The C=O stretching frequency aldehydes and ketones.
-
date post
20-Dec-2015 -
Category
Documents
-
view
236 -
download
4
Transcript of The C=O stretching frequency aldehydes and ketones.
![Page 1: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/1.jpg)
The C=O stretching frequency
aldehydes and ketones
![Page 2: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/2.jpg)
C=O aldehydes R(C=O)H 1740-1720 S(sh) 14 ketones R(C=O)R 1730-1710 S(sh) 35 esters R(CO2)R 1750-1735 S(sh) 33, 34 carboxylic acids RCO2H 1720-1680 S(sh) 26,27,30 amides (Amide I) RCONH2, RCONHR 1670-1640 S(sh) 19, 21 (Amide II) RCONH2 1650-1620 S(sh) 19, 21 (Amide II) RCONHR 1550 S(sh) 19, 21 amide RCONR2 1650-1620 S(sh) 23 anhydrides R(CO2CO)R 1820, 1750 S, S(sh) 36 carboxylates R(CO2)
-, M+ 1600, 1400 S,S(sh) 42 C=C olefins R2C=CR2 1680-1640 W(sh) 10, 39, 40 R2C=CH2 1600-1675 M(sh) 9, 35 R2C=C(OR)R 1600-1630 S(sh) 41 -NO2 nitro groups RNO2 1550, 1370 S,S(sh) 28
A summary of the principle infrared bands and their assignments. R is an aliphatic group.
![Page 3: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/3.jpg)
Wavenumbers, cm-1
5001000150020002500300035004000
% T
rans
mit
tanc
e
10
20
30
40
50
60
70
80
90
100
H-C=OImpurity peak,probably O-H
Figure IR-14. Butanal, neat liquid, thin film: CH3CH2CH2CHO
Aliphatic Aldehyde
![Page 4: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/4.jpg)
Wavenumbers, cm-1
5001000150020002500300035004000
% T
rans
mitt
ance
0
20
40
60
80
100
Figure IR-35. 5-Hexene-2-one, neat liquid: CH2=CH2CH2CH2COCH3
Aliphatic Ketone
![Page 5: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/5.jpg)
The C=O stretching frequency
esters
![Page 6: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/6.jpg)
C=O aldehydes R(C=O)H 1740-1720 S(sh) 14 ketones R(C=O)R 1730-1710 S(sh) 35 esters R(CO2)R 1750-1735 S(sh) 33, 34 carboxylic acids RCO2H 1720-1680 S(sh) 26,27,30 amides (Amide I) RCONH2, RCONHR 1670-1640 S(sh) 19, 21 (Amide II) RCONH2 1650-1620 S(sh) 19, 21 (Amide II) RCONHR 1550 S(sh) 19, 21 amide RCONR2 1650-1620 S(sh) 23 anhydrides R(CO2CO)R 1820, 1750 S, S(sh) 36 carboxylates R(CO2)
-, M+ 1600, 1400 S,S(sh) 42 C=C olefins R2C=CR2 1680-1640 W(sh) 10, 39, 40 R2C=CH2 1600-1675 M(sh) 9, 35 R2C=C(OR)R 1600-1630 S(sh) 41 -NO2 nitro groups RNO2 1550, 1370 S,S(sh) 28
A summary of the principle infrared bands and their assignments. R is an aliphatic group.
![Page 7: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/7.jpg)
Wavenumbers, cm-1
5001000150020002500300035004000
% T
rans
mit
tanc
e
0
20
40
60
80
100
Top: CHCl3 vs CHCl3
Bottom: 2.5 % v/v un CHCl3
Aliphatic Ester
Figure IR-33. Methyl acetate in 0.1 mm NaCl cells: CH3CO2CH3
![Page 8: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/8.jpg)
Wavenumbers, cm-1
5001000150020002500300035004000
% T
rans
mitt
ance
0
20
40
60
80
100
Top: CHCl3 vs CHCl3
Bottom: 2.5 % v/v un CHCl3
CCl4
neat
![Page 9: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/9.jpg)
Wavenumber, cm-1
1000150020002500300035004000
% T
rans
mit
tanc
e
0
20
40
60
80
100
120
liquid film
vapor: 106 °C
Figure IR-34. Vapor and liquid spectra of ethyl n-hexanoate: CH3CH2CH2CH2CH2CO2CH2CH3
Aliphatic Ester
![Page 10: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/10.jpg)
The C=O stretching frequency
aliphatic acids
![Page 11: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/11.jpg)
C=O aldehydes R(C=O)H 1740-1720 S(sh) 14 ketones R(C=O)R 1730-1710 S(sh) 35 esters R(CO2)R 1750-1735 S(sh) 33, 34 carboxylic acids RCO2H 1720-1680 S(sh) 26,27,30 amides (Amide I) RCONH2, RCONHR 1670-1640 S(sh) 19, 21 (Amide II) RCONH2 1650-1620 S(sh) 19, 21 (Amide II) RCONHR 1550 S(sh) 19, 21 amide RCONR2 1650-1620 S(sh) 23 anhydrides R(CO2CO)R 1820, 1750 S, S(sh) 36 carboxylates R(CO2)
-, M+ 1600, 1400 S,S(sh) 42 C=C olefins R2C=CR2 1680-1640 W(sh) 10, 39, 40 R2C=CH2 1600-1675 M(sh) 9, 35 R2C=C(OR)R 1600-1630 S(sh) 41 -NO2 nitro groups RNO2 1550, 1370 S,S(sh) 28
A summary of the principle infrared bands and their assignments. R is an aliphatic group.
![Page 12: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/12.jpg)
Aliphatic Acid
Figure IR-26. The liquid,
vapor and CCl4 soln
spectra of hexanoic acid:
CH3(CH2)4 CO2H
Wavenumber, cm-1
1000150020002500300035004000
% T
rans
mit
tanc
e
0
20
40
60
80
100
120
liquid film
vapor: 134 °C
![Page 13: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/13.jpg)
The C=O stretching frequency
aliphatic amides
![Page 14: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/14.jpg)
C=O aldehydes R(C=O)H 1740-1720 S(sh) 14 ketones R(C=O)R 1730-1710 S(sh) 35 esters R(CO2)R 1750-1735 S(sh) 33, 34 carboxylic acids RCO2H 1720-1680 S(sh) 26,27,30 amides (Amide I) RCONH2, RCONHR 1670-1640 S(sh) 19, 21 (Amide II) RCONH2 1650-1620 S(sh) 19, 21 (Amide II) RCONHR 1550 S(sh) 19, 21 amide RCONR2 1650-1620 S(sh) 23 anhydrides R(CO2CO)R 1820, 1750 S, S(sh) 36 carboxylates R(CO2)
-, M+ 1600, 1400 S,S(sh) 42 C=C olefins R2C=CR2 1680-1640 W(sh) 10, 39, 40 R2C=CH2 1600-1675 M(sh) 9, 35 R2C=C(OR)R 1600-1630 S(sh) 41 -NO2 nitro groups RNO2 1550, 1370 S,S(sh) 28
A summary of the principle infrared bands and their assignments. R is an aliphatic group.
![Page 15: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/15.jpg)
Amide I 1662 cm-1
Amide II; 1634 cm-1
KBr pellet
![Page 16: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/16.jpg)
Wavnumbers, cm-1
5001000150020002500300035004000
% T
rans
mit
tanc
e
10
20
30
40
50
60
70
80
90
100
Amide I Amide II
Figure IR-21. N-Methyl acetamide, neat liquid; thin film: CH3CONHCH3
Secondary Amide
![Page 17: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/17.jpg)
Wavenumbers, cm-1
5001000150020002500300035004000
% T
rans
mit
tanc
e
0
20
40
60
80
100
Figure IR-23. N,N-Dimethylacetamide, neat liquid; thin film: CH3CON(CH3)2
Tertiary Amide
![Page 18: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/18.jpg)
The C=O stretching frequency
anhydrides
![Page 19: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/19.jpg)
C=O aldehydes R(C=O)H 1740-1720 S(sh) 14 ketones R(C=O)R 1730-1710 S(sh) 35 esters R(CO2)R 1750-1735 S(sh) 33, 34 carboxylic acids RCO2H 1720-1680 S(sh) 26,27,30 amides (Amide I) RCONH2, RCONHR 1670-1640 S(sh) 19, 21 (Amide II) RCONH2 1650-1620 S(sh) 19, 21 (Amide II) RCONHR 1550 S(sh) 19, 21 amide RCONR2 1650-1620 S(sh) 23 anhydrides R(CO2CO)R 1820, 1750 S, S(sh) 36 carboxylates R(CO2)
-, M+ 1600, 1400 S,S(sh) 42 C=C olefins R2C=CR2 1680-1640 W(sh) 10, 39, 40 R2C=CH2 1600-1675 M(sh) 9, 35 R2C=C(OR)R 1600-1630 S(sh) 41 -NO2 nitro groups RNO2 1550, 1370 S,S(sh) 28
A summary of the principle infrared bands and their assignments. R is an aliphatic group.
![Page 20: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/20.jpg)
Wavenumber, cm-1
50010001500200025003000350040004500
% T
rans
mit
tanc
e
0
20
40
60
80
100
Figure IR-36. Propionic anhydride, neat liquid: CH3CH2CO2COCH2CH3
Anhydrides
![Page 21: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/21.jpg)
The C=O stretching frequency
carboxylates
![Page 22: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/22.jpg)
C=O aldehydes R(C=O)H 1740-1720 S(sh) 14 ketones R(C=O)R 1730-1710 S(sh) 35 esters R(CO2)R 1750-1735 S(sh) 33, 34 carboxylic acids RCO2H 1720-1680 S(sh) 26,27,30 amides (Amide I) RCONH2, RCONHR 1670-1640 S(sh) 19, 21 (Amide II) RCONH2 1650-1620 S(sh) 19, 21 (Amide II) RCONHR 1550 S(sh) 19, 21 amide RCONR2 1650-1620 S(sh) 23 anhydrides R(CO2CO)R 1820, 1750 S, S(sh) 36 carboxylates R(CO2)
-, M+ 1600, 1400 S,S(sh) 42 C=C olefins R2C=CR2 1680-1640 W(sh) 10, 39, 40 R2C=CH2 1600-1675 M(sh) 9, 35 R2C=C(OR)R 1600-1630 S(sh) 41 -NO2 nitro groups RNO2 1550, 1370 S,S(sh) 28
A summary of the principle infrared bands and their assignments. R is an aliphatic group.
![Page 23: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/23.jpg)
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
![Page 24: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/24.jpg)
C
O
O
C
O
O
-
-
1410 cm-11560 cm-1
(1560+ 1410)/2 = 1485 cm-1
![Page 25: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/25.jpg)
![Page 26: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/26.jpg)
The C=C bond stretch
![Page 27: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/27.jpg)
C=O aldehydes R(C=O)H 1740-1720 S(sh) 14 ketones R(C=O)R 1730-1710 S(sh) 35 esters R(CO2)R 1750-1735 S(sh) 33, 34 carboxylic acids RCO2H 1720-1680 S(sh) 26,27,30 amides (Amide I) RCONH2, RCONHR 1670-1640 S(sh) 19, 21 (Amide II) RCONH2 1650-1620 S(sh) 19, 21 (Amide II) RCONHR 1550 S(sh) 19, 21 amide RCONR2 1650-1620 S(sh) 23 anhydrides R(CO2CO)R 1820, 1750 S, S(sh) 36 carboxylates R(CO2)
-, M+ 1600, 1400 S,S(sh) 42 C=C olefins R2C=CR2 1680-1640 W(sh) 10, 39, 40 R2C=CH2 1600-1675 M(sh) 9, 35 R2C=C(OR)R 1600-1630 S(sh) 41 -NO2 nitro groups RNO2 1550, 1370 S,S(sh) 28
A summary of the principle infrared bands and their assignments. R is an aliphatic group.
![Page 28: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/28.jpg)
![Page 29: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/29.jpg)
![Page 30: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/30.jpg)
Wavenumbers, cm-1
5001000150020002500300035004000
% T
rans
mitt
ance
0
20
40
60
80
100
HC=Cstretches
CH3,CH2 symmetric
and asymmetric stretches
C=Cstretch
CH3,CH2
bending vibrations
(CH2)4
rocking
out of plane H wag of vinylgroup 900, 1000 cm-1)
Figure IR-9. 1-Heptene; neat sample, thin film:
H2C=CH-CH2CH2CH2CH2CH3
![Page 31: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/31.jpg)
The C=C bond stretch when next to a heteroatom
![Page 32: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/32.jpg)
C=O aldehydes R(C=O)H 1740-1720 S(sh) 14 ketones R(C=O)R 1730-1710 S(sh) 35 esters R(CO2)R 1750-1735 S(sh) 33, 34 carboxylic acids RCO2H 1720-1680 S(sh) 26,27,30 amides (Amide I) RCONH2, RCONHR 1670-1640 S(sh) 19, 21 (Amide II) RCONH2 1650-1620 S(sh) 19, 21 (Amide II) RCONHR 1550 S(sh) 19, 21 amide RCONR2 1650-1620 S(sh) 23 anhydrides R(CO2CO)R 1820, 1750 S, S(sh) 36 carboxylates R(CO2)
-, M+ 1600, 1400 S,S(sh) 42 C=C olefins R2C=CR2 1680-1640 W(sh) 10, 39, 40 R2C=CH2 1600-1675 M(sh) 9, 35 R2C=C(OR)R 1600-1630 S(sh) 41 -NO2 nitro groups RNO2 1550, 1370 S,S(sh) 28
A summary of the principle infrared bands and their assignments. R is an aliphatic group.
![Page 33: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/33.jpg)
Wavenumbers, cm-1
5001000150020002500300035004000
% T
rans
mit
tanc
e
0
20
40
60
80
100
Figure IR-40. 2,5-Dimethoxy2,5-dihydrofuran, neat liquid:
OOCH3
CH3O
![Page 34: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/34.jpg)
Wavenumbers, cm-1
5001000150020002500300035004000
% T
rans
mit
tanc
e
0
20
40
60
80
100
Figure IR-41. 2,3-Dihydrofuran, neat liquid: O
![Page 35: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/35.jpg)
![Page 36: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/36.jpg)
The cumulative C=C bond stretch
![Page 37: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/37.jpg)
![Page 38: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/38.jpg)
The NO2 stretching frequency
![Page 39: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/39.jpg)
C=O aldehydes R(C=O)H 1740-1720 S(sh) 14 ketones R(C=O)R 1730-1710 S(sh) 35 esters R(CO2)R 1750-1735 S(sh) 33, 34 carboxylic acids RCO2H 1720-1680 S(sh) 26,27,30 amides (Amide I) RCONH2, RCONHR 1670-1640 S(sh) 19, 21 (Amide II) RCONH2 1650-1620 S(sh) 19, 21 (Amide II) RCONHR 1550 S(sh) 19, 21 amide RCONR2 1650-1620 S(sh) 23 anhydrides R(CO2CO)R 1820, 1750 S, S(sh) 36 carboxylates R(CO2)
-, M+ 1600, 1400 S,S(sh) 42 C=C olefins R2C=CR2 1680-1640 W(sh) 10, 39, 40 R2C=CH2 1600-1675 M(sh) 9, 35 R2C=C(OR)R 1600-1630 S(sh) 41 -NO2 nitro groups RNO2 1550, 1370 S,S(sh) 28
A summary of the principle infrared bands and their assignments. R is an aliphatic group.
![Page 40: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/40.jpg)
N
O
O
+N
O
O
+-
-
![Page 41: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/41.jpg)
Aromatic Rings
Ring breathing motions
1600-1585
1500-1400
Both often appear as doublets
![Page 42: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/42.jpg)
Wavenumbers, cm-1
5001000150020002500300035004000
% T
rans
mit
tanc
e
20
30
40
50
60
70
80
90
overtones of the benzene ring
Benzene, neat, thin film:
![Page 43: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/43.jpg)
Wavenumbers, cm-1
5001000150020002500300035004000
% T
rans
mit
tanc
e
0
20
40
60
80
100
carbon-carbontriple bond stretch
H
![Page 44: The C=O stretching frequency aldehydes and ketones.](https://reader031.fdocuments.in/reader031/viewer/2022013103/56649d4b5503460f94a28d90/html5/thumbnails/44.jpg)
Wavenumbers, cm-1
5001000150020002500300035004000
% T
rans
mit
tanc
e
0
20
40
60
80
100
120
symmetric and asymmetric-NO2 stretch
4-Chloro-2-nitrophenol, KBr pellet: