NMR Problems 2 1. The following 3 sets of spectra were obtained from 3 isomers of a compound with formula C9H12. Identify the compounds. 3H
2H
2H
2H
8
6
4
PPM
150
1H
100
PPM
2
0
50
0
3H
2H
1H
2H
8
6
150
4
PPM
100
PPM
2
50
0
3H
2H
3H
0
1H
8
150
6
4
PPM
100
PPM
2
50
0
0
2. The following spectra were obtained from a compound of formula C5H8O. Identify the compound. 3H
2H
1H
2H
10
8
6
PPM
4
2
0
6.4 Hz
6.2 Hz
6.0 Hz
6.0 Hz
15.1 Hz
6.2 Hz
15.1 Hz
6.4 Hz
600 Mz
d
200
d
180
160
140
d
120
t
100
PPM
80
60
q
40
20
0
3. Identify the compound with the following analytical data. Elemental Analysis: C, 74.54; H, 8.53; N, 7.90; O, 9.03
3H
2H
3H
2H
3H 2H
8
7
6
5
4
PPM
J = 7.8 Hz
m
s
s
2
160
140
1
0
J = 7.8 Hz
J = 8.0 Hz
J = 8.0 Hz
J = 7.5, 1.5 Hz
d
180
3
d
t
d
120
100
PPM
80
60
40
t
q q
20
0
4. The following spectra were obtained from a compound of molecular formula C6H14O. Identify the compound. 6H
3H
2H 2H
1H
4
5. 3
2
PPM
1
0
The following spectra were also obtained from a compound of molecular formula C6H14O. Identify the compound. 6H
2H
3H
1H
4
2H
3
2
PPM
1
0
6. The following spectra were obtained from a compound with elemental analysis: C, 49.54; H, 4.80; Br, 25.35; O, 20.31 %. Identify the compound. 3H
2H
9
2H
8
1H
7
1H
6
J = 7.5
J = 7.5
1H 1H
5
PPM
2H
4
2H
3
2
1
0
J = 6.2, 10.9, 1.0
J = 6.2, 10.9, 1.0
J = 7.0
J = 6.2, 1.0
J = 6.2, 7.0, 1.0
d d
s
180
s d d s
160
140
120
d
100
PPM
80
d
60
q
t
40
20
0
7. The cyclic compound C6H8O gave the following 1H NMR spectrum. Identify it. 3H
1H
1H
7
1H
6
5
4
2H
3
PPM
2
1
J = 7.0
J = 6.7
J = 10.9
J = 6.8
J = 10.9
J = 6.2
0
J = 6.9
J = 6.7
J = 6.2
J = 7.0
J = 6.9
J = 6.8