallel to the external field
B. Anti-parallel to the external field
C. Randomly to the external field
D. Effective frequency decrease
88. Coupling causes the peaks in 1H NMR spectra to be split into
A. Two peaks
B. Multiple peaks equal to the number of hydrogens on surrounding atoms
C. Multiple peaks equal to the number of surrounding carbon atoms
D. Multiple peaks equal to the number of hydrogen on surrounding atoms, plus one
89. Characteristic of the ideal solvent:
A. Should contain no protons
B. Low boiling
C. Deuterated solvents
D. All of the above
90. Which information can NOT be obtained from 13CNMR spectrum?
A. How many different types of hydrogens?
B. What types of hydrogens?
C. How many hydrogens of each type?
D. How many neighboring hydrogens?
E. All of them
91. If the number of protons and neutrons is even the spin of the nucleus will be which of the
following?
A. Integral spin
B. Half integral spin
C. Zero spin
D. Positive spin
92. What is the incorrect about 13CNMR and 1HNMR?
A. Both utilize active nuclei to do its function
B. The downfield in both are in the left side of the spectrum
C. Both are used in chemical structure elucidation
D. Both have the same scale in the X-axis

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93. Coupling is NOT important beyond three bonds unless there is
A. Ring strain as in small rings
B. Bridged systems
C. Delocalization as in aromatic or unsaturated systems
D. Five connecting bonds in a W configuration
94. Carbon tetrachloride (CCl4) is relatively free of absorption at frequencies above 1333 cm -1
A. True
B. False
95. The number of identical proton can be calculated by dividing the total number of proton at
the total unit of integration then the number that obtained multiply by integration of each
proton
A. If the number of total area under the curve (integration unit) higher than the number of
hydrogen
B. If the number of total area under the curve (integration unit) less than the number of
hydrogen
C. Can be used in the two cases
D. Can NOT be used in the two cases
96. Tetramethyl silane (TMS) Si(CH3)4 is used as reference in NMR because
A. Soluble in most aqueous solvent
B. React with compound being analyzed
C. Given signal with the chemical shift of δ = 0
D. All the hydrogen atoms are chemically nonequivalent.
E. It has 4 equivalent hydrogens so it produces an intense peak & signal is outside the range
shown by most protons
97. Propose a structure for the following molecules given the molecular formula (C6H12O) and
respective spectra C

98. HID of C8H9Cl is

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 A. 3
B. 4
C. 5
D. 6
99. Alkali halide discs (KBr) in IR is used in case of
A. Liquid sample
B. Solid sample
C. Gas sample

100. Internal alkynes ( R-C≡C-R ) would have a band at 3200- 3300 cm-1 O
A. True
B. False
101. Match the following compound to its IR spectrum.
O

AC B
D

102. The 1HNMR of products are different because

A. They differ in the multiplicity of signals
B. They differ in the number of signals

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 C. They differ in the chemical shift of signals HO
D. They differ in the integration of signals
E. All of above H OH

BH3 ,THF OR
-
H2O , OH

Spectral Data

1. IR

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B. 1H- NMR

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C. 13 C-NMR

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