P1258716699SzBgf

1
TWELVE 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)
NOTE ON INTEGRALS
Integrals (relative number of hydrogens) are
given as 2
The integrals are the simplest ratio.
Expansions are blue and printed above the
baseline.
3
COMBINED PROBLEM 1
4
PROBLEM 1 INFRARED SPECTRUM
C4H10O
5
PROBLEM 1 NMR SPECTRUM
6
C4H10O
2
1
1
doublet
multiplet
doublet
6
COMBINED PROBLEM 2
7
PROBLEM 2 INFRARED SPECTRUM
C9H10O2
1719
8
PROBLEM 2 NMR SPECTRUM
C9H10O2
3
2
5
quartet
triplet
two multiplets
9
COMBINED PROBLEM 3
10
PROBLEM 3 INFRARED SPECTRUM
C10H12O
1688
11
6
PROBLEM 3 NMR SPECTRUM
C10H12O
5
1
doublet
septet
12
COMBINED PROBLEM 4
13
PROBLEM 4 INFRARED SPECTRUM
C5H10O2
1712
14
PROBLEM 4 NMR SPECTRUM
3
C5H10O2
1
2
two overlapping multiplets (2 2)
4
triplet
triplet
15
COMBINED PROBLEM 5
16
PROBLEM 5 INFRARED SPECTRUM
C9H12
17
PROBLEM 5 NMR SPECTRUM
C9H12
6
5
1
septet
doublet
18
COMBINED PROBLEM 6
19
PROBLEM 6 INFRARED SPECTRUM
C9H12
1610
20
PROBLEM 6 NMR SPECTRUM
3
C9H12
1
21
COMBINED PROBLEM 7
22
PROBLEM 7 INFRARED SPECTRUM
C6H10O3
1731
1719
23
PROBLEM 7 NMR SPECTRUM
3
C6H10O3
3
2
2
triplet
quartet
24
COMBINED PROBLEM 8
25
PROBLEM 8 INFRARED SPECTRUM
C5H7NO2
2266
1749
26
PROBLEM 8 NMR SPECTRUM
C5H7NO2
2
3
2
quartet
triplet
27
COMBINED PROBLEM 9
28
PROBLEM 9 INFRARED SPECTRUM
C9H12O
29
PROBLEM 9 NMR SPECTRUM
C9H12O
5
3
2
1
1
triplet
quintet
triplet
30
COMBINED PROBLEM 10
31
PROBLEM 10 INFRARED SPECTRUM
C8H12O4
1730
32
PROBLEM 10 NMR SPECTRUM
400 MHz
3
C8H12O4
1
2
quartet
triplet
33
COMBINED PROBLEM 11
34
PROBLEM 11 INFRARED SPECTRUM
C7H12O4
1735
35
PROBLEM 11 NMR SPECTRUM
400 MHz
3
C7H12O4
1
2
quartet
triplet
36
COMBINED PROBLEM 12
37
PROBLEM 12 INFRARED SPECTRUM
C8H7N
2229
38
PROBLEM 12 NMR SPECTRUM
400 MHz
3
C8H7N
4
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