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 thanthose containing chromium compounds, which are often carcinogenic.CH3СООН1. КMnO4, H,0, д2. HCІ, Н-ОClClThe 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)LOD40003000200015001000500HAVENUMBERI l3088 682667701438 66те1142 81793743054 5769141411491125 84745122973 5515935013181910523971264C- OH200e 67282560167114806B6212001268674110469564768679648 6479916 58816 7020858814756411757984560702663 6214461161CI66480B614121086.42HSP-41-134ppmChemical ShiftIntegrationMultiplet13.431S7.811d7.561d.7.551t7.451

Solution: We know DMSO is a highly polar solvent and hydrophilic one. So as principle of solubility…

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

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Question

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.

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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