Using the correlation tables attached for C13 NMR. Calculate the expected chemical shift of each set of C atoms in propiophenone(liquid) and Coumarin(solid) organic compounds.
Using the correlation tables attached for C13 NMR. Calculate the expected chemical shift of each set of C atoms in propiophenone(liquid) and Coumarin(solid) organic compounds.
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter10: Alcohols
Section: Chapter Questions
Problem 10.58P
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Question
Using the correlation tables attached for C13 NMR. Calculate the expected chemical shift of each set of C atoms in propiophenone(liquid) and Coumarin(solid) organic compounds.
Transcribed Image Text:Table 33.9
CHA
-2.3
CH3CH3
6.1
15.7
C
X
13.1
13C Chemical Shifts for Selected Hydrocarbons
24.9
24.3
16.2 Code
-1
-Br
-CI
-F
25.2
Substituent
-CH₂
-C=C
-C=C
-CH₂
-CO-NH, 22
-CO-OR 21
C=O-CO-OH 21
Terminal
a
9
20
5
23
13.8
22.0
Table 33.10 13C Shielding Constants for Groups Attached to Alkyl Chains
3
3
27.7
B
10
6
6
9 17
Internal
a
6
17
16
20
24
3
-CO-O- 24 4
-CO-R
-CO-H
-C=N
30 1
31 0
4
3
-7 11
20 11
31 11 32
68 9 63
22.5
1
Y
Terminal
B
8
4
7
2231
34.4
3
30.4
31.8
4
12
25 10
10
6
31.5
Terminal
or
internal
Y
-2
-1
-4
-2
-1
-2
-2
-2
-2
-2
-3
-1
-3
-4
-2.9
Y
S
11.5
B
Internal
Z
N -NR₂
22.4
Substituent
-NH₂
-NHR
-NH₂+
-NR₂+
-NO₂
-SH
-SR
B
Y
Terminal
29
37
42
26
31
63
11
20
26.9
-OH
48
-OR
58
51
0-0-CO-R
-O-CO-Ar 53
11
25.7
10
8
6
Internal
a
24
31
8
6
8 24
5
4
57
12 11
7
126.2
41
51
45
B
10
6
6
4
11
855
25.4
23.0
Terminal
or
internal
IT?
|
Table 33.11 13C Shielding Constants for Substituents Attached to Phenyl Rings
c=128.5 ppm + Zattach
8c2= 128.5 ppm + Zortho
Substituent
-H
-CH3
-CH₂ CH3
-CF₂
-C=C
-C=C
-C.Hs
-CO-NH2
-CO-OR
C=0 -CO-OH
-CO-C
-CO-CH3
CO-H
C
-C=N
Jattach
0
9.3
15.7
2.6
9.5
-6.2
13.0
5.5
2.1
2.4
4.6
9.1
8.7
-15.8
R stands for any alkyl groups.
Fortho
0
2
0.7 -0.1 -3.0
-2.8
-3.3
-0.6 -0.1
-2.8
-2.0
3.7
-1.1
-0.4
0.2 -0.5
0.4 -0.3
0.5 -1.0
-0.4 -1.0
1.2 0
1.6 -0.1
0.8
2.6
0.2
0.1
1.2
0.6
с
3.6
meta
0
C=O
CH3
0.7
H
Opara
0
Substituent
-H
-CH₂
-CH₂ CH₂
-CH₂OR
-C=C
-C=C
-C₂Hs
-CO-OR
-CO-OH
-CO-R
-CO-H
R stands for any alkyl group.
H
5.0
4.4
5.0
6.6
4.3
5.8
COCH,
4.3
214
0
10.6
15.5
173
&
X
Table 33.12 13C Shielding Constants for Substituents Attached to Vinyl Carbons
6.2
4.7
15.0
13.4
Compound
R-CO-H
Ar-CO-H
R-CO-R
Ar-CO-R; Ar-CO-Ar
H-CO-OH
R-CO-OH
Ar-CO-OH
H-CO-O-
R-CO-O
Ar-CO-O
N
S
O
a
-9.8
-9.7
13.6
-8.5
13.6
12.0
12.5 -11.0
-7.0
-11.0
B
209
7.0
9.0
5.9
13.0
Substituent
-I
-Br
-C
-F
8c3-128.5 ppm + O2mels
8C4 = 128.5 ppm + dzpara
163
-NH₂
-NR₂
8
200-204
185-197
206-212
196-206
166
178-185
168-178
171
182-189
171-181
-NH-CO-R
-N=N-C₂H5
-NO₂
-SH
-SR
O
-OH
-OCH3
-O-C6H5
-O-CO-R
8A-123.3 ppm +0₂
&a=123.3 ppm +2
Example of the use of Table 33.12
A
base
-COOR (₂)
-CH3 (0₂)
total
N
S
O
123.3 ppm
6.2 ppm
-9.8 ppm
119.7 ppm
Sobs-122.3 ppm
Substituent
-C=N
-Br
-a
-F
-NR₂
-NR₂+
-NO₂
-SR
-OR
-OCO-R
210
184
Jattach
-32.3
-5.6
6.4
35.0
NH
18.7
22.4
11.1
24.0
19.8
2.2
10.0
Table 33.13 13C Chemical Shifts of Carbonyls and Other Unsaturated Carbons
Compound
198
15.2
-38.1
-7.9
26
24.9
H-CO-OR
R-CO-OR
Ar-CO-OR
H-CO-NR₂
R-CO-NR₂
Ar-CO-NR₂
R-CO-C
Ar-CO-C
R-C=C-R; Ar-C=C-R
R-C=N; Ar-C=N
B
base
— COOR (₂)
-CH₂ (0₂)
total
169
26.9 -12.8
31.4 -14.6
-9.4
-6.2
29.1
23.0
dortho
9.9
3.3
0.3
-0.26
ܕܗ
-12.9
-15.6
-9.9
-5.8
-4.9
7.3
<-1.0
-5.7
-34.1
<-29.0
16.0
19.8 -10.6
-0.9
22.3
19.0
-16.0
29.0
18.0
-39.0
-27.0
NH
14.3
0.7
-1.8
123.3 ppm
7.0 ppm
10.6 ppm
140.9 ppm
obs=144.1 ppm
8
161-163
170-179
159-167
162-166
168-180
168-171
169-180
163-171
65-89
117-125
Opara
-0.4
-1.3
-2.0
-4.4
1.0
-9.5
0.9 -11.7
0.2 -5.6
0.3
0.9
meta
2.6
1.8
1.2
-13.6
0.4
0.2
1.4
1.0
0.3
1.3
2.2
6.1
3.1
-3.5
-7.3
-8.1
-5.2
-2.3
Transcribed Image Text:D
c
с
Propiophenone
B
CH 3
A
Coumarin
B
스
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