1. TWELVE EASY PROBLEMS
COMBINED PROBLEMS
FORMULA + INFRARED + NMR

2. Integrals (relative number of hydrogens) are given as: 2
Spectra in these problems were obtained from:
SDBSWeb: (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. Answer to #1
(CH3)2CHCH2OH

7. COMBINED PROBLEM #2

8. PROBLEM 2 INFRARED SPECTRUM
C9H10O2
1719

9. PROBLEM 2 NMR SPECTRUM
C9H10O2 3 2 5
two multiplets
quartet
triplet

10. Answer to 2

11. COMBINED PROBLEM #3

12. PROBLEM 3 INFRARED SPECTRUM
C10H12O
1688

13. 6
PROBLEM 3 NMR SPECTRUM
C10H12O 5 1
septet
doublet

14. Answer #3

15. COMBINED PROBLEM #4

16. PROBLEM 4 INFRARED SPECTRUM
C5H10O2
1712

17. C5H10O2 PROBLEM 4 NMR SPECTRUM 3 1 2 4 triplet triplet two overlapping
multiplets (2 + 2) 4
triplet
triplet

18. Answer

19. COMBINED PROBLEM #5

20. PROBLEM 5 INFRARED SPECTRUM
C9H12

21. PROBLEM 5 NMR SPECTRUM
C9H12 6 5 1
septet
doublet

22. Answer to 5
Isopropyl benzene

23. COMBINED PROBLEM #6

24. PROBLEM 6 INFRARED SPECTRUM
C9H12O

25. PROBLEM 6 NMR SPECTRUM
C9H12O 5 3 2 1 1
triplet
quintet
triplet

26. Answer 6

27. CORRELATION CHARTS

28. BASIC INFRARED KNOWLEDGE
EXPANDED CH
BASE VALUES
3000
OH 3600
NH 3400
CH 3000
C N 2250
C C 2150
C=O 1715
C=C 1650
C-O 1100
2750
C-H
=C-H
-C-H
-CHO
CH2 and CH3 bend : 1465 and 1365
aldehyde
acid
acid
chloride
ester
ketone
amide
anhydride : and 1760
EXPANDED C=O
benzene C=C : between 1400 and 1600
Also remember the effects of H-bonding, conjugation and ring size.

29. NMR Correlation Chart d (ppm)
-OH
-NH
DOWNFIELD
UPFIELD
DESHIELDED
SHIELDED
CHCl3 ,
TMS
d (ppm) 12 11 10 9 8 7 6 5 4 3 2 1 H
CH2F
CH2Cl
CH2Br
CH2I
CH2O
CH2NO2
CH2Ar
CH2NR2
CH2S
C C-H
C=C-CH2
CH2-C-
C-CH-C
RCOOH
RCHO
C=C 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.

30. R-CH3 0.7 - 1.3 R-N-C-H 2.2 - 2.9 R-C=C-H R-CH2-R 1.2 - 1.4 4.5 - 6.5
APPROXIMATE CHEMICAL SHIFT RANGES (ppm) FOR SELECTED TYPES OF PROTONS
R-CH
R-N-C-H
R-C=C-H
R-CH2-R
R-S-C-H
R3CH
I-C-H H
R-C=C-C-H
Br-C-H O
Cl-C-H
R-C-C-H O O
RO-C-H
R-C-N-H
RO-C-C-H
HO-C-H O O O
R-C-H
HO-C-C-H
R-C-O-C-H O
N C-C-H
O2N-C-H
R-C-O-H
R-C C-C-H
F-C-H
C-H
R-N-H Ar-N-H R-S-H
R-O-H Ar-O-H
R-C C-H

31. =C-H OUT OF PLANE BENDING m
ALKENES s s
Monosubstituted
Disubstituted
cis-1,2- s
trans-1,2- s
1,1- s
Trisubstituted m
Tetrasubstituted
=C-H OUT OF PLANE BENDING
1000
900
800
700
cm-1

32. BENZENES 10 11 12 13 14 15 m Monosubstituted s s Disubstituted ortho s m
BENZENES
Monosubstituted s s
Disubstituted
ortho s
meta m s s
para s
RING H’s
Trisubstituted
OOPS
1,2,4 m s
1,2,3 s m
1,3,5 s m
combination bands
1000
900
800
700
cm-1