Experiment #7: Classification Tests for Hydrocarbons

CAVIDA, C.M.B., *CHOSANTOS, D.B., CHUA, K.B.C., CO, E.K.T, CRISOL, D.B.

2C-MT, Faculty of Pharmacy, UST

Abstract

In this experiment 5 organic compounds which were Hexane, Heptane, Cyclohexane, Benzene,
and Toluene were used. These Organic compounds were observed in terms of its intrinsic physical
properties and its chemical properties in terms of structure and behavior. By simple observation we noted
its color and odor. Also, a test in concentrated 1 mL H 2S04 was conducted to differentiate which
compounds were immiscible or not, then observation of any change and/or warming effect was also
noted. Ignition test was also conducted to test the flammability of the organic compounds by adding 3-5
drops of the sample in an evaporating dish and lighting it with a match. Baeyer’s test and Bromine test
was also conducted to test the organic compounds for active saturation. In Baeyer’s test, 5 drops of
sample was added to 2 drops of 2% KMn0 4. The observation of any brown suspension was noted and
decolorization of the reagent was immediate if it occurred within 1 minute. While in Bromine test, 5 drops
of sample was added to 10 drops of .5% Br2 in CCl4 reagent and if the reagent failed to decolorize within
1 minute exposure to sunlight was done. Then Test for Aromaticity: Nitration was conducted to determine
the miscibility of the 5 organic compounds by mixing 5 drops of the sample and 8 drops of nitrating
mixture, formation of any yellow oily layer was observed and water bath was also conducted. Lastly test
for basic oxidation was done to note if any precipitate was formed when 4 drops of sample was added to
8 drops of 2% KMn04 & 10% NaoH solution. The organic compounds were tested if it is saturated, actively
unsaturated, aromatic or an arene.

Introduction:

Hydrocarbons are the compounds which (Figure 1: Example of a saturated Hydrocarbon)

are composed of Hydrogen and Carbon. Each
carbon atoms has four bonds. They can be
saturated (single bond), unsaturated (double or
triple bond), acyclic (without rings) and cyclic
(with rings). Saturated hydrocarbons are known
when all the valencies of carbon atoms are fully
utilized by single covalent bonds. The parent
molecule of saturated hydrocarbon is methane. (Figure 2: Example of an Unsaturated
A number of carbon atoms can be linked Hydrocarbon)
together without any limitations. Examples are :
Alkanes (methane, ethane, propane etc.)  Hexane is a chemical made from crude
Unsaturated hydrocarbons have one or more oil. Pure hexane is a colorless liquid with a
double or triple bonds between carbon atoms. slightly disagreeable odor. It evaporates very
Those with double bond are called alkenes. easily into the air and dissolves only slightly in
Those with one double bond have the formula water. Hexane is highly flammable, and its
CnH2n (assuming non-cyclic structures). Those vapors can be explosive. is a hydrocarbon with
containing triple bonds are called alkynes, with the chemical formula C6H14; that is, an alkane
general formula CnH2n-2. with six carbon atoms. In the IUPAC
nomenclature, however, hexane is the
unbranched isomer (n-hexane); the other four
structures are named as methylated derivatives
of pentane and butane.
 Benzene: Is a colorless,
liquid, inflammable, aromatic hydrocarbon of
(Figure 3: Ex. Of hexane) chemical formula C6H6 which boils at 80.1°C
(176.2°F) and freezes at 5.4–5.5°C (41.7–41.
The six carbon atoms of benzene, each with a
hydrogen atom attached, are arranged
Heptane is a volatile, colorless, highly symmetrically in a plane, forming a
flammable liquid hydrocarbon, C7H16, obtained in regular hexagon. The hexagon symbol,
the fractional distillation of petroleum and used commonly used to represent the structural
as a standard in determining octane ratings, as formula for benzene, implies the presence of a
an anesthetic, and as a solvent. It is also a
carbon atom at each of the six angles and,
straight-chain alkane. r.d. 0.684; m.p. –90.6°C;
b.p. 98.4°C. In standardizing octane numbers, unless substituents are attached, a hydrogen at
heptane is given a value zero. each carbon atom. Whereas the three double
bonds usually included in the formula are
convenient in accounting for the addition
reactions of benzene, present evidence is that
all the carbon-to-carbon bonds are identical.

(Figure 4: Example of Heptane)

Cyclohexane is a colorless
liquid cycloalkane, C6H12; r.d. 0.78; m.p. 6.5°C;
b.p. 81°C. It occurs in petroleum and is made by
passing benzene and hydrogen under pressure
over a heated Raney nickel catalyst at 150°C, or
by the reduction of cyclohexanone. It is used as
a solvent and paint remover and can be oxidized (Figure 6: Example of Benzene)
using hot concentrated nitric acid to hexanedioic
acid (adipic acid). The cyclohexane ring is not Toluene, C7H8, colorless liquid aromatic
planar and can adopt boat and hydrocarbon that melts at −95°C and boils at
chair conformations; in formulae it is 110.8°C. It is insoluble in water but highly
represented by a single hexagon. It is extremely soluble in most organic solvents. Toluene is
flammable, colorless, mobile liquid, used in the obtained from coal tar and petroleum by
manufacture of nylon and as a solvent, a paint, distillation. It is used as a solvent and as a
and a varnish remover. starting material for the synthesis of many
compounds, including dyes and explosives.
When toluene is treated with a mixture of nitric
and sulfuric acids (a process known as
nitration), trinitrotoluene (TNT) is produced. It is
formerly known as toluol, is a clear, water-
insoluble liquid with the typical smell of paint
thinners. Chemically it is a mono-substituted
benzene derivative, i.e. one in which a single
hydrogen atom from the benzene molecule has
been replaced by a univalent group, in this case
CH3. It is an aromatic hydrocarbon that is widely
used as an industrial feedstock and as a solvent.
(Figure 5: Example of Cyclohexane)

(Figure 7: Example of Toulene)
Flammability is a test where it checks a
number of properties. Almost all organic
compounds (compounds containing C and H
primarily in combination with O, N, and other
non-metals) are readily flammable (Fully
halogenated carbon compounds are notable
exception). Flammability means that the
compound can react exothermically with oxygen.
Because of the high heat of reaction, it means a
fire will result from the reaction. Most alcohols
and alkanes are prime examples. Their high
flammability is the result of their ease of reaction
with oxygen, and the large amount of heat given
out when they react. This heat results from the
formation the bonds in CO2 and H2O, which are
very stable and have less energy than the bonds
of the initial reactants. The excess energy is lost
as heat.
Hydrocarbon Solubility : The rule to use
when determining hydrocarbon solubility is: Like
dissolves like. This means that polar compounds
(water, alcohols, and carboxylic acids) dissolve
other polar compounds. Nonpolar compounds
dissolve other nonpolar compounds but tend not
to dissolve polar compounds. When you test for
solubility you are looking for either a
homogeneous solution or a heterogenous
solution. Homogeneous solutions have no layers
evident indicating the hydrocarbon being tested
is soluble. These hydrocarbons are miscible.
Heterogenous solutions have layers evident
indicating the hydrocarbons are insoluble. These
hydrocarbons are immiscible.
Miscibility is the property of liquids to
mix in all proportions, forming
a homogeneous solution. In principle, the term
applies also to other phases (solids and gases),
but the main focus is usually on the solubility of
one liquid in another. Water and ethanol, for
example, are miscible since they mix in all
proportions. By contrast, substances are said to
be immiscible if in some proportion, they do not
form a solution. For example, diethyl ether is
fairly soluble in water, but these two solvents are
not miscible since they are not soluble in all
proportions. Like any other solubility
phenomenon, miscibility depends on the forces
of attraction between the molecules of the
different liquids. The rule of thumb "like
dissolves like" means that liquids with similar
molecular structures, in particular similar
polarity, will likely dissolve in each other.
(Polarity means the extent to which partial
positive and negative charges appear on
a molecule, because of the type and
arrangement of its component atoms.) Both
water and ethyl alcohol have very polar hydroxyl
groups (-OH) on their molecules, and therefore
both undergo the strong intermolecular attraction
known as "hydrogen bonding." Hexane, on the
other hand, is not miscible with water because
its molecular structure contains no polar groups
of any kind that would be attracted to the water
molecules.
The Baeyer test for unsaturation is for
determining the presence of carbon-carbon
double bonded compounds, called alkenes or
carbon-carbon trible bonded compounds, called
alkyne bonds.  The Baeyer test uses dilute
Pottasium Permanganate to Oxidize the carbon-
carbon double or triple bond. It’s called oxidation
because the double bond is replaced by a
hydroxy group (an OH group). The carbon’s
charge goes from being +1 to +2, so it loses an
electron (and is thus oxidized) 
Reaction for alkenes
(Figure 8: Reaction of Baeyer’s Test)
An alkene is replaced with a diol (a
compound with 2 hydroxy groups). Evidence for
the reaction is there because the purple
Pottasium permanganate goes
colorless. Alkynes work the same way, but a 4
hydroxy quattrol is produced (with 2 hydroxy
groups on each carbon). 
The reaction is important because it doesn’t
work on alkanes (compounds with carbon
carbon single bonds) or aromatic compounds. 
However, the test has a few drawbacks.
Aldehydes (terminal carbonyls ... carbon double
bonded to Oxygen) will also be oxidized (to
carboxylic acids) and formic acid (ethanoic acid)
and its esters are known to give positive tests.
The Bromine test is used to determine if
the colorless organic compound contains any
double C=C bonds (the alkene functional group).
Bromine does not react with an alkane because
the alkane contains only single C-C bonds which
cannot add the bromine. Alkanes merely dilute
the red-brown bromine color to an orange or
yellow color in the absence of a strong catalyst.
Due to their C=C double bonds which can be
broken, alkenes react readily with bromine to
produce saturated dibromoalkanes. When an
alkene is reacted with bromine, the red-brown
color of the bromine is immediately lost due to
the reaction of the bromine.
Unsaturation and Alkanes and Alkenes:
Alkanes are considered saturated because they
have only single C-C bonds and cannot add
hydrogen. Alkenes are unsaturated because
they are capable of adding a hydrogen when the
C=C double bond is broken.
Aromaticity is a property associated with
the extra stability of certain types of p systems.  use a pinch amount.
Fundamentally it arises from having the
maximum number of electrons in
the p bonding molecular orbital’s. As we will see,
it is not restricted to benzene, substituted
benzenes, 6-membered rings or just
hydrocarbons. The property of aromaticity is
generally about a significant extra stability
associated with a resonance delocalized
structure. This extra stability moderates the
reactivity of these systems compared to alkenes
and means aromatics can be considered as their
own functional group. The presence of aromatic
systems can also influence the reactivity of
functional groups directly attached to the
aromatic system particularly in the benzylic
position. Therefore it is important that you are
able to recognise the aromatic systems.
Basic oxidation was done using
potassium permanganate, it is an inorganic
chemical compound with the formula KMnO 4. It
is a salt consisting of K+ and MnO4–ions. Formerly
known as permanganate of potash or Condy's
crystals, it is a strong oxidizing agent. It
dissolves in water to give intense purple
solutions, the evaporation of which gives
prismatic purplish-black glistening crystals.
NaOH was also used to help determine if the
samples used will be forming a precipitate or
not.
Methodology:
A. Physical state, color, and odor
The physical state of the organic
compounds hexane, heptanes,
cyclohexane, benzene and toluene were
physically examined at room
temperature. The color was noted with a
wafting motion of the hand over the
mouth of the test tube. The color should
be noted by physical observation.
B. Solubility in concentrated H2S04
Add a drop of the sample
cautiously to about 1 mL of conc. H 2S04
by using dry and calibrated droppers.
C. Ignition Test
Place 3-5 drops of the liquid
sample in a small evaporating dish and
light with a match. If the sample is solid,
D. Test for Active Unsaturation
a. Baeyer’s test :
Place 5 drops of the sample in a
dry tes tube. Add two drops of 2%
KMn04 solution. Shake the test tube
vigorously and observe the rate and
extent at which the reagent is
decolorized. *note the formation of a
brown suspension. Compare with water
as a negative control. Decolorization of
the reagent is immediate if it occurs
within 1 minute.
b. Bromine test:
Place 5 drops of the sample in a
dry test tube. Add 10 drops 0.5 Br 2 in
CCl4 reagent. Shake the test tube
vigorously and observe the rate and
extent (color change) by which the
reagent is decolorized: the bromine
color is discharged. Then compare with
water as a negative control. If the
reganet failed to decolorized within 1
 minute, expose the reaction mixture to
sunlight.

E. Test for Aromaticity: Nitration

Place 2 mL of conc. HN0 3 in an

Erlenmeyer flask in an evaporating dish
containing water and gradually 2 mL of
conc. H2S04. Cool the resulting mixture
to room temperature. This will serve as
the nitrating mixture.

Place 5 drops of the sample in a

dry test tube. Add 8 drops of the
nitrating mixture and shake the test tube
to ensure complete mixing. Note the
formation of yellow oily layer or droplet.
Dilute with 20 drops of water.

If there no apparent reaction

observed within a minute, place the test
tube in a water bath for 10 minutes.
Dilute with 20 drops of water.

F. Basic oxidation

To 4 drops of the sample in the

test tube, add 8 drops of 2% KMn0 4
solution and 3 drops of 10% NaOH
solution. Warm each test tube in a water
bath for 2 minutes and observe color
change and the formation of precipitate.
 Results and Discussion: www.sigmaaldrich.com/chemistry/solvents/produ
cts.html?

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References:
www.chemistryexplained.com
www.chemistry.com

www.orgchem.colorado.edu

www.chemistryabout.com

  Compounds Studied

Cyclohexan
Hexane Heptane Benzene Toluene
e

     

Condensed structural formula

A. Physical State at RT Liquid Liquid Liquid Liquid liquid

Color Colorless colorless colorless colorless colorless
Odor strong odor strong odor strong odor strong odor strong odor
B. Solubility in Concentarted no color no color
no color change yellow yellow
H2S04 change change
Inference immiscible immiscible immiscible miscible miscible
C. Ignition Test orange, 5 secs orange, 6 secs orange flame, 5 secs orange flame, 8 secs orange flame, 3 secs
Inference flammable flammable flammable flammable flammable
no no no decolorization with brown no decolorization with brown
D. Baeyer's test no decolorization
decolorization decolorization suspension suspension
decolorized, 5 decolorized, 7
Bromine test did not decolorize no decolorization decolorized, 10 mins
mins mins
Inference miscible miscible miscible miscible miscible
E. Test for aromaticity: no color no color became yellow when added with
no color change no color change
nitration change change H2S04
Inference immiscible immiscible immiscible immiscible miscible with water
F. Basic Oxidation no precipitate no precipitate no precipitate no precipitate black precipitate
Inference