The Cerric Nitrate Test

Shows positive test for:

alcohols

Reactions:
the alcohol complexes with the cerric nitrate ion

How to perform the test:

Three drops of the compound to be tested are added to 10 drops of an acidified
cerric ammonium nitrate solution (a yellow solution).

Indications of a positive test:

The immediate formation of the red or red-brown color indicates a positive test.
Note that if the unknown is not soluble in water, two layers will be present. A
red color in either layer indicates a positive test.

a negative test (left) and a positive test (right)

The Chromic Acid Test

Shows positive test for:
1o and 2o alcohols and aldehydes

Reactions:
aldehydes and primary alcohols are oxidized to carboxylic acids while the
Cr+6 ion in the chromic acid is reduced to Cr+3.

secondary alcohols are oxidized to ketones while the Cr+6 ion in the chromic
acid is reduced to Cr+3.

How to perform the test:

Three drops of the compound to be tested are mixed with 5 drops of acetone
and 5 drops of chromic acid solution (an orange solution).

Indications of a positive test:

The disappearance of the red-orange color of chromic acid and the formation of
a blue-green color of the Cr (III) ion indicates a positive test. Note that if the
unknown is not soluble in water, two layers may be present. A blue-green color
in either layer indicates a positive test.
 a negative test (left) and a positive test (right)

The 2,4 Dinitrophenylhydrazine Test

Shows positive test for:

aldehydes and ketones

Reactions:
reacts with the carbonyl group of aldehydes and ketones

How to perform the test:

Five drops of the compound to be tested are mixed with 5 drops of the
dinitrophenylhydrazine reagent (an orange solution) in 2 ml of ethanol and the
tube shaken. If no positive test is observed immediately, the mixture should be
allowed to stand for 15 minutes.

A positive test is indicated by:

The formation of a yellow, orange or orange-red precipitate.
 a negative test (left) and a positive test (right)

The KMnO4 Test

Shows positive test for:

aldehydes, alkenes and phenols

Reactions:
aldehydes are oxidized to carboxylic acids

alkenes are oxidized to glycols

monohydroxy phenols do not yield stable products but dihydroxyl phenols can
be oxidized to quinones
How to perform the test:
Three drops of the compound to be tested are dissolved in 2 ml of water or
aqueous ethanol. 2% KMnO4 solution (a purple solution) is added dropwise and
the solution is shaken.

Indications of a positive test:

The purple color of the KMnO4 solution disappears and a precipitate of
MnO2 is formed.

a negative test (left) and a positive test (right)

The Iodoform Test

Shows positive test for:

acetaldehyde and methyl ketones

Reactions:
 the methyl group of the ketone is removed from the molecule and produces
iodoform (CHI3)

How to perform the test:

Three drops of the compound to be tested are added to 3 ml of water and 10
drops of KI/I2 solution (a dark purple-brown solution). 10% NaOH solution is
added dropwise until the dark color of the solution fades to yellow. The
solution is heated at 60oC. If the color of the solution becomes colorless, more
KI/I2 solution is added.

Indications of a positive test:

The formation of a yellow precipitate or suspension of iodoform is a positive
test.

a negative test (left) and a positive test (right)

The FeCl3 Test

Shows positive test for:

phenols
Reactions:
phenols complex with the iron ion

How to perform the test:

About 20 drops of 5% FeCl3 solution (a yellow solution) are added to a tube
containing 3 drops of the substance to be tested and the tube is stirred.

Indications of a positive test:

An intense color ranging from purple to reddish brown to green is observed.

a negative test (left) and a positive test (right)

Boiling Point

A simple, although not entirely accurate, definition for boiling point is the temperature
at which a substance is readily converted from the liquid phase to the gas phase. The
boiling point of a substance is determined by how strongly the molecules are attracted
to each other. The larger the interaction between molecules, the higher the boiling
point. The magnitude of the interactions are determined by two factors:

(1) the kind of molecule

molecules that contain carbonyl or hydroxyl groups (aldehydes, ketones
and alcohols)* tend to attract each other to a greater extent than do
molecules without these groups (alkanes, alkenes and alkynes).

(2) the size of the molecule

larger molecules tend to attract each other more readily than do smaller
molecules.
The boiling point does a very good job of narrowing down the possible identity of an
unknown compound. With a short list of possible compounds, like in this lab, the
boiling point would do such a good job that you might be able to identify your
compound without using any other information. To prevent this, you will only be
given a range into which the boiling point of your compound falls. For example, if
your unknown had a boiling point of 45 degrees Celsius, you might be told that the
boiling point falls between 0 and 50 degrees.

* Many of the other functional groups only briefly mentioned in this experiment have
the same effect on boiling point.

Water Solubility

The size of the molecule and functional groups present on the molecule also
determine whether or not it will be soluble in a particular solvent. Many of the same
functional groups that raise the boiling point of a compound (carbonyl and hydroxyl
groups) also increase its solubility in water. As a general rule monofunctional
compounds with three or fewer carbon atoms will be soluble in water. Those with six
or more carbon atoms will be insoluble. Those compounds with four or five carbons
are borderline.

Using this rule we should be able to predict that methanol (an alcohol with one
carbon) will be soluble in water, octanol (an alcohol with eight carbons) will be
insoluble and that butanol (an alcohol with four carbons) may or may not be soluble.

If water and a soluble compound are added to a container, the two will mix (below
right). If water and an insoluble compound are added to a container, the two do not
mix and we observe two layers (below left).