A.

EXPERIMENT TITTLE : Alkane, Alkene, Alkyne

B. EXPERIMENT START : Friday, 01st March 2019 at 07.30 a.m.
C. EXPERIMENT FINISH : Friday, 01st March 2019 at 11.00 a.m.
D. EXPERIMENT PURPOSE :
1. Differentiate the type of reaction that occurs in alkane, alkene, and alkyne.
2. Knowing the properties of alkane, alkene, and alkyne which can be burned.
E. BASIC THEORY
Hydrocarbon compounds are the simplest organic compounds. This is
produced by its constituent atoms which consist only of hydrogen and carbon.
Hydrocarbons can be classified into 3 groups namely aliphatic hydrocarbons,
alicyclic hydrocarbons and the last is aromatic hydrocarbons (Riyanti, 2008).
Hydrocarbons are organic compounds which only consist of hydrogen and
carbon. Hydrocarbons can be classified into open chains and closed chains.
Open chains can then be classified as saturated or unsaturated. Saturated
hydrocarbons are hydrocarbons that do not have double bonds, such as Alkana.
The general formula of Alkana is CnH2n + 2. Unsaturated Hydrocarbons are
hydrocarbons that have double bonds, such as Alkene (double) has a general
formula CnH2n and Alkuna (triple ) which has the general formula CnH2n-2
(Fessenden & Fessenden, 1992).
Alkanes are saturated hydrocarbon compounds or saturated aliphatic
hydrocarbons (Rohmadi, 2012). The simplest alkane is methane which has one
C atom with the CH4 chemical formula (Rohmadi, 2012). The reaction of the
alkane with halogen elements is called a halogenation reaction. This reaction
will produce an alkyl halide compound, where the hydrogen atom from the
alkane will be substituted by halogens so that this reaction can be called a
substitution reaction. Another Halongen, fluorine reacts explosively with
organic compounds while iodine is not reactive enough to react with alkanes.
The rate of change of atom H as follows H3> H2> H1. The reactivity of
halogens in substituting H is fluorine> chlorine> bromine> iodine (Simbolon,
2012).
Halogenation reaction :

Alkane, Alkene, Alkyne | 1

 Source: Fessenden & Fessenden, 1986
CH3CH2CH3 (g) + Br2 (aq) CH3CH(Br)CH3 (aq) + HBr (aq) + other product
Source: Fessenden & Fessenden, 1986
Combustion reaction :

Source: Fessenden & Fessenden, 1986

Source: Fessenden & Fessenden, 1986

Alkene and cycloalkene are hydrocarbons that have one or more carbon-
carbon double bonds. The compound is said to be unsaturated because it does
not have the maximum number of atoms which can be accommodated by each
carbon. Alkenes are often called olefins, an old term derived from the fact that
chlorine contains in the form of gaseous ethylene (C2H4) forming a result that
resembles oil (Pine et al, 1988).
According to, the systemic nomenclature for alkenes includes an extension
of the rule applied to the alkane, namely as the parent compound is taken the
longest straight chain of carbon atoms containing double bonds; the suffix - where
from the name of the equivalent alkane hydrocarbons is replaced by suffixes, the
position of double bonds is expressed by the low number of carbon atoms; where
the bond is located, the number stating this position is placed in front of the name
of the parent compound, the alkyl group located to the parent compound is
marked as is done on alkane hydrocarbons; if a geometric isomer is to be marked,
the name starts with cis or trans (Keenan, 1984).
The physical properties of alkenes are closely related to the nature of the
corresponding alkanes. The low molecular weight alkene that is important in the
petrochemical industry in the form of gas. The most common alkene in a chemical
laboratory is a strong smelling liquid. Like alkanes, alkenes are non-polar relative
compounds which do not dissolve in water. The physical properties of some
alkene and cycloalkene are arranged in the following table:

Alkane, Alkene, Alkyne | 2

 Figure 1. Physical Properties of Alkenes
Source : Justiana, 2009
Alkyne is an aliphatic hydrocarbon group that 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 & Wahjudi, 2005).
Alkyne has the general formula CnH2n-2. The simplest alkyne is etuna
(C2H2) and has a structural formula: H-C=C-H. Alkyne is divided into three
types based on the position of the three double bonds, namely: terminal and
internal alkyne (Parlan & Wahjudi, 2005).
Giving the Alkyne name with the IUPAC system is to replace the suffix -
ana in the alkane name associated with the -una suffix. For alkyne molecules
with long chains, the longest carbon chains containing three double bonds are
numbered from one end which allows triple double bonds to have a low
number. The position of the triple double bond is indicated by the number of

Alkane, Alkene, Alkyne | 3

 carbon atoms which have a double triple bond which is lower (Parlan &
Wahjudi, 2005).

Figure 2. Nomenclature of Alkyne

Source: (Parlan & Wahjudi, 2005)
In general, alkyne physical properties are similar to the physical properties
of alkanes and alkenes. Some alkaline properties include, low alkaline alkaline
at room temperature in the form of gas, while those containing five or more
carbon atoms are liquid; the density is smaller than water; is a non-polar
compound, insoluble 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 higher the boiling point (Parlan & Wahjudi, 2005).
Alkanes, alkene, and alkyne have very wide functions and uses. Certainly
very needed for humans primarily as fuel oil (eg kerosene, gasoline, diesel) and
gas fuel (LPG) because alkanes are the main component of natural gas and oil
earth. Besides that it is used for road coating (asphalt), lubricants and paraffin
(wax). While alkene and alkyne are usually used as starting materials or
reagents Practical Organic Chemistry I "ALAKANA, ALKENA, AND
ALKUNA" | 2 early in the synthesis of a compound because of its double bond
(Riswiyantoro, 2009).
F. TOOLS AND MATERIALS
a. Tools
1. Test tube 2 pieces
2. Side pipe tube 1 piece
3. Measuring flask 1 piece
4. Spatula 1 piece
5. Pipette 2 pieces
6. Bowl 1 piece
7. LPG 1 piece
8. Matches 1 piece

Alkane, Alkene, Alkyne | 4

 9. Stick 1 piece
10. Hose 1 piece
b. Materials
1. Bromine water 10 mL
2. LPG gas sufficiently
3. Carbide granules sufficiently
4. Aquades sufficiently
G. LINE 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

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

Alkane, Alkene, Alkyne | 5

3.
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

Alkane, Alkene, Alkyne | 6

 H. OBSERVATION RESULTS

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)

Alkane, Alkene, Alkyne | 7

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

Alkane, Alkene, Alkyne | 8

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

Alkane, Alkene, Alkyne | 9

I. EXPLANATION AND ANALYSIS
Alkane, alkene, alkyne aims to differentiate the type of reaction that occurs
in alkane, alkene, and alkyne and to know the properties of alkane and alkyne
which can be burned.
1. Substitution of Alkane
The first experiment aims to determine the type of reaction that occurs
in the alkane namely halogen substitution reaction. the first step is to
prepare 5 mL of bromine water (a yellow solution) then put it in a test tube.
Furthermore, LPG gas is flowed through the hose into a test tube that has
been filled with 5 mL of bromine water and observed changes occur. After
the bromine water is drained with LPG gas it produces a color change from
the yellow solution to a colorless solution. This is because LPG gas contains
three alkane compounds, including: propane, butane and isobutane. When
LPG gas is poured into bromine water, the alkane compounds contained in
LPG gas react with bromine water so that a substitution reaction occurs. If
the alkane saturated compound is reacted with one of the halogen groups a
substitution reaction will occur. Substitution reaction is the reaction of
replacing hydrocarbon atoms by other compounds atoms. The substitution
reactions in alkane saturated compounds are as follows :
R - H + X2 R–X + H–X
Reaction of alkane compounds contained in LPG gas with bromine water :
• Propane
CH3CH2CH3 (g) + Br2 (aq) → CH3CH2CH2Br (aq) + CH3CHBrCH3 (aq)
+ HBr (aq)
• Butane
CH3CH2CH2CH3 (g) + Br2 (aq) → CH3CH2CH2CH2Br (aq) +
CH3CH2CHBrCH3 (aq) + HBr (aq)
• Isobutane
CH3CH2CH2CH3 (g) + Br2 (aq) → CH3CH2CH2CH2Br (aq) +
CH3CH2CHBrCH3 (aq) + HBr (aq)
It can be concluded that the color changes experienced by bromine
water indicate the reaction of replacing H atoms with Halogen (substitution
reaction).

Alkane, Alkene, Alkyne | 10

2. Form Acetylene Gas
In the second experiment it was intended to produce acetylene from
carbide granules (gray granules). The first step is to prepare two test tubes,
bent pipes and a tub filled with water. In the test tube A carbide granules are
added and the test tube B is filled with water placed upside down in a water
bath. Then connect the test tube A with the test tube B using the bent pipe.
Next, in the test tube A containing carbide granules added water drops by
drop using a pipette to form a white gas called esthylene gas (C2H2) which
smells pungent. Close the test tube A using a rubber cover connected to the
test tube B and a gas bubble is formed. The experiment was stopped when
the test tube inside the water bath had no gas bubbles because it had been
replaced by gas and the tube had to be reversed immediately by the mouth
of the tube above and the mouth of the tube closed by the thumb. Then the
test tube is immediately ignited by a match. The reactions that occur are :
CaC2 (s) + H2O (l) →CH CH (g) + Ca(OH)2 (aq)
When the gas in the test tube C is ignited by a match produces an
explosion, the color of the orange and soot colored flame is black. This
indicates that the combustion of acetylene gas is incomplete combustion
because it forms black soot and the resulting fire is orange. Ahen the gas is
burning there leaving black ash in the wall test tube. This occurs because the
soot flame is caused by a higher amount of carbon in the ethyne than in
methane. All carbon atoms cannot be oxidized while this combustion makes
the flame become dirty (Tewari & Vishnoi, 2017). The combustion
reactions that occur in acetylene gas are as follows:
CH CH (g) + O2 (g) → C (s) + 2CO (g) + 2H2O (l)
3. Addition Reaction of Alkyne
In the fourth experiment aims to determine the reactions that occur in
alkyne namely addition reactions. The first step is to prepare two test tubes,
hoses, carbide granules and 2 mL of bromine water. In the test tube A filled
with carbide granules (white powder) and test tube B filled with 2 mL of
bromine water (yellow solution). Then the test tube A and the test tube B are
connected by a hose and add water drop by drop to the test tube A

Alkane, Alkene, Alkyne | 11

 containing carbide granules. Close the test tube A using a rubber cover.
From the addition of the water in the test tube B which contains bromine
water there will be a change in the color of bromine water which was
originally a colored solution yellow becomes a colorless solution. The
reaction is :
CH CH (g) + Br2 (aq) → CHBr = CHBr (aq) → (CHBr)2 (g)
The discoloration of bromine water indicates that the acetylene
compound in carbide gas has undergone an addition reaction with Bromine.
In a small amount of water bromine will add alkyne to alkenes. Whereas if
the bromine is excess, it can add alkenes to alkanes. Based on the above
reaction shows that alkyne which has a triple bond will experience an
addition reaction when reacted with halogen (Br) to alkene which has a
double bond.
J. CONCLUSION
1. A substitution reaction occurs when the alkane is reacted with halogen Br2
(Halogenation) which is shown to change the color of the bromine to
colorless.
2. When carbide granules are reacted with water to produce ethylene gas and
an incomplete combustion reaction occurs.
3. Alkyne occur addition reaction with Br2.
K. REFERENCES
Justiana Sandri. 2009. Chemistry for Senior High School. Jakarta: Penerbit
Yudhistira
Keenan. 1984. Kimia Untuk Universitas Jilid 2. Jakarta: Penerbit Airlangga
Parlan & Wahjudi. 2005. Kimia Organik I. Malang: Penerbit Universitas
Negeri Malang UM Press
Fessenden, Ralp J., & Fessenden, Joan S. 1986. Kimia Organik Edisi III.
Aloysius Hadyana Pudjaatmaka, Penerjemah. Jakarta: Erlangga.
Fessenden, R.J dan Fessenden J.S., 1992. Kimia Organik, Jilid I, Edisi 3, A.B :
A.H Pudjaatmaka. Jakarta: Erlangga
Pine et al. 1988. Kimia Organik terbitan keempat. Bandung: Penerbit ITB
Riswiyantoro, 2009. Kimia Organik. Jakarta : Erlangga.

Alkane, Alkene, Alkyne | 12

Riyanti M. Zipora S. Tri RA. Subki EM. 2008. Sintesis Senyawa Hidrokarbon.
Jurnal Unila. Simbolon, Putri Laura. 2012. Reaksi Oksidasipada
Alkena dan Reaksi Asam Basa pada
senyawa Amina. Diakses melalui http://putrilaur.blogspot.co.id/. Pada
tanggal 12 Maret 2016 pukul 11.15 WIB
Rohmadi. 2012, Bab IX SMA (Senyawa Hidrokarbon Alkana, Alkena,
Alkuna), (Online), (http://kuliah.rohmadi.info/wp-
content/uploads/2012/12/Bab-IX-Kimia.pdf ), diakses 19 Agustus
2018
Tewari, K.S., & Vishnoi, N.K. 2017. A Textbook of Organic Chemistry Fourth
Edition. India: Vikas.
Tim Dosen Kimia Organik. 2016. Panduan Praktikum Kimia Organik.
Surabaya: Universitas Negeri Surabaya.

Alkane, Alkene, Alkyne | 13

L. ATTACHMENT
1. Answer of the Question
1. What is the content of LPG gas? Write down the chemical formula!
Answer :
Propane :
CH3CH2CH3
Butane:
CH3CH2CH2CH3
Isobutane:
CH3CHCH3
Br
2. What gas occurs when the carbide is given water?
Answer :
Carbide will react with water to produce acetylene gas. The reaction is :
CaC2(s) + H2O (l)→ CH2 = CH2(g)+ Ca(OH)2 (s)
3. Write down the reactions that occur from the gas after being put into
bromine water!
Answer :

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

Alkane, Alkene, Alkyne | 14

 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. Differentiate the nature of the reaction that occurs between city
gas/LPG gas & carbide gas to bromine water!
Answer :
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. 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!
Answer :
City gas/LPG gas the reaction is :

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

Alkane, Alkene, Alkyne | 15

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

CH3
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.

Alkane, Alkene, Alkyne | 16

 2. Documentation

No. Procedure of experiment Photo Information

1. - Bromine water + flowed LPG :

LPG 5 mL of Bromine
water colorless solution

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

Alkane, Alkene, Alkyne | 17

2. -Carbide granules + aquades : gas
Carbide granules
1. Put into side pipe tube -Gas ignited by matches : fire + carbon
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

Alkane, Alkene, Alkyne | 18

Alkane, Alkene, Alkyne | 19
3. -Carbide granules + aquades : gas
Carbide Bromine
granules water
-Gas + bromine water : bromine water
1. Entered into 1. Entered become colorless
side pipe into test
tube 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

Alkane, Alkene, Alkyne | 20

Alkane, Alkene, Alkyne | 21