An experiment to prepare ethene gas from ethanol and examine its

properties:
Aim:
The purpose of this experiment was to prepare samples of ethene gas by
dehydrating ethanol using aluminium oxide as a dehydrating agent and
catalyst and then to perform various tests on the gas obtained to examine its
properties.
Apparatus:
Chemicals:
Ethanol
Aluminium oxide
Lime water
Glass wool
Bromine water
Acidified potassium permanganate solution (very dilute).
Water
Additional apparatus:
Boiling tube
Rubber stopper with hole
Delivery tube
Trough
Test- tube rack
5 test tubes
5 rubber stoppers for test tubes
Retort stand
Spatula
Bunsen burner
Glass rod
Splint
Matches
Diagram:
- Preparation of ethene gas:

Method:
(1) Preparation of ethene:

Pour some ethanol into the boiling tube to a 2-3 cm depth

Add some glass wool to soak up the ethanol, using a glass rod to push the
wool down the tube.
Clamp the boiling tube in a horizontal position using a retort stand.
Put a small amount of aluminium oxide about half way along the boiling tube.
Complete the set up of the apparatus as shown in the diagram above.
Light the Bunsen burner, adjust it to a blue flame and heat the aluminium
oxide. (Make sure the test tube is filled with water when you start to collect
the gas produced.)
As the aluminium oxide gets hot the heat reaches the ethanol at the end of
the tube. The ethanol then changes to vapour, passes over the hot
aluminium oxide and is dehydrated to produce ethene gas.
Let the bubbles produced escape for a short time (these are mainly bubbles
of displaced air). Collect 5 test tubes of the gas and put a stopper on each
tube when it is filled.
When the test tubes have all been filled, loosen the retort stand and raise
the apparatus so that the delivery tube no longer dips into the water. This
avoids suck back of water as the tube begins to cool which could cause the
boiling tube to crack. Turn off the Bunsen burner.
(2) Testing the properties of ethene:
Combustion:
Remove the stopper of one of the tubes filled with ethene and apply a light
to the mouth of the test tube using a lighted splint.
Allow the gas to burn and when it has stopped burning add a small amount
of lime water to the test tube, stopper it and shake the tube a few times.
The limewater should turn milky white, showing that the gas burns in air to
produce carbon dioxide.
This is the reaction that occurs:
C2H4 + 3O2 2CO2 + 2H2O
Addition of bromine:
Taking great care, add about 1/10th of the test tube of bromine water to one
of the test tubes of ethene.
Replace the stopper and shake the tube a few times.
The yellow/red colour should disappear to form a colourless solution.
In the presence of bromine, bromine is added across the carbon carbon
double bond in ethene to form a colourless alkane called 1,2
dibromoethane and in the reaction above, when bromine in water is added to
ethene, a colourless compound called 2- bromoethanol is produced . This
means that adding bromine or bromine water is a common test for
unsaturation.
Addition of acidified potassium permanganate:

Add about 1/10th of very dilute potassium permanganate solution to one of

the test tubes of ethene and shake the tube a few times.
The purple colour of the permanganate solution should disappear to give a
colourless solution. (This colour change is evidence for the presence of a
carbon to carbon double bond.
Results:
Test:
Observations:
(1) Combustion
The gas burned with a luminous
flame and limewater turned
milky white when added showing
carbon dioxide was formed.
(2) Addition of bromine
The yellow/ red colour of the
bromine water turned to
colourless indicating
unsaturation (the carbon
carbon double bond in ethene)
(3) Addition of acidified
The purple colour of the
KMnO4
permanganate solution turned to
colourless indicating the
presence of the carbon carbon
double bond.
Discussion:
The first reaction encountered in this experiment was that for the production
of ethene by the dehydration of the alcohol, ethanol, over a heated catalyst,
in this case, aluminium oxide:
This is an elimination reaction as water is eliminated. This reaction can also
take place by using an acid catalyst such as concentrated sulphuric acid and
heating to about 180 degrees. The acid catalysts normally used are either
concentrated sulphuric acid or concentrated phosphoric(V) acid, H 3PO4.
Concentrated sulphuric acid produces inconvenient and rather messy results,
however. Not only is it an acid, but it is also a strong oxidising agent and so
it oxidises some of the alcohol to carbon dioxide and at the same time is
reduced itself to sulphur dioxide. Both of these gases have to be removed
from the alkene before it can be used industrially. These gases which are
produced are passed through sodium hydroxide solution to remove the
carbon dioxide and sulphur dioxide produced from the side reactions.
In this reaction, the acid first protonates the oxygen atom of the alcohol,
forming [CH3CH2OH2]+ , then water is lost which forms a carbocation and
finally the hydrogen ions that catalysed the reaction are regenerated. This
dehydration reaction is most likely for tertiary alcohols as the carbocation
produced is stabilised by the three alkyl groups that are attached to it.

Another example of the dehydration of an alcohol to produce an ethene is

the dehydration of cyclohexanol to produce cyclohexene and water.
Cyclohexanol is heated with concentrated phosphoric(V) acid and the liquid
cyclohexene distils off and can be collected and purified. Phosphoric(V) acid
tends to be used in place of sulphuric acid because it is safer and produces a
less messy reaction.
Dehydration can also be reversed to produce an alcohol such as ethanol from
ethene. This backwards reaction is exothermic and so favours low
temperatures and great care must be taken to provide the correct conditions
for the desired direction of the reaction so as to produce the desired
products.
The second reaction encountered in this experiment was the complete
combustion of ethene in oxygen to produce carbon dioxide and water, by the
reaction:
C2H4 + 3O2 2CO2 + 2H2O
This reaction is the same for all hydrocarbons when they are completely
combusted in oxygen; carbon dioxide and water are always produced.
The third reaction encountered was the addition of bromine water to ethene,
a common test for unsaturation. Bromine dissolves in water to form a
yellow/red solution to form what is commonly called bromine water and
this is used in the bromine water test to determine whether a hydrocarbon
is unsaturated or saturated. If the substance contains carbon-carbon double/
(triple) bonds, the solution changes to colourless as unsaturated undergo an
addition reaction with the bromine water and decolourise the bromine water.
If the substance is saturated and contains only carbon- carbon single bonds,
he colour of the bromine water remains the same and will be unaffected by
the hydrocarbon. Alkenes like ethene are much more reactive than their
alkane counterparts because of their unsaturation. Alkenes undergo rapid
addition reactions with halogens (e.g. Bromine) across their carbon-carbon
double bond whereas alkanes undergo slow substation reaction under
extreme conditions such as UV light. The reaction between ethene and
bromine, for example, occur almost spontaneously which is an electrophilic
addition reaction as an electrophile is attacking an electron rich area.

Reaction of ethene with bromine. (see conclusion for reaction with bromine
water).

The fourth and final reaction encountered was the reaction between ethene
and dilute acidified potassium permanganate. The permanganate is a purple
colour alone but when added to an alkene under acidic conditions it changes
to colourless. This is another way other than bromine water of distinguishing
between saturated and unsaturated substances, although bromine water is
more commonly used for this. Acidified potassium permangate is a very
strong oxidising agent and it oxidises an alkene such as ethene. The colour
change depends on whether the potassium manganate(VII) is used under
acidic or alkaline conditions; when under acidic conditions like in our
experiment with dilute sulphuric acid, the purple solution changes to
colourless and when made slightly alkaline (usually by adding sodium
carbonate solution), the purple solution first becomes dark green and then
produces a dark brown precipitate.
When ethene is oxidised by the permanganate ions, ethane- 1, 2-diol is
formed and the Mn7+ ions are reduced to Mn2+ ions:

However, the product, ethane-1,2-diol, is itself quite easily oxidised by

manganate(VII) ions, and so the reaction won't stop at this point unless the
potassium permanganate(VII) solution is extremely dilute, very cold and
preferably not under acidic conditions (although then permanganate would
not oxidise ethene!) This is why we had to use dilute potassium
permanganate solution and means that the reaction is not very useful as a
way of preparing ethane-1, 2-diol. The only real use for this reaction is to test
for carbon-carbon double bonds, but bromine water is usually used for this.
The results from our experiment seem accurate as they produced results that
agree with the structure and usual properties of alkenes as unsaturated
hydrocarbons: they combust completely in oxygen to produce carbon dioxide
and water, they perform addition reactions and react with bromine water
producing a colour change and indicating the presence of their carboncarbon double bond(s) and they are oxidised by permanganate ions also
causing a colour change. All of these chemical properties can be explained in
terms of the unsaturation of alkenes. The only real problem we came across
was the sucking back of water when we forgot to remove the apparatus from
the water after we had finished preparing our samples of ethene. This
happened because the boiling tube was beginning to cool as soon as the
Bunsen was turned off. Luckily we noticed in time and removed the
apparatus from the water before any damage to the tube could be made!
The fact that ethene is insoluble in water due to its bonding was essential for
our experiment as the gas was collected over the water without it dissolving.
Conclusion:
From this experiment, whose purpose was to prepare the unsaturated gas,
ethane, and test its properties, the following conclusions can be drawn:

Firstly, ethane can be prepared by dehydrating the primary

alcohol ethanol using a catalyst and dehydrating agent such as
aluminium oxide. This elimination reaction can be summarised in
the equation:
H
H
H
H
Al2O3
H--C----CH

C=C
+ H2O
-H2O
H
OH
H
H
Ethanol
Ethene
Water
This reaction is reversible, meaning under certain conditions ethene
can be hydrated to form ethanol.
When ethane is combusted, carbon dioxide is produced which was indicated
by the change of the lime water to milky white. The reaction that occurred,
which is the same for the complete combustion all hydrocarbons, was:
C2H4 + 3O2 2CO2 + 2H2O
Ethene is a colourless gas that belongs to the homologous series of the
alkenes as it contains a carbon carbon double bond it is unsaturated.
Ethene, like all unsaturated compounds, tends to undergo addition reactions
across its carbon carbon double bond. When it is reacted with bromine, for
example, bromine adds across the carbon carbon double bond to a
colourless compound called 1,2 dibromoethane, a haloalkane.
This reaction with bromine would be as follows:

When reacted with bromine water, as in this experiment, a colourless

compound called 2-bromoethanol forms.
This reaction with bromine water would be as follows:

As the colour of bromine is a yellow/red colour disappears when bromine/

bromine water is added to ethene and also in other unsaturated compounds,
and as addition reactions occur only in unsaturated compounds, adding
bromine water is often used to test for unsaturation, i.e.: to detect whether
there are any carbon-carbon double or triple bonds present in the compound.
Another way of testing for unsaturation is to add an acidified solution of
potassium permanganate solution to oxidise ethene. In this reaction the
purple colour of the permanganate changes to colourless.