Why is it better to acquire the 1H-NMR spectrum in DMSO-d6 and not in CDCl3?

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
ChapterL3: Carbon (13c) Nmr Spectroscopy
Section: Chapter Questions
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Why is it better to acquire the 1H-NMR spectrum in DMSO-d6 and not in CDCl3?

 

In the experiment, potassium permanganate is used to oxidize 2-chlorotoluene (o-chlorotoluene)
to 2-chlorobenzoic acid (o-chlorobenzoic acid). Permanganate solutions are less hazardous than
those containing chromium compounds, which are often carcinogenic.
CH3
СООН
1. КMnO4, H,0, д
2. HCІ, Н-О
Cl
Cl
The yield of the reaction observed in the literature (Clarke, H. T.; Taylor, E. R. Org. Synth. 1930,
10, 20) is 76-78 % before recrystallization and 65-67 % after recrystallization.
Transcribed Image Text:In the experiment, potassium permanganate is used to oxidize 2-chlorotoluene (o-chlorotoluene) to 2-chlorobenzoic acid (o-chlorobenzoic acid). Permanganate solutions are less hazardous than those containing chromium compounds, which are often carcinogenic. CH3 СООН 1. КMnO4, H,0, д 2. HCІ, Н-О Cl Cl The yield of the reaction observed in the literature (Clarke, H. T.; Taylor, E. R. Org. Synth. 1930, 10, 20) is 76-78 % before recrystallization and 65-67 % after recrystallization.
Spectra (Infrared in KBr, 'H-NMR in DMSO-d6, 400 MHz)
LOD
4000
3000
2000
1500
1000
500
HAVENUMBERI l
3088 68
2667
70
1438 66
те
1142 81
793
74
3054 57
691
4
1411
49
1125 84
745
12
2973 55
1593
50
1318
19
1052
39
712
64
C- OH
200e 67
2825
60
1671
1480
6B
62
1200
1268
67
41
1046
956
47
686
79
648 64
79
916 58
816 70
2085
88
1475
64
1175
79
84
560
70
2663 62
1446
1161
CI
66
480
B6
14
12
10
8
6.
4
2
HSP-41-134
ppm
Chemical Shift
Integration
Multiplet
13.43
1
S
7.81
1
d
7.56
1
d.
7.55
1
t
7.45
1
Transcribed Image Text:Spectra (Infrared in KBr, 'H-NMR in DMSO-d6, 400 MHz) LOD 4000 3000 2000 1500 1000 500 HAVENUMBERI l 3088 68 2667 70 1438 66 те 1142 81 793 74 3054 57 691 4 1411 49 1125 84 745 12 2973 55 1593 50 1318 19 1052 39 712 64 C- OH 200e 67 2825 60 1671 1480 6B 62 1200 1268 67 41 1046 956 47 686 79 648 64 79 916 58 816 70 2085 88 1475 64 1175 79 84 560 70 2663 62 1446 1161 CI 66 480 B6 14 12 10 8 6. 4 2 HSP-41-134 ppm Chemical Shift Integration Multiplet 13.43 1 S 7.81 1 d 7.56 1 d. 7.55 1 t 7.45 1
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