TABLE APPENDIX OF CONTENTS
Selected Infrared and Proton Nuclear Magnetic Resonance Spectra (200 MHz) for organic starting materials used in this course.
Experiment 2: Wittig Olefination
trans-cinnamaldehyde benzyl chloride triphenylphosphine A-2 A-4 A-6
Experiment 3: Electrophilic Aromatic Substitution
methyl benzoate A-7
Experiment 4: Sodium Borohydride Reduction
(see Experiment 2)
Selected Solvents and Reagents:
methanol dichloromethane ethanol diethyl ether pyridine xylenes A-9 A-10 A-11 A-12 A-13 A-14
A-1
Updated 5/7/2009
H
O
H
H
10.0 ppm (t1)
A-2
0.97 9.0 8.0
2.82
4.10 7.0
1.05 6.0
A-3
Cl
ppm (t1)
A-4
1.00 5.0
0.36
7.0
6.0
4.0
3.0
2.0
1.0
0.0
A-5
P
ppm (f1)
A-6
1.00 5.0 6.0 4.0 3.0 2.0 1.0 0.0
7.0
H3 CO
O
1.00 8.00 ppm (f1)
0.54 7.50
1.10
ppm (f1)
A-7
1.00 6.0
1.10 0.54 5.0
1.79
8.0
7.0
4.0
3.0
2.0
1.0
0.0
A-8
OH
H
H
H
ppm (f1)
A-9
0.93
0.32
3.50
3.00
2.50
2.00
1.50
1.00
0.50
0.00
H
7000
H
Cl
Cl
6000
5000
4000
3000
ppm (f1)
A-10
2000
1000
0
1.00 4.0 3.0 2.0 1.0 0.0
5.0
OH
ppm (f1)
A-11
1.00
0.45
1.41
4.0
3.0
2.0
1.0
...