Ir Func Group

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
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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

Ir Func Group

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IR

Common Structural Units

Stretching Vibrations (Double Bonds)

Aldehydes and ketones

1800-1850 and 1740-1790

Bending Vibrations (Diagnostic)

Stretching Vibrations Triple Bonds)

Substituted derivatives of benzene

730-770 and 690-710

Serapan gugus fungsional pada Infra merah

Regions of the Infrared Spectrum

2500-2000 cm-1 CC and C N (stretching)

Below 1500 cm-1 fingerprint region

Methyl Isopropyl Ketone

Regions of the Infrared

Infrared Spectroscopy (IR)

IR: Aromatic Compounds

The infra-red spectrum for a simple

carbon-oxygen double, C=O

Infrared Absorption Spectrum of

IR: Carbonyl Compounds

The infra-red spectrum for an

The infra-red spectrum for a

The infra-red spectrum for a primary

Analyzing the Spectrum A Suggested Approach

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

Methyl Isopropyl Ketone

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

Primary Amine Secondary

Step 3. Refine the Structure Possibilities by

Step 4. If none of the above apply then the

- Check for main absorptions

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