A.

EXPERIMENT TITLE : Alkanes, Alkene and Alkyne

B. DAY/ DATE OF EXPERIMENT : Friday, 1nd of March 2019, 07.30
a.m
C. FINISHED THE EXPERIMENT : Friday, 1nd of March 2019, 12.00
p.m
D. EXPERIMENT PURPOSE :
1. Differentiate the type of reaction that occurs in alkane, alkene, and alkyne.
2. Knowing the properties of alkane and alkyne which can be burned.

E. BASIC THEORY
Hydrocarbon compounds are the simplest organic compounds. This is
caused by its constituent atoms which consist only of hydrogen and carbon.
Hydrocarbons can be classified into 3 groups namely hydrocarbonaliphatic,
alicyclic hydrocarbons and the last is aromatic hydrocarbons. Hydrocarbons are
organic compounds whose molecules are composed of carbon and hydrogen.
Aliphatic means the end of the chain does not meet each other while saturation
means that all carbon-carbon bonds are single bonds. Alkanes, alkene and alkyne
are unsaturated hydrocarbons. And all three have very broad functions and uses.
1. Definition Alkanes, Alkene, and Alkyne.
Alkanes is commonly called a saturated hydrocarbon compound.
Hydrocarbons are called because they only contain carbon and hydrogen atoms.
Saturated because it only has a single C-H and C-C bond. Alkanes has the
general formula CnH2n+2,where n is a natural number that states the number of
carbon atoms. Alkanes are also often referred to as aliphatic compounds
(Greece = aleiphas which means fat). This is because animal fats contain long
chain carbon which is similar to alkanes (Fessenden & Fessenden,
1986).Alkanes are saturated hydrocarbon compounds, whereas alkene and
alkyne are unsaturated hydrocarbons (Underwood & Day, 2002). The boiling
point of petroleum gases are respectively at normal atmospheric pressure. That

1
 is not the case for methane and ethane, which can only be liquefied at very low
temperatures (Favennec & Jean, 2001).
Alkene or olefins in organic chemistry are unsaturated hydrocarbons
with a double bond between atomic carbon. The simplest acyclic alkene, which
forms one double bond and does not bind to any functional cluster, will form a
hydrocarbons with the general formula CnH2n. The simplest alkenics are ethene
or ethylene (C2H4) Aromatic compounds are often also described as cyclic
alkenes, but their structure and characteristics differ so that they are not
considered alkene.
Alkuna is a hydrocarbon containing three carbon double bonds. In
general, the chemical formula is CnH2n-2. All alkane molecules are tetrahedral
with bond angles close to 109.5. Compounds containing C = C bonds end with
–una(Chang, 2004). Alkyne is an aliphatic hydrocarbon group which has a
functional group in the form of carbon carbon triple bonds. Like double bonds
in alkenes, a triple bond on alkyne is also called an unsaturated bond. The lack
of saturation of carbon-carbon triple bonds is greater than the double bonds in
alkenes. Therefore the ability to react is also greater (Parlan & Wahyudi, 2005).
2. Properties of Alkanes, Alkene, and Alkyne
Alkana is the main component in natural gas and petroleum. Alkane
compounds have a single or saturated compound with a general formula.
Alkana is a nonpolar compound so it is difficult to dissolve in water but tends to
dissolve in nonpolar solvents, such as esters and CCl4. If the calcium is added
to the water, the alkane will be in the upper layer, because of the type of alkane
that is smaller than the density of the water. At room temperature, the alkane
with C1-C4 atom has gas phase, C5-C17 liquid phases and > C18 solid phase.
If the C chain has a higher viscosity (thickness), the boiling point is higher. For
alkanes containing atoms, with C atoms as much, the more number of branches
the lower the boiling point (Riswiyanto, 2009).
The properties of alkenes include double bond unsaturated
hydrocarbons, alkenes also called olefins (oil formers). The physiological

2
 properties are more active (as sleeping pills -> 2-methyl-2- butene), the same
properties as Alkana, but more reactive. Colorless gas, can be burned, a
distinctive smell, explosive in the air (at a concentration of 3 - 34%). Available
in ordinary coal gas in the "cracking" process. At room temperature, alkenes
can be added by Cl2, Br2, or I 2without a catalyst. Reacts with HCl and H2SO4
and can be oxidized by KMnO4 and K2Cr2O7.
Alkyne low temperature at room temperature in the form of gas, while
containing five or more liquid carbon atoms, the density is smaller than water,
is a non-polar compound, is not soluble in water but soluble in non-polar
organic solvents, such as ether , benzene, and carbon tetrachloride, the more the
number of atoms and branching of atoms the higher the boiling point.
3. Reaction
a. Reaction with Halogen in alkanes (Halogenation)
Alkanes can react with halogens (F2, Cl2 Br2 and I2) to
produce alkylhalides and the reaction is called halogenation.
Halogenation usually uses bromine or chlorine so it is also called
bromination and chlorination. Low substitution between alkane and
halogen produce halogenoalkane. In this reaction, one H atom in alkane is
replaced by Br. Decolorisers of bromine water after flowing with LPG
indicate the presence of bromide acid whose solution is colorless.
b. Combustion reaction
There are two types of combustion, namely complete combustion and
incomplete combustion. Complete combustion is the conversion of a
compound to CO2 and H2O. Incomplete combustion happened if the oxygen
supply insufficient for complete combustion. Incomplete combustion leads
to carbon monoxide or sometimes carbon as a carbon black or soot
(Fessenden & Fessenden, 1986).
The combustion of LPG fuels are releases a tremendous amount of
energy, but reactions won’t occur to a significant extent at ordinary

3
 temperatures. A spark or a flame must be present before ignite (Hein &
Arena, 2011).
Complete combustion of gas has a dim blue color due to the emission
of single wave-length radiation from various electron transitions in the
excited molecule formed in the flame. Incomplete combustion of gas,
incandescent solid particles called soot produce the familiar red-orange glow
of ‘fire’ (Choudury, 2014).
C3H8(g) + 5O2(l) → 3CO2(g) + 4H2O(g)
c. Reaction Addition of halogens to alkene and alkyne
One of the reaction of alkynes is addition reaction. Addition reaction
of halogens usually is bromine and chlorine (Parlan & Wahyudi, 2005).
Bromine and chlorine can contain alkene and alkyne to produce 1,2
dihalides. Fluorine and iodine cannot be used because highly reactive
fluorine and iodine are very unreactive.
C2H2(g) + 2Br(aq) → Br2CH-CHBr2(aq)
In a substitution reaction, one atom or group of atom in a molecule is
replaced by another. For example, a hydrogen atom in cyclohexane is
replaced by bromine water when the alkane is exposed to Br2 in the presence
of light or heat (Fox & Whitesell, 2004).

Picture 1: Reaction of Propane with Bromine

(Brown, 2011)
Substitution of bromine for a primary hydrogen gives 1–
bromopropane, substitution of bromine for secondary hydrogen gives 2-
bromopropane.

4
F. TOOLS AND MATERIALS
a. Tools
1. Test tube 2 piece
2. Side pipe tube 1 piece
3. Measuring flask 1 piece
4. Spatula 1 piece
5. Pipette 2 piece
6. Beaker glass 1 piece
7. LPG 1 piece
8. Matches 1 piece
9. Stick 1 piece
10. Hose 1 piece
b. Materials
1. Bromine water 10 mL
2. LPG gas sufficienly
3. Carbide granules sufficienly
4. Aquades sufficienly

G. LANES WORK
1.
LPG 5 mL of Bromine water
1. Entered into
test tube

2. Flew LPG into the test tube

until the color of bromine
water disappear
3. Observed and wrote the
color changes
Observation result

5
 2. Carbide granules
1. Put into side pipe tube
2. Connected with a hose to
tube B (filled of water )
which is placed up and
down
3. Added water into side
pipe tube using pipette
4. Closed the side pipe
tube
5. Took test tube B that
has been filled gas
6. Closed with tissue
7. Ignited by matches
8. Observed and wrote

Observation result

3. Addition reaction of alkyne

Carbide granules Bromine water

1. Entered into 1. Entered into

side pipe tube test tube B
2. Added water
using pipette

1. Test tube A and B connected by pipe

to be flew by gas from side pipe tube
to test tube B
2. Flew the gas until the color of bromine
water disappear
3. Observed and wrote
Observation result

4. Combustion of LPG.

6
 LPG

1. Open the regulator

2. Flow LPG into bunsen

Observed

7
 H. OBSERVATION RESULT

Observation result
No. Procedure of experiment Assumtion/reaction Conclusion
Before After
1. - Bromine water : - Bromine water - Propana Alkane ocur
LPG 5 mL of Bromine yellow solution + flowed LPG :
water CH3CH2CH3 (g) + Br2 (aq) substitusi reaction
colorless
 CH3CH2CH2Br (aq) + by halogene Br2
2. Entered into solution
test tube CH3CHBrCH3 (aq) + HBr (halogenation)
(aq)
4. Flew LPG into the test
tube until the color of - Butana
bromine water disappear CH3CH2CH2CH3 (g) + Br2
5. Observed and wrote the
color changes (aq)  CH3CH2CH2CH2Br
(aq) + CH3CH2CHBrCH3
Observation result
(aq) + HBr (aq)
- Isobutana
CH3CH2CH2CH3 (g) + Br2
(aq)  CH3CH2CH2CH2Br
(aq) + CH3CH2CHBrCH3
(aq) + HBr (aq)

8
2. - Carbide - Carbide  CaC2 (s) + H2O (l)  Alkyne can occur
Carbide granules
granules : white granules + CH CH (g) + Ca(OH)2 combusion in
3. Put into side pipe tube complete reaction
4. Connected with a hose to powder aquades : gas (aq)
tube B (filled of water ) - Aquades : - Gas ignited by  CH CH (g) + O2 (g) 
which is placed up and
colorless matches : fire + C (s) + 2CO (g) + 2H2O (l)
down
9. Added water into side solution carbon
pipe tube using pipette
10. Closed the side pipe
tube
11. Took test tube B that
has been filled gas
12. Closed with tissue
13. Ignited by matches
14. Observed and wrote

Observation result

9
3. - Carbide - Carbide  CH CH (g) + Br2 (aq) Alkyne occur
Carbide Bromine
granules water granules : white granules + CHBr CHBr (aq)  addition reaction
with Br2.
powder aquades : gas (CHBr)2 (g)
3. Entered into 2. Entered
side pipe into test - Bromine water : - Gas + bromine
tube tube B yellow solution water : bromine
4. Added water
water become
using pipette
colorless
4. Test tube A and B
connected by pipe to
be flew by gas from
side pipe tube to test
tube B
5. Flew the gas until the
color of bromine water
disappear
6. Observed and wrote
Observation result

LPG gas: Flame is blue

The combusition of
4. Colorless
LPG LPG is complete
1. Open the regulator combustion.
2. Flow LPG into bunsen

10
Observed

11
I. ANALYSIS AND EXPLANATIONS
1. The first experiment aims to to explain the reaction between LPG and
bromine water. The principle of this experiment is substitution reaction
between compound of LPG and bromine water. The first, put 5 mL of
bromine water into test tube. Than, flew LPG into test tube until the color of
bromine water(yellow solution) is dissapeared. Observe and note the color
changes that occur. After the experiment result mixture of LPG and bromine
water become colorless.
The reaction is:
a. Propana
CH3CH2CH3 (g) + Br2 (aq)  CH3CH2CH2Br (aq) + CH3CHBrCH3 (aq) +
HBr (aq)
b. Butana
CH3CH2CH2CH3 (g) + Br2 (aq)  CH3CH2CH2CH2Br (aq) +
CH3CH2CHBrCH3 (aq) + HBr (aq)
c. Isobutana
CH3CH2CH2CH3 (g) + Br2 (aq)  CH3CH2CH2CH2Br (aq) +
CH3CH2CHBrCH3 (aq) + HBr (aq)

Substitution of bromine for a primary hydrogen gives 1–bromobutane,

substitution of bromine for secondary hydrogen gives 2-bromobutane. Low
substitution between alkane and halogen produce halogenoalkane. In this
reaction, one H atom in alkane is replaced by Br. Decolorisers of bromine
water after flowing with LPG indicate the presence of bromide acid whose
solution is colorless.
2. The second experiment is to explain the reaction of acetylene gas
combustion. The principle of this experiment is incomplete combustion
produced from acetylene gas. The first, put carbide granules into test tube A.
Than, connected it to a bent B pipe to test tube C which down in a D
container filled water. Added water into test tube A drop by drop very

12
 quickly by using pipette until carbide granules submerged. After that, closed
test tube A by using rubber cover that has hole to put the B pipe. Shake test
tube A to make reaction faster between carbide granules and water. Take the
test tube C which has filled gas and closed it with tissue to prevent gas come
out from test tube. Then ignited by matches and observed.
The reaction is:

CaC2 (s) + H2O (l)  CH CH (g) + Ca(OH)2 (aq)

CH CH (g) + O2 (g)  C (s) + 2CO (g) + 2H2O (l)

Reaction between carbide (calsium carbide) and water is ethylene gas.
To proven it, burn the stick and insert it into test tube C. The result of this
test is, there are small exploison and flammable. It shown that, flammable
ethylene gas meets the test tube. The combustion of acetylene gas is
incomplete combustion. This can be seen from the following reaction:
(g) + O2 → C(s) + CO(g) + H2O(l)
This is in accordance with the theory that incomplete combustion leads to
carbon monoxide or sometimes carbon as a carbon black or soot. Incomplete
combustion happened if the oxygen supply insufficient for complete
combustion.
3. The third experiment is to explain the reaction of alkyne. The principle of
this experiment is addition reaction of alkyne with Br. The first, put carbide
granules into test tube A and added using pipette until carbide granules
submerged. Next, connect it to test tube B which filled bromine water use
plastic hose to drain gas from test tube A to test tube B. Then, closed test
tube A by using rubber cover that has hole to put the pipe. Shake test tube A
to make reaction faster between carbide granules and water. After that
observed and wrote. Then, flow the gas to test tube B until the color of
bromine water is dissapear. When bromine is added to acetylene, the double
bond gets saturated hydrocarbon (alkane). So that's why alkynes decolourize
bromine water.

13
 The reaction is:
CH CH (g) + Br2 (aq) CHBr CHBr (aq)  (CHBr)2 (g)
4. The last experiment aims of this experiment is to explain the combustion of
LPG. The principle of this experiment is complete combustion of alkane
compound. The first, open the regulator. After that, flow LPG(colorless) into
bunsen. Than, observed the changes that occur and the result flame is blue.
The reaction is:
C3H8(g) + 5O2(g) → 3CO2(g) + 4H2O(l)
2C4H10(g) + 13O2(g) → 8CO2(g) + 10H2O(l)
The combustion reaction of LPG gas is to produce carbon dioxide and
water gas. This is in accordance with the theory which states perfect
combustion which means that the gas to be burned is converted to CO2 and
H2O. The flame that produce is blue. it cause complete combustion of gas
has a dim blue color due.

J. CONCLUSION
1. In experiment 1, alkane ocur substitusi reaction by halogene Br2
(halogenation).
2. In experiment 2, acetylene gas can produced from carbide and water.
Alkyne can occur combusion in complete reaction.
3. In experiment 3, alkyne occur addition reaction with Br2.
4. In experiment 4, The combusition of LPG is complete combustion.

K. REFERENCES
Brown, W. H. (2011). Organic Chemistry. Belmont: Brooks/Cole Cengage

Learning.

Chang, R. (2004). Kimia Dasar Konsep-Konsep Inti Jilid 1 (3rd ed.). Jakarta:

Erlangga.

14
 Choudury, A. K. R. (2014). Principles of Colour, Appreance and Measurement,

1.

Favennec, & Jean, P. (2001). Petroleum Refining Refinery Operation and

Management. Paris: Technip.

Fessenden, R. ., & Fessenden, J. . (1986). Kimia Organik jilid 2. Jakarta:

Erlangga.

Fox, M. A., & Whitesell, J. K. (2004). Organic Chemistry. London: Jones and

Barlett inc.

Hein, M., & Arena, S. (2011). Foundation of College Chemistry. Hoboken: John

Wiley and Sons, Inc.

Parlan, & Wahyudi. (2005). Kimia organik 1. Malang: Jurusan Kimia FMIPA

Universitas Negeri Malang.

Riswiyanto. (2009). Kimia Organik. Jakarta: Erlangga.

Underwood, A. ., & Day, R. . (2002). Analisis Kimia Kuantitatif (6th ed.).

Jakarta: Erlangga.

L. ATTACHMENT
1. Answer to the questions

Answer

1) What is the content of LPG gas? Write down the chemical formula!
2) What gas occurs when the carbide is given water?
3) Write down the reactions that occur from the gas after being put into bromine
water!

15
4) Differentiate the nature of the reaction that occurs between city gas/LPG gas
& carbide gas to bromine water!
5) Write down the combustion reaction of city gas / LPG gas & carbide gas and
distinguish the flame that occurs from each of the gas combustion results on
your observation!

Questions

1) LPG gas contains:

Propane:
CH3CH2CH3
Butane :
CH3CH2CH2CH3
Isobutane:
CH3CHCH3
Br
2) Carbide will react with water to produce acetylene gas. The reaction is :
CaC2(s) + H2O (l) CH2 = CH2(g)+ Ca(OH)2 (s)
3) Reaction with propane

CH3CH2CH3(g) + Br2 (aq) CH3CH2CH2Br(aq) + HBr(aq)

(Propane) (1-bromo propane)
or
CH3CH2CH3(g) + Br2(aq) CH3CHBrCH3(aq) + HBr(aq)
(Propane) (2-bromo propane)
Reation with butane
CH3CH2CH2CH3(g) + Br2(aq) CH3CH2CH2CH2Br(aq) + HBr(aq)
(Butane) (1-bromo butane)
or
CH3CH2CH2CH3(g) + Br2(aq) CH3CHBrCH2CH3 (aq) + HBr(aq)
(Butane) (2-bromo butane)
Reaction with isobutane

16
 CH3CHCH3(g) + Br2(aq) CH3CHCHBr(aq) + HBr(aq)
CH3 CH3
(Isobutane) (1-bromo-2-methyl propane)
or
Br
CH3CHCH3(g) + Br2(aq) CH3CHCH3(aq) + HBr(aq)
CH3 CH3
(isobutene) (2-bromo-2-methyl propane)
Reaction between acetylene gas and bromine water
Br Br

H C C H

C2H2 (g) + Br2(aq)  Br Br (aq)

Acetylene gas bromine water 1,1,2,2-tetrabromo ethane
4) a. City gas / LPG which is fed with bromine water: City gas/LPG gas contain
propane, butane and isobutene which all of them is alkanes. Alkanes can
subtitued by halogen, it’s also called halogenation. So when LPG react with
bromine water, all the alkanes compound will undergo substitution reaction
with bromine.
b. Carbide gas/acetylene: is alkyne compound. As we know from alkyne’s
properties, alkyne can react with halogen with addition reaction. This is
because alkanes just have single bond for each atom carbon whereas alkyne
have triple bond for each atom carbon.
5) City gas/LPG gas the reaction is :

Propane : C3H8 (g) + 5 O2 (g)→ 3 CO2(g) + 4 H2O (l)

13
Butane : C4H10 (g) + O2 (g) → 4 CO2(g) + 5 H2O (l)
2
13
Isobutane : CH3CHCH3 (g) + O2 4CO2 + 5H2O
2

CH3

17
It can be observed by looking the color of flame. Combustion of LPG will
produce blue flame that indicate a complete combustion.
Carbide gas the reaction is :
CH2CH2 (g) + 2O2(g)  2CO(g) + 2H2O(l)
2CH2CH2(g) + 2O2(g)  4C(s) + 4H2O(l)
Carbide gas will produce orange/red flame that indicate a incomplete
combustion

18
 2. Documentation

No. Procedure of experiment Photo Information

1. - Bromine water + flowed LPG :

LPG 5 mL of Bromine
water colorless solution

3. Entered into
test tube

6. Flew LPG into the test

tube until the color of
bromine water disappear
7. Observed and wrote the
color changes
Observation result

19
2. -Carbide granules + aquades : gas
Carbide granules
5. Put into side pipe tube -Gas ignited by matches : fire + carbon
6. Connected with a hose to
tube B (filled of water )
which is placed up and
down
15. Added water into side
pipe tube using pipette
16. Closed the side pipe
tube
17. Took test tube B that
has been filled gas
18. Closed with tissue
19. Ignited by matches
20. Observed and wrote

Observation result

20
3. -Carbide granules + aquades : gas
Carbide Bromine
granules water
-Gas + bromine water : bromine water
5. Entered into 3. Entered become colorless
side pipe into test
tube tube B
6. Added water
using pipette

7. Test tube A and B

connected by pipe to
be flew by gas from
side pipe tube to test
tube B
8. Flew the gas until the
color of bromine water
disappear
9. Observed and wrote
Observation result

21
22