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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 world’s 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 C4H10 + 13 O2 --> 8 CO2 + 10 H2O + 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 Baeyer’s 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 KMnO4. The presence of clear or brown colour
indicate the presence of manganese oxide, MnO2.

Apparatus and Materials: Bunsen burner, Evaporating dish, test tubes, test tube rack, hexane
(C6H10), cyclohexene (C6H10), toluene (C7H8), 5% bromine (Br2 dissolved in either
trichloroethane or in methylene chloride; either solvent is fine), 0.5% potassium permanganate
(KMNO4) dissolved in water 98.5% H2SO4.

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:

Observations
Compounds
In the dark Exposed to sunlight
The mixture turns to pale yellow in
The mixture turns to pale yellow colour after adding bromine and
Hexane
in colour after adding bromine. turns back to colourless after
exposed to sunlight.
Pale yellow colour of bromine
Cyclohexene water becomes colourless once
added into cyclohexene solution
Toluene Two layers of mixtures are Two layers of mixtures are formed.
formed. Upper layer is cloudy Upper layer is cloudy white, lower
yellow, lower layer is colourless. layer is colourless.
The mixture turns to pale yellow in
The mixture turns to pale yellow colour after adding bromine and
Unknown A
in colour after adding bromine. turns back to colourless after
exposed to sunlight.
Pale yellow colour of bromine
Unknown B 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: 2C6H14 + 19O2 → 12CO2 + 14H2O
b. Cyclohexene: 2C6H10 + 17O2 → 12CO2 + 10H2O
c. Toluene: C7H8 + 9O2 → 7CO2 + 4H2O
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, C6H14 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,
C6H10 contain more carbon content per all atoms present in one molecule than C6H14 does. So
soot and smoke formed which indicate incomplete combustion. The toluene C7H8 contains more
carbon content per all atoms present in one molecule than C6H10 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 Br2 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 Br2 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.
Hexane (Before After) Cyclohexene (Before After) Toluene (Before After)

Unknown A (Before After) Unknown B (Before After)


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, MnO2. 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.

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 KMNO4

Hydrocarbon compounds after adding with acidified KMNO4

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, MnO2. From the experiment, we can conclude that unknown compound A is
saturated hydrocarbon while unknown compound B is unsaturated hydrocarbon.