Lab 1: The Hydrocarbons

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Pre Lab Questions:
1. Define the terms Hydrocarbon derivative, aliphatic hydrocarbon, unsaturated, and phenyl.
Hydrocarbon derivative: A Hydrocarbon derivative is a compound containing carbon,
hydrogen, and one additional element, topically O, N, S, P, F, Cl, and Br, or other
halogen gas.
Aliphatic hydrocarbon: An aliphatic hydrocarbon is a straight chain, or branched chain
hydrocarbon. These can be an Alkane, Alkene, or Alkyne.
Unsaturated: An Unsaturated hydrocarbon is a hydrocarbon that contains one or more
carbon carbon multiple (double or triple) bonds in the same molecule.
Phenyl: A phenyl is an attached group similar to the cyclic hydrocarbon of a benzene
ring, but missing one carbon atom, that is ready to attach to another molecule as a
functional group.
2. What is the evidence for reaction of potassium permanganate with alkynes?
The evidence for reaction of potassium permanganate with alkynes is that the purple
solution will turn brown, this visually signifies the chemical reaction (oxidation) taking
place.
3. What feature in its structural formula indicates weather a hydrocarbon is an alkane, alkene,
alkyne, or aromatic compound?
Alkane: Alkanes possess only carbon - carbon single bonds in a straight chain.
Alkene: Alkenes possess one or more carbon - carbon double bonds in a straight chain.
Alkyne: Alkyne possess one or more carbon - carbon triple bonds in a straight chain.
Aromatic: Aromatic hydrocarbon are arranged in a ring shape with free floating double
bonds that change position regularly throughout the “ring”.
4. Draw the electronic structure for Benzene, showing valence electrons.

5. Write equations to illustrate the reaction of bromine with these organic compounds: ethane,
C2H6; ethylene, C2H4; and acetylene, C2H2.

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 Reaction of Bromine with Ethane (C₂H₆): C2H6+ Br2 => C2H5Br + HBr
Reaction of Bromine with Ethylene (C2H4): C2H4+ Br2 => C2H4Br2
Reaction of Bromine with Acetylene (C2H2): C2H2 + 2Br2 => C2H2Br4
6. Can the combustion test be used to distinguish between an alkene and an alkyne? Explain.
Yes the combustion test cannot be used to distinguish between an alkyne and alkenes.
Alkenes will produce a “clean” flame and relatively little soot, whereas Alkynes will
produce a “sooty” flame and produce far more soot. It will be difficult to keep the
temperature and amount of alkenes and an alkynes the same to avoid deviation in how
much soot is produced between tests.

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Observation and result questions:
1. Physical Properties of Some Hydrocarbons
a. draw the structure of the three cyclic hydrocarbons and indicate which is an alkane, which is
an alkene, and which an aromatic.

b. Compare the odors if the hydrocarbons. Did you notice an odor trend among the types of
hydrocarbons? Comment.
Personally I have a very poor sense of smell, I was unable to determine any significant
difference in the odors of the hydrocarbons present. To me the organic chemistry lab
does not have any odor at all. My group members noted that cyclohexene had a mild
odor, where as cyclohexane and toluene had a strong unpleasant odor.

c. Were the hydrocarbons soluble in water? In Methylene chloride? What is your evidence that
they dissolve in one solvent and not the other?
Cyclohexane, Cyclohexene and Toluene, separate into layers distinctly separate from
water. Cyclohexane, Cyclohexene and Toluene mix with Methylene chloride and do not
form visually distinct layers. The evidence that they do not mix is the visually distinct
layers as well as the fact that Cyclohexane, Cyclohexene and Toluene, are all non-polar
molecules. As such they (Cyclohexane, Cyclohexene and Toluene) are insoluble in water.
Cyclohexane, Cyclohexene and Toluene are soluble in Methylene chloride because it is a
polar molecule.
d. Elain why they dissolve in one solvent, but not the other.
Cyclohexane, Cyclohexene and Toluene, are all non-polar molecules and as such are
insoluble in water. Cyclohexane, cyclohexene and toluene are soluble in Methylene
chloride because it is a polar molecule.

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e. Paraffin wax is primarily a mixture of long-chain hydrocarbons, an example of which is
C25H52. Draw the structure of a molecule found in this mixture.
CH3 – (CH2)23 – CH3
f. How do the odors of the cyclic hydrocarbons and paraffin compare? How do you explain the
tremendous difference in intensity of the odors of paraffin and the cyclic hydrocarbons?
To me the odors of the cyclic hydrocarbons and paraffin are comparable, both have no
odor. This may be an issue with my sense of smell more than anything else. My group
members noted that paraffin wax had little to no odor compared to cyclohexane,
cyclohexene and toluene (I wouldn’t know).
2. Reactions and Tests to Distinguish among the Hydrocarbons
a. Reaction with Bromine
Did bromine react immediately with cyclohexane? With cyclohexene? If either of the
hydrocarbons reacted immediately with bromine, write an equation for the reaction.
Bromine did not immediately react with cyclohexane. Though, under the UV light
the bromine did react with cyclohexane.
Bromine did immediately react with cyclohexene, likely due to the presence of a
carbon – carbon double bond.
Did cyclohexane react with bromine when the test tube was placed under the sunlamp?
Was the reaction rapid? If a reaction occurred, write and equation for it.
The reaction under the sunlamp was not immediate but did occur over a few
seconds. The reaction is as follows:
C6H12 + Br2 -----UV Light -----> C6H11Br + HBr
Was hydrogen bromide evolved in the reaction? What is your evidence?
Yes, hydrogen bromide evolved in the reaction as evidenced by the litmus paper
changing color from blue to red, indicating it is coming onto contact with an acid,
in this case hydrogen bromide.
b. Reaction with Oxygen (Combustion)
Which of the cyclic hydrocarbons reacted with potassium permanganate, KMnO4? Write
equations for the reactions that occurred.
The only hydrocarbon that reacted with potassium permanganate was cyclohexene, the
solution turned brown upon mixing the two together.
The reaction is as follows:
7C6H10 + 12C2H5OH + 10KMnO4 => 10MnO2 + 11C6H10(OH)2 + 10KOH

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c. Reaction with Oxygen (Combustion)
Compare the amount soot that was produced when the various cyclic hydrocarbons
burned.
Soot produced by:
Cyclohexane: Low amounts of soot
Cyclohexene: Soot produced
Toluene: Lots of soot produced.
On the basis of your observations of the burning of toluene, comment on the practical
problems associated with using toluene as fuel in your car.
Toluene will produce far more pollution in form of smog it seems. Toluene has a higher
ignition temperature than gasoline as well, which will make it less feasible to use as a
fuel. Car engines are specifically designed to burn gasoline and this disparity in physical
properties will likely adversely affect the engine health and produce waste in form of
engine deformation and wear and tear over the lifetime of the engine, in turn causing
unintended forms of pollution secondary to emissions.

d. Tests on Some Common Hydrocarbons

Record your observations on the tests of the Common Hydrocarbons with Br2, KMnO4, and O2.
Also indicate the type of hydrocarbon (alkane, alkene, or aromatic) in each case and whether it is
saturated or unsaturated.

Using your textbook and any other source, draw structures for naphthalene, polystyrene,
polyethylene, and a high-octane compound typically found in gasoline (show segments of
polymer molecules).
Drawings below:

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3. Observations on Some Common Hydrocarbon Derivatives
Relate the odor of each of the hydrocarbon derivatives to some familiar commercial or
natural material.
I could not smell any of the chemicals, I am unable to relate what I cannot smell to other
items I can also not smell.

4. Synthesis of Acetylene
Describe what happened when water was added to calcium carbide.
The calcium carbide began to bubble. After inserting the flaming splint it was
discovered flammable gas was created when the water reacted with the calcium
carbide.
Wat did you observe when the burning splint was thrust into the test tube?
When the flaming splint was thrust into the test tube, an explosion occurred. This
indicates flammable gas was created by the interaction of water and calcium
carbide.
Is acetylene unsaturated? What is your evidence?
The acetylene is unsaturated, this is shown by the reaction with potassium permanganate.
The potassium permanganate turns brown slowly in the presence of acetylene gas. This
shows an oxidation reaction the triple bond in acetylene is broken and each carbon atom
is oxidized to a carboxylic acid group when exposed to potassium permanganate.
Write and equation for the synthesis of acetylene.
CaC2 + 2H2O => C2H2 + Ca(OH)2

Write and equation for the combustion of acetylene.

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 2C2H2 + 5O2 => 4CO2 + 2H2O
Did the purple color of potassium permanganate disappear? What color product was
formed? Does this confirm acetylene is unsaturated? Write an equation for the reaction
that occurred.
The Purple KMnO4 turned brown slowly over time. Indicating the acetylene formed
reacted (oxidizes) the potassium permanganate, causing the change of color.
Discussion:
Questions and problems:
1. From a chemical standpoint, why is the hydrocarbon mixture called paraffin wax ideally suited
for a covering on a jelly jar.
From a chemical standpoint paraffin wax is ideally suited for a covering on a jelly jar
because it is hydrophobic because it is a non-polar molecule, jelly is water based and will
be easily contained by the paraffin wax. The paraffin wax is comically stable and will
not react with the jelly it is preserving. Paraffin wax is solid at room temperature and can
form an effective air tight barrier.
2. When hydrocarbons burn in insufficient oxygen, one product (along with water) is carbon
monoxide, CO. Write an equation for the combustion of acetylene with insufficient oxygen.
Why is some CO formed during combustion in an automobile engine?
The balanced chemical equation for the combustion of acetylene with insufficient oxygen
is: 2C2H2 + 3O2 → 4CO + 2H2O

CO is formed during combustion in an automobile engine because the oxygen supply

may not be adequate, weather the cold-air intake is damaged or clogged, or the car
computer is simply not pulling enough oxygen into the cylinders to facilitate full
combustion is unknown, but the carbon monoxide is formed by insufficient oxygen gas
levels present during combustion.
3. Two of the compounds in this experiment had similar odors, yet their molecular structures are
very different. Comment on factors at the molecular level which may be involved in the
mechanism of smell. (Assume that a nerve impulse to the olfactory center of the brain is initiated
by interaction of molecules, in this case the hydrocarbon with a receptor in the nose.)

The two hydrocarbons with similar odors (as verified by my group members as I do not smell
very well), were cyclohexane and toluene. Both cyclohexane and toluene have very similar
chemical structures and are cyclic hydrocarbons. Cyclohexane and toluene likely smelled very
similar because they are likely picked up by the body’s smell receptors in a similar manner
because of the structural similarities.

4. Discuss the relationship between the molecular weights of hydrocarbon molecules and the
uses of hydrocarbons in modern society.

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Discuss the relationship between the molecular weights of hydrocarbon molecules and the uses
of hydrocarbons in modern society is clearly shown by smaller hydrocarbon molecules being
used as fuel sources due to their volatility and ease of combustibility. The higher molecular
weight hydrocarbons are useful for other purposes like lubrication of machinery because they
have a higher melting point and are less volatile. Higher weight hydrocarbons like paraffin wax
have many applications like use as wax to seal food (their chemical properties make they
hydrophobic and a good packaging material), or for candle wax to limit the speed ant which the
wick burns. Hydrocarbons are not only what we are made up of as people, but are essential to
the functioning of modern society, it’s how we get around, it’s how we package our good and
food, it’s how we operate our society. Unless alternatives are found these finite resources will be
depleted, this does not bode well for humanity.

Conclusion:
In conclusion this lab demonstrated the physical properties of hydrocarbons in a real world, easy
to understand setting. I was able to learn the physical properties of hydrocarbons easily when
they are presented in a physically observable setting. Though the lab was easy to understand, I
personally, have an extremely weak sense of smell, this lead to difficulty when denoting the
odors between chemicals. All of the odors smelled the same to me, like nothing! To me the
organic chemistry lab does not have the foul odor everyone else seems to perceive, it smells like
nothing to me, I can’t even smell the gas for the Bunsen burners, combined with hearing damage
(physically induced by nerve damage) it made detecting the gas and lighting it a bit harder than
for those with properly working smell and hearing. I feel that due to my poor sensory perception
things like this were made extremely difficult if not impossible for me because my sense of smell
is not effective. I would change the lab to not include this portion as I’m sure there are other
people with a bad sense of smell. Otherwise I feel the Synthesis of Acetylene (section 4) did a
great job of capturing people’s attention by giving real world ques to otherwise unseen chemical
processes (the explosion after inserting the burning splint, or the change of potassium
permanganate from purple to brown in the acetylene gas). The combustion test was a good way
to visualize weather the hydrocarbons were saturated or unsaturated, and to visually represent the
bonds among the hydrocarbons, though combusting the same amounts was a bit difficult, putting
more of one hydrocarbon then another may lead to inaccurate results, and using a dropper bottle
was for the most part fine, though more accurate methods may yield clearer results. One drop of
the hydrocarbons tested may have considerably more weight than another single drop from a
separate hydrocarbon, but I guess this is a bit “nit-picky”.

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