Practical TITLE Aim

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4 Carboxylic Acids, Esters and Amides To prepare a sample of ester and to investigate the physical properties of ester.

Material/apparatus

absolute ethanol, glacial ethanoic acid, concentrated sulphuric acid, 5% aqueous sodium bicarbonate solution, oil, water, sodium chloride solution, beaker, distillation flask, tap funnel, round bottomed flask, conical flask, measuring cylinder, thermometer, Liebig condenser, Bunsen burner, retort stands and clamps, tripod stand, stopper with two holes, wooden block.

Introduction

1. Carboxylic acids contain a COOH group is attached either to a hydrogen atom or to an alkyl group. 2. The chemical properties of other carboxylic acids are similar to those of ethanoic acid. This is because all the carboxylic acids have the same functional group which acts in the same manner. 3. Ethanoic acid is a weak acid which reacts with a base to produce a salt and water in a reaction known as neutralization. 4. For example, the reaction between ethanoic acid and sodium hydroxide will produce sodium ethanoate and water. 5. Ethanoic acid is a weak acid and its reacts with a metal carbonate to produce a salt, carbon dioxcide and water. 6. For example, the reaction between ethanoic acid and sodium carbonate, Na 2 CO3, will produce sodium ethanoate, carbon dioxcide gas and water. Carbon dioxcide gas that is produced can be tested with limewater which it turns milky. 7. Amides are made by a chain or carbon atoms with one as a carbonyl, double bonded to oxygen, bonded to an amine group, nitrogen, which is then bonded to the next carbon to continue the chain and one hydrogen. 8. Ester is organic compounds which has fruity smell. 9. Esters are produced by esterification reactions. 10. An esterification reaction is a reaction between an alcohol and a carboxylic acid which produces an ester and water. 11. Uses of carboxylic acids in everyday life are Used in food as flavouring agents. Used to make plastics and emulsion paints. Used for making esters in perfumes and food flavourings.

Procedure

A. To investigate the physical properties of ester

1. About 2 cm of ethyl ethanoate is poured into a test tube. The smell of ester is noted. 2. About 5 Cm of distilled water is added to the ester and the mixture is shaken well. The solubility of the ester in water is noted. 3. Steps 1 to 2 are repeated using acetone and methylated spirits consecutively to replace distilled water.

Results

Solvent Water Acetone Methylated spirits

Observation Not very soluble soluble soluble

B. To prepare a sample of ester 1. About 50 cm of absolute ethanol with 50 Cm of glacial ethanoic acid flask is mixed into a 250 ml round bottomed flask. 2. 10 Cm of concentrated sulphuric acid is added carefully to the content of the flask while swirling. 3. The apparatus as shown in Figure 1 is set up.

4. The mixture is heated under reflux for 1 hour. 5. The heating source is removed and is allowed the mixture to cool to room temperature. 6. The cooled mixture is poured into a separatory funnel and add 25 Cm cold water. Shake the separatory funnel. 7. The lower aqueous layer is separated from the upper organic layer. The
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aqueous layer is discarded. 8. 25 Cm 5% aqueous sodium bicarbonate solution is added and the separator funnel is shake and the lower layer is discarded. 9. Procedure 8 is repeated 10.25 Cm of water is added and the separator funnel is shake. The aqueous layer discarded. 11.5 Cm of saturated aqueous calcium chloride is added. The mixture is stirred gently and the aqueous layer is discarded. 12. The organic layer is observed and smelled.

Discussion /Questions

1. Explain the meaning of esterification reaction. Reaction produce ester or prepared by reacting carbonxlylic acid and alcohol and the prensence of concentrated sulphuric acid.

2. Write a balanced chemical equation to represent the reaction between ethanoic acid and ethanol. CH3CH2OH + 2[O] CH3COOH + H2O

3. What is the function of concentrated sulphuric acid in this experiment? a. A drying agent to absorb the water that is produced b. A catalyst that increases the rate of reaction

4. Explain another method of preparing ethyl ethanoate . Is heating the mixture of ethanol, ethanoic and concentrated sulphuric acid

under reflux above for 20 minute. After that, the mixture is then poured into distillation flask. Distillate is collected at 70C. Distillation process is stopped when temperature reached 78C. Pure ester is distilled between 75-78C.

5. What is the function of 5% aqueous sodium bicarbonate solution in this experiment? It neutralizes all ethanoic acid and sulphuric acid so that the acid impurities can be eliminated.

6. Explain the use of calcium chloride solution in this experiment. Acts as drying agent to eliminate all water from the liquid ethyl ethanoate.

7. Compare the solubility of ethyl ethanoate in water, acetone and methylated spirits.Explain your observation. Ethyl ethanoate only soluble in acetone and metylated sprite. Ethyl ethanoate is a covalent compound which are only soluble in non-polaritic.

8. Name the ester produced from an esterification reaction between butanoic acid and ethanol. Ethyl butanoate

9. Write a balanced chemical equation o represent the reaction above.

C3H9COOH + CH5OH

CH3CH2CH2COOCH2CH3

Conclusion

Ethyl ethanoate is prepared by heating ethanoic acid and ethanol in the presence of concentrated sulphuric acid as the catalyst.

References

Chong Kum Ying & Chang See Leong. (2002). Fokus Ungu SPM Sains. Bangi, Selangor : Penerbitan Pelangi Sdn. Bhd.

Mah Chee Wai & Lim Swee Kim. (2011). Nexus SPM Chemistry. Petaling Jaya: Sasbadi Sdn. Bhd.

Tan Yin Toon,Loh Wai Leng,Tan On Tin,(2009) Success Chemistry SPM.Oxford Fajar.Shah Alam ,Selangor

S.H. Chan.(2011). Kimia SPM; Kuasai Melalui Diagram. Selangor: SAP Publications.

Suhaila Ahmad & Doris Siaw Hie Kiew. (2011). Memory Mastery Through Visual Maps & Diagrams Chemistry SPM. Selangor: PNI Neuron(M) Sdn. Bhd.

Vijaya Viswanathan & Catherine Lee. (2012). Suplemen SPM Chemistry .Selangor: Marshall Cavendish (Malaysia) Sdn. Bhd.

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