CHEMICAL PROPERTIES OF HYDROCARBONS

Garnica Isabella, Orellano Maria, Collante Catalina, Jaimes Raul

Industrial Chemistry, Faculty of Basic Sciences, Francisco de Paula Santander
University.

SUMMARY:
Hydrocarbons can be obtained naturally and synthetically by chemical methods.
Procedures are carried out to obtain a hydrocarbon, whether aliphatic, cyclic or
aromatic, which are identified by showing their release in the form of gas. If these
gases are exposed to the flame, their combustion can be seen and when they are
put in contact with different reagents, how they react according to their
characteristics can be observed.

Keywords: Hydrocarbons, alkane, benzene.

INTRODUCTION.

Organic compounds that contain only carbon and hydrogen in their molecules are
called hydrocarbons. They form a carbon structure to which hydrogen atoms are
attached. Hydrocarbons are classified into two main classes
• Aromatic Hydrocarbons, which have at least one aromatic ring (planar set of six
carbon atoms)
• Aliphatic Hydrocarbons, join together in open chains, either linear or branched.
Aliphatic Hydrocarbons in turn are classified into:
• Saturated Hydrocarbons, also known as alkanes, which do not have any double or
triple bonds between carbon atoms.
• Unsaturated hydrocarbons have one or more double or triple bonds between
carbon atoms.
Depending on whether the bonds are double or triple, they are classified as:
alkenes: contain one or more double bonds
alkynes: contain one or more triple bonds

Alkanes
The simplest family of this group is that of alkanes, which is characterized by the
general formula (CnH2n+2). Due to their structure, alkanes are also called saturated
hydrocarbons. In an alkane molecule the only chemical bonds that exist are the
simple ones between carbon atoms and between carbon and hydrogen atoms. Due
to the great stability of these bonds, alkanes are not very reactive, which is why they
are also called paraffins. Alkanes are obtained mainly from oil and natural gas,
where they are mixed as products of the anaerobic decomposition of living matter.
[1]

Methane is the simplest alkane hydrocarbon that exists. Its chemical formula is CH4.
This means that there are four hydrogen atoms and one carbon atom, which are
joined by covalent bonds. Methane occurs in nature in the form of a gas at normal
temperatures and pressures. In addition, it is colorless and odorless, despite being
produced by the rot of plants.
Among the uses of methane, the one that stands out the most is its application as
fuel. Its heat of combustion is the lowest of all hydrocarbons, but if its molecular
mass is divided it produces the same amount of heat as the most complex ones.
This makes it very useful for domestic use, being known as natural gas.

Methane can be obtained from different sources. The main one is that which is
extracted from geological deposits, created by the decomposition of organic matter.
It can also be obtained from the fermentation of organic remains, such as manure or
wastewater sludge. [2]

Hexane or n-hexane is an alkane aliphatic hydrocarbon with six carbon atoms. Its
chemical form is C6H14. It is also known as hexyl hydride.
This has application in: Extraction of edible vegetable oils, Production of
concentrated foods for animal consumption, Solvent for paints, Solvent for chemical
processes and Footwear Industry. [3]
Unsaturated hydrocarbons that have molecules with at least one carbon-carbon
double bond are known as alkenes. These compounds are alkanes that, upon losing
a pair of hydrogen atoms, begin to have a double bond formed by two carbons. They
used to be known as olefins, since the simplest compounds generate oils by
establishing a reaction with a halogen. Alkenes, on the other hand, have different
physical characteristics compared to alkanes because the carbon double bond
changes the properties linked to acidity and polarity, for example. [4]
The simplest alkene is ethylene, which under normal conditions is found in a
gaseous state and naturally in plants, and is considered a hormone in the plant world
(phytohormone). This hormone is responsible for the stress processes to which
plants are subjected, including processes as important as fruit ripening. It has a
characteristic, not unpleasant aroma. It can be considered one of the most important
chemical compounds for the industry. A characteristic reaction of ethylene is the
formation of the alcohol, ethanol, through hydration, when reacting with water, and in
the presence of a catalyst. In many cases, these reactions have commercial interest,
since ethylene is very present in the petrochemical industry, where it is transformed
into countless products, ranging from plastics to antifreeze substances, including
different polymers such as fibers and elastomers.[5]
Alkynes are hydrocarbons or organic compounds that have a triple bond between two
carbons in their structures. This triple bond (≡) is considered a functional group as it
represents an active site of the molecule, and therefore is responsible for their reactivity.
These exhibit greater acidity and polarity than alkanes and alkenes due to the nature of their
links. The precise term to describe this slight difference is what is known as unsaturation .
How as additional bonds are formed between the carbons, the number of hydrogens
bonded to them decreases. Due to its electronic characteristics, carbon seeks to
form four simple bonds, so the greater the unsaturation, the greater the tendency to
react (with the exception of aromatic compounds).
Acetylene is the simplest and smallest alkyne of all. From its chemical formula, other
hydrocarbons can be expressed by replacing the H with alkyl groups (RC≡CR'). The same
thing happens in the world of organic syntheses through a large number of reactions.

This alkyne is produced from the reaction of calcium oxide from limestone and coke,
a raw material that provides the necessary carbons within an electric furnace:

CaO + 3C => CaC2 + CO

CaC2 is calcium carbide, an inorganic compound that finally reacts with water to
form acetylene:

CaC2 + 2H2O => Ca(OH)2 + HC≡CH [6]

In aromatic hydrocarbons, benzene is found, which has six carbon atoms (C) and six
hydrogen atoms (H). Its chemical structure can be described as a hexagonal ring
with alternating double union. It is a colorless, flammable liquid with a sweet odor. It
evaporates quickly when exposed to air. This is formed from natural processes, such
as volcanoes and forest fires. It is mainly used as a starting material in the
manufacture of other chemicals, including plastics, lubricants, rubbers, dyes,
detergents, drugs and pesticides. However, its non-industrial uses are limited
because benzene is carcinogenic and toxic.[7]

MATERIALS.

In the laboratory, these reagents were used properly in each part of the practice
developed: Anhydrous sodium acetate, sodium hydroxide, n-hexane, Baeyer's
reagent, bromine in 2% carbon tetrachloride (can be replaced by bromine water),
concentrated sulfuric acid, calcium carbide, benzene, concentrated nitric acid, sand,
carrot.
 METHODOLOGY.

Part I: This part was carried out demonstratively.

Soda lime was prepared: 1 part sodium hydroxide and calcium oxide. The NaOH
(which was in the form of granules) was pulverized, then the CaO2 was added, then
sodium acetate was added, then the mixture was transferred to a side release tube
and covered with a stopper, sealed well. Previously, the Bunsen burner is lit, the gas
is released through the side hose that is connected to the tube. The hose
approaches the bunsen burner and it was observed how the gas coming out of the
hose ignites.

Part II: five test tubes were taken and approximately 2 ml of hexane was added to
each one, subsequently 3 drops of KMnO4 were added to tube #1, 5 drops of NaOH
were added to tube #2, and 5 drops of NaOH were added to tube #3. H2SO4 was
added and finally bromine water was added to tubes # 4 and 5 and they were left in
the presence and absence of light respectively.

Part III: this part was carried out demonstratively.

Approximately 10 mL of ethanol was added to the round bottom flask with lateral
detachment. Then, with great caution and avoiding splashes, approximately 20 mL of
concentrated sulfuric acid was added. A little sand was added to the previous
mixture. The sand is used in order to avoid overheating of the reaction mixture. The
balloon was covered by adapting a rubber stopper that has a thermometer to monitor
the temperature and a rubber hose was also adapted to the nose of the lateral
detachment. The joints were checked so that there were no possible places for gas
escape in the assembly. The heating plate was turned on and it was checked that
the temperature did not exceed 145 – 150 ºC. The rubber hose was submerged in a
beaker containing water approximately halfway. The hose was left in the water until
the gas bubbling was constant, once this was achieved, the hose was removed from
the water, letting a little escape. of gas and perform the combustibility test. 4 clean
and dry test tubes were prepared in the rack and containing approximately 1 mL of
the following reagents: Baeyer, Br2/CCl4, NaOH solution and H2SO4. The hose was
removed from the beaker. with water and was immediately introduced into each of
the test tubes containing the reagents, allowing the ethylene to bubble for 1 or 2
minutes.

Part IV: a little grated carrot was added to a test tube and 1 ml of n-hexane was
added and then shaken vigorously and 10 drops of this new solution were
transferred to a different test tube to add 5 drops of H2SO4 and stir.

Part V: Approximately 10 g of calcium carbide (CaC2) was placed in a balloon with

lateral release. A dispenser was adapted to the mouth of the balloon with lateral
release, and approximately 60 mL of distilled water was added. A hose was adapted
to the warhead of the lateral detachment and a beaker with approximately 20 mL of
water was available to collect the gas generated. It was verified that in none of the
joints there were spaces that could serve as a leak for acetylene. The stopcock of
the dispenser was opened to let the distilled water fall on the calcium carbide. The
combustibility test was carried out. The other points were not carried out since the
reagent was in powder form and in that state it does not react well.
Part VI:

Flammability: 3 drops of benzene were added to a porcelain capsule and carefully

brought close to the flame.

Halogenation: a test tube was taken and 1 ml of benzene and bromine water was
added.

Oxidation: KMnO4 was added to a test tube containing 1 ml of benzene.

Sulfonation: benzene was added to a test tube and H2SO4, and it was heated in a
water bath for approximately 3 minutes.

Nitration: A mixture of 10 drops of concentrated H2SO4 and 2.5 mL of concentrated

HNO3 was prepared with great caution. 10 drops of benzene were added to said
mixture and then heated in a water bath for 4 minutes. The mixture was allowed to
cool and then He poured it into a glass containing approximately 20 mL of cold
water. He perceived the smell by dragging the vapors with the palm of his hand
towards his nose.

ANALYSIS AND RESULTS.

Part I. Obtaining methane

In the laboratory to obtain methane, sodium acetate (CH3COONa) was reacted with
soda lime (NaOH and CaO). In this process, methane is obtained because the
pyrolysis of sodium acetate is carried out, that is, the breakdown of the molecules by
means of heat, giving methane as a product. (8) Methane is identified when exposed
to flame since this is a flammable gas that produces incomplete combustion.

Part II. Chemical properties of saturated hydrocarbons (n-hexane)

In test tube #1, when adding 3 drops of KMnO4, which is purple, to 10 drops of
hexane (colorless), it is observed that the two solutions do not mix or react, this is
because The Baeyer test consists of adding a solution alkaline of KMnO4 to a
sample where it is believed that there are unsaturations,[8] and hexane, being an
aliphatic alkane, is saturated, for this reason it is only observed that the two solutions
are separated.
In test tube #2, 5 drops of NaOH and 10 drops of hexane were added and it is
observed that these two do mix and the solution remains colorless. When you have a
non-polar solvent such as hexane and a polar compound (NaOH), dissolution does
not occur since the non-polar molecules of the hydrocarbon do not solvate the ions
since a lot of energy is required to break the crystals.[9] ]
In test tube #3, H2SO4 and hexane were added. These form two phases because
the acid is a polar compound and the hydrocarbon, being non-polar, is insoluble in
polar compounds and does not react.
In test tube #4 and #5, hexane and bromine water were added but they were left in
the presence of light and in the absence of light respectively. In #4, a single phase
and one reaction were observed because the alkanes They react with halogens ,
mainly chlorine and bromine; The reaction is photochemical, that is, it requires the
presence of light. Halogenation is a substitution reaction, replacing hydrogen atoms
with halogen atoms in the alkane molecule.[10] and in #5 the two phases are
observed because if they are to react in the dark they must be subjected to high
temperatures (>250°C). [10]

Part III. Preparation and chemical properties of ethylene (C2H4)

To obtain ethylene from an alcohol, in this case ethanol, dehydration was carried out
by applying heat, which led to the formation of the expected alkene. Ethylene with
potassium permanganate in this there is a color change because the permanganate
ion (purple color) is replaced by a precipitate of manganese dioxide (MnO2) that
turns dark brown. (9) When ethylene is exposed to bromine water, a double bond
rupture occurs and by the addition reaction a bromine is added to each carbon,
obtaining dibromoethane, evidenced in the discoloration of bromine water. Ethylene
in bromine water. In This reaction (halogenation) involves the electrophilic addition of
Br+ to the alkene and the double bond of ethylene is eliminated. When hexane is
exposed to H2SO4, a penetrating odor is perceived, due to the formation of SO2 that
causes the odor and thus reveals the reaction since there was no color change or
precipitate.

Part IV. Qualitative determination of beta-carotenes in carrots

A small amount of carrot was added to a test tube and 1 ml of hexane was added
and it was shaken vigorously. It was observed that the solution that was colorless
initially turned translucent yellow. A few drops of this solution were passed to a test
tube. different test and H2SO4 is added where two phases are observed, one
aqueous and the other a little oily, this when stirred you begin to observe how the
translucent yellow changes to a darker color almost green and thus changes to a
dark gray, this indicates the separation or breakdown of beta-carotene.

Part VI. Chemical properties of benzene (C6H6)

- Flammability:
 Most organic solvents are highly flammable and toxic. In carrying out the practice, it
was verified by exposing benzene to the flame, which produced incomplete
combustion.

- Halogenation: 2% Br2/CCl4.

1 ml of benzene and bromine water were added to a test tube, two phases were
observed. Both chlorine and bromine produce derivatives by substitution of
hydrogens from benzene, giving what is known as aryl halides . Halogenation
reactions are favored by low temperatures, in the presence of a catalyst, such as
iron or some Lewis acid, in order to be able to polarize the halogen to produce the
reaction. Like nitration, halogenation is also a monosubstitution reaction. [11]

- Oxidation: Baeyer's reagent.

Benzene and KMnO4 were added to a test tube where two phases were observed,
the purple one due to the permanganate remaining at the bottom because it was
denser than the benzene. Potassium permanganate and potassium dichromate allow
alkyl groups of benzene to be oxidized. The chain breaks at the benzylic position
regardless of its length, generating benzoic acid.[12]

- Sulfonation.

Benzene and H2SO4 were added to a test tube, the solution first turned yellow and
then turned brown. Two phases were observed where the benzene, being less
dense, remained at the top. The SO3, a good electrophile, was attacked. through the
aromatic ring, producing the electrophilic addition, a final stage of recovery of
aromaticity due to the loss of a proton gives us benzenesulfonic acid.[13]

- Nitration.

By adding HNO3 to benzene in the presence of H2SO4 as a catalyst, the nitronium

cation is formed, which causes the nitration of the benzene. When it is allowed to
cool and cold water is added, a pleasant odor similar to that of almonds is perceived
due to the nitrobenzene.

CONCLUSIONS

∙ Each of the reactions carried out in this report confirmed the presence of a certain type of
hydrocarbon upon contact with the reagents.
∙ The type of combustion caused by each of the hydrocarbons (methane and ethylene) was
identified.

∙ The type of reaction and interaction presented in a mixture of a reactant and an organic
compound is given by its properties and characteristics .

References

[1] Geocities.ws. (2019). [online] Available at:

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[2] OKDIARIO. (2019). What is methane? Properties of natural gas . [online] Available at:
https://okdiario.com/curiosidades/propiedades-metano-gas-natural-1038131 [Accessed 20 Sep.
2019].

[3] Marketizer.com, Q. (2019). Uses and applications of hexane | QuimiNet.com . [online]

Quiminet.com. Available at: https://www.quiminet.com/articulos/usos-y-aplicaciones-del-hexano-
44406.htm [Accessed 20 Sep. 2019].

[4] Definition.of. (2019). Definition of alkenes — Definicion.de . [online] Available at:

https://definicion.de/alquenos/ [Accessed 20 Sep. 2019].

[5] Quimica.laguia2000.com. (2019). Ethylene | The Chemistry Guide . [online] Available at:
https://quimica.laguia2000.com/quimica-organica/ethylene [Accessed 20 Sep. 2019].

[6] Life Persona. (2019). Alkynes: properties, structure, uses and examples - Life Persona . [online]
Available at: https://www.lifeder.com/alquinos/ [Accessed 20 Sep. 2019].

[7] Benzene. (2019). What is Benzene? - Main Uses and Health Risks . [online] Available at:
https://www.benzene.net/ [Accessed 20 Sep. 2019].

[8] Quimicaorganica.org. (2019). Baeyer test . [online] Available at:

https://www.quimicaorganica.org/foro/13-alquenos/7924-proba-de-baeyer.html [Accessed 20 Sep.
2019].

[9] Coursehero.com. (2019). When you have a non-polar solvent like hexane and a polar solute like |
Course Hero . [online] Available at: https://www.coursehero.com/file/p10gsrt/when-se-tiene-un-
dissolvente-no-polar-como-el-hexano-y-un-soluto-polar-como- on/ [Accessed 20 Sep. 2019].

[10] Chemistry | Inorganic chemistry. (2019). Chemistry | Inorganic Chemistry: Main reactions of
alkanes . [online] Available at: https://www.fullquimica.com/2012/09/reacciones-principales-de-los-
alcanos.html [Accessed 20 Sep. 2019].
[11] Quimica.laguia2000.com. (2019). Reactions of Benzene | The Chemistry Guide . [online]
Available at: https://quimica.laguia2000.com/reacciones-quimicas/reacciones-del-benzeno [Accessed
20 Sep. 2019].

[12] Quimicaorganica.net. (2019). BENZENE | Organic Chemistry . [online] Available at:

http://www.quimicaorganica.net/benzene.html [Accessed 20 Sep. 2019].

[13] Quimicaorganica.net. (2019). Sulfonation of Benzene | Organic Chemistry . [online] Available at:
http://www.quimicaorganica.net/sulfonacion-benzene.html [Accessed 20 Sep. 2019].

Annexes
1.Write the balanced chemical equations for the reactions of

obtaining methane, ethylene and acetylene.

Methane

CH3 COONa + 2NaOH + CaO CH4 + CaO+ Na2O3

Incomplete combustion

2CH4 + 3O2 2CO + 4H2O

Ethylene

(Ethene)

C2H5OH H2SO4 C2H4 + H2O

Complete combustion

C2H4 + 3O2 2CO2 + 2H2O

2. Write the balanced equations for the reactions in part II, III, and

V where the positive tests resulted.

Part II. Chemical properties of saturated hydrocarbons (n-

hexane)
Part III. Preparation and chemical properties of ethylene (C2H4)

∙ Ethylene (ethene) is obtained by the distillation of ethanol (alcohol

ethyl)

3. In part IV, for the qualitative test of β-carotenes does it occur or not?

discoloration of the solution? If discoloration occurs, what is the cause?

freak? Explain.

♣ Yes, discoloration of the solution occurs for the qualitative β-test.

carotenes because n-hexane acts as an organic solvent and

breaks the double bonds of β-carotene

4. Write the five balanced chemical reactions corresponding to the tests carried out
in part VI with benzene.