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Objective

To identify hydrocarbons and determine their properties.



Introduction

Hydrocarbons are organic compounds that contain only carbon and hydrogen atoms.
These includes, alkanes, alkenes, alkynes and arenes. There are teo classes of hydrocarbons.
They are saturated and unsaturated. A saturated hydrocarbon contains only single bonds
between its atoms. This classes is represented by alkanes and cycloalkanes.



An unsaturated hydrocarbon contain at least one carbon-carbon double bond or triple bond in
its molecule. Alkenes, alkynes and arenes are representatives of this class.


Hydrocarbons are divided into 2 classes known as aliphatic compound and aromatic
compounds. Aliphatic compound, the carbon atoms are arranged in an open chain structure
and not in closed rings. alkanes alkenes, and alkynes are aliphatic hydrocarbons. Alkanes are
the simplest family of hydrocarbon compounds containing carbon and hydrogen only.
Aromatic compounds at least one benzene ring in their structures. The simplest example is
benzene.




Materials

1. Cyclohexane
2. Cyclohexene
3. Concentrated H
2
SO
4

4. 2% Bromine in tetrachloromethane
5. 0.50 % KMnO
4

6. 10% NaOH
7. 10% Na
2
CO
3

8. Distilled water
9. Blue litmus paper

Apparatus

1. Test tubes (10 per group)
2. Test tube rack
3. 100ml beaker
4. Test tube holder (clamp)

Procedure

A.) Bromine test

1. In a clean test tube, add 1 ml of cyclohexane to 5 10 drops of 2% bromine in
tetrachloromethane (Br
2
/CCl
4
). Shake well and observe after two or three minutes.
2. Prepare a second similar tube. Place the first tube in your laboratory locker and the
second in bright sunlight.
3. Allow both tubes to stand for 10 - 15 minutes and compare them.
4. Observe the colour of the solution in each tube.
5. Test whether or not hydrogen bromide was evolved by placing a blue litmus paper into
the test tube. Record the results.
6. Repeat steps 1-5 with cyclohexene, with just one test tube of sample. ( No need for
sunlight reaction)

B.) Aqueous Potassium Permanganate (Baeyer's Test)
1. In a clean test tube, add 1 ml of cyclohexane to a mixture of 5 10 drops of dilute
potassium permanganate solution (0.5 % KMnO
4
solution) and 3 drops of dilute sodium
carbonate solution (10% Na
2
CO
3
solution).
2. Shake the tube for 1-2 minutes, and note the results.
3. Repeat steps 1-2 with cyclohexene and note the results.

C.) Sulfuric Acid Test
1. In a clean test tube add 1 ml of cyclohexane, and with gentle shaking, add 5 drops of
concentrated sulfuric acid very cautiously.
2. Shake the tubes well and note the results.
3. Observe whether heat evolved and whether the hydrocarbon dissolves.
4. Discard the contents by pouring them into a beaker containing at least 50 ml of water.
5. Repeat steps 1-4 with cyclohexene and note the results.

D. Sodium Hydroxide Test
1. In a clean test tube, add 1 ml of cyclohexane to 5 drops of dilute sodium hydroxide
solution (10% NaOH solution) and shake well.
2. Observe the changes and note the results.
3. Repeat steps 1-2 with cyclohexene and note the results.

.
Results
Reagent Used Observation
Cyclohexane Cyclohexene
0.50%

+ 10%


The solution contains
double layers and
remains purple in
colour.

The solution contains
double layers. The purple
solution turns
brown colour and there
are brown precipitates
present.
Concentrated

The solution is clear. It


has double layers. There
is no heat
evolved. (hydrocarbon
not dissolve)
The solution contains
double layers. The
solution turns cloudy
and there is heat released
10% NaOH The solution remains
colourless with double
layers
The colourless solution
turns
yellow with double
layers






Discussion

Hydrocarbons are organic compounds that contain only carbon and hydrogen atoms.
These includes, alkanes, alkenes, alkynes and arenes. There are teo classes of hydrocarbons.
They are saturated and unsaturated. A saturated hydrocarbon contains only single bonds
between its atoms. This classes is represented by alkanes and cycloalkanes.

Hydrocarbons are divided into classes know as aliphatic compounds and
aromatic compounds. Aliphatic compounds are namely alkanes and alkenes. Alkanes are the
simplest family of hydrocarbons-compounds containing carbon and hydrogen only. They
only contain carbon-hydrogen bonds and carbon-carbon single bonds. The first is methane,
followed by ethane, and propane. C
n
H
2n+2.
The simplest alkane, which is methane is a natural
product of the anaerobic bacterial decomposition of vegetable matter under water. Another
proven source of methane is termites. When termites consume wood, the microorganisms that
inhabit their digestive system break down cellulose ( a component wood ) into methane,
carbon dioxide and other compunds.


The first test conducted is Baeyers Test which is aqueous potassium permanganate
test. This test is been done by adding 1 ml of cyclohexane to a mixture of 3 ml of dilute
potassium permanganate solution and 3 ml of dilute sodium carbonate solution in a clean test
tube. The test tube is then shaken for 1 to 2 minutes. The test tubes must be shaken
thoroughly so that the reaction is equal.


There is no reaction in the solution. Thus, it remains purple in colour. However, there
is a double layer which is formed on the surface of the solution. The double layer formed is
due to the oil present in the benzene ring of the cyclohexane.

The test is then repeated by using cyclohexene instead of cyclohexane. The reaction
that takes places is oxidation which causes the purple solution to turn brown colour. There is
also brown precipitate formed and the surface of the solution has double layers. The purple
solution changes colour to brown because potassium permanganate is reduced to manganese
dioxide, which is the brown precipitate. The double layers exist due to the same reason as in
the cyclohexane.


3C6H10+ KMnO4+ 2H2O 3C6H10OH + MnO2+ KOH


After that is the sulphuric acid test . 1 ml of cyclohexane is added into a clean test
tube and with gently shaking, 3 ml of concentrated sulphuric acid is added cautiously. The
tubes are then shaken for a while. Then, quickly the test tube is placed on the palm of my
hand to test whether heat evolved.

Alkanes are not reactive as this reaction is an addition reaction. Hence the solution remains
colourless but there is a double layer that formed on the surface of the solution.

For cyclohexene, the solution turns cloudy and there is heat released. Cyclohexene reacts
with concentrated sulphuric acid to produce alkyl hydrogensulphates. There is heat released
due to the breaking down of the carbon-carbon double bond in cyclohexene which releases
energy that produces a net evolution of heat energy. The mixture of solution is then discarded
into a beaker containing with at least 50 ml of distilled water to dilute the concentrated
sulphuric acid in the mixture as it is too acidic before pouring it into the sink.

The last test is sodium hydroxide test that is conducted by adding 1 ml of cyclohexane
to 3 ml of dilute sodium hydroxide solution and is then shaken well. There was no change or
reaction occurs in the solution except that a double layer is formed on the surface of the
solution.

The test is then repeated by using cyclohexene to replace cyclohexane. The colourless
solution turns yellow and has a double layer on the surface of the solution for cyclohexene.

Throughout all the tests, it is noted that cyclohexane is compared with cyclohexene to
identify and determine their properties. It can be seen that cyclohexene is much more reactive
compared to cyclohexane as it undergoes addition reactions. However, cyclohexane does not
participate in any addition reaction due to its carbon-carbon single bond. Instead,
cyclohexane undergoes halogenation which is a substitution reaction in the first test but
remain unreactive on the other tests. There is reaction between alkanes and chlorine or
bromine. The interesting reactions happen in the presence of ultraviolet light (sunlight will
do). These are photochemical reactions and happen at room temperature. It is known as free
radical substituition.

The reddish-brown bromine is decolourised as it reacts with the alkene.
A liquid alkene (like cyclohexene) can be shaken with liquid bromine or its solution in
tetrachloromethane.
Chlorine reacts faster than bromine, but the chemistry is similar. Iodine reacts much, much
more slowly, but again the chemistry is similar. This decolourisation of bromine is often used
as a test for a carbon-carbon double bond. If an aqueous solution of bromine is used (bromine
water), a mixture of products. The other halogens, apart from fluorine, behave similarly.
(Fluorine reacts explosively with all hydrocarbons - including alkenes - to give carbon
and hydrogen fluoride.)
The mechanism for the reaction between ethene and bromine
The reaction is an example of electrophilic addition.


Precautions

1. Lab coat and closed shoes need to wear before entering the lab
2. The eyes to the scale graduated measuring cylinder need to be placed
perpendicularly during the measuring of hydrochloric acid to avoid parallax error.
3. Use only small amount of the substances as it is harmful. This experiment need to
get under supervision from lecturer.
4. Hydrochloric acid is corrosive as it strong acidic solution, it need to be handle
with care.
5. The test tubes must be shaken thoroughly so that the reaction is equal.
6. Make sure that the conical flask is in a clean and dry condition before using it.
7. Clean all the apparatus after using it.


Conclusions
In this experiment, the properties and the difference between an alkane and alkene can
be identified. Thus, this experiment is a succeed. Alkane is identified from alkene by its
properties. It can be seen from the tests conducted in the experiment that alkene is much more
reactive than alkane. Alkanes are unreactive because they are saturated hydrocarbon. Their
carbon-carbon single bonds are unreactive and they undergo substituition reaction. Alkenes
are reactive because they are unsaturated hydrocarbons. Their carbon-carbon double bonds
are reactive. Thus, alkenes undergo a lot of addition reaction while alkane does not undergo
any addition reaction in the experiments conducted. Instead, alkane only undergo
halogenation which is a substitution reaction when react with bromine water. Thus, alkene is
more reactive than alkane.




Questions
1. Why is there a difference in reaction when the bromine test is done in the dark and in
the presence of sunlight? Explain your answer.
Because, there is no reaction of bromine in the dark condition. There is only reaction
when there is presence of ultraviolet light, (sunlight will do ). These are photochemical
reactions, and happen at room temperature. It is known as free radical substituition.

2. Write the equation for the reaction between cyclohexane and sodium hydroxide.
There is no reaction, therefore there is no equation.
3. Explain why the hydrocarbons dissolve in one solvent, but not the other.
Explain why alkenes are more reactive compared to alkanes.
Hydrocarbons are dissolve in organic solvent, but not in water. Polarity plays the biggest
role. Like substances dissolve other like substances. Hydrocarbons (which are non-polar)
are soluble in non-polar solvents such as benzene and carbon tetrachloride. They are not
soluble in polar solvents, such as water or ether. It is like the concept of hydrophobic and
hydrophilic. Hydrophilic have the affinity towards water, while hydrophobic does not
have the affinity towards water. In this context, hydrocarbons are hydrophobic which
means it does not react with water.
Alkanes are unreactive because they are saturated hydrocarbons. Their carbon-carbon
single bonds are unreactive. They undergo substituition reaction. However, alkenes are
reactive because they are unsaturated hydrocarbon and their carbon-carbon double bonds
are reactive. They undergo addition reaction.

References
1. http://www.quora.com/Organic-Chemistry/Why-is-alkene-more-reactive-than-
alkane
2. http://wiki.answers.com/Q/Why_are_hydrocarbons_soluble_in_one_solvent_and_
not_on_the_other?#slide=3
3.

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