Presents a sequence of procedures for identifying an unknown organic liquid using mass, NMR, IR, and UV spectroscopy, along with specific examples of unknowns and their spectra

138. 112 CHAPTER 2 INFRARED SPECTROMETRY
Problem 2.3 Spectrum A
Problem 2.3 Spectrum B
Problem 2.3 Spectrum C
Problem 2.3

139. PROBLEMS 113
Problem 2.3 Spectrum D
Problem 2.4 Spectrum E
Problem 2.4 Spectrum F
Problems 2.3 and 2.4

140. 114 CHAPTER 2 INFRARED SPECTROMETRY
Problem 2.4 Spectrum G
Problem 2.4 Spectrum H
Problem 2.4 Spectrum I
Problem 2.4

141. PROBLEMS 115
Problem 2.5 Spectrum J
Problem 2.5 Spectrum K
Problem 2.5 Spectrum L
Problem 2.5

142. 116 CHAPTER 2 INFRARED SPECTROMETRY
Problem 2.5 Spectrum M
Problem 2.6 Spectrum N
Problem 2.6 Spectrum O
Problems 2.5 and 2.6

143. PROBLEMS 117
Problem 2.6 Spectrum P
Problem 2.6 Spectrum Q
Problem 2.6
Problem 2.6 Spectrum R

144. 118 CHAPTER 2 INFRARED SPECTROMETRY
Problem 2.7 Spectrum S
Problem 2.8 Spectrum T
Problems 2.7 and 2.8

518. Chapter 8 Additional Problems 1
2.83.03.23.43.63.84.04.24.44.64.8 ppm
45505560657075 ppm
13
C/DEPT
1
H NMR
MASS
IR
m/z
4000 3000 2000 1000
Wavenumber (cm-1)
50
100
%Transmittance
663
1126
1304
1458
2877
3440
10050
50
100
45
63
75 89 107
137
139
200190180170
50
100
169
171
195
197
CI Reagent gas methane
13
C/DEPT NMR 75.5 MHz
1
H NMR 300 MHz
1

519. Chapter 8 Additional Problems 2
23456789 ppm
20406080100120140160180 ppm
MASS
IR
1
H NMR 600 MHz
13
C/DEPT NMR 150.9 MHz
%ofBasePeak
m/z 10050
0
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 1000
Wavenumber (cm-1)
80
90
100
%Transmittance
2954
2931
2870
1712
1458
1149
1103
670680 Hz18701880 Hz 17901800 Hz 390400410420430440 Hz
13
C/DEPT NMR 75.5 MHz
1
H NMR 300 MHz
2

520. Chapter 8 Additional Problems 3
4.55.05.56.06.57.07.58.08.59.09.510.010.5 ppm
5060708090100110120130140150160170 ppm
MASS
46804700 Hz
IR
1
H NMR 600 MHz
13
C/DEPT NMR 600 MHz
4120 Hz41804200 Hz4460 Hz
%ofBasePeak
m/z
4000 3000 2000 1000
Wavenumber (cm-1)
50
100
%Transmittance
702
760
1092
1215
1304
1442
1616
1678
2954
3190
1501401301201101009080706050
50
100
53
65
92
120
152
3A

521. Chapter 8 Additional Problems 4
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

522. Chapter 8 Additional Problems 5
2.02.53.03.54.04.55.05.56.06.57.0 ppm
2030405060708090100110120130140 ppm
MASS
IR
1
H NMR 600 MHz
3660 Hz41204140 Hz
11201140 Hz
38003820 Hz
13
C/DEPT NMR 150.9 MHz
%ofBasePeak
m/z
1601501401301201101009080706050
50
100
164
149
131
1211039177
65
55
4000 3000 2000 1000
Wavenumber (cm-1)
50
100
%Transmittance
3514
3016
2935
2850
1597
1512
1427
1265
1153
1034
856
791
4A

523. Chapter 8 Additional Problems 6
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

524. Chapter 8 Additional Problems 7
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

525. Chapter 8 Additional Problems 8
1.52.02.53.03.54.04.55.05.56.0 ppm
2030405060708090100110120130140 ppm
MASS
IR
1500 Hz 600620 Hz17401760 Hz
%ofBasePeak
m/z
15010050
50
100
168
140125
111
97
83
705541
4000 3000 2000 1000
Wavenumber (cm-1)
50
100
%Transmittance
3078
2924
2854
1643
1466
910
260280 Hz
13
C NMR 75.5 MHz
1
H NMR 300 MHz
2030405060708090100110120130140 ppm
29.029.229.429.629.8 ppm
13
C/DEPT NMR 75.5 MHz
5A

526. Chapter 8 Additional Problems 9
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

527. Chapter 8 Additional Problems 10
2.02.53.03.54.04.55.05.5 ppm
2030405060708090100110120130140150 ppm
MASS
11001150120012501300 Hz
IR
%ofBasePeak
m/z
140130120110100908070605040
50
100
53
68
77
79
93
107 121
136
4000 3000 2000 1000
Wavenumber (cm-1)
100
%Transmittance
795
887
1373
1442
1643
2924
3078
85090095010001050 Hz
30.531.0 ppm
1
H NMR 600 MHz
13
C/DEPT NMR 150.9 MHz
6A

528. Chapter 8 Additional Problems 11
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

529. Chapter 8 Additional Problems 12
1.41.51.61.71.81.92.02.1 ppm
F2
F1
HMBC 600 MHz
4.85.05.25.45.6
ppm
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

530. Chapter 8 Additional Problems 13
1.01.11.21.31.41.51.61.71.81.92.02.12.22.32.42.52.62.7 ppm
406080100120140160180200 ppm
MASS
IR
1
H NMR 600 MHz
13
C/DEPT NMR 600 MHz
%ofBasePeak
m/z
4000 3000 2000 1000
Wavenumber (cm-1)
50
100
1134
1211
1288
1373
1450
1612
1682
2870
2924
1501401301201101009080706050
50
100
41
53
67
81
109
123
137
152
13
C/DEPT NMR 150.9 MHz
7A

531. Chapter 8 Additional Problems 14
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

532. Chapter 8 Additional Problems 15
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

533. Chapter 8 Additional Problems 16
2.53.03.54.04.55.05.56.06.57.0 ppm
30405060708090100110120130140150160170180 ppm
MASS
IR
1
H NMR 600 MHz
13
C/DEPT NMR 600 MHz
42204230 Hz 14101420 Hz36603670 Hz
%ofBasePeak
m/z
120110100908070605040
50
100
124
109
81
5343
4000 3000 2000 1000
Wavenumber (cm-1)
50
100
%Transmittance
3124
2924
1674
1520
1296
1026
802
13
C/DEPT NMR 150.9 MHz
8A

534. Chapter 8 Additional Problems 17
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

535. Chapter 8 Additional Problems 18
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

536. Chapter 8 Additional Problems 19
6.66.76.86.97.07.17.27.37.47.57.67.77.87.9 ppm
120125130135140145150155160165170175180185190195 ppm
MASS
IR
1
H NMR 600 MHz
13
C/DEPT NMR 600 MHz
129130 ppm
%ofBasePeak
m/z
4000 3000 2000 1000
Wavenumber (cm-1)
70
80
90
100
%Transmittance
3286
1635
1597
1442
1281
1149
702
20015010050
50
100
198
121
105
93
7765
13
C/DEPT NMR 150.9 MHz
9A

537. Chapter 8 Additional Problems 20
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

538. Chapter 8 Additional Problems 21
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

539. Chapter 8 Additional Problems 22
1.82.02.22.42.62.83.03.23.43.63.84.04.24.4 ppm
406080100120140160180200 ppm
MASS
IR
1
H NMR 600 MHz
13
C/DEPT NMR 600 MHz
26802700 Hz
%ofBasePeak
m/z
140130120110100908070605040
50
100
43
55 69
79
97
140
4000 3000 2000 1000
Wavenumber (cm-1)
50
100
%Transmittance
764
1072
1358
1682
1720
2854
2924
25202540 Hz
13
C/DEPT NMR 150.9 MHz
10A

540. Chapter 8 Additional Problems 23
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

541. Chapter 8 Additional Problems 24
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

542. Chapter 8 Additional Problems 25
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
13
C/DEPT NMR 150.9 MHz
1
H NMR 600 MHz
%ofBasePeak
m/z
4000 3000 2000 1000
Wavenumber (cm-1)
80
90
100
%Transmittance
949
1188
1404
1705
1728
2962
3178
15010050
50
100
x 20
43
69
71
83
98
114
125
166
169
184
x64
30.130.2 ppm
30.130.2 ppm
11A

543. Chapter 8 Additional Problems 26
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

544. Chapter 8 Additional Problems 27
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

545. Chapter 8 Additional Problems 28
1.52.02.53.03.54.04.55.05.5 ppm
2030405060708090100110120130 ppm
MASS
IR
%ofBasePeak
m/z
4000 3000 2000 1000
Wavenumber (cm-1)
100
%Transmittance
825
980
1134
1373
1450
2870
2924
2993
1401301201101009080706050
50
100
53 65
77
79
93
105
121
136
0.91.01.11.21.31.41.51.61.71.81.9 ppm
13
C/DEPT NMR 150.9 MHz
1
H NMR 600 MHz
12A

546. Chapter 8 Additional Problems 29
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

547. Chapter 8 Additional Problems 30
0.81.01.21.41.61.82.0 ppm
F2
F1
HMBC 600 MHz
5.65.7
ppm
ppm
16
18
20
22
24
26
28
30
ppm
67 ppm
120
130
140
0.81.01.21.41.61.82.0 ppm
12C