C8H10O

C12H26O

C9H7NO

Procedure for obtaining IR spectra

Liquid Samples: The simplest method for mounting the sample consists of placing a thin film of the liquid between two transparent windows. The most common material used for the windows is NaCl(transparent within 10000 to 650 cm-1)

Vibration

Frequency (cm-1 )

Intensity Stretching 2850 - 3000 Medium 1450-1475 Medium Bending 1375 and 1450 Weak to medium Bending (Not useful for interpretation - too many bands Stretching Stretching Stretching Stretching Stretching Stretching Bending 3000 - 3100 1600 - 1680 3300 2100-2250 3030 1450-1600 690-900 Weak to medium Weak to medium Medium to strong Weak Weak to medium Medium Strong

Hydrocarbon Alkane C-H CH2 CH3 C-C Alkene C-H C= C Alkyne C-H C C Arene C-H C= C C-H

Alkanes
Infrared spectrum of decane.

Alkenes
Infrared spectrum of cyclohexene.

Alkynes
Infrared spectrum of 1-octyne.

Aromatics
Infrared spectrum of toluene.

Alcohols
Bond Intensity
O- H (free) O- H (H bonded) C-O

Frequency, cm-1 3600-3650 3200 - 3500 1000 - 1250

Weak Medium, broad Medium

Ethers
Infrared spectrum of dibutyl ether.

Ethers
Infrared spectrum of anisole.

Amines
Infrared spectrum of 1-butanamine, a 1 amine.

IR of Molecules with C=O Groups

Carbonyl Group Vibration Stretching Stretching Stretching 1630-1820 1630-1820 2720 1700-1725 2500-3300 O RCR' Ketones C=O Aldehydes C=O C-H Carboxylic acids C=O Stretching O H Stretching O RCH O RCOH Frequency (cm-1 ) Intensity Strong Strong Weak Strong Strong (broad)

IR of Molecules with C=O Groups

O RCNH2 Amides C=O Stretching 1630-1680 Stretching 3200, 3400 N H (1 amides have two N-H stretches) (2 amides have one N-H stretch) O RCOR' Carboxylic esters Stretching C=O 2 Stretching sp C O sp C O O O RCOCR C=O C O RC N Nitriles CN
3

Strong Medium

1735-1800 1200-1250 Stretching Acid anhydrides Stretching Stretching Stretching 1740-1760 and 1800-1850 900-1300 2200-2250 1000-1100

Strong Strong Strong Strong Strong Medium

Aldehydes and Ketones

Infrared spectrum of menthone.

Carbonyl groups
The position of C=O stretching vibration is sensitive to its molecular environment.
as ring size decreases and angle strain increases, absorption shifts to a higher frequency.
O O O O

1715 cm-1

1745 cm-1

1780 cm-1

1850 cm-1

conjugation shifts the C=O absorption to lower frequency.

O O O H 1717 cm-1 1690 cm-1 1700 cm-1

Carboxylic acids
Infrared spectrum of pentanoic acid.

Esters
Infrared spectrum of ethyl butanoate.

toluene

Some characteristic infrared absorption frequencies BOND C-H COMPOUND TYPE alkanes alkenes RCH=CH2 R2C=CH2 cis-RCH=CHR trans-RCH=CHR aromatic rings monosubst. ortho-disubst. meta-disubst. para-disubst. alkynes O-H C=C alcohols or phenols alkenes aromatic rings C C C-O alkynes primary alcohols secondary alcohols tertiary alcohols phenols alkyl ethers aryl ethers all abs. strong unless marked: m, moderate; v, variable; b, broad 3300 3200-3640 (b) 1640-1680 (v) 1500 and 1600 (v) 2100-2260 (v) 1050 (b) 1100 (b) 1150 (b) 1230 (b) 1060-1150 1200-1275(b) and 1020-1075 (m) 675-730 (v) 965-975 3000-3100 (m) and 690-710 and 730-770 735-770 690-710 and 750-810 (m) 810-840 (m) FREQUENCY RANGE, cm-1 2850-2960 and 1350-1470 3020-3080 (m) and 910-920 and 990-1000 880-900

IR spectra of ALKANES CH bond saturated (sp3) 2850-2960 cm-1 + 1350-1470 cm-1

-CH2-CH3 -CH(CH3)2 -C(CH3)3 + + +

+ 1430-1470 and 1375 and 1370, 1385 and 1370(s), 1395 (m)

n-pentane

2850-2960 cm-1
3000 cm-1 satd C-H 1470 &1375 cm-1

CH3CH2CH2CH2CH3

n-hexane

CH3CH2CH2CH2CH2CH3

2-methylbutane

(isopentane)

2,3-dimethylbutane

cyclohexane

no 1375 cm-1 no CH3

IR of ALKENES =CH bond, unsaturated vinyl (sp2) 3020-3080 cm-1 + 675-1000 RCH=CH2 R2C=CH2 cis-RCH=CHR + 880-900 + 675-730 (v) + 910-920 & 990-1000

trans-RCH=CHR + 965-975

C=C bond

1640-1680 cm-1 (v)

1-decene

unsatd C-H

30203080 cm-1 C=C 1640-1680

910-920 & 990-1000 RCH=CH2

4-methyl-1-pentene

910-920 & 990-1000 RCH=CH2

2-methyl-1-butene

880-900
R2C=CH2

2,3-dimethyl-1-butene

880-900
R2C=CH2

IR spectra BENZENEs =CH bond, unsaturated aryl (sp2) 3000-3100 cm-1 + 690-840 mono-substituted + 690-710, 730-770 ortho-disubstituted + 735-770 meta-disubstituted + 690-710, 750-810(m) para-disubstituted + 810-840(m)

C=C bond

1500, 1600 cm-1

ethylbenzene

30003100 cm-1 Unsatd C-H

1500 & 1600 Benzene ring

690-710, 730-770
mono-

o-xylene

735-770
ortho

p-xylene

810-840(m)
para

m-xylene

meta

690-710, 750-810(m)

styrene

no satd C-H 1640 C=C

910-920 & 990-1000 RCH=CH2 mono

2-phenylpropene

Satd C-H

880-900
R2C=CH2 mono

p-methylstyrene

para

IR spectra ALCOHOLS & ETHERS

CO bond

1050-1275 (b) cm-1 1o ROH 2o ROH 3o ROH ethers 1050 1100 1150 1060-1150

OH bond

3200-3640 (b)

1-butanol

3200-3640 (b) O-H

C-O 1o

CH3CH2CH2CH2-OH

2-butanol

O-H C-O 2o

tert-butyl alcohol

O-H

C-O 3o

methyl n-propyl ether

no O--H C-O ether

2-butanone

C=O ~1700 (s)

C9H12

1500 & 1600 benzene C-H unsatd & satd mono C9H12 C6H5 = -C3H7

isopropylbenzene n-propylbenzene?

n-propylbenzene

isopropylbenzene

isopropyl split 1370 + 1385

C8H6

C-H unsatd 1500, 1600 benzene 3300 C8H6 C6H5 = C2H C-H

mono

phenylacetylene

C4H8

Unstd 16401680 C=C

880-900
R2C=CH2

isobutylene

CH3 CH3C=CH2

Which compound is this? a) 2-pentanone b) 1-pentanol c) 1-bromopentane d) 2-methylpentane

1-pentanol

What is the compound? a) 1-bromopentane b) 1-pentanol c) 2-pentanone d) 2-methylpentane

2-pentanone

In a matching problem, do not try to fully analyze each spectrum. Look for differences in the possible compounds that will show up in an infrared spectrum.

H2 C C CH2 H biphenyl allylbenzene

H2 H2 C C

1,2-diphenylethane

CH3 CH3 B D CH3CH2CH2CH2CH3 F CH2CH2CH2CH3

o-xylene

n-pentane

n-butylbenzene