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Generic Carbon-13 data is provided for various products produced in the Junior Sophister Organic Chemistry Practical Course
A standard cabon-13 spectrum (proton decoupled) is provided. Routine Carbon-13 nmr spectra are not run because of time constraints. Remember that the carbon-13 nuclide only constitutes 1% of all carbon isotopes. All the samples were prepared in CDCl3. The CDCl3 solvent signal is observed as a triplet centred at 77.0 ppm. The relevant peaks are listed in ppm The excitation frequency for the 9.4T magnet is 100.62MHz Additional carbon spectra to determine the number of protons attached to a given signal are provided using the Carbon-13 DEPT 135° and Carbon-13 DEPT 90° experiments. These spectra are displayed in a comparative format. Carbon DEPT experiments are read as follows: DEPT 135° CH2 resonances are inverted
CH3 and CH remain normal upward phase
DEPT 90° CH resonances only are observed C with no protons attached are NOT seen in DEPT experiments A phosphorous-31 spectrum is also provided for DethylBenzylphosphonate (3A) Phosphorous-31 is an NMR active spin ½ nuclide The excitation frequency for the 9.4T magnet is 162 MHz Carbon-13 are provided for the following products Experiment Compound 1 Cis-5,5,10,10-Tetrachlorotricyclo[7.1.0.04,6]decane 2A Benzoin 3A Diethyl Benzylphosphonate 3B (E,E)-1,4-Diphenyl-1,3-butadiene 4A cis-Cyclohex-4-ene-1,2-dicarboxylic acid anhydride 4B cis-Cyclohex-4-ane-1,2-dicarboxylic acid anhydride 5 2,6-Dimethyl-5-hydroxy-heptan-3-one 6A 1-Phenyl-1,4-butanediol 6B γ-Phenyl-γ-butyrolactone 7 (-)cis-Caran-trans-4-ol
Experiment 1 Cis-5,5,10,10-Tetrachlorotricyclo[7.1.0.04,6]decane
65.9
299
30.9
422
21.2
727
(ppm)101520253035404550556065707580
Experiment 1 Cis-5,5,10,10-Tetrachlorotricyclo[7.1.0.04,6]decane
1520253035404550556065707580
1520253035404550556065707580
1520253035404550556065707580(ppm)
File 1 : E:\ASPX32\JS13C01\013001.1RFile 2 : E:\ASPX32\JS13C01\014001.1RFile 3 : E:\ASPX32\JS13C01\015001.1R
Experiment 2A Benzoin
198.
8968
138.
9482
133.
9106
133.
3986
129.
1242
128.
6702
128.
5687
127.
7476
76.1
789
(ppm)708090100110120130140150160170180190200210
76.1
789
(ppm)76.077.0
Experiment 2A Benzoin
8090100110120130140150160170180190200
8090100110120130140150160170180190200(ppm)
File 1 : E:\ASPX32\JS13C02\013001.1RFile 2 : E:\ASPX32\JS13C02\014001.1R
Experiment 3A DiethylBenzylphosphonate
131.5
198
131.4
232
129.6
844
129.6
168
128.4
190
128.3
900
126.7
575
126.7
189
62.02
7361
.9597
34.32
3132
.9514
16.27
8616
.2207
(ppm)2030405060708090100110120130140
34.32
31
32.95
14
(ppm)33.034.035.0
J(13C- 31P) = Hz
Experiment 3A DiethylBenzylphosphonate
102030405060708090100110120130
102030405060708090100110120130
102030405060708090100110120130(ppm)
File 1 : C:\NMR\ASPX32\JS13C03A\013001.1RFile 2 : C:\NMR\ASPX32\JS13C03A\014001.1R
File 3 : C:\NMR\ASPX32\JS13C03A\015001.1R
Experiment 3A DiethylBenzylphosphonate Phosphorous-31 NMR 162MHz
27.6
374
8.53
62
0.29
52
(ppm)-4-2024681012141618202224262830323436
Note : the large peak is the product, the peak at 8.5 ppm is the starting material
Experiment 3B (E,E)-1,4-Diphenyl-1,3-butadiene
137.3
157
132.7
949
129.2
208
128.6
412
127.5
497
126.3
615
(ppm)126.0127.0128.0129.0130.0131.0132.0133.0134.0135.0136.0137.0138.0139.0140.0
Experiment 3B (E,E)-1,4-Diphenyl-1,3-butadiene
126.0127.0128.0129.0130.0131.0132.0133.0134.0135.0136.0137.0138.0
126.0127.0128.0129.0130.0131.0132.0133.0134.0135.0136.0137.0138.0(ppm)
File 1 : C:\NMR\ASPX32\JS13C03B\013001.1R File 2 : C:\NMR\ASPX32\JS13C03B\014001.1R
Experiment 4A cis-Cyclohex-4-ene-1,2-dicarboxylic acid anhydride
174.
1967
127.
5689
39.4
717
23.2
626
(ppm)2030405060708090100110120130140150160170180
Experiment 4A cis-Cyclohex-4-ene-1,2-dicarboxylic acid anhydride
2030405060708090100110120130140150160170180
2030405060708090100110120130140150160170180
2030405060708090100110120130140150160170180(ppm)
File 1 : C:\NMR\ASPX32\JS13C04A\013001.1RFile 2 : C:\NMR\ASPX32\JS13C04A\013001.1R
File 3 : C:\NMR\ASPX32\JS13C04A\015001.1R
Experiment 4B cis-Cyclohex-4-ane-1,2-dicarboxylic acid anhydride
172.
9023
40.3
894
23.6
490
21.8
813
(ppm)2030405060708090100110120130140150160170180190
Experiment 4B cis-Cyclohex-4-ane-1,2-dicarboxylic acid anhydride
2030405060708090100110120130140150160170
2030405060708090100110120130140150160170
2030405060708090100110120130140150160170(ppm)
File 1 : C:\NMR\ASPX32\JS13C04B\013001.1RFile 2 : C:\NMR\ASPX32\JS13C04B\014001.1R
File 3 : C:\NMR\ASPX32\JS13C04B\015001.1R
Experiment 5 2,6-Dimethyl-5-hydroxy-heptan-3-one
216.5
259
72.24
74
43.51
9241
.5293
32.96
10
18.36
5118
.0174
17.99
8017
.7662
(ppm)102030405060708090100110120130140150160170180190200210220230
18.36
51
18.01
7417
.9980
17.76
62
(ppm)17.518.018.5
Experiment 5 2,6-Dimethyl-5-hydroxy-heptan-3-one
102030405060708090100110120130140150160170180190200210220
102030405060708090100110120130140150160170180190200210220
102030405060708090100110120130140150160170180190200210220(ppm)
File 1 : C:\NMR\ASPX32\JS13C05\013001.1RFile 2 : C:\NMR\ASPX32\JS13C05\014001.1R
File 3 : C:\NMR\ASPX32\JS13C05\015001.1R
Experiment 6A 1-Phenyl-1,4-butanediol
144.6
474
128.4
287
127.4
723
125.7
529
74.36
29
62.82
91
36.21
64
29.16
47
(ppm)253035404550556065707580859095100105110115120125130135140145150
Experiment 6A 1-Phenyl-1,4-butanediol
30405060708090100110120130140150
30405060708090100110120130140150
30405060708090100110120130140150(ppm)
File 1 : C:\NMR\ASPX32\JS13C06A\013001.1RFile 2 : C:\NMR\ASPX32\JS13C06A\014001.1R
File 3 : C:\NMR\ASPX32\JS13C06A\015001.1R
Experiment 6B γ-Phenyl-γ-butyrolactone
176.9
594
139.2
766
128.7
088
128.3
997
125.2
216
81.21
17
30.92
2828
.9136
(ppm)30405060708090100110120130140150160170180
Experiment 6b γ-Phenyl-γ-butyrolactone
30405060708090100110120130140150160170
30405060708090100110120130140150160170
30405060708090100110120130140150160170
(ppm)
Experiment 7 (-)cis-Caran-trans-4-ol
74.7
878
36.5
061
30.5
267
28.8
073
28.4
016
21.8
426
20.0
652
17.7
275
17.6
212
15.9
211
(ppm)1520253035404550556065707580
17.7
275
17.6
212
(ppm)17.217.618.0
Experiment 7 (-)cis-Caran-trans-4-ol
15202530354045505560657075
15202530354045505560657075
15202530354045505560657075(ppm)
File 1 : C:\NMR\ASPX32\JS13C07\013001.1RFile 2 : C:\NMR\ASPX32\JS13C07\014001.1R
File 3 : C:\NMR\ASPX32\JS13C07\015001.1R
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