Experiment Properties of Alkenes

Discussion
Alkenes are unsaturated hydrocarbons that contain at least one carbon-carbon double bond
which is known as olefinic bond or ethylenic bond. Alkenes have the fewer number of hydrogen per
carbon and their general formula is C
n
H
2n
. alkene is also known as olefin. Alkanes which is also known as
paraffin are saturated aliphatic hydrocarbons with general formula of C
n
H
2n+2
. They have only carbon-
carbon single bond and carbon hydrogen bond with the maximum possible number of hydrogen per
carbon. Alkenes are more reactive than alkanes due to the presence of electrons in the ethylenic bond
which is a weak bond that can easily undergo additional reaction such as electrophilic addition. Alkenes
are connected to each other by ethylenic bond so they are having free electrons in the outer shell.
Alkenes have more bond energy compared to alkanes because of the presence of bond in addition to
sigma bond. The presence of the bond does not allow free movement of molecules. Hence a strain
builds up in the alkene molecules which makes it more reactive. The bond of alkenes is a very weak
bond that make the electrons of bond are more exposed to be attacked by an electrophile. Therefore,
alkenes are more reactive than alkanes.
In the combustion reaction, cyclohexene was burnt with a yellow-orange and very sooty flame.
Alkenes burn completely in excess oxygen to produce carbon dioxide and water. However, the
incomplete burning of alkenes will produce carbon monoxide and carbon. The carbon produced are the
soots that can be observed during the experiment. For example, the thermochemical equation of the
combustion of cyclohexene are
(i) 2C
6
H
10 (l)
+ 17O
2(g)
12CO
2(g)
+ 10H
2
O
(l)
(complete combustion)
(ii) C
6
H
10 (l)
+ 4O
2(g)
CO
2(g)
+ CO
(g)
+ 4C
(g)


+ 5H
2
O
(l)
(incomplete combustion)
Alkenes (cyclohexene) burn with more sooty flame compared to alkanes (cyclohexane). This is because
alkenes have higher percentage of carbon in their molecules than alkanes.
The reaction by adding bromine to cyclohexene is an additional reaction which is known as
bromination (halogenation). When an alkene is mixed with bromine, brown colour of bromine is rapidly
decolourised. whenever the reaction is carried in dark or light, there are no differences because reaction
with bromine is very reactive. The bromination starts when the electron cloud of the bond in the
hexane molecule first polarises an approaching bromine molecule. Electrophilic addition the occurs
when a weak sigma bond is formed between the positive end of the polarised molecule, Br
+
and one of
the carbon atoms in the double bond. The carbocation or carbonium ion formed then react rapidly with
the nucleophile. The example of mechanism of bromination is shown as below :



The example of chemical equation of bromination of cyclohexene is :

diethyl ether
C
6
H
10
Br
2 (l)

C
6
H
10 (l)
+ Br
2(l)
The product formed is only in single layer because both organic solvent which are bromine and
cyclohexene are mixed.
The reaction of adding bromine water to cyclohexene is an additional reaction of alkene. The
brown colour of bromine water decolourised and two colourless layer of solution are formed. The
solution formed two layer because the bromine water are inorganic solvent while cyclohexene is organic
solvent which cannot mix together. The chemical equation of this experiment is :
C
6
H
10 (l)
+ Br
2(aq)
C
6
H
10
Br
2 (aq)

Moreover, the reaction between cyclohexene and potassium manganate(VII) is known as
hydroxylation. The purple colour of potassium manganate(VII) decolourised and 2 layer of solution are
formed. In reaction with potassium manganate (VII), cyclohexene is oxidized and produce diol which two
hydroxyl groups are added to the double bond. The chemical reaction of this reaction is :
C
6
H
10
+ KMnO
4
C
6
H
10
(OH)
2
+ MnO
2
Hexene react with potassium manganate (VII) will produce diol. However, hexane will not react with
potassium manganate (VII) because hexane does not contain any carbon-carbon double bond and it has
reached maximum number of hydrogen per carbon.

In addition, when cycloalkene react with concentrated sulphuric acid, 3 layer of different colour
of solution are formed. the colour of the solution formed are dark brown, yellow and colourless. The
dark brown colour of solution is due to the presence of the precipitate which is dark in colour known as
cyclohexane hydrogen sulphate. This reaction is an oxidatihexn reaction. The chemical equation for this
reaction is
C
6
H
10
+ H
2
SO
4
C
6
H
11
OSO
2
OH
Hexane react with concentrated sulphuric acid will produce alkyl hydrogensulphates while hexane will
not react with concentrated sulphuric acid. This is because alkane is non-polar molecule while sulphuric
acid is polar molecule. There are no interaction between non-polar and polar molecule. Thus, hexane
will not react with concentrated sulphuric acid.
There are some tests can be used to distinguish between cyclohexene and cyclohexane. Firstly,
react these two organic compound with concentrated sulphuric acid. Cyclohexene will react with
concentrated sulphuric acid and produce three layer of colour solution while there is no reaction for the
cyclohexane. Secondly, react these two organic compound with bromine. Cyclohexene will decolourise
the reddish-brown bromine but cyclohexane will not decolourise the reddish-brown. Besides, reaction
with acidified potassium manganate (VII) solution also can be used to distinguish between cyclohexene
and cyclohexane. Cyclohexene will decolourise purple potassium manganate (VII) solution but
cyclohexane will not have any reaction.
During the experiment, there are some safety and precaution steps that must be done to
minimize the danger and error that will occur. During the experiment do not handle the chemical with
bare hand because the chemical solution such as concentrated sulphuric acid and bromine dissolved in
diethyl ether are corrosive. A pair of gloves must be worn. When shaking the solution, a cork is used to
close the mouth of the test tube before shaking. The solutions such as cyclohexene and concentrated
sulphuric acid must be handle in the fume chamber. After using the cyclohexene and bromine, the
reagent bottle needed to close quickly to avoid the organic vapors come out. Do not shake the test tube
when concentrated sulphuric acid is added to the cyclohexene. After finishing the experiment, the
solutions cannot be pour into the sink, it must be pour into a reagent bottle which is used to keep the
chemical waste.