TWELVE EASY PROBLEMS

COMBINED PROBLEMS
FORMULA + INFRARED + NMR
 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.

COMBINED PROBLEM #1
 PROBLEM 1 INFRARED SPECTRUM

C4H10O
PROBLEM 1 NMR SPECTRUM
6

C4H10O 2

doublet multiplet doublet

 Answer to #1
• (CH3)2CHCH2OH
COMBINED PROBLEM #2
 PROBLEM 2 INFRARED SPECTRUM

C9H10O2

1719
 PROBLEM 2 NMR SPECTRUM

C9H10O2 3
2

two multiplets quartet triplet

Answer to 2
COMBINED PROBLEM #3
 PROBLEM 3 INFRARED SPECTRUM

C10H12O

1688
 6
PROBLEM 3 NMR SPECTRUM

C10H12O

5 1

septet doublet
Answer #3
COMBINED PROBLEM #4
 PROBLEM 4 INFRARED SPECTRUM

C5H10O2

1712
 PROBLEM 4 NMR SPECTRUM 3

1 C5H10O2
2
two overlapping
multiplets (2 + 2)
4

triplet triplet
Answer
COMBINED PROBLEM #5
 PROBLEM 5 INFRARED SPECTRUM

C9H12
 PROBLEM 5 NMR SPECTRUM

C9H12 6

septet doublet
 Answer to 5
• Isopropyl benzene
COMBINED PROBLEM #6
 PROBLEM 6 INFRARED SPECTRUM

C9H12O
 PROBLEM 6 NMR SPECTRUM

C9H12O

3
2
1 1

triplet quintet triplet

Answer 6
CORRELATION CHARTS
 BASIC INFRARED KNOWLEDGE
EXPANDED CH
BASE VALUES 3000
OH 3600 3300 3100 2900 2850
NH 3400 C-H =C-H -C-H 2750
-CHO
CH 3000
CH2 and CH3 bend : 1465 and 1365
C N 2250
C C 2150 1800 1735 1725 1715 1710 1690
aldehyde acid
acid ester ketone amide
C=O 1715 chloride

C=C 1650 anhydride : 1810 and 1760

EXPANDED C=O

C-O 1100 benzene C=C : between 1400 and 1600

Also remember the effects of H-bonding, conjugation and ring size.

 NMR Correlation Chart
-OH -NH
DOWNFIELD UPFIELD
DESHIELDED SHIELDED
CHCl3 , H

TMS

12 11 10 9 8 7 6 5 4 3 2 1 0 d (ppm)
H
CH2F CH2Ar C-CH-C
RCOOH RCHO C=C CH2Cl CH2NR2
CH2S C
CH2Br
CH2I C C-H C-CH2-C
CH2O C=C-CH2 C-CH3
CH2NO2 CH2-C-
O
Ranges can be defined for different general types of protons.
This chart is general, the next slide is more definite.
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-C=C-H

R-CH2-R 1.2 - 1.4 R-S-C-H 2.0 - 3.0 4.5 - 6.5
R3CH 1.4 - 1.7
I-C-H 2.0 - 4.0
H
R-C=C-C-H 1.6 - 2.6
Br-C-H 2.7 - 4.1
O 6.5 - 8.0
R-C-C-H 2.1 - 2.4 Cl-C-H 3.1 - 4.1 O
O RO-C-H 3.2 - 3.8 R-C-N-H
5.0 - 9.0
RO-C-C-H 2.1 - 2.5
HO-C-H 3.2 - 3.8 O
O
O 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 O
O2N-C-H 4.1 - 4.3 R-C-O-H
R-C C-C-H 2.1 - 3.0
F-C-H 4.2 - 4.8 11.0 - 12.0
C-H 2.3 - 2.7 R-N-H 0.5 - 4.0 Ar-N-H 3.0 - 5.0 R-S-H
R-C C-H 1.7 - 2.7 R-O-H 0.5 - 5.0 Ar-O-H 4.0 - 7.0 1.0 - 4.0
 10 11 12 13 14 15 m
ALKENES
R H
Monosubstituted C C s s
H H
Disubstituted
R R
cis-1,2- C C s
H H
H R
trans-1,2- C C s
R H
R H
1,1- C C s
R H
R R
Trisubstituted C C m
R H
R R
Tetrasubstituted C C =C-H OUT OF PLANE BENDING
R R
1000 900 800 700 cm-1
 BENZENES 10 11 12 13 14 15 m

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