NMR Problem Set

Problem Set 1 - NMR Spectra
Reich
Chem 345
Two Isomers of C4H8O2

Problem R-16A: C4H8O2
300 MHz 1H NMR Spectrum in CDCl3
Source: Aldrich Spectral Viewer/Reich
IHD = 1
3
O
30
20
10
Hz
CH2 CH3
X
CH3
Observed protons are circled

protons causing splitting are underlined
2
O
CH2 CH3
quartet
4.2
10
4.1
Problem R-16B: C4H8O2

2.05 2.00
5
ppm
1.30 1.25
IHD = 1
3
CH2 CH3
O
3
O
CH3
X
30
20
10
CH2 CH3
Hz
1.20 1.15 1.10
2
2.4
3.70 3.65
10
2.3
5
ppm
Two Isomers of C4H8O2
Problem R-16C: C4H8O2

IHD = 1
CH2 CH2 CH3
CH2 CH3
O
H
O
30
20
10
Hz
O
3.00
H
1.8
1.7
1.6
2.06
2.11
8.1
8.0
CH2 CH2
O
1.00 0.95
1.01
4.15 4.10
10
Problem R-16D: C4H8O2

100 MHz 1H NMR Spectrum
Source: Reich
5
ppm
IHD = 1
1.17
O
1.00
OH
CH2 CH3
CH2 CH2 CH3
CH2 CH2
0.94
0.32
OH
12
2.4
11
1.7
2.3
10
1.0
1.6
6
ppm
Problem R-18L C4H9Br

300 MHz 1H NMR spectrum in CDCl3
Source: Aldrich Spectra Viewer/Reich
Br
30
20
10
Hz
CH2 CH3
IHD = 0
CH2 CH2 CH2
CH2 CH2 CH3

sextet
pentet
1.95 1.90 1.85 1.80 1.75 1.70 1.65 1.60 1.55 1.50 1.45 1.40 1.35
CH2 CH3
1.00 0.95 0.90

2.20
1.42
1.00
3.45 3.40 3.35
100
ppm
80
60
40
CDCl3
Problem R-18L: C4H9Br

75 MHz 13C NMR spectrum
Solv: CDCl3
Source: ASV/Reich
13.2
21.3
34.8
33.6
10
200
180
160
140
120
20
US
Problem R-7N C8H10O

Source: Aldrich Spectra Viewer 33-09
IHD = 4
CH2 CH3
7.3
7.2
7.1
7.0
6.9
6.8
O CH2 CH3
3
R
120.6
129.5
Problem R-7N: C8H10O

Solv: CDCl3
Source: ASV/Reich
ppm
Infrared Spectrum:
210 200 190 180 170 160 150 140 130 120 110 100
ppm
90
80
70
60
14.9
3.9
63.3
4.0
114.6
1.4
50
40
30
20
10
Problem R-7R: C5H9BrO2

X
IHD = 1
CH2 CH2
30
3.6
3.5
3.4
20
10
3.3
Hz
3.2
3.1
O
Br
CH2 CH3
CH2 CH2
3.0
2
O
1.00
2.9
1.05
1.43
1.00
1.3
O
CH2 CH3
4.2
10
9
Infrared Spectrum:
5
ppm
100
60
40
20
1600
1400
1200
1000
800
600
400
200
14.2
25.9
cm-1
CDCl3
Problem R-7R: C5H9BrO2

Solv: CDCl3
Source: ASV/Reich
1800
37.8
Change of scale
at 2000 cm-1
61.0
4000 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000
170.4
Percent Transmittance
80
210 200 190 180 170 160 150 140 130 120 110 100
ppm
90
80
70
60
50
40
30
20
10
Problem R-7P C9H10O

US
IHD = 5
R = electron withdrawing group
30
20
10
Hz
CH2 CH3
3
8.0
7.9
7.8
7.7
7.6
7.5
7.4
2.32
2
5
1.54
CH2 CH3
1.00
Problem R-7P C9H10O

Solv: CDCl3
Source: ASV/Reich
5
ppm
1.25 1.20
31.8
3.0
132.8
128.5
127.9
136.9
200.6
10
Infrared Spectrum:
3.0
8.2
3.1
1
4
CDCl3
O
1
210 200 190 180 170 160 150 140 130 120 110 100
ppm
90
80
70
60
50
40
30
20
10
Problem R-7M: C11H14O

300 MHz 1H NMR
Solv: CDCl3
Source: A. Fiedler/Reich
IHD = 5
30
20
10
Hz
nonet
Ph
CH2
CH (CH3)2
R = electron withdrawing group
CH (CH3)2
R
X
CH2
CH
6.14
7.95 7.90
ppm
7.60
7.55
7.50 7.45
ppm
7.40
7.35
2.40
2.35
2.30
ppm
2.25
2.20
2.98
2.00
2.03
1.01
2.85
1.00
ppm
2.80
ppm
4
ppm
210 200 190 180 170 160 150 140 130 120 110 100
ppm
90
80
70
60
50
25.1
22.8
47.4
132.7
128.5
128.0
137.3
199.9
Problem R-7M C11H14O

Solv: CDCl3
Source: ASV/Reich
40
30
20
10
Problem R-7K C5H9ClO2

Source: Adam Fiedler/Reich
IHD = 1
30
20
10
Hz
O
O
Cl
O
3.26
3.13
Cl
CH2 CH3
Correct structure
This is a reasonable alternative

structure - also fits the 1H NMR
data
X = O, Cl
CH CH3
2.16
CH2 CH3
CH CH3
4.45
4.40
1.00
4.35
4.30
ppm
4.25
4.20
4.15
1.35
1.70 1.65
ppm
4
ppm
1.30
ppm
1.25
Infrared Spectrum:
100
60
40
20
1800
1600
1200
1000
800
600
400
200
14.0
CDCl3
21.5
62.0
Problem R-7K: C5H9ClO2

Solv: CDCl3
Source: ASV/Reich
1400
cm-1
Change of scale
at 2000 cm-1
52.6
4000 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000
170.1
Percent Transmittance
80
220
210
200
190
180
170
160
150
140
130
120
110
ppm
100
90
80
70
60
50
40
30
20
10
Problem R-7O C5H8

40
20
CH2 CH3
Hz
triplet of doublets (td)

H
CH2 CH2
CH2
CH2 CH2 CH3
2
2
2.2
2.1
2.0
1.9
1.8
1.7
1.6
1.5
1.4
1.3
1.2
1.1
1.0
0.9
IHD = 2
There is a long-range coupling

(over 4 bonds) between the
alkyne proton and the CH2 group
10
5
ppm
Problem R-7O: C5H8

Solv: CDCl3
Source: ASV/Reich
H
C
210 200 190 180 170 160 150 140 130 120 110 100
ppm
90
80
70
60
50
40
30
20
10
Problem R-18C C10H12O

Source: Aldrich Spectra Viewer/Reich
IHD = 5
CH2 CH3
CH2 CH3
quartet
O
30
Ph
20
10
Hz
2.50 2.45 2.40
2.51
CH2
3
1.05 1.00 0.95

2
1.02
7.35 7.30 7.25 7.20 7.15
100
80
7.8
35.1
49.8
134.4
129.3
128.6
126.8
1.00
3.70 3.65 3.60
208.8
10
1.52
Problem R-18C: C10H12O

75 MHz 13C NMR spectrum CDCl3
Source: ASV/Reich
CDCl3
220
200
180
160
140
120
ppm
60
40
20
Reich
Chem 345
Problem R-18R: C5H10O2

CH2 CH3
CH2 CH2 CH3
IHD = 1
O
O
30
Propyl acetate
20
10
Hz
O
1.70 1.65 1.60
CH2 CH2
CH3
1.57
1.49
1.09
1.00
3
2
Problem R-18S: C5H10O2

5
ppm
2.05 2.00
4.05 4.00
10
IHD = 1
CH2 CH2 CH3
CH2 CH3
O CH3
CH2 CH2
O
methyl butyrate
30
20
10
Hz
1.7
1.00
5
ppm
0.96
0.95 0.90
2.35 2.30 2.25
3.70 3.65
1.6
0.66
0.64
10
1.00 0.95 0.90

NMR Problem Set

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NMR Problem Set

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Problem Set 1 - NMR Spectra

Two Isomers of C4H8O2

Observed protons are circled

Problem R-16B: C4H8O2

1.20 1.15 1.10

Two Isomers of C4H8O2

Problem R-16C: C4H8O2

Problem R-16D: C4H8O2

CH2 CH2 CH3

Problem R-18L C4H9Br

CH2 CH2 CH2

CH2 CH2 CH3

1.00 0.95 0.90

3.45 3.40 3.35

Problem R-18L: C4H9Br

Problem R-7N C8H10O

Problem R-7N: C8H10O

Problem R-7R: C5H9BrO2

Problem R-7R: C5H9BrO2

Problem R-7P C9H10O

R = electron withdrawing group

Problem R-7P C9H10O

Problem R-7M: C11H14O

R = electron withdrawing group

Problem R-7M C11H14O

Problem R-7K C5H9ClO2

This is a reasonable alternative

Problem R-7K: C5H9ClO2

Problem R-7O C5H8

triplet of doublets (td)

CH2 CH2 CH3

There is a long-range coupling

Problem R-7O: C5H8

Problem R-18C C10H12O

2.50 2.45 2.40

1.05 1.00 0.95

7.35 7.30 7.25 7.20 7.15

3.70 3.65 3.60

Problem R-18C: C10H12O

Problem R-18R: C5H10O2

CH2 CH2 CH3

1.70 1.65 1.60

Problem R-18S: C5H10O2

CH2 CH2 CH3

2.35 2.30 2.25

1.00 0.95 0.90

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