The C=O stretching frequency

aldehydes and ketones

C=O aldehydes R(C=O)H 1740-1720 S(sh) 14
ketones R(C=O)R 1730-1710 S(sh) 35
esters R(CO
2
)R 1750-1735 S(sh) 33, 34
carboxylic acids RCO
2
H 1720-1680 S(sh) 26,27,30
amides (Amide I) RCONH
2
, RCONHR 1670-1640 S(sh) 19, 21
(Amide II) RCONH
2
1650-1620 S(sh) 19, 21
(Amide II) RCONHR 1550 S(sh) 19, 21
amide RCONR
2
1650-1620 S(sh) 23
anhydrides R(CO
2
CO)R 1820, 1750 S, S(sh) 36
carboxylates R(CO
2
)
-
, M
+
1600, 1400 S,S(sh) 42
C=C olefins R
2
C=CR
2
1680-1640 W(sh) 10, 39, 40
R
2
C=CH
2
1600-1675 M(sh) 9, 35
R
2
C=C(OR)R 1600-1630 S(sh) 41
-NO
2
nitro groups RNO
2
1550, 1370 S,S(sh) 28

A summary of the principle infrared bands and their assignments.
R is an aliphatic group.








Wavenumbers, cm
-1
500 1000 1500 2000 2500 3000 3500 4000
%

T
r
a
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s
m
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a
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c
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10
20
30
40
50
60
70
80
90
100
H-C=O
Impurity peak,
probably O-H
Figure IR-14. Butanal, neat liquid, thin film: CH
3
CH
2
CH
2
CHO
Aliphatic Aldehyde
Wavenumbers, cm
-1
500 1000 1500 2000 2500 3000 3500 4000
%

T
r
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s
m
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a
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c
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0
20
40
60
80
100
Figure IR-35. 5-Hexene-2-one, neat liquid: CH
2
=CH
2
CH
2
CH
2
COCH
3

Aliphatic Ketone
The C=O stretching frequency
esters
C=O aldehydes R(C=O)H 1740-1720 S(sh) 14
ketones R(C=O)R 1730-1710 S(sh) 35
esters R(CO
2
)R 1750-1735 S(sh) 33, 34
carboxylic acids RCO
2
H 1720-1680 S(sh) 26,27,30
amides (Amide I) RCONH
2
, RCONHR 1670-1640 S(sh) 19, 21
(Amide II) RCONH
2
1650-1620 S(sh) 19, 21
(Amide II) RCONHR 1550 S(sh) 19, 21
amide RCONR
2
1650-1620 S(sh) 23
anhydrides R(CO
2
CO)R 1820, 1750 S, S(sh) 36
carboxylates R(CO
2
)
-
, M
+
1600, 1400 S,S(sh) 42
C=C olefins R
2
C=CR
2
1680-1640 W(sh) 10, 39, 40
R
2
C=CH
2
1600-1675 M(sh) 9, 35
R
2
C=C(OR)R 1600-1630 S(sh) 41
-NO
2
nitro groups RNO
2
1550, 1370 S,S(sh) 28

A summary of the principle infrared bands and their assignments.
R is an aliphatic group.








Wavenumbers, cm
-1
500 1000 1500 2000 2500 3000 3500 4000
%

T
r
a
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s
m
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a
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c
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0
20
40
60
80
100
Top: CHCl
3
vs CHCl
3
Bottom: 2.5 % v/v un CHCl
3
Aliphatic Ester
Figure IR-33. Methyl acetate in 0.1 mm NaCl cells: CH
3
CO
2
CH
3

Wavenumbers, cm
-1
500 1000 1500 2000 2500 3000 3500 4000
%

T
r
a
n
s
m
i
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a
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c
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0
20
40
60
80
100
Top: CHCl
3
vs CHCl
3
Bottom: 2.5 % v/v un CHCl
3
CCl
4
neat
Wavenumber, cm
-1
1000 1500 2000 2500 3000 3500 4000
%

T
r
a
n
s
m
i
t
t
a
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c
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0
20
40
60
80
100
120
liquid film
vapor: 106 C
Figure IR-34. Vapor and liquid spectra of ethyl n-hexanoate:
CH
3
CH
2
CH
2
CH
2
CH
2
CO
2
CH
2
CH
3

Aliphatic Ester
The C=O stretching frequency
aliphatic acids
C=O aldehydes R(C=O)H 1740-1720 S(sh) 14
ketones R(C=O)R 1730-1710 S(sh) 35
esters R(CO
2
)R 1750-1735 S(sh) 33, 34
carboxylic acids RCO
2
H 1720-1680 S(sh) 26,27,30
amides (Amide I) RCONH
2
, RCONHR 1670-1640 S(sh) 19, 21
(Amide II) RCONH
2
1650-1620 S(sh) 19, 21
(Amide II) RCONHR 1550 S(sh) 19, 21
amide RCONR
2
1650-1620 S(sh) 23
anhydrides R(CO
2
CO)R 1820, 1750 S, S(sh) 36
carboxylates R(CO
2
)
-
, M
+
1600, 1400 S,S(sh) 42
C=C olefins R
2
C=CR
2
1680-1640 W(sh) 10, 39, 40
R
2
C=CH
2
1600-1675 M(sh) 9, 35
R
2
C=C(OR)R 1600-1630 S(sh) 41
-NO
2
nitro groups RNO
2
1550, 1370 S,S(sh) 28

A summary of the principle infrared bands and their assignments.
R is an aliphatic group.







Aliphatic Acid
Figure IR-26. The liquid,
vapor and CCl
4
soln
spectra of hexanoic acid:
CH
3
(CH
2
)
4
CO
2
H
Wavenumber, cm
-1
1000 1500 2000 2500 3000 3500 4000
%

T
r
a
n
s
m
i
t
t
a
n
c
e
0
20
40
60
80
100
120
liquid film
vapor: 134 C
The C=O stretching frequency
aliphatic amides
C=O aldehydes R(C=O)H 1740-1720 S(sh) 14
ketones R(C=O)R 1730-1710 S(sh) 35
esters R(CO
2
)R 1750-1735 S(sh) 33, 34
carboxylic acids RCO
2
H 1720-1680 S(sh) 26,27,30
amides (Amide I) RCONH
2
, RCONHR 1670-1640 S(sh) 19, 21
(Amide II) RCONH
2
1650-1620 S(sh) 19, 21
(Amide II) RCONHR 1550 S(sh) 19, 21
amide RCONR
2
1650-1620 S(sh) 23
anhydrides R(CO
2
CO)R 1820, 1750 S, S(sh) 36
carboxylates R(CO
2
)
-
, M
+
1600, 1400 S,S(sh) 42
C=C olefins R
2
C=CR
2
1680-1640 W(sh) 10, 39, 40
R
2
C=CH
2
1600-1675 M(sh) 9, 35
R
2
C=C(OR)R 1600-1630 S(sh) 41
-NO
2
nitro groups RNO
2
1550, 1370 S,S(sh) 28

A summary of the principle infrared bands and their assignments.
R is an aliphatic group.







Amide I
1662 cm
-1
Amide II; 1634 cm
-1
KBr
pellet
Wavnumbers, cm
-1
500 1000 1500 2000 2500 3000 3500 4000
%

T
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c
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10
20
30
40
50
60
70
80
90
100
Amide I Amide II
Figure IR-21. N-Methyl acetamide, neat liquid; thin film:
CH
3
CONHCH
3

Secondary Amide
Wavenumbers, cm
-1
500 1000 1500 2000 2500 3000 3500 4000
%

T
r
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s
m
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c
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0
20
40
60
80
100

Figure IR-23. N,N-Dimethylacetamide, neat liquid; thin film:
CH
3
CON(CH
3
)
2

Tertiary Amide
The C=O stretching frequency
anhydrides

C=O aldehydes R(C=O)H 1740-1720 S(sh) 14
ketones R(C=O)R 1730-1710 S(sh) 35
esters R(CO
2
)R 1750-1735 S(sh) 33, 34
carboxylic acids RCO
2
H 1720-1680 S(sh) 26,27,30
amides (Amide I) RCONH
2
, RCONHR 1670-1640 S(sh) 19, 21
(Amide II) RCONH
2
1650-1620 S(sh) 19, 21
(Amide II) RCONHR 1550 S(sh) 19, 21
amide RCONR
2
1650-1620 S(sh) 23
anhydrides R(CO
2
CO)R 1820, 1750 S, S(sh) 36
carboxylates R(CO
2
)
-
, M
+
1600, 1400 S,S(sh) 42
C=C olefins R
2
C=CR
2
1680-1640 W(sh) 10, 39, 40
R
2
C=CH
2
1600-1675 M(sh) 9, 35
R
2
C=C(OR)R 1600-1630 S(sh) 41
-NO
2
nitro groups RNO
2
1550, 1370 S,S(sh) 28

A summary of the principle infrared bands and their assignments.
R is an aliphatic group.




Wavenumber, cm
-1
500 1000 1500 2000 2500 3000 3500 4000 4500
%

T
r
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s
m
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c
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0
20
40
60
80
100
Figure IR-36. Propionic anhydride, neat liquid:
CH
3
CH
2
CO
2
COCH
2
CH
3

Anhydrides
The C=O stretching frequency
carboxylates
C=O aldehydes R(C=O)H 1740-1720 S(sh) 14
ketones R(C=O)R 1730-1710 S(sh) 35
esters R(CO
2
)R 1750-1735 S(sh) 33, 34
carboxylic acids RCO
2
H 1720-1680 S(sh) 26,27,30
amides (Amide I) RCONH
2
, RCONHR 1670-1640 S(sh) 19, 21
(Amide II) RCONH
2
1650-1620 S(sh) 19, 21
(Amide II) RCONHR 1550 S(sh) 19, 21
amide RCONR
2
1650-1620 S(sh) 23
anhydrides R(CO
2
CO)R 1820, 1750 S, S(sh) 36
carboxylates R(CO
2
)
-
, M
+
1600, 1400 S,S(sh) 42
C=C olefins R
2
C=CR
2
1680-1640 W(sh) 10, 39, 40
R
2
C=CH
2
1600-1675 M(sh) 9, 35
R
2
C=C(OR)R 1600-1630 S(sh) 41
-NO
2
nitro groups RNO
2
1550, 1370 S,S(sh) 28

A summary of the principle infrared bands and their assignments.
R is an aliphatic group.




C
O
O
C
O
O
-
-
C=O in an acid 1700 cm
-1;
C-O-C stretch 1300 to 1000 cm
-1
,
say in ethers 1150 cm
-1
. Averaging a C=O with a C-O-C results
in: (1700 + 1150)/2 = 1425 cm
-1
. Naively, we would estimate a
bond and a half would have a frequency of 1425 cm
-1


C
O
O
C
O
O
-
-
1410 cm
-1
1560 cm
-1
(1560+ 1410)/2 = 1485 cm
-1


The C=C bond stretch
C=O aldehydes R(C=O)H 1740-1720 S(sh) 14
ketones R(C=O)R 1730-1710 S(sh) 35
esters R(CO
2
)R 1750-1735 S(sh) 33, 34
carboxylic acids RCO
2
H 1720-1680 S(sh) 26,27,30
amides (Amide I) RCONH
2
, RCONHR 1670-1640 S(sh) 19, 21
(Amide II) RCONH
2
1650-1620 S(sh) 19, 21
(Amide II) RCONHR 1550 S(sh) 19, 21
amide RCONR
2
1650-1620 S(sh) 23
anhydrides R(CO
2
CO)R 1820, 1750 S, S(sh) 36
carboxylates R(CO
2
)
-
, M
+
1600, 1400 S,S(sh) 42
C=C olefins R
2
C=CR
2
1680-1640 W(sh) 10, 39, 40
R
2
C=CH
2
1600-1675 M(sh) 9, 35
R
2
C=C(OR)R 1600-1630 S(sh) 41
-NO
2
nitro groups RNO
2
1550, 1370 S,S(sh) 28

A summary of the principle infrared bands and their assignments.
R is an aliphatic group.



Wavenumbers, cm
-1
500 1000 1500 2000 2500 3000 3500 4000
%

T
r
a
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s
m
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t
a
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c
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0
20
40
60
80
100
HC=C
stretches
CH
3
,CH
2
symmetric
and asymmetric stretches
C=C
stretch
CH
3
,CH
2

bending
vibrations
(CH2)
4
rocking
out of plane
H wag of vinyl
group 900, 1000 cm
-1
)
Figure IR-9. 1-Heptene; neat sample, thin film:
H
2
C=CH-CH
2
CH
2
CH
2
CH
2
CH
3

The C=C bond stretch when next to a heteroatom
C=O aldehydes R(C=O)H 1740-1720 S(sh) 14
ketones R(C=O)R 1730-1710 S(sh) 35
esters R(CO
2
)R 1750-1735 S(sh) 33, 34
carboxylic acids RCO
2
H 1720-1680 S(sh) 26,27,30
amides (Amide I) RCONH
2
, RCONHR 1670-1640 S(sh) 19, 21
(Amide II) RCONH
2
1650-1620 S(sh) 19, 21
(Amide II) RCONHR 1550 S(sh) 19, 21
amide RCONR
2
1650-1620 S(sh) 23
anhydrides R(CO
2
CO)R 1820, 1750 S, S(sh) 36
carboxylates R(CO
2
)
-
, M
+
1600, 1400 S,S(sh) 42
C=C olefins R
2
C=CR
2
1680-1640 W(sh) 10, 39, 40
R
2
C=CH
2
1600-1675 M(sh) 9, 35
R
2
C=C(OR)R 1600-1630 S(sh) 41
-NO
2
nitro groups RNO
2
1550, 1370 S,S(sh) 28

A summary of the principle infrared bands and their assignments.
R is an aliphatic group.

Wavenumbers, cm
-1
500 1000 1500 2000 2500 3000 3500 4000
%

T
r
a
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s
m
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a
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c
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0
20
40
60
80
100
Figure IR-40. 2,5-Dimethoxy2,5-dihydrofuran, neat liquid:
O
OCH
3
CH
3
O
Wavenumbers, cm
-1
500 1000 1500 2000 2500 3000 3500 4000
%

T
r
a
n
s
m
i
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t
a
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c
e
0
20
40
60
80
100
Figure IR-41. 2,3-Dihydrofuran, neat liquid:
O
The cumulative C=C bond stretch
The NO
2
stretching frequency
C=O aldehydes R(C=O)H 1740-1720 S(sh) 14
ketones R(C=O)R 1730-1710 S(sh) 35
esters R(CO
2
)R 1750-1735 S(sh) 33, 34
carboxylic acids RCO
2
H 1720-1680 S(sh) 26,27,30
amides (Amide I) RCONH
2
, RCONHR 1670-1640 S(sh) 19, 21
(Amide II) RCONH
2
1650-1620 S(sh) 19, 21
(Amide II) RCONHR 1550 S(sh) 19, 21
amide RCONR
2
1650-1620 S(sh) 23
anhydrides R(CO
2
CO)R 1820, 1750 S, S(sh) 36
carboxylates R(CO
2
)
-
, M
+
1600, 1400 S,S(sh) 42
C=C olefins R
2
C=CR
2
1680-1640 W(sh) 10, 39, 40
R
2
C=CH
2
1600-1675 M(sh) 9, 35
R
2
C=C(OR)R 1600-1630 S(sh) 41
-NO
2
nitro groups RNO
2
1550, 1370 S,S(sh) 28

A summary of the principle infrared bands and their assignments.
R is an aliphatic group.


N
O
O
+
N
O
O
+
-
-
Aromatic Rings
Ring breathing motions
1600-1585
1500-1400
Both often appear as doublets
Wavenumbers, cm
-1
500 1000 1500 2000 2500 3000 3500 4000
%

T
r
a
n
s
m
i
t
t
a
n
c
e
20
30
40
50
60
70
80
90
overtones of
the benzene
ring
Benzene, neat, thin film:
Wavenumbers, cm
-1
500 1000 1500 2000 2500 3000 3500 4000
%

T
r
a
n
s
m
i
t
t
a
n
c
e
0
20
40
60
80
100
carbon-carbon
triple bond stretch
H
Wavenumbers, cm-1
500 1000 1500 2000 2500 3000 3500 4000
%

T
r
a
n
s
m
i
t
t
a
n
c
e
0
20
40
60
80
100
120
symmetric and asymmetric
-NO
2
stretch
4-Chloro-2-nitrophenol, KBr pellet: