OBJECTIVE

1. To synthesize methane, ethane, and ethyne

2. To characterize the prepared methane, ethane and ethyne

SUMMARY

The purpose of the experiment was to synthesize methane‚ ethane and ethyne and to
characterize the prepared methane‚ ethane and ethyne. The experiment was divided into two
part which was Part A and Part B. Part A involved preparation of methane by reduction of
chloroform‚ preparation of ethane and preparation of ethyne while Part B required the
characterization test for methane‚ ethane and ethyne. In Part A‚ for the preparation of
methane by reduction of chloroform‚ a few step have been done to collect methane gas
especially by using zinc dust to avoid from boilied aggressively and to increase reactivity
with water with the presence of ethanol. For preparation of ethene‚ dehydration reaction was
involved with the presence of aluminium oxide as drying reagent. Preparation of ethyne
required calcium dicarbide. The function of calcium carbide was the desulfurisation of iron
and as a powerful deoxidizer at ladle treatment facilities. The action of water on the calcium
dicarbide then results in the formation of ethyne. For Part B experiment in characterization of
methane‚ each of the test tubes have been divided into five set which is Set 1A‚ Set 1B‚ Set
2A‚ Set 2B and Set 2C for the characterization tests. Set 1A‚ Set 1B‚Set 2B and Set 2C gave
the positive results based on the theory while Set 2A did not obey the theory given due to
some error that might could happen. For characterization of ethene‚ all of the sets followed
the the theory by giving the correct results based on the present of ethene. Last but not least‚
some of the method used to identify the characterization of ethyne did not showed the present
of ethyne when mixed with a few solution to detect the colour change of the solution due to
some error happened. Overall‚ some of the error happened in this experiment were due to
technically error during conducting the experiment and some recommendation should be
done to obtain the correct results for the next experiment so that the mission and objective of
conducting the experiment can be achieved.
 INTRODUCTION

Alkane

Alkane consist of carbon and hydrogen only. However, unlike other hydrocarbons, alkanes
have only carbon-carbon single bonds. Alkanes are saturated hydrocarbons with each carbon
atom bonded to four other atoms by four single covalent bonds. However, alkanes can
undergo combustion reactions and substitution reactions.

Saturated Aliphatic Hydrocarbon

Methane is first member of the family of hydrocarbons. It can be prepared in the laboratory
by the reduction of any halogenated derivatives of alkane. This type of reaction involves the
replacement of one or more atoms of halogen. The generalized scheme is :

RX HX

reduction

The chemical properties of methane are characteristic of the alkanes as groups. A convenient
test for alkanes which distinguishes them from unsaturated aliphatic hydrocarbons consist of
treatment with bromine in carbon tetrachloride. If it is an alkane; almost no reaction occurs in
the dark. In bright artificial light or in sunlight, the bromine colour is gradually discharged as
the substitution reaction proceeds and hydrogen bromide (HBr) is evolved. To the test the
HBr, blow your breath gently across the mouth of the reaction tube. If the HBr present, it will
dissolve in the moisture of your breath to form a cloud of droplets.

Unsaturated Aliphatic Hydrocarbons

Unsaturated aliphatic hydrocarbons have one or more multiple (double or triple) carbon-
carbon bonds per molecules.

Alkenes

The distinguishing feature of the alkene hydrocarbons is the carbon-carbon double bond. The
synthesis of alkene can be accomplished by elimination of atoms or groups from two adjacent
carbon atoms the productions of 2-methyl-2-butane from t-amyl alcohol is an example the
acid catalysed dehydration of alcohols.
 Two test can be carried for and alkene :

1) Bromine, dissolved in carbon tetra chloride, adds rapidly to alkenes at room

temperature to form dibromides.

2) Baeyer test. Alkenes react with neutral permanganate solution to form glycols.

Alkynes

The distinguishing features of an alkynes is a carbon-carbon triple bond. Alkynes give

positive Baeyer Test for unsaturation with aqueous potassium permanganate. This experiment
contains two parts : Part A, you will synthesize methane, ethane, and ethyne; Part B, you will
characterize prepared methane, ethane and ethyne.

FLOW CHART

Part A

1. Preparation of Methane by reduction of chloroform.

Fit the flask with a

Add 10 g zinc
Add 10 ml of rubber stopper and a
of dust into a
ethanol and 10 delivery tube for
50 ml round-
ml of water. collection of the gas
bottomed flask
over water.
mounted in a
ring stand.

After the air in the

If the reaction Add to the mixture
flask has been
too rapid, cool 5 ml of
displaced, collect (
the flask in a chloroform and 1
over water ) at least 6
pan of cool ml of 10% 𝐶𝑢𝑆𝑂4
test test tube of
water. solution.
methane by keeping
the bottles ( or test
tubes ) inverted over
the water.
2. Preparation of Ethene

Place Rocksil wool at Fit a cork and

Place about 1 g
the bottom of test tube. delivery tube to
of aluminium
Drop 8-10 drop of the test tube and
oxide halfway
ethanol until the rocksil heat the
along the test
wool has been soaked aluminium oxide
tube.
up with ethanol. with a gentle
flame.

Collect at least 6 test tube of ethene by

displacement of water.
3. Preparation of Ethyne

• Place 2 or 3 small pieces of calsium dicarbide in a test tube and

arrange the apparatus for collection of ethyne.
1

• Add 2 or 3 drop water at the time.

2

•Collect at least 6 test tubes of ethyne by displacement of water.

3
 Part B : Characterization Tests for Methane, Ethene and Ethyne

Prepared FIVE sets of tubes, each set consists of 3 test tubes containing
methane,ethene and ethyne.

To set 1A and 1B, add 1 ml of 4% solution of bromine in carbon

tetrachloride. Then, stopper all the test tube.

Place set 1A in drawer for 15 minutes. Then, leave set 1B in bright light for 15
minutes. Observe the result and then open the stopper and blow your breath
across the mouth of each tube. Note and record any difference.

Swirl about 2 ml of a 0.3% solution of potassium permanganate in set 2A.

Record any observation.

Shake the tubes in Set 2B with alkaline potassium permanganate solution.

Record the observation.
 Add about 1𝑐𝑚3 of acidified potassium permanganate ( by adding 1𝑐𝑚3 of
sulphuric acid to 0.5 ml of 1% potassium permanganate solution ). Record the
observation.
No Test Observation
Methane Ethene Ethyne
1. Set 1A
Tubes left in darkness
2. Set 1B
Tubes left in a bright light
3. Set 1A and 1B
Blowing across the mouth of
each of the test tubes.
4. Set 2A
2 ml of 3.0% potassium
permanganate solution
5. Set 2B
1 ml alkaline potassium
permanganate
6. Set 2C
2 ml acidified potassium
permanganate solution
RESULTS

Observation

No. Test Methane Ethene Ethyne

1 SET 1A
Tubes left in darkness Bubble is Bubble is
No reaction. produced. produced.

2 SET 1B
Tubes left in a bright light Bromine orange Bromine orange Bromine orange
colours turn to colours turn to colours turn to
colourless. colourless. colourless.

3 SET 1A & 1B
Blowing across the mouth of Both solutions No reaction No reaction
each of the test tubes turn into water occurs. occurs.
droplets.
 4 SET 2A
2mL of 0.3% potassium Black dark
permanganate solution Dark purple Dark brown brown

5 SET 2B
1mL alkaline potassium Light dark
permanganate Dark purple brown Dark brown

6 SET 2C
2mL acidified potassium Very soft light
permanganate solution Light pink Soft light pink pink

DISCUSSION

The purpose of the experiment was to synthesize methane‚ ethane and ethyne and to
characterize the prepared methane‚ ethane and ethyne. The experiment was divided into two
part which was Part A and Part B. Part A involved preparation of methane by reduction of
chloroform‚ preparation of ethane and preparation of ethyne while Part B required the
characterization test for methane‚ ethane and ethyne. In Part A‚ for the preparation of methane
by reduction of chloroform‚ the zinc dust has been used to increase reactivity with water with
the presence of ethanol. The copper sulphate solution act as catalyst which increases the rate
of reaction without undergoes any permanent chemical change. The methane has been
collected into five test tubes for the characterization test.

CH4 + Cl2 CH3Cl + HCl (chloromethane)

CH3Cl + Cl2 CH2Cl2 + HCl (dichloromethane)

CH2Cl2 + Cl2 CHCl3 + HCl (chloroform)

CHCl3 + Cl2 CCl4 + HCl (carbon tetra chloride)

For preparation of ethene‚ rocksil wool was used to increase the absorbance of ethanol.The
rocksil wool also can be replaced with glass wool. Aluminium oxide also was placed at the
middle of the test tube followed by strongly heating. When ethanol was flowed over heated
aluminium oxide‚ dehydration occurs to produce ethane. The aluminium oxide functions as
catalyst and drying agent in this reaction. The ethene produced was collected into five test
tubes for the characterization test.

Aluminium oxide
C2H5OH C2H4 + H2O

Preparation of ethyne required calcium dicarbide. The function of calcium carbide was
the desulfurisation of iron and as a powerful deoxidizer at ladle treatment facilities. Calcium
dicarbide is prepared by the reaction between calcium oxide and coke at very high
temperatures in an electric furnace. The action of water on the calcium dicarbide then results
in the formation of ethyne. Because calcium oxide and coke are obtained from limestone and
coal, respectively, acetylene gas is obtained in a few steps from three abundant cheap raw
materials such as water, coal, and limestone.

coal + coke + Ca(OH) 2 ==> CaC2

carbon limestone calcium carbide

CaC2 + 2 H2O → C2H2 + Ca(OH)2

This reaction was the basis of the industrial manufacture of acetylene, and is the major
industrial use of calcium carbide.At high temperatures, CaC2 reacts with water vapour to give
calcium carbonate, carbon dioxide and hydrogen. Today acetylene is mainly manufactured by
the partial combustion of methane or appears as a side product in the ethylene stream from
cracking of hydrocarbons. The acetylene gas used for this purpose is distributed as a solution
of acetylene in acetone under pressure. Acetylene gas is also the starting material for the large
scale synthesis of important organic compounds. The ethyne gas produced was collected into
five test tubes for the characterization test.

For Part B experiment‚ each of the test tubes have been divided into five set which is Set 1A‚
Set 1B‚ Set 2A‚ Set 2B and Set 2C for the characterization tests. All the test tubes for Set 1A
and Set 1B have been added with 1mL of 4% solution of bromine in carbon tetrachloride
followed by closing them with stopper. Then‚ all the test tubes in Set 1A and1B have been
placed in two different places which Set1A was left in darkness while the Set1B left in a
bright light for about 15 minutes. All of the test tubes had give positive results indicate all the
gaseous were present especially for Set 1B based on the occurance of substitution method.
Next to test the for HBr‚ all the test tube in Set 1A and Set 1B mouth had been blow across
and the results also shown that all the gaseous were present. Next‚ for Set 2A ‚2mL of 0.3%
solution of potassium permanganate was swirl into each of the test tubes containing methane‚
ethane and ethyne. The observation shown that purple coloured potassium permanganate
solution remain unchanged but according to the theory‚ the result must turns purple potassium
permanganate solution to light purple because of saturated hydrocarbon. Purple coloured
potassium permanganate solution turns into brown precipitate indicate a positive test for
unsaturation of ethene because of the MnO2 formed the appearance of brown precipitate. The
characterization of ethyne also did not follow the theory which should give a positive result
such as ethene. An alkaline potassium permanganate solution had been poured into all the test
tubes in Set 2B followed by shaking them properly. The results prove that all the gaseous had
presents in each of the test tubes. Last but not least‚ for Set 2C‚1 cm3 of acidified potassium
permanganate was added into all the test tubes and observation also gave the positive results
which follow the theory. Overall‚ some of the error happened in this experiment were due to
technically error during conducting the experiment and some recommendation should be
done to obtain the correct results for the next experiment so that the mission and objective of
conducting the experiment can be achieved.

CONCLUSION

The conclusion of the experiment shown that Set 1A and Set 1B gave the possible positive
results which all the methane‚ ethane and ethyne showed their presence either in darkness or
in the bright light based on some chemical reaction that take placed. For Set 2A‚only ethene
showed the presence while methane and ethyne did not and this causes might came from
some error that happened. Both Set 2B and Set 2C gave the positive results based on the
observation that has been recorded by detecting the colour change of alkaline potassium
permanganate solution and acidified potassium permanganate. Some of the error has been
detected and a few recommendations has been listed out to improve the results for upcoming
experiments.

RECOMMENDATION
Through this experiment, there are some possible sources of error identified after the results
have been obtained. First, when the reactions occurred, the glassware contains the reactions
did not connected by the delivery tube with the test tubes immediately resulting the gas
collection later takes long time. To improve this situation for the next experiment, the
glassware should be immediately connected to the delivery tube and can proceed easily with
the gas collection. Second, when the gases have been collected error happen when the test
tubes were exposed with the atmosphere resulting other gases mixed with the gases. To make
improvement for this error, the stopper must be put immediately when the gases have been
collected. Moreover , the most important thing is to make sure that confusion did not happen
as there are 15 test tubes with the 3 different gases, so the best way is to label the test tubes
with the sticker.

TUTORIALS

1. What do ‘saturated’ and ‘unsaturated’ mean when applied to hydrocarbons? Give

examples of a saturated hydrocarbon and an unsaturated hydrocarbon.

Saturated hydrocarbon consists of carbon and hydrogen atoms that are bonded by a
single covalent bond only. Example is alkane.

Unsaturated hydrocarbon contains least one double covalent bond or triple covalent
bond between two carbon atoms. Example is alkene.

2. Give five (5) sources of methane.

 Five sources of methane:
1. Decay of plant material in wetlands.
2. The seepage of gas from underground deposits .
3. The digestion of food by cattle.
4. Oil and gas production.
5. Rice farming.

3. Describe reactions that are characteristics of alkanes‚ alkenes and alkynes.

In the absence of a spark or a high-intensity light source, alkanes are generally inert to
chemical reactions. In the presence of light, or at high temperatures, alkanes react with
halogens to form alkyl halides. Reaction with chlorine gives an alkyl chloride.
Reaction with bromine gives an alkyl bromide. Unsaturated hydrocarbons such as
alkenes and alkynes are much more reactive than the parent alkanes. They react
rapidly with bromine, for example, to add a Br2 molecule across the C=C double
bond. This reaction provides a way to test for alkenes or alkynes. Solutions of
bromine in CCl4 have an intense red-orange color. When Br2 in CCl4 is mixed with a
sample of an alkane, no change is initially observed. When it is mixed with an alkene
or alkyne, the color of Br2 rapidly disappears.

The reaction between 2-butene and bromine to form 2,3-dibromobutane is just one
example of the addition reactions of alkenes and alkynes. Hydrogen bromide (HBr)
adds across a C=C double bond to form the corresponding alkyl bromide, in which the
hydrogen ends up on the carbon atom that had more hydrogen atoms to begin with.
Addition of HBr to 2-butene, for example, gives 2-bromobutane. H2 adds across
double (or triple bonds) in the presence of a suitable catalyst to convert an alkene (or
alkyne) to the corresponding alkane.

In the presence of an acid catalyst, it is even possible to add a molecule of water

across a C=C double bond.Addition reactions provide a way to add new substituents
to a hydrocarbon chain and thereby produce new derivatives of the parent alkanes.In
theory, two products can form when an unsymmetric reagent such as HBr is added to
an unsymmetric C=C double bond. In practice, only one product is obtained. When
HBr is added to 2-methylpropene, for example, the product is 2-bromo-2-
methylpropane, not 1-bromo-2-methylpropane.

4. Write a balanced equation for the reaction which methane was obtained by the
reduction of chloroform.

CHCl3 + 3H2 → CH4 + 3HCl

5. Provide two(2) other methods of collecting gas that can be used in this experiment.
1. Upward delivery gas collection
2 .Downward delivery gas collection

REFERENCES

 Lab Manual
 Yeap Tok Kheng,Chemistry SPM Highlights,Pearson Malaysia Sdn.Bhd,2014,
p341-390