35- 40 40- 45- 2980.65 4000 3500 3000 2500 2000 1500 1000 500 Wavenumbers (cm-1) 00 50- 55 59 %Transmittance 99 60 99 65- 2889.03 88 80- 95 85- 3657.47 3854.47 3752.13 1496.34 1473.06 1382.11 1135.85 1452.27 1251.24 1072.73 955.08 00 90- 2045.26 1030.49 811.05 762.19 689.35 626.06 596.85 550.97 500.48 480.70 455.36 426.77 417.04 407.47 Tue Oct 22 16:14:00 2024 (GMT-04:00) 10 8 10.5644 Figure 2. 1H NMR spectrum in CDCl3 of meso-stilbene dibromide. 2.0000 3.7702 Figure 1. 1H NMR spectrum in CDCl3 of d/-stilbene dibromide, 8 5.0-8.0 ppm region. 6 4 2 0 [ppm] .2598 5.4826 (1R, 2R)-1,2-dibromo-1,2-diphenylethane 1H NMR in CDC13 with SiMed (27/09/08] 7.26 7.18 T . 7.8 7.6 7.14 7.2 7.0 6.8 6.6 6.1 6.2 6.0 5.8 5.6 5.4 ppm 4.5599 -0.0005 enantiomer -5.48
35- 40 40- 45- 2980.65 4000 3500 3000 2500 2000 1500 1000 500 Wavenumbers (cm-1) 00 50- 55 59 %Transmittance 99 60 99 65- 2889.03 88 80- 95 85- 3657.47 3854.47 3752.13 1496.34 1473.06 1382.11 1135.85 1452.27 1251.24 1072.73 955.08 00 90- 2045.26 1030.49 811.05 762.19 689.35 626.06 596.85 550.97 500.48 480.70 455.36 426.77 417.04 407.47 Tue Oct 22 16:14:00 2024 (GMT-04:00) 10 8 10.5644 Figure 2. 1H NMR spectrum in CDCl3 of meso-stilbene dibromide. 2.0000 3.7702 Figure 1. 1H NMR spectrum in CDCl3 of d/-stilbene dibromide, 8 5.0-8.0 ppm region. 6 4 2 0 [ppm] .2598 5.4826 (1R, 2R)-1,2-dibromo-1,2-diphenylethane 1H NMR in CDC13 with SiMed (27/09/08] 7.26 7.18 T . 7.8 7.6 7.14 7.2 7.0 6.8 6.6 6.1 6.2 6.0 5.8 5.6 5.4 ppm 4.5599 -0.0005 enantiomer -5.48
Macroscale and Microscale Organic Experiments
7th Edition
ISBN:9781305577190
Author:Kenneth L. Williamson, Katherine M. Masters
Publisher:Kenneth L. Williamson, Katherine M. Masters
Chapter45: Synthesis And Bioassay Of Sulfanilamide And Derivatives
Section: Chapter Questions
Problem 5Q
Related questions
Question
a) Indicate which absorption bands in the IR spectrum of the recrystallized product (meso-stilbene dibromide) are due to (i) Csp2 -H stretches, (ii) Csp3 -H stretches, and (iii) C=C stretches.
b) The 1H NMR spectra in CDCl3 of dl-stilbene dibromide (Fig 1, 5.0-8.0 ppm region) and the
purified product, meso-stilbene dibromide (Fig 2) are shown below. Assign the peaks in these
spectra.
c) Based on the NMR spectrum and melting point of your purified sample, derive an estimate of
the purity (in mole %) of the material you have synthesized.
Reaction:
Trans-Stilbene + Bromine → Meso-Stilbene Dibromide
Transcribed Image Text:35-
40
40-
45-
2980.65
4000
3500
3000
2500
2000
1500
1000
500
Wavenumbers (cm-1)
00
50-
55
59
%Transmittance
99
60
99
65-
2889.03
88
80-
95
85-
3657.47
3854.47
3752.13
1496.34 1473.06
1382.11
1135.85
1452.27
1251.24
1072.73
955.08
00
90-
2045.26
1030.49
811.05
762.19
689.35
626.06
596.85
550.97
500.48 480.70
455.36 426.77 417.04
407.47
Tue Oct 22 16:14:00 2024 (GMT-04:00)
![10
8
10.5644
Figure 2. 1H NMR spectrum in CDCl3 of meso-stilbene dibromide.
2.0000
3.7702
Figure 1. 1H NMR spectrum in CDCl3 of d/-stilbene dibromide, 8 5.0-8.0 ppm region.
6
4
2
0
[ppm]
.2598
5.4826
(1R, 2R)-1,2-dibromo-1,2-diphenylethane
1H NMR in CDC13 with SiMed (27/09/08]
7.26
7.18
T
.
7.8
7.6
7.14
7.2
7.0
6.8
6.6
6.1
6.2
6.0
5.8 5.6 5.4
ppm
4.5599
-0.0005
enantiomer
-5.48](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F21bfbeb3-7edb-4f33-b014-040a82ff0b99%2F488daf0a-7407-49b5-81f7-f0bbee754ca1%2Farxvzh_processed.jpeg&w=3840&q=75)
Transcribed Image Text:10
8
10.5644
Figure 2. 1H NMR spectrum in CDCl3 of meso-stilbene dibromide.
2.0000
3.7702
Figure 1. 1H NMR spectrum in CDCl3 of d/-stilbene dibromide, 8 5.0-8.0 ppm region.
6
4
2
0
[ppm]
.2598
5.4826
(1R, 2R)-1,2-dibromo-1,2-diphenylethane
1H NMR in CDC13 with SiMed (27/09/08]
7.26
7.18
T
.
7.8
7.6
7.14
7.2
7.0
6.8
6.6
6.1
6.2
6.0
5.8 5.6 5.4
ppm
4.5599
-0.0005
enantiomer
-5.48
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