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This experiment will introduce you to some of the more common functional groups of organic chemistry.
The functional group is that portion of the molecule that undergoes a structural change during a chemical
reaction. The functional groups that will be studied in this experiment are carboxylic acid, amines
aldehyde, ketone, alcohols and alkenes.
You will learn chemical tests that will allow you to distinguish one functional group from another. You
will use the chemical tests to identify the functionality of an unknown organic compound. In addition, you
will use a water solubility test to determine whether your organic compound is of high or low formula
weight.
The chemical tests you will perform make up a sequence of experiments designed to determine the
absence of or suggest the presence of particular functional groups. The complete sequence is shown in the
flow diagram on page 8. This diagram can serve you in several ways:
It is a summary of the procedure that you are to follow in classifying your unknown as one of the
functional group types.
It can order your thoughts as you read the discussion of each test, and help you to understand the
significance of that test.
It can enhance your appreciation for and enjoyment of this experiment. Your role is that of chemist
and detective: you will employ this cleverly devised scheme to sleuth out the identity of your unknown's
functionality.
Experiment 1 2
O O
R C OH + H2O R C O- + H3O+
O O
R C OH + NaOH R C O- Na+ + H2O
If the compound is not soluble in either dilute acid or dilute base, then it is a neutral compound (ketone,
aldehyde, alcohol, alkene) of high molecular weight.
H
R' C O + H2N N NO2 R' C N N NO2 + H2O
H
R R
O2N O2N
O O
-
R C H + 2 Ag(NH3)2+ + 2 OH− R C O + NH4+ + 2 Ag(s) + H2O + 3NH3
An aldehyde is indicated by the appearance of a silver mirror on the wall of the test tube or a precipitate
of silver metal.
O O
H2CrO4 H2CrO4
primary alcohol: R−CH2−OH R C H R C OH
O
H2CrO4
secondary alcohol: R' CH OH R' C R
R
R''
H2CrO4
tertiary alcohol: R' C OH no visible reaction
R
An alcohol is indicated by disappearance of the orange color of the chromic acid reagent and the
formation of a green or blue-green solution.
Experiment 1 5
Br Br
H H
C C + Br2 H C C H
H H H H
colorless red solution colorless or light yellow solution
Bromine solutions are reddish-brown; alkenes and bromoalkanes are colorless. Rapid decolorization of
bromine is a positive indication of an alkene.
III. PROCEDURE
The following procedures are to be carried out first on samples of known compounds so that positive
responses for each test can be observed. When you feel confident that you can recognize a positive test for
each procedure, obtain an unknown from your instructor. Substitute your unknown for the known
compound in each test. Use the flow diagram on page 8 to follow your progress in identifying the
functionality and molecular weight (high or low) of your unknown.
Known compounds to be tested for solubility properties: ethanoic acid, propanone, cyclohexene,
diethylamine, benzaldehyde, 1-pentanol.
provided and rinse the test tube thoroughly. It may deposit explosive products upon standing or drying
out.
enthanoic acid
diethylamine
propanone
benzaldehyde
1-pentanol
cyclohexene
Chemical equation:
Experiment 1 10
Chemical equation:
Chemical equation:
Chemical equation:
Chemical equation:
Chemical equation:
Experiment 1 11
Unknown Number___________________
Water Solubility/Litmus
5% NaOH Solubility
5% HCl Solubility
Tollen’s Test
Decolorization of Bromine