Sitasi Online_zotero_pku 17_ulfa Nur Afifah_17030194033.docx

A. EXPERIMENT TITLE

: Alkanes, Alkene and Alkyne

B. DAY/ DATE OF EXPERIMENT

: Friday, 1nd of March 2019, 07.30 a.m : Friday, 1nd of March 2019, 12.00

C. FINISHED THE EXPERIMENT

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 2bromopropane.

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 Bromine water

Carbide granules

1. Entered into test tube B

1. Entered into side pipe tube 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

No. 1.

Procedure of experiment

LPG

5 mL of Bromine water 2. Entered into test tube

Observation result Before - Bromine water : yellow solution

Assumtion/reaction

After - Bromine water + flowed LPG : colorless solution

Conclusion

- Propana

Alkane

CH3CH2CH3 (g) + Br2 (aq) substitusi reaction  CH3CH2CH2Br (aq) + by

halogene

CH3CHBrCH3 (aq) + HBr (halogenation) (aq)

4. Flew LPG into the test tube until the color of bromine water disappear 5. Observed and wrote the color changes

- Butana CH3CH2CH2CH3 (g) +

Br2

(aq)  CH3CH2CH2CH2Br (aq)

Observation result

+

CH3CH2CHBrCH3

(aq) + HBr (aq) - Isobutana CH3CH2CH2CH3 (g) +

Br2

(aq)  CH3CH2CH2CH2Br (aq)

+

CH3CH2CHBrCH3

(aq) + HBr (aq)

8

ocur

Br2

2.

Carbide granules

- Carbide

granules : white 3. Put into side pipe tube 4. Connected with a hose to powder tube B (filled of water ) - Aquades : which is placed up and colorless down solution 9. Added water into side 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

 CaC2 (s) + H2O (l)  Alkyne can occur in granules + CH CH (g) + Ca(OH)2 combusion complete reaction aquades : gas (aq)

- Carbide

- Gas ignited by  CH

matches : fire + carbon

Observation result

9

CH (g) + O2 (g) 

C (s) + 2CO (g) + 2H2O (l)

3.

Carbide granules

Bromine water

3. Entered into 2. Entered into test side pipe tube B tube 4. Added water using pipette

- Carbide

 CH

- Carbide

granules : white

granules

+

powder

aquades : gas

- Bromine water :

- Gas + bromine

yellow solution

water : bromine water

CH (g) + Br2 (aq) Alkyne CHBr CHBr (aq)  addition with Br2. (CHBr)2 (g)

occur reaction

become

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: 4.

LPG

Flame is blue

Colorless

The combusition of LPG is complete

1. Open the regulator 2. Flow LPG into bunsen

combustion.

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)

+

(aq)

 CH3CH2CH2CH2Br

(aq)

+

CH3CH2CHBrCH3 (aq) + HBr (aq) c. Isobutana CH3CH2CH2CH3

(g)

+

Br2

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

CH (g) + Ca(OH)2 (aq)

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) (Propane)

CH3CH2CH2Br(aq) + HBr(aq) (1-bromo propane)

or CH3CH2CH3(g) + Br2(aq)

CH3CHBrCH3(aq) + HBr(aq)

(Propane)

(2-bromo propane)

Reation with butane CH3CH2CH2CH3(g) + Br2(aq) (Butane)

CH3CH2CH2CH2Br(aq) + HBr(aq) (1-bromo butane)

or CH3CH2CH2CH3(g) + Br2(aq) (Butane)

CH3CHBrCH2CH3 (aq) + HBr(aq) (2-bromo butane)

Reaction with isobutane 16

CH3CHCH3(g) + Br2(aq) CH3

CH3CHCHBr(aq) + HBr(aq) CH3

(Isobutane)

(1-bromo-2-methyl propane) or Br

CH3CHCH3(g) + Br2(aq) CH3

CH3CHCH3(aq) + HBr(aq) CH3

(isobutene)

(2-bromo-2-methyl propane)

Reaction between acetylene gas and bromine water

H

C2H2

(g)

Acetylene gas

Br2(aq) 

+

bromine water

Br

Br

C

C

Br

Br

H

(aq)

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) Butane : C4H10 (g) +

13 2

O2 (g) → 4 CO2(g) + 5 H2O (l)

Isobutane : CH3CHCH3 (g) +

13 2

O2

CH3

17

4CO2 + 5H2O

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. 1.

Procedure of experiment

LPG

Photo

Information - Bromine water + flowed 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 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

-Gas ignited by matches : fire + carbon

Observation result

20

3.

Carbide granules

-Carbide granules + aquades : gas

Bromine water

-Gas + bromine water : bromine water become colorless

5. Entered into 3. Entered into test side pipe tube B tube 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