PRACTICAL 3: ALCOHOL, ETHER AND AMINES

Aim: To prepare samples of ethanol and to investigate the chemical properties of ethanol. Theoretical Knowledge: People have used fermentation in brewing and baking for more than 5000 years. The action of yeast or other microorganisms converts disaccharides such as sucrose or maltose to ethanol and carbon dioxide (CO2). In brewing, the desired product is ethanol; in baking, the desired product is CO2. In 1789, Lavoisier first showed that sugar undergoes fermentation to yield ethanol and CO2. Gay- Lussac quantified that process in 1815 to show that each mole of glucose gives two moles of ethanol and two moles of CO2. Pasteur demonstrated in 1857 that the process requires yeast. Then in 1897, Bchner found that a yeast extract not containing living organisms could cause the conversion. Twentieth- century chemists continued these studies to identify the enzymes and reaction intermediates that are part of the chemical pathways involved. Ethanol is a straight-chain alcohol, and its molecular formula is C2H5OH. Its empirical formula is C2H6O. An alternative notation is CH3-CH2-OH, which indicates that the carbon of a methyl group (CH3-) is attached to the carbon of a methylene group (-CH2-), which is attached to the oxygen of a hydroxyl group (OH). It is a constitutional isomer of dimethyl ether. Ethanol is often abbreviated as EtOH, using the common organic chemistry notation of representing the ethyl group (C2H5) with Et. Problem Statement: Does the ethanol can be prepared by process of fermentation and distillation? Hypothesis: The preparation of ethanol involved the fermentation process and distillation process with the boling point of 78OC and melting point of -115OC and the specific gravity of 0.79 gcm-3.

Variables: Manipulated variable: Types of ingredients (mashed banana, glucose,tapioca,mashed pineapple,rice and others) Responding variable: Colour and smell of distillate collected Fixed variable: Amount of yeast used Materials and Apparatus: Glucose, cooked potatoes, mashed pineapple, rice, tapioca, mashed banana, yeast, lime water, distilled water, tap water, potassium dichromate (VI) solution, concentrated sulphuric acid, filter paper, conical flask, beaker, measuring cylinder, distillation flask, stopper with delivery tube, stopper with one hole, thermometer, Liebig condenser, fractioning column, retort stands and clamps, tripod stand, wire gauze, Bunsen burner, rubber tubing, filter funnel, boiling tube, blue litmus paper, evaporating dish, test tube holder, dropper, forceps. Procedures: A. To prepare samples of ethanol. 1) About 20g of glucose is dissolved in 150 cm of distilled water in a clean conical flask. 2) Approximately about 10g of yeast is added to the mixture and had shake well. 3) The conical flask has been closed with a stopper connected to a delivery tube. The other end of the delivery tube was dip into lime water in a boiling tube as shown in Figure 1(a). 4) The apparatus was leaved in a warm place (35C) for about 4-5 days. 5) Any changes which are taking place are observed for time to time. 6) The content of the conical flask is filtered after about 4-5 days. The filtrate was poured into a distillation flask. 7) The apparatus for the distillation was set up as shown in Figure 1 (b). 8) The filtrate was heat in the water bath and the ethanol that boils over at 78 to 80C are collected. 9) The color and the smell of the distillate collected are examined.

10) Steps 1 to 9 are repeated using cooked potatoes, mashed pineapple, rice, tapioca or mashed banana to replace glucose.

Figure 1(a): Preparation of ethanol

Figure 1(b): Set-up for distillation of ethanol

Results: Types of ingredients Glucose Cooked potatoes Mashed pineapple Rice Tapioca Mashed banana Colour of the distillate collected Very cloudy Cloudy A little bit of cloudy A little bit of cloudy A little bit of cloudy Cloudy

B. To investigate the chemical properties of ethanol. B-1 To investigate the combustion of ethanol. 1) About 2cm of the prepared ethanol was pour into an evaporating dish. 2) A lighted wooden splinter is used to ignite the ethanol (Figure 2). 3) The combustibility of ethanol is noted.

Figure 2 : Combustion of ethanol.

Test Combustibility Colour of the flame Sootiness of the flame

Observation Occured very fast Blue colour None

B-2 To investigate the oxidation of ethanol. Variables: Manipulated variable: Prepared ethanol Responding variable: Smell of products after boiled Fixed variable: Volume of potassium permanganate solution/ Drops of concentrated sulphuric acid and Volume of ethanol 1) About 10cm of potassium permanganate solution are pour into a boiling tube. 2) About 10 drops of concentrated sulphuric acid are add into the boiling tube by using a dropper. 3) About 3cm of ethanol is added to the mixture. 4) The apparatus was set up as shown in Figure 3. 5) The boiling tube was heat carefully with a gentle flame until the mixture boils. 6) The product is smelled.

Figure 3 : Oxidation of ethanol

Discussion: Ethanol is a colourless liquid with a pleasant smell. It is completely miscible with water and organic solvents and is very hydroscopic. It has melting point of -1150C and boilong point 780C. Its specific gravity is 0.79.As we know, ethanol is used in the manufacture of alcoholic drinks. Besides that, it is widey used as solvent for paint, varnish and drugs and in the manufacture of ethanal, for example acetaldehyde), and ethanoic acid.Ethanol also is used as a fuel in gasohol and in preserving biological specimens. Ethanol burns in air with a blue flame, forming carbon dioxide and water. It reacts with active metals to form the metal ethoxide and hydrogen, e.g., with sodium it forms sodium ethoxide. It reacts with certain acids to form esters, e.g., with acetic acid it forms ethyl acetate. It can be oxidized to form acetic acid and acetaldehyde. It can be dehydrated to form diethyl ether.

Conclusion: The preparation of ethanol involved the fermentation process and distillation process with the boling point of 78OC and melting point of -115OC and the specific gravity of 0.79 gcm-3. Hypothesis is accepted. Precautions: 1) 2-propanol (rubbing alcohol) is generally safe; however, it is flammable, toxic, and requires care in handling. 2) Use open flames with caution since the alcohol and some alcohol-water mixtures are flammable. 3) Wear protective goggles throughout the laboratory activity. 4) Wash your hands thoroughly with soap or detergent before leaving the laboratory. 5) Always use caution in the laboratory. Many chemicals are potentially harmful. 6) Avoid ingesting any of the reagents.

Questions: 1. Name the enzyme present in yeast that decomposes glucose into ethanol. Zymase enzyme

2.

Write a balanced chemical equation to represent the decomposition of glucose into ethanol. C6H12O6 (s) 2 CH3CH2OH (aq) + 2 CO2 (g) + 2 ATP

3.

Explain the use of fractional distillation in this experiment. To separate a mixture of two miscible liquids (liquids that mix in all proportions) with different boiling points. For example, in this experiment it was use to separate ethanol from water and its compounds. To produce ethanol we have to prepare a fermentation of glucose. The ethanol from this fermentation will be isolated by fractional distillation. The fractional distillation must repeat, in order to remove water, which, unfortunately predominates during the first fractional distillation. Once you have

repeated your fractional distillation, you can determine the amount of alcohol in your final distillate sample. To produce alcoholic beverages. This is because it also has several parts that are important in the experiment like this. The part is like this: A container for the original mixturecalled a retort. a condenser to cool the vapors a receiver to collect the distillate

4.

Write a balanced chemical equation to represent the combustion of ethanol. C2H5OH (l) + 3O2 (g) 2CO2 (g) + 3H2O (g)

5.

What is function of potassium permanganate solution in this experiment? Potassium permanganate solution was functioning as an oxidizing agent which is to oxidize the ethanol to acetic acid. For your information, it is difficult for us to stop the reaction at the acetaldehyde at high yield.

6.

Write a balanced chemical equation to represent the oxidation of ethanol. CH3CH2OH CH3COOH

7.

Predict your observation when apparatus set-up in Figure 1 is left for more than a week and explain your answers. I think that the lime water will be silkier and has a milky precipitate because of the carbon that has been released. Other than that, the smell will also stinkier. This is because the yeast has been fermenting the ingredients for a long time. It means that there were a pour ethanol gas has been produced. It can also have the high color of flammable.

8.

Can ethanol be used as vehicle fuel? Explain your answer. In my opinion, ethanol can be used as vehicle fuel.This is because it is volatile which has boling point of 78C. Besides that, ethanol is highly flammable and it has high heat content. So, as a fuel, it is a clean fuel, biofuel and gasohol.For example, the largest single use of ethanol is as a motor fuel and fuel additive. Brazil has the largest national fuel ethanol industry. Gasoline sold in Brazil contains at least 25% anhydrous ethanol. Hydrous ethanol (about 95% ethanol and 5% water) can be used as fuel in more than 90% of new cars sold in the country. Brazilian ethanol production is praised for the high carbon sequestration capabilities of the sugar plantations, thus making it a real option to combat climate change.

REFERENCES

Bah Hock Guan, Tor Siong Hoon (2008). Matriculation Chemistry 1. Kuala Lumpur Oriental Academic Publication. Chook Jack Bee, Mary Khoo (2006). Chemistry The Essential Study Guide Form 4 Selangor Darul Ehsan. Federal Publications Sdn. Bhd. Kho Chin He,(1998). Pendekatan Komprehensif Kimia Organik STPM. Selangor Darul Ehsan.Federal Publications Sdn.Bhd. Low Swee Neo, Lim Yean Ching, Eng Nguan Hong (2005). Chemistry Academic Notes Form 4, Pulau Pinang, Abadi Ilmu Sdn Bhd. Ooi Theng Theng. (1997). Sukses Lengkap Terkini SPM Kimia. Selangor Darul Ehsan. Pustaka Delta Pelajaran Sdn Bhd.

http://en.wikipedia.org/wiki/Ethanol

10 July 2011. 15 July 2011.

http://wiki.answers.com/Q/What_are_the_properties_of_Ethanol http://www.infoplease.com/ce6/sci/A0858037.html\ scifun.chem.wisc.edu/chemweek/pdf/ethanol.pdf

23 July 2011. 23 July 2011.

www.distill.com/ethanolproperties.html 26 July 2011. en.wikipedia.org/wiki/Ethanol 26 July 2011.

www.distill.com/ethanolproperties.html 28 July 2011. en.wikipedia.org/wiki/Ethanol_fuel 28 July 2011. 1 August 2011.

www.cleanairtrust.org/E85-Chemical-Properties-Production.html www.energyrefuge.com/archives/ethanol-fuel.htm

1 August 2011