Title: Experiment 12, Properties of hydrocarbons.

Objective: To determine the properties of hydrocarbons.

Introduction:
Hydrocarbons are organic compounds that consist of only C and H atoms.
They include the alkanes, alkenes, alkynes and the aromatic hydrocarbons. Almost
all useable supplies of hydrocarbons are obtained from fossil fuels. These compounds are
classified as saturated or unsaturated hydrocarbons. This classification only applies to the
aliphatic compounds (alkanes, alkenes and alkenes), that is the straight or branch chain
hydrocarbons depending on the number of bonds in between the carbon atom which is
the basis of hydrocarbons structural differences. Since alkanes have only single bonds, thus it
is said to be saturated, alkenes and alkynes which have carbon-carbon double or triple bonds
are said to be unsaturated. For aromatic hydrocarbons, they are cyclic compounds whose
structure is related to that of benzene, with 6 electrons in a six-membered ring.

In this experiment, hexane will be used as an example of saturated hydrocarbons
(alkanes),cyclohexene will be used as an unsaturated hydrocarbon (alkenes) and toluene as an
aromatic hydrocarbon.

i. Combustion
Hydrocarbons are currently the main source of the worlds electric energy and heat sources
(such as home heating) because of the energy produced when burnt. Often this energy is
used directly as heat such as in home heaters, which use either petroleum or natural gas.
Common properties of hydrocarbons are the facts that they produce steam, carbon dioxide
and heat during combustion and that oxygen is required for combustion to take place.

Typical combustion reaction: 2 C
4
H
10
+ 13 O
2
--> 8 CO
2
+ 10 H
2
O + heat energy

ii. Reaction with bromine
Bromine reacts readily with alkenes at room temperature in the absence of light to form the
corresponding dibromide compound. This reaction can be followed by the disappearance of
the brown bromine colour from the reaction medium, as long as the alkene is in excess.


Alkanes and toluene on the other hand can show reaction in the presence of sunlight only,
which will produce hydrogen bromide (HBr) as a side product when react with bromine.

The presence of HBr can be tested for by placing a piece of moist blue litmus paper above
the reaction vessel. Evolution of HBr will turn the litmus paper red, which indicate the HBr is
acidic. This can be used as an additional test for alkanes. Aromatic hydrocarbons will not react
with bromine either in the dark, or in the sunlight.

iii. Reaction with potassium permanganate
Potassium permanganate reacts readily with alkenes to form glycols or other oxidation
products. This is referred to as Baeyers test for alkenes. Neither alkanes nor aromatic
hydrocarbons show reaction with potassium permanganate. The reaction can be followed by
the disappearance of the purple colour of the KMnO
4
. The presence of clear or brown colour
indicate the presence of manganese oxide, MnO
2
.


Apparatus and Materials: Bunsen burner, Evaporating dish, test tubes, test tube rack, hexane
(C
6
H
10
), cyclohexene (C
6
H
10
), toluene (C
7
H
8
), 5% bromine (Br
2
dissolved in either
trichloroethane or in methylene chloride; either solvent is fine), 0.5% potassium permanganate
(KMNO
4
) dissolved in water 98.5% H
2
SO
4
.




Results:
i. Combustion:
a. Hexane: Burn in orange flame with little amount of smoke and soot.
b. Cyclohexene: Burn vigorously in orange flames with large amount of smoke and
soot.
c. Toluene: Burn very vigorously in orange flames with large amount of smoke and
soot.
d. Unknown compound A: Burn in orange flames with little amount of smoke and soot.
e. Unknown compound B: Burn vigorously in orange flames with large amount of
smoke and soot.

ii. Reaction with bromine:

Compounds
Observations
In the dark Exposed to sunlight
Hexane
The mixture turns to pale yellow
in colour after adding bromine.
The mixture turns to pale yellow
in colour after adding bromine
and turns back to colourless after
exposed to sunlight.
Cyclohexene
Pale yellow colour of bromine
water becomes colourless once
added into cyclohexene solution

Toluene
Two layers of mixtures are
formed. Upper layer is cloudy
yellow, lower layer is colourless.
Two layers of mixtures are
formed. Upper layer is cloudy
white, lower layer is colourless.
Unknown A
The mixture turns to pale yellow
in colour after adding bromine.
The mixture turns to pale yellow
in colour after adding bromine
and turns back to colourless after
exposed to sunlight.
Unknown B
Pale yellow colour of bromine
water becomes colourless once
added into unknown B solution




iii. Reaction with potassium permanganate:
a. Hexane: Two layers of mixtures are formed with upper layer is colourless while
lower layer is dark purple colour.
b. Cyclohexene: Two layers of mixture are formed with upper layer is colourless while
lower layer is brown colour with brown precipitate.
c. Toluene: Two layers of mixtures are formed with upper layer is colourless while
lower layer is dark purple colour.
d. Unknown compound A: Two layers of mixtures are formed with upper layer is
colourless while lower layer is dark purple colour.
e. Unknown compound B: Two layers of mixture are formed with upper layer is
colourless while lower layer is brown colour with brown precipitate.

Discussion:
For the part of combustion, we know that all hydrocarbons undergo combustion with
producing carbon dioxide, water and heat energy in complete combustion.
Equation:
a. Hexane: 2C
6
H
14
+ 19O
2
12CO
2
+ 14H
2
O
b. Cyclohexene: 2C
6
H
10
+ 17O
2
12CO
2
+ 10H
2
O
c. Toluene: C
7
H
8
+ 9O
2
7CO
2
+ 4H
2
O
From the observation, alkenes and aromatic hydrocarbon produced more soot and smoke than
alkanes when undergo combustion. Soot and smoke that produced was carbon monoxide and
even carbon, which produced when there is insufficient oxygen for those hydrocarbon
undergo complete combustion. Incomplete combustion is more likely to occur in aromatic
than alkenes than alkanes. The hexane, C
6
H
14
contain relatively less carbon atoms per all atoms
present in a molecule, so there is a more complete combustion and little soot is observed. The
cyclohexene, C
6
H
10
contain more carbon content per all atoms present in one molecule than
C
6
H
14
does. So soot and smoke formed which indicate incomplete combustion. The toluene
C
7
H
8
contains more carbon content per all atoms present in one molecule than C
6
H
10
does, so
more soot is observed, indicating that there is much incomplete combustion. The following
pictures show the sequence in increasing order of the time taken required for the completion
of combustion reaction of hydrocarbon. Accurate sequence is hexane, unknown A, cyclohexene,
unknown B and toluene.







For the part of reaction with bromine, alkanes react with bromine only when it is
exposed to sunlight. It undergoes free radical substitution by replacing one of the hydrogen in
hydrocarbon with one bromine atom. Sunlight will act as catalyst to break the bond, which
called as photochemical reaction. This is because alkanes contain sigma-bonds, which is
stronger bond and thus need sunlight to act as catalyst to break the bond. The mechanism is
shown below


For alkenes, from the observations we noted, alkenes react readily with bromine
although did not exposed to sunlight. This is because it undergo halogenations by addition
reaction due to it contain pi-bonds, which can be broken easily result from their imperfect
overlap. So, no sunlight is needed to act as catalyst to break the pi-bonds. Cyclohexene reacts
with bromine to form 1,2-dibromocyclohexane as a product. The mechanism is shown below.


For toluene, it is also undergo free radical substitution, which means react with bromine
with the presence of sunlight but, the reaction happens to the methyl group instead of the
benzene ring. The organic product formed is (bromomethyl)benzene. The mechanism is shown
below.
Step 1 (Initiation)
Heat or uv light cause the weak halogen bond to undergo homolytic cleavage to generate two
bromine radicals and starting the chain process.

Step 2 (Propagation)
(a) A bromine radical abstracts a hydrogen to form HBr and a benzyl radical, then
(b) The benzyl radical abstracts a bromine atom from another molecule of Br
2
to form the
benzyl bromide product and another bromine radical, which can then itself undergo reaction
2(a) creating a cycle that can repeat.

Step 3 (Termination)
Various reactions between the possible pairs of radicals allow for the formation of Br
2
or the
product, benzyl bromide. These reactions remove radicals and do not perpetuate the cycle.

Unknown compound A showed same observation with hexane while Unknown compound B
showed same observation with cyclohexene.




For reaction with potassium permanganate, alkenes is the only one that showed positive
result, thus it is called Baeyer permanganate test. The appearance of brown colour indicate the
presence of manganese dioxide, MnO
2.
This is because acidified potassium permanganate that
act as oxidizing agent is reduced into brown precipitate which is manganese dioxide and
cyclohexene is oxidized to diol.
Hexane (Before After) Cyclohexene (Before After) Toluene (Before After)
Unknown A (Before After) Unknown B (Before After)


Toluene can produce carboxylic acid from the reaction of potassium permanganate but it is
necessary to heat the mixture first. If not, no reaction will occur. Unknown A liquid got the
same observation as hexane and unknown B liquid got the same as cyclohexene.


Hydrocarbons compounds before adding with acidified KMNO
4


Hydrocarbon compounds after adding with acidified KMNO
4

Conclusion:
For combustion reaction, all compounds produced smoke, soot and orange flames. However,
hexane and compound A produce less soot compare to the other three compounds.
Cyclohexene and compound B produced more soot than the others three compound due to
more carbon content per atoms present. For the reaction with bromine, reaction is only occur
in the presence of UV light for alkanes and aromatic compounds by free radical substitution
reaction but cyclohexene react readily with bromine by addition reaction. For the reaction with
acidified potassium permanganate, hexane and toluene has no reaction but cyclohexene react
with potassium permanganate with leaving brown colour solution that indicate the presence of
manganese dioxide, MnO
2.
From the experiment, we can conclude that unknown compound A
is saturated hydrocarbon while unknown compound B is unsaturated hydrocarbon.