TWELVE MORE EASY PROBLEMS

1
TWELVE MORE EASY PROBLEMS
COMBINED PROBLEMS
FORMULA INFRARED NMR
2
Spectra in these problems were obtained from
SDBSWeb http//www.aist.go.jp/RIODB/SDBS/
(Mar 2002)
3
COMBINED PROBLEM 13
4
PROBLEM 13 INFRARED SPECTRUM
C7H14O
1713
5
PROBLEM 13 NMR SPECTRUM
400 MHz
C7H14O
3
2
2
triplet sextet triplet
6
COMBINED PROBLEM 14
7
PROBLEM 14 INFRARED SPECTRUM
C7H14O
1716
8
6
PROBLEM 14 NMR SPECTRUM
C7H14O
1
septet doublet
9
COMBINED PROBLEM 15
10
PROBLEM 15 INFRARED SPECTRUM
C4H10O
11
PROBLEM 15 NMR SPECTRUM
3
C4H10O
1
3
2
1
triplet
quintet
sextet
doublet
12
COMBINED PROBLEM 16
13
PROBLEM 16 INFRARED SPECTRUM
C5H12O
14
PROBLEM 16 NMR SPECTRUM
90 MHz
C5H12O
two overlapping multiplets a singlet
6
at 300 MHz you see a nonet, a quartet and a
singlet
4
2
triplet
doublet
15
COMBINED PROBLEM 17
16
PROBLEM 17 INFRARED SPECTRUM
C8H10O2
17
PROBLEM 17 NMR SPECTRUM
C8H10O2
3
2
4
1
18
COMBINED PROBLEM 18
19
PROBLEM 18 INFRARED SPECTRUM
C8H10O
20
PROBLEM 18 NMR SPECTRUM
3
C8H10O
1
4
2
quartet
triplet
21
COMBINED PROBLEM 19
22
PROBLEM 19 INFRARED SPECTRUM
C6H15N
23
6
PROBLEM 19 NMR SPECTRUM
C6H15N
4
1
4
triplet
triplet
sextet
24
COMBINED PROBLEM 20
25
PROBLEM 20 INFRARED SPECTRUM
C7H9N
26
PROBLEM 20 NMR SPECTRUM
3
C7H9N
4
2
27
COMBINED PROBLEM 21
28
PROBLEM 21 INFRARED SPECTRUM
C6H12O2
1737
29
PROBLEM 21 NMR SPECTRUM
C6H12O2
3
1
30
COMBINED PROBLEM 22
31
PROBLEM 22 INFRARED SPECTRUM
C8H8O2
32
PROBLEM 22 NMR SPECTRUM
3
C8H8O2
4
1
33
COMBINED PROBLEM 23
34
PROBLEM 23 INFRARED SPECTRUM
C9H8O
1678
1627
35
PROBLEM 23 NMR SPECTRUM
NOT AVAILABLE AT THIS TIME
See if you cant solve it anyway !
36
COMBINED PROBLEM 24
37
PROBLEM 24 INFRARED SPECTRUM
C5H6O3
1808
1755
1697
38
PROBLEM 24 NMR SPECTRUM
C5H6O3
4
2
triplet quintet
39
CORRELATION CHARTS
40
BASIC INFRARED KNOWLEDGE
EXPANDED CH
3000
BASE VALUES
OH 3600 NH 3400 CH 3000 C N 2250 C
C 2150 CO 1715 CC 1650 C-O 1100
3300 3100 2900 2850
2750
C-H
-C-H
C-H
-CHO
CH2 and CH3 bend 1465 and 1365
1800 1735 1725 1715 1710 1690
acid
aldehyde
ester
acid chloride
amide
ketone
anhydride 1810 and 1760
EXPANDED CO
benzene CC between 1400 and 1600
Also remember the effects of H-bonding,
conjugation and ring size.
41
NMR Correlation Chart
-OH
-NH
DOWNFIELD
UPFIELD
DESHIELDED
SHIELDED
CHCl3 ,
TMS
d (ppm)
12
11
10
9
8
7
6
5
4
3
2
1
0
H
CH2Ar CH2NR2 CH2S C C-H CC-CH2 CH2-C-
CH2F CH2Cl CH2Br CH2I CH2O CH2NO2
C-CH-C
RCOOH
RCHO
CC
C
C-CH2-C C-CH3
O
Ranges can be defined for different general types
of protons. This chart is general, the next slide
is more definite.
42
APPROXIMATE CHEMICAL SHIFT RANGES (ppm) FOR
SELECTED TYPES OF PROTONS
R-CH3 0.7 - 1.3
R-N-C-H 2.2 - 2.9
R-CC-H
R-CH2-R 1.2 - 1.4
4.5 - 6.5
R-S-C-H 2.0 - 3.0
R3CH 1.4 - 1.7
I-C-H 2.0 - 4.0
H
R-CC-C-H 1.6 - 2.6
Br-C-H 2.7 - 4.1
6.5 - 8.0
Cl-C-H 3.1 - 4.1
R-C-C-H 2.1 - 2.4
R-C-N-H
RO-C-H 3.2 - 3.8
5.0 - 9.0
RO-C-C-H 2.1 - 2.5
HO-C-H 3.2 - 3.8
R-C-H
HO-C-C-H 2.1 - 2.5
9.0 - 10.0
R-C-O-C-H 3.5 - 4.8
N C-C-H 2.1 - 3.0
O2N-C-H 4.1 - 4.3
R-C-O-H
R-C C-C-H 2.1 - 3.0
11.0 - 12.0
F-C-H 4.2 - 4.8
C-H 2.3 - 2.7
R-N-H 0.5 - 4.0 Ar-N-H 3.0 - 5.0 R-S-H
R-O-H 0.5 - 5.0 Ar-O-H 4.0 - 7.0
1.0 - 4.0
R-C C-H 1.7 - 2.7
43
m
10 11 12 13 14
15
ALKENES
s
s
Monosubstituted
Disubstituted
cis-1,2-
s
trans-1,2-
s
1,1-
s
Trisubstituted
m
C-H OUT OF PLANE BENDING
Tetrasubstituted
1000
900
800
700
cm-1
44
m
10 11 12 13 14
15
BENZENES
Monosubstituted
s
s
Disubstituted
s
ortho
s
s
m
meta
para
s
RING Hs
Trisubstituted
OOPS
s
m
1,2,4
1,2,3
s
m
1,3,5
s
m
combination bands
1000
900
800
700
cm-1