Infra Red Spectroscopy

Infrared Spectroscopy of Organic

Molecules
IR region lower energy than visible light (below red

produces heating as with a heat lamp)

2.5 106 m to 2.5 105 m region used by organic
chemists for structural analysis
IR energy in a spectrum is usually measured as
wavenumber (cm-1), the inverse of wavelength and
proportional to frequency

Infrared Energy Modes

IR energy absorption corresponds to specific

modes, such as bending and stretching of

bonds
Energy is characteristic of the atoms in the
group and their bonding
Corresponds to vibrations and rotations

Interpreting Infrared Spectra

Most functional groups absorb at about the

same energy and intensity independent of the

molecule they are in
IR spectrum has lower energy region
characteristic of molecule as a whole
(fingerprint region)

Regions of the Infrared Spectrum

4000-2500 cm -1 N-H, C-H, O-

H (stretching)
3300-3600 N-H, O-H
3000 C-H
2500-2000 cm -1 CC and C
N (stretching)

2000-1500 cm-1 double

bonds (stretching)
C=O 1680-1750
C=C 1640-1680 cm-1
Below 1500 cm-1
fingerprint region

12.8 Infrared Spectra of Hydrocarbons

C-H, C-C, C=C, C

C have characteristic peaks

absence helps rule out C=C or C C

Cyclohexane (top), cyclohexene (bottom)

IR: Aromatic Compounds

Weak CH stretch at 3030 cm1
Weak absorptions 1660 - 2000 cm1 range
Medium-intensity absorptions 1450 to 1600 cm 1
See spectrum of phenylacetylene, Figure 12.15

IR: Alcohols and Amines

OH 3400 to 3650 cm1

Usually broad and intense

NH 3300 to 3500 cm1
Sharper and less intense than an OH

Cyclohexanol

IR: Carbonyl Compounds

Strong, sharp C=O peak 1670 to 1780 cm 1
Exact absorption characteristic of type of carbonyl

compound
1730 cm1 in saturated aldehydes
1705 cm1 in aldehydes next to double bond or
aromatic ring

Benzaldehyde

C=O in Ketones
1715 cm1 in six-membered ring and acyclic ketones
1750 cm1 in 5-membered ring ketones
1690 cm1 in ketones next to a double bond or an aromatic

ring

C=O in Esters
1735 cm1 in saturated esters
1715 cm1 in esters next to aromatic ring or a

double bond

C=O in Carboxylic Acids

Also OH

Alcohol and Amine

OH

3330 cm-1

NH2

3370 cm-1
3270 cm-1
24

Double Bonds
O

1715 cm-1

CH2

1650 cm-1

25

More Examples
CH3CH2CH2CH2 C C H

3310 cm-1
2120 cm-1

O
CH3CH2CH2CH2CH2 C

OH

3500 2500 cm-1

1710 cm-1

26

diethylbenzene

styrene

benzoic acid

methanol

acetone

aniline

phenol