Experiment 4

Preparation of Hydrocarbons

Joshell Mharielle C. Sion/ Group 4

September 26, 2019

1. Introduction

Hydrocarbons are the most widely used organic compound on the planet. They are considered the driving
force for modern civilization, because of the makeup fossil fuels. Hydrocarbons can be classified based on
the number of carbon bonds; alkanes are those that do not contain functional group, alkenes contain C-C
double bonds, alkynes contain C_C triple bonds and aromatic hydrocarbons contain aromatic ring.

These type of compounds also possess different properties and characterization. Physical properties
include flammability and solubility. Flammability can be observed through the presence of the black soot.
Unsaturated hydrocarbons( compounds that have C-C multiple bonds) produce a black sooty flame when
burned. This is due to the incomplete combustion of carbon. Saturated hydrocarbons leave no mark. The
solubility of these compounds can also be determined. Hydrocarbons are also known for their low solubility
in water, and that is due to their lack in hydrogen carbons that would react with H2O. In some cases,
hydrocarbons can undergo certain reactions. Bromination and oxidation are some common examples in
which hydrocarbons can be distinguished. These reactions however, does not require any catalyst, and
may happen even at a low temperature at dark. There are some conditions however for an alkane to
undergo bromination, that is through heating or presence of light. It is also known as the mechanism named
as free – radical substitution. Oxidation reactions can occur in very mild conditions with alkenes and
alkynes.

In this experiment, the researchers aim to ;

• To differentiate alkanes, alkenes, alkynes, and aromatic hydrocarbons, through their properties
• To visualize the characteristic reactions of alkanes, alkenes, alkynes, and aromatic hydrocarbons
• To prepare acetylene gas

Through this objectives, the researchers would identify the effects of different Carbon atoms bonds to the
overall properties and characteristics of a compound.

2. Materials and Methods

2.1 Physical Properties

2.1.1 Flammability

Two(2) drops of the test compounds (cyclohexane, cyclohexene, and benzene) were placed in an
evaporating dish. Each compound was ignited using a match. The observation whether the
compound is flammable or not was recorded. The color of the flame was also observed.

2.1.2 Solubility

Two (2) drops of the test compounds (cyclohexane, cyclohexene, and benzene were transferred in
separate micro test tubes. One (1) millimeter of distilled water was added to the micro test tube
along with the compound. The two solutions were mixed. The observation whether the compound is
miscible or not was recorded.
2.2 Reactions

2.2.1 Bromination

Two (2) drops of the test compounds (cyclohexane, cyclohexene, and benzene were transferred in
separate micro test tubes. One (1) drop of 1.0 M bromine in CCl4 was continuously added to the
micro test tube until it changes its color. The observation was recorded.

2.2.2 Oxidation

Two (2) drops of the test compounds (cyclohexane, cyclohexene, and benzene were transferred in
separate micro test tubes. One (1) drop of 1.0 M potassium permanganate KMnO4 was added to
the micro test tube. The solution was observed for 2 minutes and the results were recorded.

2.2.3 Sulfuric Acid Test

Two (2) drops of the test compounds (cyclohexane, cyclohexene, and benzene were transferred in
separate micro test tube. Half of 1 millimeter (0.50) of concentrated sulfuric acid was added to the
solution compound. The heat released by the reaction was observed and recorded.

2.3 Acetylene
2.3.1 Preparation of the sample

The setup for the preparation of acetylene was shown in Figure 1. Two(2) grams of calcium carbide
was placed inside the 8inch generation tube which is attached to the iron stand. Ten(10) millimeters
of distilled water was poured into to the test tube. It was closed with a cork and connected to into a
small water reservoir using a rubbing tubing. Five (5) micro test tubes with corks were submerged in
the water reservoir. The acetylene gas was collected through downward water displacement. The
first test tube was discarded and the remaining four were used in the following procedure.

2.3.2 Ammoniacal Silver Nitrate Test

The prepared acetylene gas was attained from one of the test tubes in procedure 2.3.1. One (1)
millimeter of ammoniacal silver nitrate was added in the test tube. The reaction and observation
were recorded.

2.3.3 Bromination

The prepared acetylene gas was attained from one of the test tubes in procedure 2.3.1.One (1)
millimeter of bromine solution was transferred in the test tube along with the acetylene gas. The
reaction and observation were recorded.

2.3.4 Oxidation

The prepared acetylene gas was attained from one of the test tubes in procedure 2.3.1.One (1)
millimeter of 1.0 M KMnO4 was transferred in the test tube along with the acetylene gas. The
reaction and observation were recorded.

Figure 1: Acetylene Preparation Set up

https://www.studyrankersonline.com/62944/figure-given-below-showing-laboratory-preparation-acetylene
 3. Results and Discussion

Table 1.1: Physical Properties of Alkane, Alkene, and Aromatic Hydrocarbons

Test Compounds Observations

Flammability Solubility
Cyclohexane -yellow red flame
-ignited for 10 seconds
Cyclohexene yellow red flame
-ignited for 6 seconds
Benzene yellow red flame
-ignited for 5 seconds

The physical properties of hydrocarbons are first tested to determine the effects of its structure. The
two physical properties observed are flammability and solubility. Hydrocarbons which are bonded by single
carbons are saturated, and the ones with double to triple bonds are unsaturated. In this experiment, each of
the test compounds present the type of bonding there is between the carbon atoms. As shown in Table 1.1,
all of the test compounds are flammable because of the presence of reduced carbons. However,
Cyclohexane ignited for 10 seconds, while benzene only lasted for 5 seconds. This is because benzene has
more stable structure than cyclohexane. The double bonds in between the carbon atoms in benzene allows
for a resonance, which makes it stable. Thus, it is harder for the flame to linger and burn the interactions
between the bonds. On the other hand, cyclohexane is more unstable allowing oxygen in the air to react with
the carbon atoms. This is also the reason why it lasted longer than benzene.

For the solubility of the test compounds in water. Cyclohexane and Cyclohexane are two compounds
that are immiscible in water. This is due to the polarity of both compounds which are found to show a non-
polar behavior. The symmetrical structure of both of these compounds caused no dipole moment or difference
in electronegativity. Thus, it would not dissolve in a polar water. Contrarily, benzene is only slightly soluble in
water. At some temperatures, the mixture of benzene and water is possible. But it does not suggest that
benzene is entirely immiscible since the two compounds have different polarity.

Table 1.2: Reactions of Alkane, Alkene, and Aromatic Hydrocarbons

Test Observations
Compounds Bromination Oxidation
Cyclohexane -turned brown after 2 -did not blend with
drops KMnO4

Cyclohexene -remained colorless -the solution turned

brown
-did not blend with
KMnO4
Benzene -turned brown after 1 -slightly blend with
drop KMnO4
 Test Compounds Observations
Reaction with
concentrated H2SO4
Cyclohexane -heat was produced and observed

Cyclohexene -no heat was observed

Benzene -slight heat was observed

Figure 2.1: Solubility of Cyclohexane Figure 2.2: Solubility of Cyclohexene Figure 2.3: Solubility of Benzene

Figure 3.1: Bromination of Cyclohexane Figure 3.2: Bromination of Cyclohexene Figure 3.3: Bromination of Benzene

Figure 4.1: Oxidation of Cyclohexane Figure 4.2: Oxidation of Cyclohexene Figure 4.3: Oxidation of Benzene
 The reaction of hydrocarbons revolves around bromine solution, potassium permanganate and
concentrated sulfuric acid. In the Bromination reaction, only cyclohexene compound changes color when
bromine solution is added. The reaction between an alkene and bromine involves the breaking open of the
alkene’s double bond and the inclusion of bromine in its structure (an addition reaction).This results in the
production of an alkane with two bromine functional groups. Thus, when alkenes come into contact with
bromine, they cause it to decolorize. While, cyclohexane and benzene do not have any reaction with
bromine. Benzene can only react with bromine with the presence of a catalyst. Cyclohexane cannot react
with bromine without heat or any form of light applied.

For the oxidation of hydrocarbons, the same results occurred. Only cyclohexene changes color
when KMnO4 is added. Potassium permanganate can convert cyclohexene into glycols, thus changing its
color to brown as shown in Table 1.2. On the other hand, cyclohexane and benzene both have strong
carbon bonds. This would hinder the reaction of oxygen with the carbon atoms, resulting to minimal to
reaction with the compounds.

The reaction of hydrocarbons with concentrated sulfuric acid in the experiment, only cyclohexene
and benzene can react with sulfuric acid. This is because of the presence of double bonds in both of these
compounds. Thus, the reactions of cyclohexene and benzene do not release any heat. While, cyclohexane
produce heat. Cyclohexane only contains single bond carbon atoms, that sulfuric acid cannot convert into
another compound. Thus, it released heat as a result of the concentrated sulfuric acid not being able to
react.

Table 2.1 Preparation of Acetylene

Reaction Involved Observation

CaC2 + H2O (l) → Ca(OH)2(aq) + C2H2(g) After adding water in the test tube containing
Calcium carbide, it quickly reacted with water. It
turned white and formed bubbles. There is also
an increase in temperature

Table 2.2: Reactions of Acetylene

Properties Reactions Involved Observation

Ammoniacal Silver Ag(NO3)2 + C2H2+2NH4OH → -formed white precipitate

Nitrate Ag2C2 + 2NH4NO3 + 2H2O(l) -formed rock-like precipitate
-some brown solids floated
Bromination C2H2 + Br2(aq) → C2H2Br2 -it became darker (yellow to golden yellow)

Oxidation 4C2H2 + 5KMnO4 → 4C2H2O2 + -solution on the sides became solid

5KMnO2 + 2H2O -no further reaction occurred
Figure 5.1: Reaction with Silver Nitrate Figure 5.2: Bromination of Acetylene Figure 5.3: Oxidation of Acetylene

The results shown in Table 2.1 and Figure 5.1 suggest the successful reaction of acetylene gas with
Ammoniacal Silver nitrate. The end product of the reaction is white precipitate which is expected when a
Tollen’s reagent is added. Acetylene gas reacts with the acid to form silver acetylide which is the white
precipitate observed during the experiment. In Figure 5.2, the reaction of acetylene gas with a bromine
solution occurred. There is a color change observed from yellow to golden yellow which suggest that there
is a reaction happened. This is because of the addition of Br2 to C2H2 which affected its physical property.
Lastly, for the oxidation of acetylene gas, the researchers observe minimal changes. There is only
solidification of some solution at the sides of the test tubes. The expected product of this reaction is an
oxalic acid.
4. Conclusion

Based on the results of the experiment, the objectives are successfully met by the researchers. They
were able to distinguish the characteristics of alkanes, alkenes, alkynes, and aromatic hydrocarbons. The
structure of a compound can affect its physical properties and how it reacts with other compounds. The
attraction between carbon atoms can deviate the end product of a reaction. In flammability and solubility of
hydrocarbons, the presence of carbon bonds and stability of the compound affects the ability of each
hydrocarbons to be ignited and dissolved in water. The reactions with bromine solution, potassium
permanganate, and sulfuric acid suggest that the chemical structure of a compound has an effect to the its
reaction. Double bonded carbon atoms can react with two of the reagents because of the presence of its
double bond. Cyclohexane and benzene both cannot react with these reagents due to the stable structure
of the compounds.

To further improve this experiments, the researchers are suggesting to use other reagents to see its
reaction with different hydrocarbons. There are also some errors committed that can be reduced through
careful manipulation of the procedure.

References:

Opentextbc.ca. (2019). 20.1 Hydrocarbons – Chemistry. [online] Available at:

https://opentextbc.ca/chemistry/chapter/20-1-hydrocarbons/ [Accessed 10 Oct. 2019].

BYJUS. (2019). Hydrocarbons - Types, Classification, Properties, Preparation, Uses. [online] Available at:
https://byjus.com/jee/hydrocarbons/ [Accessed 10 Oct. 2019].