Problem 1: Mass Spec
C9H12
MW = 120
Organic Chemistry:
CHEM2322
Structural Problems
Dr. Christopher J. O’Brien
203 CRB, [email protected]
CHEM2322
Slide 1
© C. J. O’Brien
CHEM2322
Problem 1: 1H-NMR
CHEM2322
Slide 3
Slide 2
© C. J. O’Brien
Problem 1 13C-NMR
© C. J. O’Brien
CHEM2322
Slide 4
© C. J. O’Brien
Problem 1: Answer
Problem 1: IR
8
CHEM2322
Slide 5
© C. J. O’Brien
CHEM2322
7
6
5
4
PPM
3
2
Slide 6
1
0
© C. J. O’Brien
Problem 2: 1H-NMR
Problem 2: Mass Spec
C9H10O3
MW = 166
CHEM2322
Slide 7
© C. J. O’Brien
CHEM2322
Slide 8
© C. J. O’Brien
Problem 2: 13C-NMR
CHEM2322
Slide 9
Problem 2: IR
© C. J. O’Brien
CHEM2322
Problem 2: Answer
Slide 10
© C. J. O’Brien
Problem 2: Answer
ChemNMR 1H Estimation
6.99
7.34
2.65
O
OH 11.0
4.21
7.01
O
6.99
7.34
Estimation quality is indicated by color: good, medium, rough
12
CHEM2322
10
8
6
PPM
Slide 11
4
2
0
© C. J. O’Brien
CHEM2322
Slide 12
© C. J. O’Brien
Problem 3: 1H-NMR
Problem 3: Mass Spec
C14H14O2
MW = 214
CHEM2322
Slide 13
© C. J. O’Brien
CHEM2322
Problem 3: 13C-NMR
CHEM2322
Slide 15
Slide 14
© C. J. O’Brien
Problem 3: IR
© C. J. O’Brien
CHEM2322
Slide 16
© C. J. O’Brien
Problem 3: Answer
Problem 3: Answer
ChemNMR 1H Estimation
7.05
7.68
ChemNMR 13C Estimation
O
130.1
3.83
7.68
7.05
7.05
7.68
114.8
O159.5
7.05
133.1
130.1
130.1
114.8
3.83
55.8
Estimation quality is indicated by color: good, medium, rough
8
55.8
114.8
7.68
O
114.8
159.5O
130.1
133.1
7
CHEM2322
6
5
4
PPM
Estimation quality is indicated by color: good, medium, rough
3
2
1
Slide 17
0
© C. J. O’Brien
160
CHEM2322
140
120
100
PPM
80
60
40
20
Slide 18
0
© C. J. O’Brien
Problem 4: 1H-NMR
Problem 4: Mass Spec
C8H19N
MW = 129
CHEM2322
Slide 19
© C. J. O’Brien
CHEM2322
Slide 20
© C. J. O’Brien
Problem 4: 13C-NMR
CHEM2322
Slide 21
Problem 4: IR
© C. J. O’Brien
CHEM2322
Slide 22
Problem 4: Answer
© C. J. O’Brien
Problem 4: Answer
ChemNMR 13C Estimation
49.6
H
N
32.7
49.6
20.1
13.8
20.1
32.7
13.8
Estimation quality is indicated by color: good, medium, rough
50
CHEM2322
Slide 23
© C. J. O’Brien
CHEM2322
40
30
PPM
Slide 24
20
10
0
© C. J. O’Brien
Problem 5: 1H-NMR
Problem 5: Mass Spec
C3H7OCl
MW = 94
CHEM2322
Slide 25
© C. J. O’Brien
CHEM2322
Problem 5: 13C-NMR
CHEM2322
Slide 27
Slide 26
© C. J. O’Brien
Problem 5: IR
© C. J. O’Brien
CHEM2322
Slide 28
© C. J. O’Brien
Problem 5: Answer
Problem 5: Answer
ChemNMR 13C Estimation
O
58.5
43.0
71.4
Cl
Estimation quality is indicated by color: good, medium, rough
70
CHEM2322
Slide 29
© C. J. O’Brien
CHEM2322
60
50
40
PPM
Slide 30
30
20
10
0
© C. J. O’Brien