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Interpreting An Infra

This document explains how to interpret infrared spectra to identify common organic bonds. It provides infrared spectra for several compounds as examples: - Ethanoic acid's spectrum shows absorptions for C=O, C-O, O-H, and C-H bonds. The O-H absorption is broad between 2500-3300 cm-1. - Ethanol's spectrum has a higher O-H absorption of 3230-3550 cm-1 compared to acids. - Ethyl ethanoate (an ester) lacks an O-H peak. Its C=O absorption is at 1740 cm-1 and C-O peak is around 1240 cm-1.

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Аружан Жарылқап
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22 views4 pages

Interpreting An Infra

This document explains how to interpret infrared spectra to identify common organic bonds. It provides infrared spectra for several compounds as examples: - Ethanoic acid's spectrum shows absorptions for C=O, C-O, O-H, and C-H bonds. The O-H absorption is broad between 2500-3300 cm-1. - Ethanol's spectrum has a higher O-H absorption of 3230-3550 cm-1 compared to acids. - Ethyl ethanoate (an ester) lacks an O-H peak. Its C=O absorption is at 1740 cm-1 and C-O peak is around 1240 cm-1.

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Аружан Жарылқап
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© © All Rights Reserved
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INTERPRETING AN INFRA-RED SPECTRUM

This page explains how to use an infra-red spectrum to identify the presence of a few simple bonds in
organic compounds.
The infra-red spectrum for a simple carboxylic acid
Ethanoic acid. Ethanoic acid has the structure:

You will see that it contains the following bonds:


carbon-oxygen double, C=O carbon-oxygen single, C-O
oxygen-hydrogen, O-H carbon-hydrogen, C-H
carbon-carbon single, C-C
The carbon-carbon bond has absorptions which occur over a wide range of wavenumbers in the
fingerprint region - that makes it very difficult to pick out on an infra-red spectrum.
The carbon-oxygen single bond also has an absorption in the fingerprint region, varying
between 1000 and 1300 cm-1depending on the molecule it is in. You have to be very wary about
picking out a particular trough as being due to a C-O bond.
The other bonds in ethanoic acid have easily recognised absorptions outside the fingerprint
region.
The C-H bond (where the hydrogen is attached to a carbon which is singly-bonded to
everything else) absorbs somewhere in the range from 2853 - 2962 cm -1. Because that bond is present
in most organic compounds, that's not terribly useful! What it means is that you can ignore a trough
just under 3000 cm-1, because that is probably just due to C-H bonds.
The carbon-oxygen double bond, C=O, is one of the useful absorptions, found in the range
1680 - 1750 cm-1. Its position varies slightly depending on what sort of compound it is in.
The other useful bond is the O-H bond. This absorbs differently depending on its environment.
It is easily recognised in an acid because it produces a very broad trough in the range 2500 - 3300 cm-1.
The infra-red spectrum for ethanoic acid looks like this:

The possible absorption due to the C-O single bond is queried because it lies in the fingerprint
region. You couldn't be sure that this trough wasn't caused by something else.
The infra-red spectrum for an alcohol. Ethanol

The O-H bond in an alcohol absorbs at a higher wavenumber than it does in an acid -
somewhere between 3230 - 3550 cm -1. In fact, this absorption would be at a higher number still if the
alcohol isn't hydrogen bonded - for example, in the gas state. All the infra-red spectra on this page are
from liquids - so that possibility will never apply.
Notice the absorption due to the C-H bonds just under 3000 cm -1, and also the troughs between
1000 and 1100 cm-1 - one of which will be due to the C-O bond.

The infra-red spectrum for an ester. Ethyl ethanoate

This time the O-H absorption is missing completely. Don't confuse it with the C-H trough fractionally
less than 3000 cm-1. The presence of the C=O double bond is seen at about 1740 cm-1.
The C-O single bond is the absorption at about 1240 cm -1. Whether or not you could pick that out
would depend on the detail given by the table of data which you get in your exam, because C-O single
bonds vary anywhere between 1000 and 1300 cm -1 depending on what sort of compound they are in.
Some tables of data fine it down, so that they will tell you that an absorption from 1230 - 1250 is the
C-O bond in an ethanoate.
The infra-red spectrum for a ketone. Propanone

You will find that this is very similar to the infra-red spectrum for ethyl ethanoate, an ester.
Again, there is no trough due to the O-H bond, and again there is a marked absorption at about 1700
cm-1 due to the C=O.
Confusingly, there are also absorptions which look as if they might be due to C-O single bonds
- which, of course, aren't present in propanone. This reinforces the care you have to take in trying to
identify any absorptions in the fingerprint region.
Aldehydes will have similar infra-red spectra to ketones.

The infra-red spectrum for a hydroxy-acid/ 2-hydroxypropanoic acid (lactic acid)

This is interesting because it contains two different sorts of O-H bond - the one in the acid and
the simple "alcohol" type in the chain attached to the -COOH group.
The O-H bond in the acid group absorbs between 2500 and 3300, the one in the chain between
3230 and 3550 cm-1. Taken together, that gives this immense trough covering the whole range from
2500 to 3550 cm-1. Lost in that trough as well will be absorptions due to the C-H bonds.
Notice also the presence of the strong C=O absorption at about 1730 cm-1.
The infra-red spectrum for a primary amine. 1-aminobutane

Primary amines contain the -NH2 group, and so have N-H bonds. These absorb somewhere
between 3100 and 3500 cm-1. That double trough (typical of primary amines) can be seen clearly on
the spectrum to the left of the C-H absorptions.

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