Experiment # 7: Classification of Test for Hydrocarbons
Gonong, D.A. G., Gutierrez, H.A. G., Hagiwara, K. L., Javier, C.B. DLR., Labajo, A.M. F .
2C-MT, Faculty of Pharmacy, UST
Abstract
The experiment was performed to first, differentiate hydrocarbons in terms of its intrinsic
physical properties and chemical properties in terms of its structure and behavior and secondly, to
analyze a hydrocarbon and determine if it is saturated, actively unsaturated, aromatic or an arene.
Hexane, Heptane, Cyclohexane, Benzene and Toluene were subjected to three of the basic areas of
experimental inquiry: Physical Properties of compounds, Classification by solubility and Classification
test for functional groups. The Physical properties of each organic compounds such as physical state,
color and odor was observed and were noted down, the solubility of each compound was classified
using concentrated H2SO4 and test for functional groups were determined by the use of different test.
Ignition Test, Baeyer’s test and Bromine Test were applied to determine the presence of active
unsaturated hydrocarbons, Nitration was utilized to determine Aromaticity and basic oxidation was
applied to determine presence of alkyl side chain in an aromatic hydrocarbon. All organic compounds
sample were clear, colorless liquids. Also, all the organic compounds were immiscible in concentrated
H2SO4 and all exhibited to be flammable with benzene and toluene producing soot. All compounds
exhibited negative reaction for active unsaturation test except for Cyclohexane and Toluene. Except
again for Benzene and Toluene which showed to be aromatic, the rest of the organic compounds are
aliphatic compounds. And lastly, only toluene showed a positive result for basic oxidation .
Introduction
Hydrocarbons are organic
compounds that contain only carbon and
hydrogen and are divided into two main
classes: Aliphatic hydrocarbons and
aromatic hydrocarbons. Because of their
relatively non-polarity, all hydrocarbons
are insoluble in water.
Aliphatic hydrocarbons include
three major groups namely alkanes Figure2. Structure of a typical alkene
(paraffins), alkenes (olefins) and alkynes
(acetylenes). Alkanes are hydrocarbons in
which all the bonds are single bonds;
alkenes contain one or more carbon-
carbon double bonds and alkynes contain
one or more carbon-carbon triple bond.
They do not incorporate aromatic rings.
Figure3. Structure of a typical alkyne
Aromatic hydrocarbons, also known
as Arene is a cyclic conjugated
unsaturated molecule that is stabilized by
pi electron delocalization. Benzene is the
most typical of the aromatic
hydrocarbons.
Figure1. Structure of a typical alkane
Two common types of unsaturated
compounds are alkenes and alkynes,
characterized by the carbon – carbon
double and triple bond respectively, as the
functional groups. The two common
qualitative tests for unsaturation are the
Figure4. Structure of Benzene reaction of compounds with bromine in
carbon tetrachloride (Bromine test) and
The main structural difference with potassium permanganate (Baeyer’s
among hydrocarbon families is the Test). In both cases, a positive test is
presence of double or triple bonds denoted by decolorization of agent.
between carbon atoms. The alkanes are
saturated organic compounds, or those There are no suitable general
with only single bonds while unsaturated classification tests for alkanes. Saturated
organic compounds are those which have hydrocarbons are best identified through
double or triple bonds. ruling out other possible functional
groups. Alkanes are insoluble in conc.
In conducting a classification test Sulfuric acid and give a negative test for
for hydrocarbons, it is vital to conduct a
halogens.
preliminary examination first because that
will determine the intrinsic physical
properties of an unknown. The physical Aromaticity is a chemical property
state insofar as it relates to solubility and in which a conjugated ring of unsaturated
volatility is an aid to choice or purification bonds, lone pairs, or empty orbital exhibit
method is provided; The original color as stabilization stronger than would be
well as any changes observed which may expected by the stabilization of
occur in the determination of boiling point conjugation alone. It can also be
and identification of the presence of considered a manifestation of cyclic
chromophoric groups in the molecule; delocalization and of resonance. Since
Odor is also an important property in Benzene is non-reactive because of its
determining the unknown since many stability yet can be nitrated, Nitration is
types of organic compound have a used for determining the presence of
characteristic odor especially aromatic compounds. Nitration introduces
hydrocarbons which possesses a unique, a functional group that provides synthetic
distinctive odor. access to a number of substituted
aromatics. Basic Oxidation, on the other
A study of the solubility behavior of hand is a test conducted to determine the
an unknown substance determines the presence or an alkyl side–chain because
following: the presence of a functional Aromatic compounds are bearing
group, more specific information about the oxidizable alkyl substituent, are selectively
functional group due to solubility in oxidized, and by reacting the same with
certain solvents and certain deductions appropriate oxidizing agents, in an
about molecular weight may sometimes aqueous reaction medium, in the presence
be made. of a catalytically effective amount of a
solid, palladium-containing oxidation
Ignition Test indicates the presence catalyst.
of unsaturation or high carbon to
hydrogen ratio. The higher the carbon- The analyzed organic compounds were:
hydrogen ratio, the more luminous the
flame is, the more sooty. The degree of Hexane is a hydrocarbon with the
luminosity can be assessed by the chemical formula C6H14; that is, an alkane
presence of yellow flame and soot. with six carbon atoms. Hexanes are
significant constituents of gasoline. They
are all colorless liquids at room
temperature, with boiling points between in itself is rather unreactive, being a non-
50 and 70 °C, with gasoline-like odor. polar, hydrophobic hydrocarbon
They are widely used as cheap, relatively substituted cyclohexanes, however, may
safe, largely unreactive, and easily be reactive under a variety of
conditionsCyclohexane is highly
flammable.
evaporated non-polar solvents.
Figure7. structure of cyclohexane
Figure5. Structure of hexane Benzene is an organic chemical
compound with the molecular formula
Heptane is a volatile, colorless, C6H6. Benzene is a colorless and highly
flammable liquid with a sweet smell and a
highly flammable liquid hydrocarbon,
relatively high melting point. Because it is
with a chemical formula of C7H16, which is a known carcinogen, its use as an additive
obtained in the fractional distillation of in gasoline is now limited, but it is an
petroleum and used as a standard in important industrial solvent and precursor
determining octane ratings, as an in the production of drugs, plastics,
anesthetic, and as a solvent. Heptane (and synthetic rubber, and dyes. Benzene is a
its many isomers) is widely applied in natural constituent of crude oil, and may
laboratories as a totally non-polar solvent. be synthesized from other compounds
As a liquid, it is ideal for transport and present in petroleum. Benzene is an
storage. In the grease spot test, heptane aromatic hydrocarbon, a cyclic
is used to dissolve the oil spot to show the hydrocarbon with a continuous pi bond. It
previous presence of organic compounds is also related to the functional group
on a stained paper. Heptane is arene which is a generalized structure of
commercially available as mixed isomers benzene.
for use in paints and coatings
Figure6. skeletal structure of heptane
Cyclohexane is a cycloalkane with
the molecular formula C6H12. Cyclohexane
is used as a nonpolar solvent for the Figure8. Structure of benzene
chemical industry, and also as a raw
material for the industrial production of Toluene is a clear, water-insoluble
adipic acid and caprolactam, both of which liquid with the typical smell of paint
are intermediates used in the production thinners. Chemically it is a mono-
of nylon. On an industrial scale, substituted benzene derivative. It is an
cyclohexane is produced by reacting aromatic hydrocarbon that is widely used
benzene with hydrogen.Pure cyclohexane
as an industrial feedstock and as a and the color of the flame produces was
solvent. Like other solvents, toluene is noted.
sometimes also used as an inhalant drug
for its intoxicating properties; Toluene D. Test for Active Unsaturation
reacts as a normal aromatic hydrocarbon
towards electrophilic aromatic 1. Baeyer’s Test
substitution. Toluene also occurs naturally
at low levels in crude oil and is usually 5 drops of the sample was placed in a
produced in the processes of making dry test tube. 2 drops of 2% KMnO 4
gasoline via a catalytic reformer, in an solution was also added in the sample.
ethylene cracker or making coke from The test tube was shook vigorously and
coal. the rate and extent at which the reagent
was decolorized was observed and noted.
The formation of brown suspension was
noted. It was compared with water as a
negative control. The decolorization of the
reagent was immediate since it occurred
within 1 minute. The results were noted.
2. Bromine Test
5 drops of the sample was placed in a
dry test tube. 10 drops of 0.5% of
Bromine tetrachloride was added. The test
tube was also shook vigorously and the
Figure9. Structure of Toluene
rate and extent (change in color) by which
Methodology the reagent was decolorized was
observed; the bromine color is discharged.
A. Physical State, Color and Odor It was compared water as a negative
control. The reagent failed to decolorize
The physical state of the samples within a minute thus, the reaction mixture
(Hexane, Heptane, Cyclohexane, Benzene was exposed to the sunlight. The results
and Toluene) was observed at room were noted.
temperature and was noted. The odor and
color were also described and noted. E. Test for Aromaticity: Nitration
B. Solubility in Concentrated H2SO4 2 ml of concentrated HNO 3 was placed
in an Erlenmeyer flask. The flask was
A drop of about 1ml of concentrated immersed in an evaporating dish
H2SO4 was added cautiously with the use containing water and 2 ml of concentrated
of a dry and calibrated dropper. The H2SO4 was added gradually. The resulting
change in color and the warming effect mixture was cooled in room temperature.
were noted. concentrated H2SO4 is The solution served as the nitrating
corrosive and dehydrating so the solution mixture.
was carefully neutralized with 10% NaOH
and was placed in a solution container 5 drops of the sample was introduced
provided. in a dry test tube. 8 drops of the nitrating
mixture was added and the test tube was
C. Ignition Test shook which ensured that the solution was
completely mixed. The formation of an
3-5 drops of the liquid sample is oily layer or droplet was noted. The
placed in a small evaporating dish and solution was diluted with 2 drops of water.
was lighted with a match. The If no reaction was observed within a
flammability of the sample is observed minute, the test tube should be placed in
a water bath for 10 minutes and should characteristic flame that assists in
also be diluted with 20 drops of water. determining the nature compound. An
Results should also be noted. aromatic hydrocarbon which has relatively
high carbon content burns with a yellow
Since concentrated H2SO4 is sooty flame while aliphatic hydrocarbons
corrosive and dehydrating and burn with flames which are yellow but
concentrated HNO3 is corrosive and much less sooty.
oxidizing, the solution was placed in a
large beaker and was slowly diluted with Complete combustion is indicated
20 ml of water. Sodium Carbonate was by a blue flame (non-luminous) and there
also added until the foaming ceased and is more heat than light; the carbon is
was transferred in the aqueous solution completely oxidized.
container provided.
F. Basic Oxidation
Figure10. Complete Combustion Reaction
8 drops of 2% KMnO4 solution and 3
drops of 10% NaOH solution was added to Incomplete combustion is indicated
4 drops of the sample in a test tube. Each by a yellow flame (luminous) and there is
test tube was warmed in a water bath for much light than heat; the carbon is not
2 minutes. The change in color and the completely oxidized.
formation of a brown precipitate was
observed and noted.
Result and Discussion
Figure11. Incomplete Combustion reaction
All organic compounds tested were
clear, colorless liquid. Hexane exhibited a Two of the test for active
menthol odor; Heptane is odorless; unsaturation is Baeyer’s test and bromine
Cyclohexane, a strong gasoline scent; Test. All compounds exhibited negative
Benzene and toluene smell like faint reaction for active unsaturation test
rugby. except for Cyclohexane and Toluene.
All organic compounds were In bromine test, the reagent used
immiscible in concentrated H2SO4. Sulfuric is bromine tetrachloride and is widely
Acid is used as a solvent for neutral, used to test for the presence of olefinic or
water-insoluble compound. If the acetylinic linkages. Aromatic compounds
compound is unsaturated, is readily do not react because of their stability;
sulfonated or possesses functional group however, aromatic compounds will react
containing oxygen, it will dissolve in slowly upon using FeBr3 or through the
concentrated H2SO4. Solution in sulfuric action of UV light. The advantage of
acid frequently is accompanied by Bromine water over bromine in carbon
reactions such as sulfonation, tetrachloride is that the more polar
polymerization, and dehydration. Simple solvent greatly increases the rate of
aromatic hydrocarbon and their halogen bromination by the ionic mechanism. A
derivatives do not go undergo sulfonation positive result is decolorization to an
under these conditions and are therefore, orange solution. Alkenes react with Br2 to
insoluble. form a trans-dibromoalkane. Bromine will
add to the carbon-carbon double or triple
All organic compounds exhibited to
bond, when this occurs, molecular
be flammable with benzene and toluene
bromine is destroyed and its characteristic
producing soot. Many liquid burns with a
color disappears. The rapid disappearance
of the color of bromine is a positive test References:
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reactive but one of its properties is that it http://library.thinkquest.org/3659/orgche
can be nitrated. The reagent used were m/hydrocarbons.html. Retrieved:
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globule/yellow oily layer. In nitration,
H2SO4 acts as a catalyst and facilitates the http://faculty.swosu.edu/william.kelly/pdf
formation of nitronium ion (NO2+), an /qo7.pdf. Retrieved: September 18, 2010
electrophile. Only Benzene and toluene
http://www.scribd.com/doc/37474567/Fin
exhibited a positive result for Aromaticity.
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Basic Oxidation test is employed to
http://www.scribd.com/doc/25377353/Cla
test for alkyl aromatic or arenes. The
ssification-Tests-for-Hydrocarbons.
reagents utilized were 2% KMnO4, 10%
Retrieved: September 19, 2010
NaOH because aromatic hydrocarbons
that have side chains maybe oxidized by http://www.scribd.com/doc/24691082/Po
the following acid. A positive result is st-Lab-Notes. Retrieved: September 19,
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(MnO2). NaOH provides a basic
environment. The alkyl group of the http://www.patentgenius.com/patent/535
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carboxylic acid. Reaction occurs only with
primary and secondary alkyl side-chain
but not with tertiary. Only toluene
illustrated a red-brown precipitate, a
positive result for basic oxidation.
