1. Each of the following IR spectra is associated with one of the aromatic compounds below.

Identify the
compound associated with each spectrum. (10 points)

O O
NH2 OH
H N OH

m-toluidine m-tolualdehyde 3-methylpyridine m-toluic acid m-cresol

Spectrum A _____________________
MICRONS NICOLET 20SX FT-IR
2.5 2.6 2.7 2.8 2.9 3 3.5 4 4.5 5 5.5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 21 22
100 0.0

90 .05

80 0.1

70
%
T
0.2
R A
60 A B
N S
S O
M R
50 0.3
I B
T A
T N
A C
40 0.4
N E
C
E
0.5
30
0.6

20 0.7

0.8
0.9
10 1.0

0 2.0
4000 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000 1800 1600 1400 1200 1000 800 600 450
WAVENUMBERS

Spectrum B _____________________
MICRONS NICOLET 20SX FT-IR
2.5 2.6 2.7 2.8 2.9 3 3.5 4 4.5 5 5.5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 21 22
100 0.0

90 .05

80 0.1

70
%
T
0.2
R A
60 A B
N S
S O
M R
50 0.3
I B
T A
T N
A C
40 0.4
N E
C
E
0.5
30
0.6

20 0.7

0.8
0.9
10 1.0

0 2.0
4000 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000 1800 1600 1400 1200 1000 800 600 450
WAVENUMBERS

This work by Dr. James S. Nowick, Professor of Chemistry, University of California, Irvine, is licensed under a Creative Commons Attribution 4.0 International License.
Spectra are from Sigma-Aldrich (www.sigmaaldrich.com) under fair use.
Spectrum C _____________________
MICRONS NICOLET 20SX FT-IR
2.5 2.6 2.7 2.8 2.9 3 3.5 4 4.5 5 5.5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 21 22
100 0.0

90 .05

80 0.1

70
%
T
0.2
R A
60 A B
N S
S O
M R
50 0.3
I B
T A
T N
A C
40 0.4
N E
C
E
0.5
30
0.6

20 0.7

0.8
0.9
10 1.0

0 2.0
4000 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000 1800 1600 1400 1200 1000 800 600 450
WAVENUMBERS

Spectrum D _____________________
MICRONS NICOLET 20SX FT-IR
2.5 2.6 2.7 2.8 2.9 3 3.5 4 4.5 5 5.5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 21 22
100 0.0

90 .05

80 0.1

70
%
T
0.2
R A
60 A B
N S
S O
M R
50 0.3
I B
T A
T N
A C
40 0.4
N E
C
E
0.5
30
0.6

20 0.7

0.8
0.9
10 1.0

0 2.0
4000 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000 1800 1600 1400 1200 1000 800 600 450
WAVENUMBERS

Spectrum E _____________________
MICRONS NICOLET 20SX FT-IR
2.5 2.6 2.7 2.8 2.9 3 3.5 4 4.5 5 5.5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 21 22
100 0.0

90 .05

80 0.1

70
%
T
0.2
R A
60 A B
N S
S O
M R
50 0.3
I B
T A
T N
A C
40 0.4
N E
C
E
0.5
30
0.6

20 0.7

0.8
0.9
10 1.0

0 2.0
4000 3800 3600 3400 3200 3000 2800 2600 2400 2200 2000 1800 1600 1400 1200 1000 800 600 450
WAVENUMBERS

This work by Dr. James S. Nowick, Professor of Chemistry, University of California, Irvine, is licensed under a Creative Commons Attribution 4.0 International License.
Spectra are from Sigma-Aldrich (www.sigmaaldrich.com) under fair use.