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Infrared Spectroscopy
Infrared Spectroscopy is a type of imaging technique that uses infrared light that
causes the bonds of a molecule to vibrate, or stretch. The energy that is absorbed
to stretch the bonds of a molecule is measured through a spectrum, which can be
used to analyze properties of the molecule of interest. An infrared spectrum is
the actual graph that shows the energy absorbed by the molecule in relation to the
wavelength of light used. Below is an example of what an IR spectrum looks like
Usually, you will see the IR spectrum graph the transmittance (absorbance) versus
the wavenumber (inverse of wavelength, in units of cm -1). Notice the region
between 400 cm-1 and 1400 cm-1. This region is called the fingerprint region,
because the bands (the peaks representing the different stretches of the molecule),
is unique to each different molecule. As far as O.Chem II is concerned, you will
NEVER use the fingerprint region because it is too complex to memorize
each specific peak within that region! The region that will be commonly used is
the region from 1500 cm-1 to 4000 cm-1. This region contains peaks that
indicate specific functional groups that you will be responsible for! Ive
listed some important facts about IR that you should keep in mind below.
I will separate the guide into the type of bonds (functional groups) that can be seen
from the IR spectrum, and Ill emphasize which ones to know
Carbon-Carbon Bond stretching
There are 3 types of carbon-carbon bond stretching you can see from an IR: a
single, double, or triple C-C bond. The wavenumber for the specific stretches are
listed below. Keep in mind that the higher bond strength, the higher
wavenumber (energy) it is required to absorb.
C-C single bond: 1200 cm-1 (you will never use this peak)
C-C double bond: 1600-1660 cm-1 (depending on degree of conjugation).
Benzene (3 double bonds in conjugation) is around 1600 cm -1
C-C triple bond: slightly below 2200 cm-1
The most useful C-C bonds that you will need able to recognize are the C-C
double and triple bonds.
A carbon-carbon double bond is shown as a weak to moderately
strong, sharp peak around 1640-1680 (not absolute, but very close
enough). An example is shown below (2-hexene)
The alcohol O-H bond is a BROAD and strong stretch usually centered
around 3300 cm-1, covering the region between 3000 cm-1 to about 3500
cm-1. An example is shown below
Ketone
Aldehyde
Ester
Carboxylic Acid
Amide
Acid chloride (dont need to know until Exam 3)
Anhydride (dont need to know until Exam 3)
-A ketone has a strong, sharp peak around 1710 cm-1. This is the only
indicative peak of a ketone.
-An Aldehyde also has a strong, sharp peak around 1725 cm-1 (slightly higher
than ketone, but still very close making it hard to differentiate the two). However,
the most indicative peaks of an aldehyde are 2 sharp C-H spikes around
2700-2800 cm-1, slightly to the right of the sp3 hybridized C-H peaks
An ester has a strong, sharp peak around 1740-1750 cm-1. The peak is higher
in wavenumber compared to aldehyde/ketones, and is usually far enough to be able
to differentiate them apart. Just like ketone, this is the only peak indicative of
an ester
Carboxylic acids have a strong, sharp peak around 1710 cm -1, similar to
ketones/aldehydes. However, carboxylic acids have a broad O-H stretch from
2500-3500 cm-1, as mentioned previously
Amides have a strong, sharp peak that absorb around 1640-1680 (1660 on
average) cm-1. Also, there will be two amine N-H spikes/stretches around
3300-3500. These N-H peaks are usually stronger in absorbance than regular
amines N-H spikes
Acid chloride has a strong, sharp peak carbonyl peak around 1800 cm -1,
much higher than an ester or ketone/aldehyde carbonyl spike. This is due to
the increased stiffness of the bond. Again, you dont need to know this peak until
Exam 3.
Carbon-Nitrogen bond stretches are similar to C-C bond stretches in location. The
main diference is that C-N peaks are stronger in absorbance since there is
a greater dipole moment. The three types of C-N bond stretches and their
wavenumber position are shown below
Miscellaneous alterations
There are two types of alterations that can occur with functional groups
that can alter the location of the peak. The two alterations are:
Resonance: Resonance allows delocalization of the electrons in a functional
group. This allows the bonds of the functional group to be LESS stif,
making the location of the peak LESS in wave number. Each additional
resonance structure will lower the peak location about 20 cm-1. Keep this in
mind when you are looking in IR spectrums, because a peak could represent
multiple functional groups if there is a possibility of resonance. For example:
o
- Carbonyl peak at 1690 cm-1
Ring structure: A functional group placed in a ring will place strain on the
functional group, increasing the energy of the compound. This causes the
bond to become MORE stif, making stretching frequency of the peak
HIGHER. The amount increased in wavenumber depends on the amount of
strain placed on the compound. The more strain placed by the ring, the
higher the stretching frequency will be.