IR

Elusidasi

Common Structural Units

Stretching Vibrations
O

H (alcohols)

Stretching Vibrations (Double Bonds)

3200-3600
C

H (carboxylic
acids)

2500-3600

3350-3500

3310-3320

sp2 C

3000-3100

sp

sp3 C

C
1620-1680

2850-2950

sp2 C

1200

sp3 C

1025-1200

Aldehydes and ketones

1710-1750

Carboxylic acids

1700-1725

Acid anhydrides

1800-1850 and 1740-1790

Acyl halides

1770-1815

Esters

1730-1750

Amides

1680-1700

Bending Vibrations (Diagnostic)

Alkenes:
cis-disubstituted

665-730

trans-disubstituted

960-980

trisubstituted

790-840

Stretching Vibrations Triple Bonds)

C

2100-2200

2240-2280

Substituted derivatives of benzene

monosubstituted

730-770 and 690-710

ortho-disusbstituted
meta-disubstituted
para-substituted

735-770
750-810 and 680-730
790-840

Serapan gugus fungsional pada Infra merah

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

Spectra Infrared

Methyl Isopropyl Ketone

Regions of the Infrared

Spectrum

Spectra Infrared
IR Spectrum Peak Characteristics
1.Primary Examination Regions of the Spectrum
High Frequency Region
- 4000 to
1300 cm-1
Intermediate (Fingerprint Region) - 1300 to
900 cm-1
2.High Frequency Region (Functional Group
Region)
Characteristic Stretching frequencies of such
groups as:
=CH, OH, NH, C=O, CO, CN, CC,
C=C
3.The Fingerprint Region
Absorption patterns frequently complex
Bands originate from interacting vibrational
modes

Infrared Spectroscopy (IR)

IR Spectrum Peak Characteristics (cont)
Shape
Sharp (narrow)
Broad
Intensity
Weak (w)
Medium
(m)
Strong (s)
Note: Peak intensity is dependent on amount of
sample
and sensitivity of instrument;
therefore, the actual
intensity can vary from
spectrum to spectrum

Infrared Spectra of
Hydrocarbons
C-H, C-C, C=C, C C have characteristic
peaks

Hexane

Alkenes

1-Hexene

Alkynes

IR: Aromatic Compounds

Weak CH stretch at 3030 cm1
Weak absorptions 1660 - 2000 cm1 range
Medium-intensity absorptions 1450 to
1600 cm1

Phenylacetylene

Cyclohexane or
Cyclohexene?

The infra-red spectrum for a simple

carboxylic acid

Ethanoic
acid

carbon-oxygen double, C=O

carbon-oxygen single, C-O
oxygen-hydrogen, O-H
carbon-hydrogen, C-H
carbon-carbon single, C-C

IR: Alcohols

Infrared Absorption Spectrum of

Ethanol

IR: Carbonyl Compounds

Strong, sharp C=O peak 1670 to 1780 cm1
Exact absorption characteristic of type of
carbonyl compound
1730 cm1 in saturated aldehydes
1705 cm1 in aldehydes next to double bond
or aromatic ring

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

The infra-red spectrum for an

ester
Ethyl ethanoate

Practice problem:

Phenylacetaldehyde

The infra-red spectrum for a

ketone
Propanone

Amines

The infra-red spectrum for a primary

amine
1-aminobutane

Analyzing the Spectrum A Suggested Approach

Step 1.
Check for the presence of the
Carbonyl group (C=O) at 1715 cm-1. If molecule is
conjugated, the strong (C=O) absorption will be

shifted to the right by ~30 cm-1, i.e. ~1685 cm-1

If the carbonyl absorption is present, check for:
Carboxylic Acids
- Check for OH group (broad
absorption
near 3300-2500 cm-1)
Amides Check for NH group
(1 or 2 absorptions near
3500 cm-1)
Esters Check for C-O group (medium
absorptions near 1300-1000
cm-1)
Anhydrides
- Check for 2 C=O absorptions
near
1810 and 1760 cm-1
Aldehydes
- Check for Aldehyde CH group
(2 weak
absorptions near 2850

IR Spectrum
Carboxylic Acids

Isobutyric Acid

C4H8O2

IR Spectrum
Amides

Benzamide

C7H7NO

IR Spectrum
Esters

Methyl Benzoate

C8H8O2

IR Spectrum
Aldehydes

Nonanal

C9H18O

IR Spectrum
Ketones

Methyl Isopropyl Ketone

C5H10O

Step 2. - If the Carbonyl Group is Absent Check for

Alcohols,
Amines, or Ethers.
Alcohols & Phenols - Check for OH group
(Broad
absorption near 36003300 cm-1
Confirm present of CO
near
1300-1000 cm-1
Amines
- Check for NH stretch
(Medium
absorptions) near 3500
cm-1

2 Peaks
Amine

Primary Amine Secondary

- 1 Peak
Tertiary Amine -

IR Spectrum
Alkynes (CC)

Propargyl Alcohol

C3H4O

HC CCH2OH

IR Spectrum
Alcohols & Phenols

2-Naphthol

C10H9O

IR Spectrum
Amines

n-butylamine

C4H11N

IR Spectrum
Ethers

Butyl Ether

C8H18O

CH3(CH2)3 O (CH2)3CH3

Step 3. Refine the Structure Possibilities by

Looking for
Double Bonds, Triple Bonds and Nitro
Groups
Double Bonds
- C=C is weak absorption near
1650 cm-1
Aliphatics occur on right side of
3000 cm-1.
Unsaturated C=C or CC bonds show
an
absorption on the left side of 3000
cm-1.
Triple Bonds
- CN (medium, sharp
absorption near
2250 cm-1
CC (weak, sharp absorption
near
2150 cm-1
Nitro Groups
- Two strong absorptions 1600-

Step 3 (Cont)
Aromatic Ring Absorptions
Aromatic unsaturated C=C bonds show an
absorption on the left side of 3000 cm-1, but
the aromaticity must be verified in the
overtone region (1667 - 2000cm-1) and the
out-of-plane (OOP) region (900 - 690 cm-1)
Medium to strong absorption in region 1650 1450 cm-1
Many weak combination and overtone
absorptions appear between 2000 and 1667
cm-1
The relative shapes and numbers (1 - 4) of the
overtone absorptions can be used to tell
whether the aromatic ring is monosubstituted
or di-, tri-, tetra-, penta-, or hexasubstituted.
Positional (ortho-, meta-, para-) isomers can
also be distinguished.

Step 3 (Cont)
Aromatic Ring Absorptions (Cont)
The unsaturated =C-H Out-of-Plane (OOP)
bending absorptions in the region 900 690
can also be used to determine the type of
ring substitution.
The number of absorptions and their relative
positions are unique to each type of
substitution.
Although these absorptions are in the
fingerprint region they are particularly
reliable for rings with alkyl group
substitutions.
They are less reliable for polar substituents.

IR Spectrum
Nitriles

Benzonitrile

C7H5N

IR Spectrum
Alkynes (CC)

Propargyl Alcohol

C3H4O

HC CCH2OH

IR Spectrum
Nitro Compounds

Nitro Benzene

C6H5NO2

Step 4. If none of the above apply then the

compound is
most likely a hydrocarbon.
Generally, very simple spectrum
Hydrocarbons
near

- Check for main absorptions

right side of 3000 cm-1

IR Spectrum
Alkane

Decane

C H

CH (CH2) CH