Silverstein - Spectrometric Identification of O..

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112 CHAPTER 2 INFRARED SPECTROMETRY

Problem 2.3 Spectrum A

Problem 2.3 Spectrum B

Problem 2.3 Spectrum C

Problem 2.3

PROBLEMS 113

Problem 2.3 Spectrum D

Problem 2.4 Spectrum E

Problem 2.4 Spectrum F

Problems 2.3 and 2.4


Problem 2.4 Spectrum G

Problem 2.4 Spectrum H

Problem 2.4 Spectrum I

Problem 2.4

PROBLEMS 115

Problem 2.5 Spectrum J

Problem 2.5 Spectrum K

Problem 2.5 Spectrum L

Problem 2.5


Problem 2.5 Spectrum M

Problem 2.6 Spectrum N

Problem 2.6 Spectrum O


PROBLEMS 117

Problem 2.6 Spectrum P

Problem 2.6 Spectrum Q

Problem 2.6

Problem 2.6 Spectrum R


Problem 2.7 Spectrum S

Problem 2.8 Spectrum T


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Chapter 8 Additional Problems 1

2.83.03.23.43.63.84.04.24.44.64.8 ppm

45505560657075 ppm

13C/DEPT

1H NMR

MASS

IR m/z

4000 3000 2000 1000Wavenumber (cm-1)

50

100

%T

rans

mitt

ance

663

1126

1304

1458

2877

3440

10050

50

100

45

63

75 89 107137139

200190180170

50

100

169

171

195

197

CI Reagent gas methane

13C/DEPT NMR 75.5 MHz

1H NMR 300 MHz

1


23456789 ppm

20406080100120140160180 ppm

MASS

IR

1H NMR 600 MHz


% o

f B

ase

Peak

m/z 100500

50

100 41

51

55

65

70 81

83

97

98 111

150140130120110

50

100

113

141 153

m/z

CI Reagent gas methane

4000 3000 2000 1000Wavenumber (cm-1)

80

90

100

%T

rans

mit

tanc

e

29542931

2870 1712

1458

11491103

670680 Hz18701880 Hz 17901800 Hz 390400410420430440 Hz


1H NMR 300 MHz

2


4.55.05.56.06.57.07.58.08.59.09.510.010.5 ppm

5060708090100110120130140150160170 ppm

MASS

46804700 Hz

IR

1H NMR 600 MHz

13C/DEPT NMR 600 MHz

4120 Hz41804200 Hz4460 Hz

% o

f B

ase

Peak

m/z

4000 3000 2000 1000Wavenumber (cm-1)

50

100

%T

rans

mit

tanc

e

702760

1092

12151304

1442

16161678

2954

3190

1501401301201101009080706050

50

100

5365

92120

152

3A


4567891011ppm ppm

4

5

6

7

8

9

10

4

5

6

7

8

9

10

ppm

4567891011 ppm

60

80

100

120

140

160

60

80

100

120

140

160

F2

F2

F1

F1

HMQC 600 MHz

COSY 600 MHz

3B


2.02.53.03.54.04.55.05.56.06.57.0 ppm

2030405060708090100110120130140 ppm

MASS

IR

1H NMR 600 MHz

3660 Hz41204140 Hz11201140 Hz

38003820 Hz


% o

f B

ase

Peak

m/z1601501401301201101009080706050

50

100

164

1491311211039177

6555

4000 3000 2000 1000Wavenumber (cm-1)

50

100

%T

rans

mitt

ance

3514

301629352850

159715121427

1265

1153

1034

856791

4A


2.02.53.03.54.04.55.05.56.06.57.0ppm ppm

2

3

4

5

6

7

2

3

4

5

6

7

ppm

2.02.53.03.54.04.55.05.56.06.57.0 ppm

20

40

60

80

100

120

140

20

40

60

80

100

120

140

F2

F2

F1

F1

HMQC 600 MHz

COSY 600 MHz

4B


ppm

6.06.57.0 ppm

105

110

115

120

125

130

135

140

145

150

3.94.0 ppm 1.81.9 ppm

6.06.57.0ppm ppm

20

30

40

50

3.94.0 ppm 1.81.9 ppm

HMQC 600 MHz

F1

F2

4C


1.52.02.53.03.54.04.55.05.56.0 ppm

2030405060708090100110120130140 ppm

MASS

IR

1500 Hz 600620 Hz17401760 Hz

% o

f B

ase

Peak

m/z15010050

50

100

168140125

111

9783

705541

4000 3000 2000 1000Wavenumber (cm-1)

50

100

%T

rans

mitt

ance

3078

29242854

1643

1466

910

260280 Hz

13C NMR 75.5 MHz

1H NMR 300 MHz

2030405060708090100110120130140 ppm

29.029.229.429.629.8 ppm


5A


1.01.52.02.53.03.54.04.55.05.56.06.5ppm ppm

1

2

3

4

5

6

1

2

3

4

5

6

ppm

20406080100120140 ppm

1

2

3

4

5

6

1

2

3

4

5

6

F2

F2

F1

F1

COSY 300 MHz

HETCO 300 MHz

5B


2.02.53.03.54.04.55.05.5 ppm

2030405060708090100110120130140150 ppm

MASS

11001150120012501300 Hz

IR

% o

f B

ase

Peak

m/z140130120110100908070605040

50

100

53

68

77

79

93

107 121

136

4000 3000 2000 1000Wavenumber (cm-1)

100

%T

rans

mit

tanc

e795

887

13731442

1643

2924

3078

85090095010001050 Hz

30.531.0 ppm

1H NMR 600 MHz


6A


1.52.02.53.03.54.04.55.05.5ppm ppm

1.5

2.0

2.5

3.0

3.5

4.0

4.5

5.0

5.5

1.5

2.0

2.5

3.0

3.5

4.0

4.5

5.0

5.5

ppm

1.52.02.53.03.54.04.55.05.5 ppm

20

40

60

80

100

120

140

20

40

60

80

100

120

140

F2

F2

F1

F1

HMQC 600 MHz

COSY 600 MHz

ppm

1.61.82.02.2 ppm

20

25

30

35

40

45

ppm

1.61.82.02.2 ppm

1.6

1.8

2.0

2.2

6B


1.41.51.61.71.81.92.02.1 ppm

F2

F1

HMBC 600 MHz

4.85.05.25.45.6ppm

ppm

20

25

30

35

40

ppm

4.85.05.25.45.6 ppm

110

115

120

125

130

135

140

145

150

1.41.51.61.71.81.92.02.1 ppm

6C


1.01.11.21.31.41.51.61.71.81.92.02.12.22.32.42.52.62.7 ppm

406080100120140160180200 ppm

MASS

IR

1H NMR 600 MHz


% o

f B

ase

Peak

m/z

4000 3000 2000 1000Wavenumber (cm-1)

50

100

11341211128813731450

16121682

28702924

1501401301201101009080706050

50

10041

53

6781

109

123137

152


7A


1.01.21.41.61.82.02.22.42.62.83.0ppm ppm

1.0

1.2

1.4

1.6

1.8

2.0

2.2

2.4

2.6

2.8

1.0

1.2

1.4

1.6

1.8

2.0

2.2

2.4

2.6

2.8

ppm

1.01.21.41.61.82.02.22.42.62.83.0 ppm

20

25

30

35

40

45

50

20

25

30

35

40

45

50

F2

F2

F1

F1

HMQC 600 MHz

COSY 600 MHz

7B


F2

F1

HMBC 600 MHz

ppm

0.81.01.21.41.61.82.02.22.42.62.8 ppm

150

200

0.81.01.21.41.61.82.02.22.42.62.8ppm ppm

21

22

23

24

25

26

27

28

29

30

31

32

33

ppm

50

52

7C


2.53.03.54.04.55.05.56.06.57.0 ppm

30405060708090100110120130140150160170180 ppm

MASS

IR

1H NMR 600 MHz


42204230 Hz 14101420 Hz36603670 Hz

% o

f B

ase

Peak

m/z120110100908070605040

50

100

124

109

815343

4000 3000 2000 1000Wavenumber (cm-1)

50

100

%T

rans

mit

tanc

e

3124

2924

1674

1520

1296

1026

802


8A


2.02.53.03.54.04.55.05.56.06.57.07.5ppm ppm

2

3

4

5

6

7

2

3

4

5

6

7

ppm

2.02.53.03.54.04.55.05.56.06.57.07.5 ppm

20

40

60

80

100

120

140

20

40

60

80

100

120

140

F2

F2

F1

F1

HMQC 600 MHz

COSY 600 MHz

8B


2.32.4 ppm

2.32.4 ppm

20

30

40

50

60

70

80

90

100

110

120

130

140

150

160

170

180

F2

F1

HMBC 600 MHz

6.26.46.66.87.07.2ppm

6.26.46.66.87.07.2 ppm

20

30

40

50

60

70

80

90

100

110

120

130

140

150

160

170

180

8C


6.66.76.86.97.07.17.27.37.47.57.67.77.87.9 ppm

120125130135140145150155160165170175180185190195 ppm

MASS

IR

1H NMR 600 MHz


129130 ppm

% o

f B

ase

Peak

m/z

4000 3000 2000 1000Wavenumber (cm-1)

70

80

90

100

%T

rans

mit

tanc

e

3286

16351597

1442

1281

1149

702

20015010050

50

100198

121

105937765


9A


6.66.87.07.27.47.67.88.0ppm ppm

6.6

6.8

7.0

7.2

7.4

7.6

7.8

6.6

6.8

7.0

7.2

7.4

7.6

7.8

ppm

6.66.87.07.27.47.67.88.0 ppm

115

120

125

130

135

140

115

120

125

130

135

140

F2

F2

F1

F1

HMQC 600 MHz

COSY 600 MHz

9B


ppm

128

130

132

134

136

138

F2

F1

HMBC 600 MHz

ppm

6.56.66.76.86.97.07.17.27.37.47.57.67.77.87.98.0 ppm

180

200

6.56.66.76.86.97.07.17.27.37.47.57.67.77.87.98.0ppm ppm

115

120

9C


1.82.02.22.42.62.83.03.23.43.63.84.04.24.4 ppm

406080100120140160180200 ppm

MASS

IR

1H NMR 600 MHz


26802700 Hz

% o

f B

ase

Peak

m/z140130120110100908070605040

50

100

43

55 69 79

97

140

4000 3000 2000 1000Wavenumber (cm-1)

50

100

%T

rans

mit

tanc

e764

1072

1358

16821720

28542924

25202540 Hz


10A


2.02.53.03.54.04.5ppm ppm

2.0

2.5

3.0

3.5

4.0

4.5

2.0

2.5

3.0

3.5

4.0

4.5

ppm

2.02.53.03.54.04.5 ppm

20

30

40

50

60

70

80

90

20

30

40

50

60

70

80

90

F2

F2

F1

F1

HMQC 600 MHz

COSY 600 MHz

ppm

1.82.02.2 ppm

18

20

22

24

26

28

1.71.81.92.02.1ppm ppm

1.7

1.8

1.9

2.0

10B


ppm

90

100

110

120

130

140

150

F2

F1

HMBC 600 MHz

ppm

2.02.53.03.54.04.5 ppm

210

215

2.02.53.03.54.04.5ppm ppm

20

25

10C


1.01.11.21.31.41.51.61.71.81.92.02.12.22.32.42.52.62.72.82.9 ppm

200 180 160 140 120 100 80 60 40 20 ppm

MASS

IR

910111213 ppm


1H NMR 600 MHz

% o

f B

ase

Peak

m/z

4000 3000 2000 1000Wavenumber (cm-1)

80

90

100

%T

rans

mitt

ance

949

1188

1404

17051728

2962

3178

15010050

50

100

x 2043

69 71

83

98

114 125

166

169 18

4

x64

30.130.2 ppm

30.130.2 ppm

11A


1.01.21.41.61.82.02.22.42.62.83.0ppm ppm

1.0

1.2

1.4

1.6

1.8

2.0

2.2

2.4

2.6

2.8

1.0

1.2

1.4

1.6

1.8

2.0

2.2

2.4

2.6

2.8

ppm

1.01.21.41.61.82.02.22.42.62.83.0 ppm

15

20

25

30

35

40

45

50

55

15

20

25

30

35

40

45

50

55

F2

F2

F1

F1

HMQC 600 MHz

COSY 600 MHz

ppm

1.21.41.61.82.02.22.4 ppm

30.0

30.5

11B


0.81.01.21.41.61.82.02.22.42.62.83.03.2ppm ppm

20

25

30

35

40

45

50

55

F2

F1

HMBC 600 MHz

ppm

0.81.01.21.41.61.82.02.22.42.62.83.03.2 ppm

180

190

200

210

11C


1.52.02.53.03.54.04.55.05.5 ppm

2030405060708090100110120130 ppm

MASS

IR

% o

f B

ase

Peak

m/z

4000 3000 2000 1000Wavenumber (cm-1)

100

%T

rans

mit

tanc

e825

980

113413731450

28702924

2993

1401301201101009080706050

50

100

53 65

7779

93

105

121

136

0.91.01.11.21.31.41.51.61.71.81.9 ppm


1H NMR 600 MHz

12A


1.01.52.02.53.03.54.04.55.05.56.0ppm ppm

1

2

3

4

5

1

2

3

4

5

ppm

1.01.52.02.53.03.54.04.55.05.56.0 ppm

20

40

60

80

100

120

20

40

60

80

100

120

F2

F2

F1

F1

HMQC 600 MHz

COSY 600 MHz

ppm

1.01.52.02.5 ppm

15

20

25

30

0.81.01.21.41.61.82.0ppm ppm

1.0

1.5

12B


0.81.01.21.41.61.82.0 ppm

F2

F1

HMBC 600 MHz

5.65.7ppm

ppm

16

18

20

22

24

26

28

30

ppm

67 ppm

120

130

1400.81.01.21.41.61.82.0 ppm

12C

Silverstein - Spectrometric Identification of O..

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