IR Spectros

Infrared spectroscopy
(IR spectroscopy)
Chapter 12 - IR spectroscopy
How to identify a given organic molecule ???

A combination of techniques need to be used to determine the molecular structure of an organic compound. The following gives a list. Method C, H, N analysis Mass spectroscopy UV spectroscopy IR spectroscopy
1H
Information obtained Empirical formula Molecular mass Conjugation Functional groups Number and arrangement of atoms
and 13C NMR spectroscopy
The last three rely on interaction of light with matter

Electromagnetic spectrum
What is the nature of light ?

Light acts as waves
Light also has particle character
Energy (E) of a single photon is given by the following formula
E = h = hc/
Where, h = Plancks constant, = frequency c = velocity of light = wavelength
Interaction of light with matter

All organic compounds absorb electromagnetic radiation, of only certain wavelengths and transmit the rest. When organic molecules absorb energy in the UV-vis region, they undergo electronic transitions (electrons in the ground state go to higher states known as excited state) (Absorption spectroscopy) Photon energies associated with infrared are not large enough to excite electrons, but may induce vibrational excitation of covalently bonded atoms and groups. -(Infrared spectroscopy)
Shown below is a cartoon representation of light waves of different wavelength showing which region causes what transition
Electronic Transitions
Vibrational Transitions
Absorption spectroscopy
Infrared spectroscopy
Infrared spectroscopy IR spectroscopy is an useful tool to identify functional groups in organic molecules IR spectroscopy is a result of molecular vibrational transitions that occur when light interacts with matter Molecules are always vibrating For a molecule to be IR active, the vibrations should give rise to a net change in dipole moment
Molecular vibrations
The covalent bonds in molecules are not rigid sticks or rods, but are more like stiff springs that can be stretched and bent. bond length changes bond angle changes
stretching (symmetric and asymmetric) bending (scissoring, rocking, wagging and twisting)
Cartoon representation of the stretching and bending vibrations
Check this link for animation: http://en.wikipedia.org/wiki/Infrared_spectroscopy

By considering the atoms as point masses, linked by a 'spring' having a force constant f (sometimes denoted as k) and following Hooke's Law, equation shown below can be utilized to approximate the characteristic stretching frequency (in cm-1) of a diatomic molecule with the masses of two atoms being m1 and m2,
where, = m1m2/(m1+m2) = reduced mass

or
c = velocity of light. IR energy in a spectrum is usually measured as wavenumber (cm-1), the inverse of wavelength and proportional to frequency
1/ =
IR spectra of ethyl alcohol
The above figure shows the range of frequency used by organic chemists for structural analysis
Specific IR absorbed by an organic molecule is related to its structure

Shown below is the IR of a simple alkane. Note the important IR peaks
-C-C1490 cm-1 -C-H 2850 - 3000 cm-1 n-hexane
Not all vibrations can be assigned

IR of an alkene
Important peaks are shown here
IR of an alkyne
C-H stretch 2850 to 2960 cm-1 C-C 800-1300 cm-1
3100 cm-1
C=C 1630 cm-1
3300 cm-1
C C
2150 cm-1
The previous slide highlights the differences between the IR spectra of alkane, alkene and an alkyne. Note that C-C single bond has lower stretching frequency than a C=C double bond which in turn vibrates at lower energy than CC triple bond
Other important examples are listed in the following
Hydrocarbons
2850-3300 cm-1 (Sharp, strong to medium)
Note that IR vibration of O-H is greater than N-H which in turn is greater than C-H
Differences in the force constants lead to this trend

IR spectra of n-octanol CH3-(CH2)7-OH
-O-H, broad and intense
NH2
IR spectra of 3-methyl butamine

-N-H, Sharp and medium intensity
Carbonyls
Carbonyls give a strong, sharp peak in the wavenumber
range 1670 to 1780 cm1
O R NH2
O R OH
Amides
1630 1690 cm-1
Carboxylic acid
1670 1720 cm-1
Regions of Infrared spectrum
Most functional groups absorb at about the same energy and intensity, independent of the molecule they are in Characteristic higher energy IR absorptions (1500 to 4000 cm-1) can be used to confirm the presence of a functional group in a molecule IR spectrum has lower energy region (400 to 1500 cm-1) characteristic of molecule as a whole. This region is called fingerprint region
Some General Trends
Stretching frequencies are higher than corresponding bending frequencies. Bonds to hydrogen have higher stretching frequencies than those to heavier atoms. Triple bonds have higher stretching frequencies than corresponding double bonds, which in turn have higher frequencies than single bonds.
Sample problems Predict the IR absorptions for the following by using the IR chart
Which IR spectrum corresponds to what molecule ?
IR spectroscopy can be used to monitor the progress of a reaction Assume that you are dehydrating 1-methylcyclohexanol to yield 1-methylcyclohexene. How could you use IR spectroscopy to determine when the reaction is complete ?
OH - OH

IR Spectros

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Infrared spectroscopy

How to identify a given organic molecule ???

and 13C NMR spectroscopy

The last three rely on interaction of light with matter

What is the nature of light ?

Light acts as waves

Light also has particle character

Energy (E) of a single photon is given by the following formula

Where, h = Plancks constant, = frequency c = velocity of light = wavelength

Interaction of light with matter

Cartoon representation of the stretching and bending vibrations

Check this link for animation: http://en.wikipedia.org/wiki/Infrared_spectroscopy

where, = m1m2/(m1+m2) = reduced mass

IR spectra of ethyl alcohol

Specific IR absorbed by an organic molecule is related to its structure

-C-C1490 cm-1 -C-H 2850 - 3000 cm-1 n-hexane

Not all vibrations can be assigned

Important peaks are shown here

C-H stretch 2850 to 2960 cm-1 C-C 800-1300 cm-1

C=C 1630 cm-1

Other important examples are listed in the following

2850-3300 cm-1 (Sharp, strong to medium)

Differences in the force constants lead to this trend

IR spectra of n-octanol CH3-(CH2)7-OH

-O-H, broad and intense

IR spectra of 3-methyl butamine

range 1670 to 1780 cm1

Regions of Infrared spectrum

Some General Trends

Which IR spectrum corresponds to what molecule ?

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