Annotated Biblography 301
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Annotated Biblography 301
Suzanne Varughese
The source I will be discussing is the ‘Resolution of Racemic Phenylsuccinic Acid Using (-)-Proline as a Resolving Agent by Ralph Stephani and Victor Cesare. This source details the success behind the resolution of enantomiers using (+)-phenylsuccinic acid-bis proline salt from 2-propanol. It explains that this experiment offers advantages compared to other resolution procedures such as the use of toxic alkaloids that are not unpleasant in smell, utilizing (-)-proline as the resolving agent, and the usage of (+)-
phenylsuccinic acid that is nontoxic solid that is easy to work with. The paper then details a procedure like the one we performed in the lab. Surprisingly this procedure is based on the procedure published by Shiraiwa et al. Although they do not perform the exact procedure, they believe that this procedure will allow anyone to produce a high yield and optical rotation value. In relation to our experiment and the prior paper, it gives an adaptation that is similar in techniques and materials. It also encourages us that the way that our procedure in lab was performed is the best way to do the resolution of enantiomers. Cesare, V.; Stephani, R. Resolution of Racemic Phenylsuccinic Acid Using (-)-
Proline as a Resolving Agent: An Introductory Organic Chemistry Experiment. Journal of Chemical Education
1997
, 74
(10), 1226. https://doi.org/10.1021/ed074p1226.
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Related Questions
Figure 1 shows a 1H NMR spectrum of a solution that was prepared by dissolving 1,3,5-trimethoxybenzene (10.22 mg) in CDCl3 (1.470 g).T
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DEPT-135
DEPT - 90
DEPT - 45
T
200
CDS-03-521
180
4/5
160
140
-
H₂CO
T
120
75% +
100
ppm
U
80
LL
60
40
20
0
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3. 'H-NMR interpretation
When dissolved in CDC13, phenacetin shows 6 signals. All of the peaks are sharp, except for the signal f not
below.
Draw the chemical structure of phenacetin, labeling each hydrogen with an alphabetical letter.
Make a larger version of the chart below (half or full page), and complete it with the missing information.
Explanation of splitting patter
8 (ppm)
Letter
# H
(integration
Splitting pattern
value)
7.94
f
1
Broad singlet
7.36
e
6.80
d
3.98
с
2.09
b
1.38
a
Extra Credit Question
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7.4 7.2 7.0 6,8
4.0 3.8
1.4 1.2
TMS
Impurity
8.
7
5
4
3
2
&H (ppm)
100
90
80
70
60.
50
40
30
20
10
4000 3600 3200 2800 2400 2000 1800 1600 1400 1200 1000 800 650
Wavenumber (cm-)
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S
...
8
0
SPEC
CHCHỊCH CÔ, H
4
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OH
N
H
acetaminophen
phenacetin
100.0
90
80
70
60
30
40
30
20
10
0.0
40000
3000
2000
1500
1000
400.0
em-1
LOD
D
4D00
3000
s0o
2000
1500
1000
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Recrystallized Phenacetin
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110-115
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92-95
Recrystallized Benzil + Reference Benzil
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Questions:
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H3C.
TH.
nonanal
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Spectrum 1
100
2000
1000
4000
3000
BAVENUERIl
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1068 57
375 50
866 79
775 84
723 57
676 1
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2956 10
670 01
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1467 25
1411 44
1390
1979
70
2926
13
44
41
2872
2856
36
1305
2716
1251
72
1728 10
1146 47
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3.
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10
(i)
(ii)
(iii)
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Ha
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7
6
5
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H2N
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phenol
biphenyl
benzoic acid
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ether
aq
20)
CO,(g)
H2O
HIDDEN COMPOUND 1
HIDDEN COMPC
HIDDEN COMPOUND 3
trace 21)
|6.0 М НСI
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22)
NaCl
H20
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유
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CH-O
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V
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THE
NCH,
non-isolation
VI
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VII
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CI
XXIII
EtOAc/HCI
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80-
60-
40-
8
Acetonitrile Water (9:1)
6h
100
BocHN,
CH₂
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m/z
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TFA DCM (19)
1h
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