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ANALYSIS OF

HYDROCARBONS
(Alkanes, Alkenes, Alkynes and
Aromatics)

INTRODUCTION
HYDROCARBONS are the simplest
organic compounds consisting of the C
and H atoms only. Hydrocarbons are
generally insoluble in water because of
their non-polarity. They are generally
classified either as aliphatic or aromatic
hydrocarbons.
Aliphatic hydrocarbons are
derived by chemical degradation of
fats or oils. These are hydrocarbons
which does not contain a benzene
ring. Aliphatic hydrocarbons can
further be classified either as
Saturated or Unsaturated
hydrocarbons.
Saturated hydrocarbons are whose
compounds of carbon and hydrogen having
only single bond between carbon to carbon
bond with the standard formula C(n)H(2n+2).

ALKANES are compounds containing at least 2
carbons that are bonded through single covalent
bond. Also called as PARAFFINS- derived from Latin
word meaning little activity that sates that alkane
compounds are very unreactive compare to alkene
and alkyne
R C C R


Unsaturated hydrocarbons are those
compounds of carbon and hydrogen that
contains one double or triple bond
between carbon atoms (carbon-carbon ).
ALKENES are compounds containing carbon that
are bonded through double bonds. Also called as
OLEFINS forming oily liquids on reaction with chlorine
gas.
R C C R
ALKYNES are compound containing carbon
bonded through triple bonds. Also called
as ACETYLENES ( C
2
H
2
) simplest alkyne
R C C R






Aromatic hydrocarbons are obtained by
chemical degradation of certain pleasant
smelling plant extracts. They are compound
containing special six carbons arranged in a
ring formation with three alternating double
bonds. Aromatic hydrocarbons can further
be classified as Alkylated or Non-alkylated
hydrocarbons.
Alkylated hydrocarbons contains an alkyl
group. It is formed when an aromatic ring
with an alkyl halide undergoes alkylation.
Non-alkylated hydrocarbons has no alkyl
substituent attached to it and is less reactive
than the alkylated one


Many hydrocarbons occur in nature like
petroleum, asphalt, natural gas, etc. In
addition to making up fossil fuels, they
are present in trees and plants.

PARALLEL CHEMICAL TEST
A chemical test perform in a way that
different parameters are observed
simultaneously.

There are three tests that can be performed
to identify hydrocarbons. These are the
Nitration test, Bromine Test and the
Permanganate test.

NITRATION TEST is used to test the
aromacity of the compound. A positive result
yields a yellow oil or precipitate describing
an aromatic hydrocarbon.
BROMINE TEST detects the presence of
unsaturation or phenols in the compound.
The positive result is a colorless solution.
OXIDATION TEST/ PERMANGANATE
TEST detect the presence of unsaturation.
The positive result yields a brown precipitate
or a blue green solution.
Objectives
To be able to differentiate various
types of hydrocarbons
To be able to device a scheme to
distinguish one hydrocarbon from the
other
Characterize an unknown
hydrocarbon through parallel chemical
tests
Materials
Test tubes
Test tube rack
Dropper
Beaker
1:1 H2SO4
HNO3 (Nitrating
reagent)
5% Br2 in
CH2Cl2
2% aq. KMnO4
Hexane
Cyclohexene
Naphthalene
Toluene
10% NaOH
Unknown liquids
Procedure
Hexane
(5 drops)
Cyclohexene
(5 drops)
Napthalene
(5 drops)
Toluene
(5 drops)
Unkown #1
(5 drops)
Unkown #2
(5 drops)
Unkown #3
(5 drops)
Unkown #4
(5 drops)
Record
observation
Nitrating
Mixture
(8 drops)
Place in warm
water bath for
8 minutes
Add 20 drops
of H
2
O


Nitration Test
Bromine
Reagent
(5 drops)
Hexane
(5 drops)
Cyclohexene
(5 drops)
Napthalene
(5 drops)
Toluene
(5 drops)
Unkown #1
(5 drops)
Unkown #2
(5 drops)
Unkown #3
(5 drops)
Unkown #4
(5 drops)
Record observation
Bromine Test
Hexane
(5 drops)
Cyclohexene
(5 drops)
Napthalene
(5 drops)
Toluene
(5 drops)
Unkown #1
(5 drops)
Unkown #2
(5 drops)
Unkown #3
(5 drops)
Unkown #4
(5 drops)
Record
observation
KMnO
4
(1 drop)
10 % NaOH

(4 drops)
Place in warm
water bath for
2 minutes
Permanganate
Test
Set-up
Test tube
Test tube rack
RESULTS
Hydrocarbon Nitration
Reaction test
Bromine Reaction
test
Permanganate
Reaction test
Hexane - - -
Cyclohexene - + +
Naphthalene + - -
Toluene + - -
1 + - -
2 + - -
3 - - -
4 - +

+
Group 1
Hydrocarbon Nitration
Reaction test
Bromine
Reaction test
Permanganate
Reaction test
Hexane - - -
Cyclohexene - + +
Naphthalene - - +
Toluene + - -
5 + - -
6 - - +
7 - + +
8 - - +
Group 2
Hydrocarbon Nitration
Reaction test
Bromine
Reaction test
Permanganate
Reaction test
Hexane - - +
Cyclohexene - + +
Naphthalene + - +
Toluene + - -
9 + - -
10 - + +
11 - - +
12 + - +
Group 3
Hydrocarbon Nitration
Reaction test
Bromine
Reaction test
Permanganate
Reaction test
Hexane - - -
Cyclohexene - + +
Naphthalene + - -
Toluene + - -
13 + - -
14 - + +
15 - - -
16 + - -
Group 4
Hydrocarbon Nitration
Reaction test
Bromine
Reaction test
Permanganate
Reaction test
Hexane - - -
Cyclohexene - + +
Naphthalene + - +
Toluene + - -
17 + - +
18 + - -
19 - - -
20 - + +
Group 5
Hydrocarbon Nitration
Reaction test
Bromine Reaction
test
Permanganate
Reaction test
Hexane - - -
Cyclohexene - + +
Naphthalene + - +
Toluene + - -
21 + - -
22 + - +
23 - + +
24 - - -
Group 6
Hydrocarbon Nitration
Reaction test
Bromine Reaction
test
Permanganate
Reaction test
Hexane - - -
Cyclohexene - + +
Naphthalene + - -
Toluene + - -
25 + - -
26 - + -
27 - - -
28 + - -
Group 7
Hydrocarbon Nitration
Reaction test
Bromine
Reaction test
Permanganate
Reaction test
Hexane - - -
Cyclohexene - + +
Naphthalene + - -
Toluene + - -
29 + - -
30 - + +
31 - - -
Group 8
Hydrocarbon Nitration
Reaction test
Bromine
Reaction test
Permanganate
Reaction test
Hexane - - -
Cyclohexene - + +
Naphthalene + - -
Toluene + - +
32 + - -
33 - - -
34 - + +
Group 9
Nitration
Test
Bromine
Test
Oxidation
Test
Hexane - - -
Cyclohexen
e
- + +
Naphthalene + - -
Toluene + - +
DISCUSSION OF
RESULTS
There are three tests that were performed in
the analysis of hydrocarbons. These are the
Nitration test, Bromine Test and the
Permanganate test.
NITRATION TEST is used to test the
aromacity of the compound. A positive result
yields a yellow oil or precipitate describing
an aromatic hydrocarbon.
BROMINE TEST detects the presence of
unsaturation or phenols in the compound.
The positive result is a colorless solution.
OXIDATION TEST/ PERMANGANATE
TEST detect the presence of unsaturation.
The positive result yields a brown precipitate
or a blue green solution.
SATURATED ALIPHATIC
HYDROCARBON
(HEXANE)
C
6
H
14

Hexane only has a C-C single bond
Straight or branched carbon thus
opposite to aromatics
Most aliphatic compounds are
flammable
Characterize by a substitution reaction
Colorless liquid with petrolic odor


SATURATED ALIPHATIC
HYDROCARBON
HEXANE
Bromine test (-)
The structure shows that the
compound is aliphatic since it only
contains a single bond between carbons
and will not yield a colorless solution.


Nitration Test (-)
The structure of hexane is not
characterized by an aromatic ring.

Permanganate/oxidation test (-)
the same as the bromine test it
detects the presence of double and
triple bond furthermore it test the
presence of alkyl groups
UNSATURATED ALIPHATIC
HYDROCARBON
(CYCLOHEXENE)

UNSATURATED -hydrocarbons containing either
double or triple bond
ALIPHATIC - hydrocarbons joined together in straight
or branched chains
HYDROCARBON - Simplest organic compound
containing carbon and hydrogen
- The carbon serves as its backbone
where hydrogen is attach
- They are characterize by addition or
bond rupture reactions

CYCLOHEXENE
Commercially used as a starting material in the
production of chemicals, polymers ( plastics,
rubbers, resins ).
Properties :
- more reactive than alkanes ( saturated
aliphatic hydrocarbons)
- strong oxidizers react vigorously with them
- low toxicity but acts as asphyxiants
- physical state in room temperature changes
by increase in molecular weight ( gaseous
to waxy solid )
Asphyxiants gas/ vapor that can cause
unconsciousness and/or death if inhaled
CYCLOHEXENE
colorless liquid with a sharp smell
insoluble in water and less dense than
water
produced by partial hydrogenation of
benzene
not very stable upon long term storage with
exposure to light and air for it forms
peroxides
inhalation of high concentration may have
narcotic effect
highly flammable

C
6
H
10



NITRATION TEST ( - )
C
6
H
10
+ HNO
3
+ H
2
SO
4
NO REACTION

Since nitration tests for the presence of
aromatic in a solution and cyclohexene does
not exhibit aromatic structure, cyclohexene
yields a negative result because when treated
with nitric and sulfuric acid there was no
formation of yellow oil or precipitate nitrate
test only reacts with aromatic compounds

BROMINE TEST ( + )
C
6
H
10
+ Br
2
C
6
H
10
Br
2
(1,4-dibromocyclohexane )




Cyclohexene has the presence of carbon-
carbon double bond that indicates that is has
unsaturation.
The solution bromine decolorizes as it was
mixed with cyclohexene indicating a positive
result.
Decoloration of bromine happens because
bromine undergoes electrophilic addition to
the double bonds of cyclohexene
OXIDATION/PERMANGANATE TEST (
+ )
C
6
H
10
+ KMnO
4
( potassium permanganate ) C
6
H
10
(OH)
2

(1,2dihydroxicyclohexANE) + MnO
2
(manganese dioxide )

- cyclohexene has the presence of unsaturation
because there is a double bond between
carbon-carbon atoms
- when cyclohexene was treated with
potassium permanganate there was the
presence of a brown precipitate
- permanganate converted the cyclohexene
into a diol
- cyclohexene stated postive in permanganate
test




NON-ALKYLATED AROMATIC
HYDROCARBON
(NAPHTHALENE)

NON-ALKYLATED hydrocarbon that has no
alkyl substituent attached to it
AROMATIC hydrocarbon with alternating double
and single bonds between carbon atoms
forming ring/rings. An aromatic hydrocarbon is
also called an arene.
Characteristics of aromatic hydrocarbons:
Cyclic the contributing atoms are
connected forming a ring/rings
Coplanar all contributing atoms are in
the same plane
Hckels rule
Number of delocalized -electrons
should be 4n+2 where n=0,1,2
Total number of delocalized -electrons
should be even but not a multiple of 4
Delocalized conjugated system an
arrangement of alternating single and
double bonds

NAPHTHALENE
white crystalline solid
simplest polycyclic aromatic hydrocarbon (fused
aromatic rings)
from coal tar and crude oil
byproduct of fuel burning either fossil fuel or biomass
used as insecticide, pest repellant and was once a
widely used ingredient for mothballs
Naphthalene
C
10
H
8

NITRATION TEST ( + )







Cyclic
Coplanar
Hckels rule
Delocalized conjugated system

NO
2

HNO
3

H
2
SO
4

Substantial resonance stabilization
BROMINE TEST ( )

UNSATURATION unsaturated compound is a
chemical compound that contains carbon-carbon
double bonds or triple bonds
PHENOL chemical compounds consisting of a
hydroxyl group (OH) directly bonded to an
aromatic hydrocarbon
Br
2

NO REACTION
Naphthalene is an unsaturated compound, so
why did it test negative?
Since naphthalene is an aromatic compound, it is stable and
will resist addition reaction with bromine
It has 3 resonance structures



10 electrons of naphthalene are
delocalized and it has substantial
resonance energy


Aromatic compounds can react with bromine via substitution
reaction rather than the addition reaction which will
produceHBr (Hydrogen Bromide) gas
For the reaction to occur there must be presence of heat and
catalyst

OXIDATION/PERMANGANATE TEST ( )






Naphthalene is an aromatic compound, therefore
it is stable and will not react with KMNO
4

Since naphthalene is a non-alkylated
hydrocarbon, it will not test positive
This would only test positive if the reaction occurs
with aromatic hydrocarbons that contain alkyl
substituents at a very high temperature, because
then it can react with the alkyl substituent

KMNO
4

NO REACTION
ALKYLATED AROMATIC
HYDROCARBON
(TOLUENE)
ALKYLATED hydrocarbon contains
an alkyl substituent
AROMATIC - hydrocarbon with
alternating double and single bonds
between carbon atoms forming
ring/rings
TOLUENE
also known as Methylbenzene
colorless liquid with a paint thinner like
odor
water insoluble aromatic
flammable
obtained from petroleum and coal tar
used as solvent for gums and lacquers,
in high octane fuels such as medicines,
dyes, explosives and detergents
NITRATION TEST ( + )

methyl group acts as the activating group
produces poly substituted nitro-products








BROMINE TEST ( - )

negative since Br
2
is not electrophilic
enough to attack the benzene ring of
Toluene
a catalyst (FeBr
2
) is required for the
reaction to follow through

OXIDATION TEST ( +)

The methyl group in the side chain of the
aromatic ring is oxidized to become a
carboxyl group in the presence of a strong
oxidizing agent which in this case is
KMnO
4.

EXPERIMENTAL ERRORS
Inaccurate quantities of reagents
Contamination of droppers used to
transfer reagents
Contamination of test tubes
UNKNOWNS
HEXANE 8 11 15 19 24 27 31 33
CYCLOHEXENE 7 10 14 20 23 26 30
34
NAPHTHALENE 6 12 16 17 22 28 32
TOLUENE 5 9 13 18 21 25 29

REINFORCEMENT
EXERCISE
Indicate which sample best suits the description






The hydrocarbon structure above will yield yellow
oil when subjected to Nitration test since it is an
aromatic hydrocarbon. It will decolorize KMnO
4

because it contains an alkyl substituent indicating
that it is an alkylated aromatic hydrocarbon.
The sample above is aliphatic and it will turn the
bromine solution to colorless because it is unsaturated
containing a C-C triple bond, thus, it is an Unsaturated
Aliphatic hydrocarbon.
The hydrocarbon sample above will yield yellow oil
with HNO
3
/ H
2
SO
4
because it is an aromatic and will
not decolorize KMnO
4
because there is no an alkyl
group attached to it and is therefore a Non-alkylated
aromatic hydrocarbon.
CONCLUSION
Through the help of Nitration, Bromine
and Permanganate tests, different
hydrocarbons were differentiated from
one another.
Parallel chemical test was used to
compare the unknowns to the known
chemicals
SAMPLE
AROMATIC ALIPHATIC
ALKYLATED
NON-
ALKYLATED
SATURATED
UNSATURATE
D
NITRATION TEST
+ -
+ - - +
PERMANGANATE TEST
BROMINE TEST
References
http://cameochemicals.noaa.gov/react/28
http://chemistry.about.com/od/chemistrygloss
ary/g/Aliphatic-Hydrocarbon-Definition.htm
http://www.elmhurst.edu/~chm/vchembook/50
0hydrocarbons.htm
http://cameochemicals.noaa.gov/react/29
http://en.wikipedia.org/wiki/Aromaticity
http://en.wikipedia.org/wiki/Naphthalene
http://npic.orst.edu/factsheets/naphgen.html
http://chemistry.tutorvista.com/organic-
chemistry/toluene.html?view=simple