Experiment 8

HYDROCARBONS

CHY52 (Organic Chemistry I)

MF (1:00 PM – 4:00 PM)

A Formal Laboratory Report

Presented to:

PROF. JANET DUNGOG

November 4, 2019
I. INTRODUCTION

Hydrocarbons are organic

compounds that are composed only
of hydrogen and carbon. According to
IUPAC nomenclature, there are two
classifications of hydrocarbons
namely, aliphatic and aromatic
hydrocarbons. Aliphatic compounds
are carbon compounds arranged in
open chains and can be
straight chained, branched and can Figure 1. Classification of Hydrocarbons
contain single, double or triple bonds.
Saturated hydrocarbons, the alkanes, contain only carbon-carbon single bonds with the maximum
number of hydrogen attached to each carbon atoms. Meanwhile, unsaturated hydrocarbons have
double or triple carbon-carbon bonding hence containing less than the maximum number of
hydrogen attached to each carbon. These are the alkenes and alkynes. Lastly, aromatic hydrocarbons
contain a closed loop (sextet) of electrons. They follow Huckel’s rule, and their structure is stabilized
through pi electron delocalization or resonance, and all are cyclic (McMurry, 2011).

Saturated and unsaturated hydrocarbons have similar physical properties, but their chemical
properties are different. Unsaturated hydrocarbons are chemically more reactive than saturated
ones. This is because of the presence of carbon-carbon multiple bonds in such compounds and these
multiple bonds serve as locations were chemical reactions can occur.

In addition, hydrocarbons encompass various physical properties such as nonpolarity, in

which electrons are equally shared entailing no electronegativity difference. As a result, alkane is not
soluble in water due to the close electronegativities of C and H atoms (Gallant & Yaws, 1995).
Hydrocarbons also undergo relatively few chemical reactions other than combustion and their
chemical properties are mostly determined by the type of bond in the compound. All hydrocarbons
undergo combustion and burn in the presence of oxygen.

The physical states of hydrocarbons are generally affected by the intramolecular forces of
attraction (IMFA) that are present between their atoms. The strength of the IMFA is directly
proportional to the melting and boiling point of the hydrocarbon. The numbers of carbon atoms also
affect the physical state of the hydrocarbon. The greater the number of carbon atoms presents in a
given compound, the higher the boiling and melting point of the said compound.

In this experiment, five samples of hydrocarbon used to conduct this experiment, namely:
methane, ethylene, acetylene, cyclohexane, and toluene. Before conducting the experiment, the
physical properties of the sample like physical state, odor and color are the first data to be use in
identifying and classifying the compound and there are few ways introduced to identity classes of
hydrocarbons: ignition test, Baeyer’s test and Tollen’s test. The ignition test indicates the presence
of unsaturation or high carbon to hydrogen ration. The Baeyer’s Test is a test for the presence of
unsaturation (double bonds). Baeyer’s test uses a solution called the Baeyer’s reagent, which is a
solution of alkaline potassium permanganate. Reaction with double or triple bonds in an organic
material causes the color to fade from purplish-pink to brown. The reaction with tollen’s reagent,
ammoniacal AgNO3 exclusive to alkynes forming white precipitates-an indication of a positive result.

II. OBJECTIVES

Considering the mentioned concepts in the introduction section, an investigation was then
carried out through laboratory experiment. The objectives of the experiment are as follows: (a) to
differentiate hydrocarbons in terms of intrinsic physical properties and chemical properties
concerning to its structure and behaviour; (b) to observe the characteristic reaction of alkanes,
alkenes, alkynes and aromatic hydrocarbons through chemical tests and reactions (ignition
/flammability) tests, Baeyer’s test, Tollen’s test; and (c) to prepare ethylene gas by dehydration of
alcohol (water displacement method).

III. MATERIALS (Chemicals and Apparatus)

Prior in performing this experiment, the chemicals/substances needed were: (a) methane
(CH4); (b) ethylene (C2H4); (c) acetylene (C2H2); (d) cyclohexane (C6H12); (e) toluene (C7H8); (f)
potassium permanganate (KMnO4); (g) concentrated sulphuric acid (H 2SO4); (h) ethyl alcohol
(C2H5OH); (i) calcium carbide (CaC2); (j) silver reagent, (k) tollen’s reagent; (l) distilled water (H2O),

This experiment utilized as well the following apparatuses: (a) porcelain crucible cover; (b)
crucible tongs; (c) dropper; (d) match stick; (e) hot plate; (f) test tube with stopper; (g) 250-mL
distilling flask; (h) test tube; (i) test tube rack; (j) test tube holder; (k) test tube brush; (l) iron stand;
(m) iron ring; (n) clamp; (o) wire gauze; (p) rubber tubing/delivery tube; (q) boiling chips; (r)
Erlenmeyer flask; (s) thermometer; (t) basin; (u) graduated cylinder; (v) dropping funnel.
IV. PROCEDURE

Different tests were performed to determine the type of hydrocarbon used in each sample.
The hydrocarbon samples (methane, ethylene, acetylene, cyclohexane, and toluene) were examined
and each compound was subjected to the tests described below.

A. Ignition Test

For liquid samples, three (3) drops of each hydrocarbon were placed in a porcelain cover and
brought with crucible tongs to the edge of a burner flame. All observations were recorded regarding
each sample's flammability and the nature of the flame (color and sootiness). In gaseous samples,
The test tube was filled with gas in an upright position, the stopper was removed and by using a
match, the gas inside was ignited. Thereafter, the color and luminosity of the flame was carefully
observed.
B. Reaction with Cold Dilute Permanganate
One (1) mL of dilute KMnO4 solution was placed in a test tube, adding five (5) drops of the
sample and shaking to mix. The tube content was examined after five (5) minutes of intermittent
shaking.
C. Reaction with Ammoniacal Silver Nitrate Solution
The silver reagent was placed in a clean, small test tube with ten (10) drops and added with
two (2) drops of hydrocarbon. The tube contents were thoroughly mixed and observed. Any
precipitate obtained by the laboratory instructor was transferred to a vessel.

D. Preparation of Ethylene Gas

In a 250-mL distilling flask, 15 mL of 95% ethyl alcohol was placed. Then, 45 mL of

concentrated sulfuric acid was added slowly while constantly shaking and cooling under the tap
water. Boiling chips were added to the mixture in the flask to prevent frothing. A flask and a delivery
tube were inserted. The mixture was heated into a temperature range of 165-170C. (No sample was
collected during this experiment for it failed due to some errors.

E. Preparation and Testing of Acetylene Gas

Approximately 5 g of calcium carbide limps were inserted into a dry 250-mL distilling flask
and the rest of the acetylene generation set-up was assembled. Approximately 100 mL of water was
added to the dropping funnel, and then a few drops were allowed to fall on the solid and waited for
the air to be removed from the apparatus for a few minutes. (The acetylene gas was collected via
downward water displacement method.) The gas evolved was used to test B, C and D to add water
when necessary. The gas was bubbled for a full minute through the test tube contents, wherever the
hydrocarbons were added to the procedure.

V. EXPERIMENTAL DATA AND RESULTS

The results of this experiment were recapitulated in tables below (all tables presented
display all the data taken in different stages of the experiment).

Table 1. Sample Description and Sample Structures

Description Structural
Sample Formula
Color Odor Physical State
Methane
Colorless Odorless Gas

Ethylene
Colorless Sweet odor Gas

Acetylene Colorless Ethereal odor Gas

Colorless Petroleum-like odor Liquid

Cyclohexane

Toluene Colorless Aromatic odor Liquid

Table 2. Ignition Test

Observation
Sample
Color of the Flame Soot

Methane Blue colored flame No soot observed

Ethylene Blue colored flame No soot observed
Black soot observed inside the walls of
Acetylene Orange colored flame the test tube and some escaped into
gas
Black soot observed at the porcelain
Cyclohexane Yellow-orange colored flame crucible cover
Plenty of black soot remained at the
Toluene Intense yellow-orange colored flame porcelain crucible cover and some
escaped into gas

Table 3. Oxidation Reaction with Baeyer’s Reagent (cold, dilute, neutral, aqueous KMnO 4)
 Sample Final Appearance of the Mixture

Methane The solution remained deep violet. Therefore, the reaction is

negative.
Ethylene The color changed from deep violet solution to brown solution.
Therefore, the reaction is positive.
Acetylene The color changed from deep violet solution to brown solution.
Therefore, the reaction is positive.
Cyclohexane The solution remained deep violet. Therefore, the reaction is
negative.
Toluene The solution remained deep violet. Therefore, the reaction is
negative.

Table 4. Reaction with Ammoniacal Silver Nitrate (Tollen’s Test)

Sample Final Appearance of the Mixture

Methane Colorless solution, no solid precipitate formed. Therefore, the

reaction is negative.
Ethylene Colorless solution, no solid precipitate formed. Therefore, the
reaction is negative.
Acetylene Gray solid precipitate formed. Therefore, the reaction is
positive.
Cyclohexane Presence of effervescence, no solid precipitate formed.
Therefore, the reaction is negative.
Toluene Droplets observed on the side of test tube, o solid precipitate
formed. Therefore, the reaction is negative.

Table 5. Generation of Acetylene

Mixture Description
During the reaction Calcium carbide(s) + distilled water(l) → white gas with strong pungent smell
After the reaction The gas captured with the use of water displacement method was colorless

Table 6. Summary of Results

Aromatic
Reagent Alkanes Alkenes Alkynes Cycloalkanes
Hydrocarbons
1. Baeyer’s reagent: is
X / / X X
there a reaction?
2. Ammoniacal AgNO3 : is
X X / X X
there a reaction?
VI. DISCUSSION AND INTERPRETATION OF RESULTS
 To be able to determine if the given organic sample compounds aromatic or aliphatic, a
closer look to the definition of aromatic and aliphatic should be considered first. An aromatic
hydrocarbon or arene (aryl hydrocarbon) is a hydrocarbon characterized by general alternating
double and single bonds between atoms. The configuration of six carbon atoms in aromatic
compounds is known as a benzene ring. Many of these compounds have sweet scent. An aliphatic
hydrocarbon is characterized by joined carbon atoms in straight chains, branched chains or non-
aromatic rings. They can be joined by single bonds (alkanes), double bonds (alkenes), or triple bonds
(alkynes).

For this experiment, methane (alkane), ethylene (alkene), acetylene (alkyne), cyclohexane
(member of cycloalkane family), and toluene (an aromatic hydrocarbon) are used for identification
and determination of hydrocarbon properties.

The physical characteristics of each sample were noted as reflected in Table 1. Each
compound has their own characteristic odor that makes them distinguishable from the others. The
methane is odourless, ethylene has a sweet odor, acetylene has an ethereal odor, cyclohexane is
petroleum-like and toluene has an aromatic odor. Table 1 also showed the structural formula of the
different compounds. Methane is the simplest hydrocarbon, consisting of one carbon atom and four
hydrogen atoms. Ethylene is used in chemical synthesis, especially in the manufacture of
polyethylene. Acetylene is a chemical compound that forms from the bonding of two carbon and
two hydrogen atoms. Cyclohexane is cyclic and has the lowest angle and torsional strain of all the
cycloalkanes. Lastly, toluene reacts as a normal aromatic hydrocarbon towards electrophilic
aromatic substitution.

Methane gas was collected from the LPG and was placed into three test tubes using the
water displacement method. This method was used since liquids are generally denser than gases, in
which, the gas will impel the liquid to move down, thus, efficiently acquiring gases with minimal
leaks (McMills, 2018). The same method was also applied in the collection of acetylene, which
source came from calcium carbide (CaC2) and it was then submerged to water, and let the bubbles
(C2H2) from the carbide to displace the water inside the test tubes underwater and covering it with a
cork stopper; and the collection of ethylene, which source came from the dehydration of ethyl
alcohol with concentrated sulphuric acid which acts as a catalyst.

In this test, all the compounds are flammable. Dispersion forces contribute to the overall
flammability of the hydrocarbon. The more electrons a molecule has, the more polarizable it is.
Longer hydrocarbons exhibit stronger dispersion forces between them than the shorter
hydrocarbons. As the number of carbon atoms increases, it become harder for the molecules to
diffuse or escape the solid or liquid phase and become a vapor. The more easily a hydrocarbon
vaporizes, the better it burns.

The collected sample of both methane and ethylene were used in the ignition test and it
showed the appearance of a blue flame at the brim of the test tube without the formation of any
visible soot. This occurrence is due to the low percentage of carbon present in methane and
ethylene and sufficient amount of oxygen present in the air (Kay, 2010). The blue flame also
indicates the combustibility efficiency of methane and ethylene which formed water and carbon
dioxide. The balanced chemical reaction of methane and ethylene combustion is shown respectively
below:

CH4(g) + 2O2(g) → CO2(g) + 2H2O(l) + energy

C2H4(g) + 3O2(g) → 2CO2(g) + 2H2O(l) + energy

Acetylene, cyclohexane, and toluene produced a yellow flame with visible soot. The yellow
sooty flame produced means; it was an incomplete combustion, which also produces carbon
monoxide. The flame was known as carburizing flame. This indicates that combustion of acetylene,
cyclohexane, and toluene occurred inside the test tube, wherein the gas expanded then air entered.
However, toluene is burnt and large amount of soot is produced. This indicate that the toluene
undergo incomplete combustion causes unburn carbon appear as soot. Base on this observation,
toluene with a benzene ring appears to be stable towards combustion that leads to incomplete
combustion. Besides, water vapour and carbon dioxide gas is produced. Since unsaturated
hydrocarbons have carbon-carbon pi bond (McMurry, 2011), this functionality results to incomplete
combustion when burnt in air with very sooty luminous flames due to high degree of unsaturation.
This further resulted to the production of carbon monoxide, carbon, and water as shown in the
balanced chemical reaction of acetylene, cyclohexane, and toluene below respectively:

C2H2(g) + O2(g) → CO(g) + C(soot) + H2O(l)

C6H12(g) + 4O2(g) → 2CO(g) + 4C(soot) + 6H2O(l)

2C7H8(l) + 5O2(g) → 2CO(g) + 12C(soot) + 8H2O(l)

Ignition test checks a number of properties. Almost all organic compounds are readily
flammable. Flammability is when the compounds react exothermically with oxygen. Because of the
high heat of reaction, it means a fire will result from the reaction. 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 CO 2 and H2O, which are very stable and have less
energy than the bonds of the initial reactants. The excess energy is lost as heat.

Yellow flames are luminous. Although they can get at some oxygen, they cannot get as much
as they need to turn all of the carbon that's being burnt up into carbon dioxide. This is why this kind
of flame produces soot. Since it cannot release all of the carbon as CO 2, some of it gets released as
the black stuff in smoke, which is the soot.  On the other hand, blue flames are non-luminous. These
flames have access to as much oxygen as they could possibly use, so they can burn very efficiently.
All of the carbon that gets used can be turned into CO 2, so there will be no soot.

Luminous flames do not produce much energy because they do not burn as efficient as non-
luminous. This just means that the non-luminous flames have a lot more energy than luminous ones,
and their flames are actually hotter. This is why the luminous ones look yellow and the non-luminous
ones look blue.

The degree of luminosity can be assessed by the presence of yellow flame and soot.
Aromatic compounds burn with sooty flame due to the incomplete combustion which causes the
formation of an unburned carbon. In terms of degree of luminosity, aromatic compound >
unsaturated hydrocarbon, unsaturated hydrocarbon > saturated hydrocarbon

If the flame is blue or non-luminous, then it results to a complete combustion, and the
carbon is completely oxidized. On the other hand, incomplete combustion is indicated by a yellow
flame (luminous), and the carbon is not completely oxidized.

According to Caringal (2013), in terms of luminosity aromatic compound is greater than

unsaturated hydrocarbon and unsaturated hydrocarbon is greater than the saturated hydrocarbons.
Contradict to the result of the cyclohexane and ethylene in the experiment, the ethylene which is an
unsaturated hydrocarbon produce a blue color flame (non-luminous) and cyclohexane which is a
saturated hydrocarbon did not undergo to complete combustion and produced a yellow flame
(luminous). Since the ignition test involves a combustion reaction it does not only include the test for
identification of unsaturated hydrocarbon but it also includes the oxidation, a combustion reaction is
said to be complete when all carbon atoms were oxidized, since cyclohexane has 6 carbons while
ethylene has only two, then ethylene has enough carbon to be oxidized completely while the
cyclohexane has a lot of carbon that only few of it were oxidized the remaining carbons were in the
form of soot. So for the luminosity of the following hydrocarbons methane < ethylene < acetylene
<cyclohexane<toluene.
 For the test in active unsaturation, chemical test, the Baeyer’s test was done. In this test, the
presence of carbon-carbon double bonded compounds, called alkenes or carbon-carbon triple
bonded compounds, called alkyne bonds was determined. It uses dilute Potassium Permanganate to
oxidize the carbon-carbon double or triple bond. It's called oxidation because the double bond is
replaced by a hydroxyl group. The carbon's charge goes from being +1 to +2, so it loses an electron
(and is thus oxidized).

Baeyer's reagent is an alkaline solution of cold potassium permanganate, which is a powerful

oxidant making this a redox reaction. A positive result for this kind of test is the decolorization of a
violet solution and formation of brown precipitate (MnO 2). Bayer’s test involves a redox reaction
were in Mn7+ is reduced to Mn4+ and alkene is oxidized to a diol. The reaction of alkenes with KMnO 4
yields MnO2 and a diol.

The Baeyer reagent is a cold dilute aqueous solution of potassium permanganate which is a
deep purple color. Potassium permanganate does not react with alkanes because they are saturated
(single bonds which are all taken). When it is added to alkanes the purple color does not change.
When it is added to an alkene, the purple color slowly disappears and a brown MnO 2 precipitate
forms. The appearance of the brown precipitate indicates a positive test for unsaturation.

In the experiment, results as shown in Table 3, the reaction of methane, cyclohexane and
toluene with Baeyer’s reagent had no color changes, the solution still remained violet, and no layers
were formed. Alkanes are saturated, thus potassium permanganate does not react with it. For
ethylene and acetylene, the color changed from deep violet solution to brown solution. Therefore,
the reaction is positive.

Ethylene reacted with the Baeyer's reagent changing the violet-colored solution into brown
due to the reaction with the double bond in the organic compound. The decolorization of the violet
solution and the formation of a brown precipitate (MnO 2) is considered as a positive result. This
redox reaction lowers Mn7+ to Mn4+ and oxidizes the alkene to a diol. Alkenes’ reaction to KMnO 4
yields a diol and MnO2.

With KMnO4, acetylene reacted to form a diol and a brown precipitate, magnesium oxide.
The presence of the triple bond had a major impact on the reactivity of acetylene so that it changed
from violet to brown in the presence of permanganate. In addition, acetylene is unsaturated; it is
possible to react to oxidation with KMnO 4.

An alkene is replaced with a diol. There is an evidence for the reaction because the purple
potassium permanganate goes colorless. Alkynes work the same way, but a 4 hydroxy quattrol is
produced. The reaction is important because it does not work on alkanes (compounds with carbon-
carbon single bonds) or aromatic compounds.

Alkanes and aromatic compounds did not react with potassium permanganate. Reactivity
towards oxidation of cyclohexene signifies that alkenes are predisposed to addition reactions. The
presence of a double bond in an alkene allows addition reactions to proceed. Pi electrons in a double
bond are loosely held between atoms accounting for alkene reactivity. Alkanes possess single bonds
or σ electrons which are tightly bound to atoms and hence, demonstrate no reactivity under normal
conditions. Toluene, although comprised of double bonds, displays stability or chemical unreactivity
because of resonance present in its conjugated planar ring system. Its pi electrons are not as reactive
as the pi electrons of alkenes. Also, toluene has sp 2 hybridized carbon atoms forming a perfect
hexagon. The stability is accounted for by the delocalization. As a general principle, the more you
can spread electrons around - in other words, the more they are delocalized - the more stable the
molecule becomes. The extra stability of benzene is often referred to as "delocalization energy".
More rigorous conditions such as elevated temperature will be required to elicit a reaction from
benzene or aromatic compounds.

In Table 4, Tollen’s test results were presented. To determine the presence of a triple bond
(alkyne), the reaction with ammoniacal silver nitrate must be observed. In the reaction, there is a
release of terminal proton of the alkyne so that the acetylide ion can form an insoluble precipitate
with Ag+. For instance, acetylene reacts with ammoniacal solution of AgNO 3 forming acetylide of
silver and resulted to the immediate formation of a white milky precipitate which later on turned to
a grayish stone-like precipitate at the bottom of the test tube.

H-C C-H + 2 AgNO3 + 2 NH4OH AgC CAg + 2NH4NO3 + 2H20

(White precipitate)
 Addition of ammoniacal AgNO3 to each sample caused precipitates to form. When
ammoniacal AgNO3 was added to cyclohexane and toluene, the solution became cloudy. In methane,
the solution became light yellow and thus it simply tells a negative result. Since the reaction with
ammoniacal AgNO3 is exclusive to alkynes, the cyclohexane, methane and toluene resulted in a
negative test in which there is no reaction.

VII. CONCLUSIONS

Based on the findings of the experiment, the objectives of this experiment were successfully
met. The hydrocarbons were classified according to the test results successfully. Moreover, their
properties were also demonstrated through the use of the different tests.

There are different types of hydrocarbons, and there are different tests that can be
conducted to show the different properties that each type possesses. In this experiment, methane,
ethylene, acetylene, cyclohexane, and toluene were the sample used and were subjected to
different tests. First, ignition test brings about a chemical change; some decompose and blacken,
while others burst into flame. As a rule, the higher the oxygen contents of a compound, the bluer its
flame; as hydrogen increases, the flame becomes more yellow. Cyclohexane, acetylene and toluene
produced soot after combustion, indicating their high carbon to hydrogen ratio. Baeyer’s test was
conducted to test for a hydrocarbon’s active unsaturation. Potassium permanganate reacts readily
with alkenes to form glycols or other oxidation products. Neither alkanes nor aromatic hydrocarbons
show reaction with potassium permanganate. The reaction can be followed by the disappearance of
the purple colour of the KMnO 4. The presence of clear or brown colour indicates the presence of
manganese oxide, MnO2. Results show that ethylene and acetylene is the actively unsaturated
sample used. Toluene, although they contain double bonds, are already stable; therefore, they are
not actively unsaturated. Tollen’s test reaction is exclusive to alkynes and only acetylene is the
alkyne in the sample, therefore it is the only one that is positive in this test. Thus, these chemical
reactions such as oxidation help us predict what type of hydrocarbon is being tested (saturated or
unsaturated).

VIII. REFERENCES
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Hydrocarbons. (2014). Retrieved November 16, 2019 from https://www.academia.edu/

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Kay, W.B. (2010). Pressure-Volume-Temperature Relations for n-Butane. Ind. Eng, Chem.
32 (3), pp 358–360.

Properties of Hydrocarbons. (2011). Retrieved November 16, 2019 from

http://www.mendelset.com/articles/689/properties_hydrocarbons

Shriner, R.L. & Curtin, D.Y. (1980).Chemical Classification Tests and For Derivatization. 6th ed. New
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McMills (2018). Simplicity and Elegance of the Wash Bottle in Water Displacement Scheme. Journal
of Laboratory Chemical Education, 6(1), pp. 67-68
McMurry, J. (2011). Organic chemistry with biological applications. USA: Mary Finch.
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