CHME 237

EXPERİMENT 8

Name: Çiğdem Burçin

Surname: İŞLER
ID:2256238
Date:20/12/17
 FUNCTIONAL GROUPS AND INFRARED SPECTROSCOPY OF UNKNOWN ONE

Purpose of the experiment

Determine the identity of unknown one compound by identifying its functional groups by their
chemical properties and with their interaction with infrared light.
Theory
Organic compounds are mostly carbon and hydrogen containing compounds. Atoms or a group
of atoms on the hydrocarbon chain that shows a characteristic set of physical and chemical
properties and generally determine the chemical properties of the hydrocarbon are called
functional groups.

Functional Groups

Hydroxyl (-OH group)-divided into:

 Alcohols-the -OH group is bonded to a hydrocarbon chain

 Phenols -the -OH is bonded directly to benzene ring, are more acidic than
alcohols
Carbonyl groups(R-C=O)-obtained from mild oxidation of alcohols, divided into:

 Aldehydes-have a hydrogen directly bonded to the carbonyl group, are

active ingredients of perfumes and flavours such as vanilla, are easily
oxidised to carboxylic acids (a property that distinguishes them from
ketones), most common aldehyde is formaldehyde.
 Ketones -have no hydrogen bonded to the carbonyl group, most common
ketone is acetone.
Carboxylic acids-have relatively high boiling points and a tendency towards water solubility,
react with sodium bicarbonate to release carbon dioxide, most common acid is ethanoic acid
(mostly found in vinegar), aspirin is a carboxylic acid as well.

Unsaturated hydrocarbons-contain double and /or triple bonds between carbon atoms, are
highly reactive with halogens through addition reactions.

Infrared spectroscopy

Infrared spectroscopy-is the analysis of infrared light interacting with a molecule.

Main use in in organic and inorganic chemistry by chemist to determine the presence of
functional groups.
Measures the vibrations of atoms and based on this it is possible to determine the functional
groups.

Covalent bonds can be stretched and bent in addition to the mobile nature of organic
molecules and facile rotation of groups about single bonds molecules experience vibrational
motions unique for each component atom.

Infrared spectrometers allow chemists to obtain an absorption specta od compounds that are
unique to them.

Stronger bonds and asymmetric stretches absorb energy of higher wavenumbers than weaker
bonds and symmetric stretches. The presence of bands in regions gives direct information while
their absences may be used to deduce absence of functional groups.

Apparatus and Chemicals

Chemical test
Apparatus: test tubes, Dropper, Water bath, Thermometer.
Chemicals: Ceric Nitrate, Known Alcohol, 0.5M silver Nitrate, 6M Ammonia solution, Known
aldehyde, Sodium Bicarbonate, Known Carboxylic acid, 2% potassium permanganate, Known
unsaturated hydrocarbon.
Infrared Spectroscopy
Apparatus: Mortar and pestle, Dropper, Infrared Spectrometer.
Chemicals: Unknown, Dry potassium bromide (KBr).

Procedure
Chemical Identification
Hydroxyl group

Add 3 drops of ceric nitrate solution to 3 small test tubes.

To the first add 2 drops of a known alcohol, the second add 2 drops of a saturated
hydrocarbon and the third 2 drops of the unknown.
Let them stand for 2 min and record observations.
Carbonyl group

Add 10 drops of dinitrophenylhydrazine reagent(DNP) to 4 small test tubes.

To the first add 1 drop of a known ketone, the second add 1 drop of a known aldehyde
and the third 1 drop of the saturated hydrocarbon and to the fourth add 1 drop of the
unknown.
 Record your observations.
Aldehyde
Add 5 drops of 0.1M silver nitrate and 6 drops of 6 M ammonia.
Add 2 or 3 drops of known aldehyde and mix the contents thoroughly
Allow the test tube to stand in a hot water bath for about 10 min and a silver mirror
should be deposited if aldehyde is present.
Ketone
If carbonyl group is positive and aldehyde negative unknown is a ketone
Carboxylic acids

Add a few drops of the carboxylic acid in a small test tube, a saturated hydrocarbon to
the second test tube and a few drops of unknown in the third test tube.
Add a few drops of 10% sodium bicarbonate to each test tubes and record your
observations.
Unsaturated hydrocarbon

Add a few drops of the known unsaturated hydrocarbon in a small test tube, a
saturated hydrocarbon to the second test tube and a few drops of unknown in the third
test tube.
Add to each test tube one drop of ethyl alcohol and a drop of 2 % potassium
permanganate.
Record your observations.
Saturated hydrocarbons

If all of the above tests are negative then substance is a saturated hydrocarbon.
Infrared Identification

Preparation of Samples for FTIR

Solid
Obtained by mixing the solid with dry KBr, grinding to a fine, well mixed powder, and then
forming a disk of the mixture by applying high pressure. The disk will then be inserted to the
infrared spectrometer.
Liquid
Make a disk of dry KBr. Drop 1 or 2 drops of your unknown onto the disk spread it throughout
the disk. The disk will then be inserted to the infrared spectrometer.
Data

Infrared Spectroscopy

Benzaldehyde
PEAKS INTENSITY IDENTITY OF GROUP
1500-1650 MEDIUM C=C
1700-1750 HIGH C=O
2850-3000 MEDIUM C-H

Cyclohexene
PEAKS INTENSITY IDENTITY OF GROUP
1500-1650 MEDIUM C=C
2850-3000 HIGH C-H
3080-3140 HIGH =C-H

CHEMICAL PROPERTIES TEST

See attached.
Result and Conclusion
In our experiment we were able to identify the unknown by using both chemical properties of
the functional groups and infrared spectroscopy
In the chemical properties data collected pointed to presence of both Aldehydes and
Unsaturated Hydrocarbons. The data collected from the infrared spectroscopy of Benzaldehyde
and Cyclohexene when counter matched with those from chemical properties test conclusively
points to the identity of our unknown to be Benzaldehyde
References
 https://www2.chemistry.msu.edu/faculty/reusch/virttxtjml/spectrpy/infrared/
infrared.htm
 http://www.webassign.net/sample/ncsumeorgchem1/lab_2/manual.html