*For diagrams, Watson, S. (n.d.).

Qualitative Tests for Hydrocarbons: Unknown

Hyodrocarbon. Retrieved on October 12, 2016 from
http://myweb.brooklyn.liu.edu/swatson/
*Specific rxns Carey, F.A. Organic Chemistry, Sixth Edition. New York, NY: McGraw Hill. 2006..
The organic compounds cyclohexane, methylcyclohexane, cyclohexene, benzene,
and toluene were subjected to different physical and chemical tests to differentiate
their intrinsic physical properties and chemical properties in terms of structure and
behavior. The physical state, color, and odor were recorded by simple physical

observation.

1. Combustion: Ignition Test

Hydrocarbons can be determined by the characteristics of their flame, such as its
flammability, the color of the flame and the amount of soot produced, when they
burn.
Combustion is one of the most important energy-conserving processes in which the
energy in a fuel is released through an exothermic chemical reaction, while
flammability is a measure of the extent at which a substance is able to undergo
combustion. The flammability of a compound can be quantified through subjectin g
the said compound to ignition tests (Dizon, et al., 2010).
2

C7H14 + 21O2 ----> 14CO2

14H2O

During the
experiment, it was
observed that two of
the
featured solvents did
not produce soot upon combustion, which are cyclohexane and methylcyclohexane.

All hydrocarbons will burn in the presence of air. However, if an excess of oxygen is
absent in the reaction, an incomplete combustion will occur and produce byproducts
such as soot (unburned carbon). As illustrated in Figure 5.something, it is evident
that the bonds present in a substance plays a part on how much soot is yielded
from an incomplete combustion of a hydrocarbon as higher energy is required to
break multiple bonds that are present in an atom. Therefore when a specific energy
threshold for a hydrocarbon containing multiple double bonds is not met, more
carbon atoms will be left unburnt and result into more soot.
As for color, all of the solvent exhibited orange flames of differing hues upon
catching fire. Carbon, when subjected to a flame test, gives off an yellow/orange
color, therefore the more carbon atoms that are present in a compound, a more
intense orange is expected to be emitted by that certain compound. As indicated in
Table 5.something, cyclohexane and methylcyclohexane emitted an orange color
that is lighter than the rest. This is implies that the bright orange flame that is
characteristic to the combustion of the other compounds may be due to the carboncarbon double bonds that are present.
While lastly for flammability, only toluene failed to sustain a combustion reaction
upon contact with a flame. Vapor pressure is an important parameter in determining
the flammability of a substance. The higher the vapour pressure, the more
flammable the vapour released by a free liquid surface. Toluene, among all of the
solvents, has the highest boiling point which stands at 110.6 degrees Celsius. It is
dictates by trends in the physical properties of compounds that the higher the
boiling point of a substance, the lower its vapour pressure. This explains why
toluene was the least flammable: its low vapour pressure results to a less
flammable vapour.
Any inconsistent information that had been recorded may be attributed to bias while
performing the experiment.
Dizon, S., Donato, A.K. Dy, A., Enriquez, K.B. and Fauni, M.B. (2010). Classification
tests for hydrocarbons. p 3.
2. Reaction with Bromine: Effects of Light
Hydrocarbons were reacted with bromine, with light as a catalyst. In two clean, dry
test tubes for each solvent, 5-7 drops of a bromine-dichloromethane solution was
added, and 3 drops of a chosen hydrocarbon was added afterwards. One of the
tubes was wrapped in carbon paper in order to prevent the exposure of the
hydrocarbon-halogen mixture to light. These will serve as the control groups. These
test tubes were exposed to light until the fading of the red-orange color of the
bromide was observed. Upon comparison of the wrapped and unwrapped test tubes,
it was observed that fading occurred in all of the test tubes which were not
wrapped. These were tested further through the addition 10 drops of distilled water
and later, agitation. The acidity of the resulting solutions were tested through the
application of the liquid to blue litmus paper, wherein only benzene did not cause a
change from blue to pink.

The bromination of the hydrocarbons takes place through a free-radical addition or

substitution mechanism. When the reaction mixture is exposed to light, the bromine
molecules absorb radiant energy and use that energy to break bonds and convert
into free radicals.
Bromine reacted with carbon-carbon double and triple bonds by addition where it
places itself at the site of the double or triple bond, and cause the disappearance of
its characteristic red-orange color.

Alkenes and alkynes react readily with Br2 therefore, bromination occurs at a faster
rate and does not need light as a catalyst.
Bromine reacted with carbon-carbon single bonds in alkanes by replacing a H with
Br by substitution, however, the reaction is generally slow and requires light to act
as a catalyst.

It had been stated that benzene faded but failed the acidity test. This is due to
benzenes stable resonance structure.

As no bromination reaction occurred in benzene, this explains why benzene had

failed to turn blue litmus paper into pink. This color change indicates the formation
of an acid. which in the case of toluene, cyclohexene, methylcyclohexane and
cyclohexane is HBr.
It can be asserted that the bromine test determines the presence of unsaturated
hydrocarbons or alkenes/alkynes as the most reactive, rendering the presence of a
catalyst in the form of light unnecessary. The second most reactive are the
saturated hydrocarbons, which need light in order to undergo bromination, with
benzene as the least reactive.
McLaughlin, J. (n.d.). Che 102: Properties of Alkanes, Alkenes and Alkynes. Colorado
Northwestern Community College. Retrieved on Ocotober 12 , 2016 from
www.chemhaven.org/che102
3. Reaction with Cold Dilute Neutral Potassium Permanganate: Baeyers Test
Potassium permanganate is an oxidizing agent that reacts with unsaturated
aliphatic hydrocarbons, but does not react with alkanes or aromatic hydrocarbons.
The dilute KMnO solution has a deep purple color. If no reaction had occurred, no
color change should be observed. With regards to the collected data, when
potassium permangate reacts with unsaturated hydrocarbons, such as alkenes and
alkynes, it produces MnO, a brown precipitate, which makes this reaction useful as a
test for the presence of multiple bonds, if there is no other easily oxidizable group,
such as an alcohol or aldehyde.
Its mechanism is shown by Figure 5.something below.

According to Table 5.something, only two compounds had exhibited changes upon
the addition of potassium permanganate, which are methylcyclohexane that had
taken on a red violet color upon consistent agitation, and cyclohexene which acted
as predicted and produces a brown precipitate (MnO2).

Potassium permanganate is a strong oxidizing agent, which upon addition to an

unsaturated hydrocarbon will oxidize its carbon-carbon double and/or triple bonds to
form alcohol and diols. The evidence that the oxidation reaction had occurred is the
disappearance of the mixtures deep purple color and the precipitation of a brown
solid. The cyclohexene mixture, after the addition of potassium permanganate, had
started off as a deep purple color, which
gradually turned into red, and finally, a
brown mixture was also an indication that
an oxidation reaction had been taking
place.

4. Reaction with Ammoniacal Silver Nitrate Solution: Tollens Test

B. Preparation and Testing of Acetylene Gas

C. Relative Rates of Light-Catalyzed Bromination

D. Demonstration
The blue colour of the lowest layer in the rainbow is thought to be due to the
predominance of the CT complex. (A complex between two organic molecules in
which an electron from one (the donor) is transferred to the other (the acceptor),
becoming generally distributed throughout the latter; subsequent transfer of a
hydrogen atom completes the reduction of the acceptor; such complex's are
generally highly coloured and may be so observed.) In the layer above, the
concentration of the yellow bromine water is sufficiently high that its mixture with
the blue gives the green colour observed. In the top layers, there would be a
gradual break up of lipid aggregates causing the release of the carotenoids into the
aqueous medium where they would be rapidly brominated and become colourless.
The thickness of the natural tomato juice is sufficient to maintain the concentration
gradient indefinitely.
It is concluded that the tomato juice rainbow is caused by the stabilization of the CT
complex formed in the first step of the bromination of carotenoids.
The double bonds of this red pigmented molecule can be broken using a solution of
bromine water. When bromine water is added to tomato juice, bromine is added
across the double bonds of lycopene. As this occurs a spectrum of colours emerge
depending on the concentration of lycopene. The experiment illustrated the
halogenation of alkenes in a very colourful experiment.
MacBeath, M.E. and Richardson A.L. (1986). Tomato juice rainbow: A colorful and
instructive demonstration. Retrieved on October 12, 2016 from
http://pubs.acs.org/doi/pdf/10.1021/ed063p1092