NMR Practice Problem (Part II)

Winter 2016
(Problems from former Chem 30BL finals)

1
 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 212 2 3

2
DEPT 135

DEPT 90

DEPT 45

# of attached 0 1 2 3
hydrogens
DEPT 135 0 up down up
DEPT 90 0 up 0 0
DEPT 45 0 up up up

Final Answer

3
 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.

15

14

13

12

11

10

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 0.5 0.0

4
 120

115

110

105 129.64 119.51

100

95

90

85

80

75

70

65

60

55 61.52 20.70 14.27

50

45

40

35

30

25

20
132.47
154.18 135.60
15

10

0
160 150 140 130 120 110 100 90 80 70 60 50 40 30 20 10

DEPT 135

DEPT 90

DEPT 45

# of attached 0 1 2 3
hydrogens
DEPT 135 0 up down up
DEPT 90 0 up 0 0
DEPT 45 0 up up up

Final Answer

5
 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.

15.0

14.5

14.0

13.5

13.0

12.5

12.0

11.5

11.0

10.5

10.0

9.5

9.0

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

0.5

0.0
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 0.5

Multiplet: d t t
Integration: 2 2 1 2 2 3
6
 120

115

110

128.93
105 129.44

100

95

90

85

80

75

70

65

60

55
132.90 61.20 45.39 13.80
50

45

40

35

30

25

20

15 192.22 167.80 138.09

10

0
150 100 50 0

DEPT 135

DEPT 90

DEPT 45

# of attached 0 1 2 3
hydrogens
DEPT 135 0 up down up
DEPT 90 0 up 0 0
DEPT 45 0 up up up

Final Answer

7
 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 sd m d
Integration: 2 2 32 1 6

8
DEPT 135

DEPT 90

DEPT 45

# of attached 0 1 2 3
hydrogens
DEPT 135 0 up down up
DEPT 90 0 up 0 0
DEPT 45 0 up up up

Final Answer

9
 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 tt s
Integration: 5 2 22 3

10
DEPT 135

DEPT 90

DEPT 45

# of attached 0 1 2 3
hydrogens
DEPT 135 0 up down up
DEPT 90 0 up 0 0
DEPT 45 0 up up up

Final Answer

11
 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 td
Integration: 2 2 1 36

12
DEPT 135

DEPT 90

DEPT 45

# of attached 0 1 2 3
hydrogens
DEPT 135 0 up down up
DEPT 90 0 up 0 0
DEPT 45 0 up up up

Final Answer

13
 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

14
DEPT 135

DEPT 90

DEPT 45

# of attached 0 1 2 3
hydrogens
DEPT 135 0 up down up
DEPT 90 0 up 0 0
DEPT 45 0 up up up

Final Answer

15
 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

16
DEPT 135

DEPT 90

DEPT 45

# of attached 0 1 2 3
hydrogens
DEPT 135 0 up down up
DEPT 90 0 up 0 0
DEPT 45 0 up up up

Final Answer

17
 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 dm d

18
DEPT 135

DEPT 90

DEPT 45

# of attached 0 1 2 3
hydrogens
DEPT 135 0 up down up
DEPT 90 0 up 0 0
DEPT 45 0 up up up

Final Answer

19
 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

20
DEPT 135

DEPT 90

DEPT 45

# of attached 0 1 2 3
hydrogens
DEPT 135 0 up down up
DEPT 90 0 up 0 0
DEPT 45 0 up up up

Final Answer

21
 Answers

1 Summer 2010

H
N O

2 Fall 2010
O
H3 C

3 Winter 2011

4 Spring 2011
O
O

5 Summer 2011 O

O
6 Fall 2011
O O
H
O N

7 Winter 2012 O

O
O
8 Spring 2012 O
O

9 Summer 2012

10 Fall 2012

22