Scribd
Upload
768 views

NMR Problem Set

The document contains 1H NMR spectra for various compounds. Problem R-16A and R-16B show the spectra of two isomers of C4H8O2 that can be distinguished based on differences in peak positions and splitting patterns. Problem R-18R and R-18S show the spectra of propyl acetate and methyl butyrate, respectively, which also differ in their peak positions and splitting patterns due to structural differences.

Uploaded by

Jules Bruno
Copyright
© Attribution Non-Commercial (BY-NC)
Available Formats
Download as PDF, TXT or read online on Scribd
768 views

NMR Problem Set

The document contains 1H NMR spectra for various compounds. Problem R-16A and R-16B show the spectra of two isomers of C4H8O2 that can be distinguished based on differences in peak positions and splitting patterns. Problem R-18R and R-18S show the spectra of propyl acetate and methyl butyrate, respectively, which also differ in their peak positions and splitting patterns due to structural differences.

Uploaded by

Jules Bruno
Copyright
© Attribution Non-Commercial (BY-NC)
Available Formats
Download as PDF, TXT or read online on Scribd
You are on page 1/ 11

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


300 MHz 1H NMR Spectrum in CDCl3
Source: Aldrich Spectral Viewer/Reich

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


300 MHz 1H NMR Spectrum in CDCl3
Source: Aldrich Spectral Viewer/Reich

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


300 MHz 1H NMR spectrum in CDCl3
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


75 MHz 13C NMR spectrum
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


300 MHz 1H NMR spectrum in CDCl3
Source: Aldrich Spectra Viewer 33-09
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


75 MHz 13C NMR spectrum
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


300 MHz 1H NMR spectrum in CDCl3
Source: Aldrich Spectra Viewer 33-09

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


75 MHz 13C NMR spectrum
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


75 MHz 13C NMR spectrum
Solv: CDCl3
Source: ASV/Reich

40

30

20

10

Problem R-7K C5H9ClO2


250 MHz 1H NMR spectrum in CDCl3
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


75 MHz 13C NMR spectrum
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


300 MHz 1H NMR spectrum in CDCl3
Source: Aldrich Spectra Viewer 33-09

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


75 MHz 13C NMR spectrum
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


300 MHz 1H NMR spectrum in CDCl3
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


300 MHz 1H NMR Spectrum in CDCl3
Source: Aldrich Spectral Viewer/Reich

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


300 MHz 1H NMR Spectrum in CDCl3
Source: Aldrich Spectral Viewer/Reich

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

You might also like