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NMR Practice Problem Set II
Fall 2014
2
Summer 2010
1. Compound W has an empirical formula of C11H10O2. Given are the following spectra. Show
all your work (= label peaks in the spectra!)
a. Determine the degree of unsaturation for the compound.
b. Assign the six pertinent peaks in the infrared spectrum.
c. Suggest a structure for compound W based on the spectra given. Place your final answer
in the box provided below. Only the molecule placed is this box will receive credit!
Partial structures and structures, which do not meet the molecular formula, will not
any receive credit.
Integration 2 1 2 2 3
3
DEPT 135
DEPT 90
DEPT 45
# of attached
hydrogens
0 1 2 3
DEPT 135 0 up down up
DEPT 90 0 up 0 0
DEPT 45 0 up up up
Final Answer
4
Fall 2010
2. Compound W has an empirical formula of C10H13NO2. Given are the following spectra. Show
all your work (= label peaks in the spectra!)
a. Determine the degree of unsaturation for the compound.
b. Assign the six pertinent peaks in the infrared spectrum.
c. Suggest a structure for compound W based on the spectra given. Place your final answer
in the box provided below. Only the molecule placed is this box will receive credit!
Partial structures and structures, which do not meet the molecular formula, will not
any receive credit.
7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.5 0.00
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160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 100
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10
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14.2720.7061.52
119.51129.64
132.47135.60154.18
DEPT 135
DEPT 90
DEPT 45
# of attached
hydrogens
0 1 2 3
DEPT 135 0 up down up
DEPT 90 0 up 0 0
DEPT 45 0 up up up
Final Answer
6
Winter 2011
3. Compound W has an empirical formula of C11H12O3. Given are the following spectra. Show
all your work (= label peaks in the spectra!)
a. Determine the degree of unsaturation for the compound.
b. Assign the six pertinent peaks in the infrared spectrum.
c. Suggest a structure for compound W based on the spectra given. Place your final answer
in the box provided below. Only the molecule placed is this box will receive credit!
Partial structures and structures, which do not meet the molecular formula, will not
any receive credit.
8.5 8.0 7.5 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 0.50.0
0.5
1.0
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
6.5
7.0
7.5
8.0
8.5
9.0
9.5
10.0
10.5
11.0
11.5
12.0
12.5
13.0
13.5
14.0
14.5
15.0
Multiplet: d t t
Integration: 2 2 1 2 2 3
7
150 100 50 00
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10
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105
110
115
120
13.8045.3961.20
128.93129.44
132.90
138.09167.80192.22
DEPT 135
DEPT 90
DEPT 45
# of attached
hydrogens
0 1 2 3
DEPT 135 0 up down up
DEPT 90 0 up 0 0
DEPT 45 0 up up up
Final Answer
8
Spring 2011
4. Compound W has an empirical formula of C12H16O. Given are the following spectra. Show all
your work (= label peaks in the spectra!)
a. Determine the degree of unsaturation for the compound.
b. Assign the four pertinent peaks in the infrared spectrum.
c. Suggest a structure for compound W based on the spectra given. Place your final answer
in the box provided below. Only the molecule placed is this box will receive credit!
Partial structures and structures, which do not meet the molecular formula, will not
any receive credit.
Multiplet: d d s d m d
Integration: 2 2 3 2 1 6
9
DEPT 135
DEPT 90
DEPT 45
# of attached
hydrogens
0 1 2 3
DEPT 135 0 up down up
DEPT 90 0 up 0 0
DEPT 45 0 up up up
Final Answer
10
Summer 2011
5. Compound W has an empirical formula of C12H14O3. Given are the following spectra. Show
all your work (= label peaks in the spectra!)
a. Determine the degree of unsaturation for the compound.
b. Assign the five pertinent peaks in the infrared spectrum.
c. Suggest a structure for compound W based on the spectra given. Place your final
answer in the box provided below. Only the molecule placed is this box will
receive credit! Partial structures and structures, which do not meet the
molecular formula, will not any receive credit.
Multiplet: “m” s t t s
Integration: 5 2 2 2 3
11
DEPT 135
DEPT 90
DEPT 45
# of attached
hydrogens
0 1 2 3
DEPT 135 0 up down up
DEPT 90 0 up 0 0
DEPT 45 0 up up up
Final Answer
12
Fall 2011
6. Compound W has an empirical formula of C8H14O3. Given are the following spectra. Show all
your work (= label peaks in the spectra!)
a. Determine the degree of unsaturation for the compound.
b. Assign the five pertinent peaks in the infrared spectrum.
c. Suggest a structure for compound W based on the spectra given. Place your final answer in
the box provided below. Credit is given only if work is shown (=clearly labeling peaks in
the NMR spectra). Place your final answer in the box provided below. Only a molecule
placed is this box will receive credit! Incomplete molecules, a molecule with incorrect
molecular formulas and messy work will not receive any credit.
Multiplet: q s m t d
Integration: 2 2 1 3 6
13
DEPT 135
DEPT 90
DEPT 45
# of attached
hydrogens
0 1 2 3
DEPT 135 0 up down up
DEPT 90 0 up 0 0
DEPT 45 0 up up up
Final Answer
14
Winter 2012
7. Compound W has an empirical formula of C9H11NO2. Given are the following spectra. Show
all your work (= label peaks in the spectra!)
a. Determine the degree of unsaturation for the compound.
b. Assign the five pertinent peaks in the infrared spectrum.
c. Suggest a structure for compound W based on the spectra given. Place your final answer
in the box provided below. Credit is given only if work is shown (=clearly labeling
peaks in the NMR spectra). Place your final answer in the box provided below. Only a
molecule placed is this box will receive credit! Incomplete molecules, a molecule with
incorrect molecular formulas and messy work will not receive any credit.
Integration: 1/1/1/1 1 3 3
Multiplet: t/d/s/d s s s
15
DEPT 135
DEPT 90
DEPT 45
# of attached
hydrogens
0 1 2 3
DEPT 135 0 up down up
DEPT 90 0 up 0 0
DEPT 45 0 up up up
Final Answer
16
Spring 2012
8. Compound W has an empirical formula of C12H14O4. Given are the following spectra. Show
all your work (= label peaks in the spectra!)
a. Determine the degree of unsaturation for the compound.
b. Assign five pertinent peaks in the infrared spectrum.
c. Suggest a structure for compound W based on the spectra given. Place your final answer
in the box provided below. Credit is given only if work is shown (=clearly labeling
peaks in the NMR spectra). Place your final answer in the box provided below. Only
a molecule placed is this box will receive credit! Incomplete molecules, a molecule
with an incorrect molecular formula and messy work will not receive any credit.
Integration: 2 2 2 2 3 3
Multiplet: d d t t s s
17
DEPT 135
DEPT 90
DEPT 45
# of attached
hydrogens
0 1 2 3
DEPT 135 0 up down up
DEPT 90 0 up 0 0
DEPT 45 0 up up up
Final Answer
18
Summer 2012
9. Compound W has an empirical formula of C12H16O. Given are the following spectra. Show all
your work (= label peaks in the spectra!)
a. Determine the degree of unsaturation for the compound.
b. Assign five pertinent peaks in the infrared spectrum.
c. Suggest a structure for compound W based on the spectra given. Place your final answer
in the box provided below. Credit is given only if work is shown (=clearly labeling
peaks in the NMR spectra). Place your final answer in the box provided below. Only
a molecule placed is this box will receive credit! Incomplete molecules, a molecule
with an incorrect molecular formula and messy work will not receive any credit.
Integration: 2/1/2 2 2 1 6
Multiplet: t/t/d s d m d
19
DEPT 135
DEPT 90
DEPT 45
# of attached
hydrogens
0 1 2 3
DEPT 135 0 up down up
DEPT 90 0 up 0 0
DEPT 45 0 up up up
Final Answer
20
Fall 2012
10. Compound W has an empirical formula of C10H12O3. Given are the following spectra. Show
all your work (= label peaks in the spectra!)
a. Determine the degree of unsaturation for the compound.
b. Assign five pertinent peaks in the infrared spectrum.
c. Suggest a structure for compound W based on the spectra given. Place your final answer
in the box provided below. Credit is given only if work is shown (=clearly labeling
peaks in the NMR spectra). Place your final answer in the box provided below.
Only a molecule placed is this box will receive credit! Incomplete molecules,
a molecule with an incorrect molecular formula and messy work will not receive any
credit.
Integration: 1 1 1 1/1 2 2 3
Multiplet: s d t d/t t m t
21
DEPT 135
DEPT 90
DEPT 45
# of attached
hydrogens
0 1 2 3
DEPT 135 0 up down up
DEPT 90 0 up 0 0
DEPT 45 0 up up up
Final Answer
22
Answers
Summer 2010
Fall 2010
H3C
HN O
O
Winter 2011
Spring 2011
O Summer 2011
O
O
O
Fall 2011
O
O O Winter 2012 O
HN
O
Spring 2012
O
O
O
O
Summer 2012
Fall 2012
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