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