00222-091

May 2010

DESIGN LABREPORT: HOMOLOGOUS SERIES

Aim: To carry out an investigation of any aspect of a homologous series Research Question:
How does the rate of the Esterification reaction between ethanol chosen acids change with an increase in the number of Carbon atoms present in the carboxylic acid? Independent Variable: Length of Carbon chain of Carboxylic Acid Dependant Variable: Rate Controlled Variables: Initial Concentration of the acid Pressure Temperature Same alcohol to be used for all reactions

Background Information
Esterification is the reaction between alcohols and carboxylic acid when heated in presence of an acid catalyst. The catalyst is concentrated Sulphuric acid. Esterification reaction is a slow and reversible reaction. The equation for the reaction between an acid RCOOH and an alcohol R'OH (where R and R' can be the same or different) is:

Esters are insoluble in water apart from the very small esters. Small esters smell like typical organic solvents and the bigger esters smell like artificial fruit flavours, esters are also use in artificial flavourings An Esterification reaction would come to equilibrium, with significant amounts of both reactants and products present in the mixture. Ordinarily in the making of ester its high volatility is used as an advantage. The reaction mixture is distilled causing the form ester to evaporate and removing it from the system. This reduces the concentration of the product from the mixture and thereby causes the equilibrium to move to the right utilizing the reactants. Once the ester is condensed it must be kept free form moisture in order to prevent the reverse reaction form occurring.

00222-091 Given below is the reaction mechanism of esters visually.

May 2010

00222-091

May 2010

In the second step of the reacton mechanism the

Hypothesis
The rate of reaction should decrease; this is because as the length of the carbon chain of the carboxylic acid increases there is a large amount of positive charge induced on the chain due to the inductive effect. This makes it harder for the OH group to detach form the ester and hence the activation energy of the reaction increases. With increased activation energy more time would be required for all the molecules in the solution gain enough energy to react.

Apparatus & Reagents

1. 2. 3. 4. 5. 6. 1 moldm-3 ethanol 2 large measuring cylinders Conical flask Rubber stoppers (2 nos) Concentrated sulphuric acid Reflux apparatus a. Bunsen burner b. Round bottom flask c. Thermometer d. Clamp stand e. Fractionating column f. Condenser with connecting pipes

Procedure
1. Prepare 0.15 dm3 of 1 molar ethanoic acid solution by dissolving 0.15 mol of ethanoic acid (9g) in 0.15dm-3 (150 cm3) of water. 2. Measure 100cm3 of this acid and pour into a round bottom flask 3. Measure 100cm3 of the 1 molar ethanol using a measuring cylinder and pour into the round bottom flask. 4. Pour 20 ml of Sulphuric acid into the flask 5. Attach the fractionating column to the flask and connect both to a clamp stand securely. 6. Put a rubber stopper on top of the fractionating column and fix a thermometer in it. 7. Connect the condensers to the fractionating column 8. Place a conical flask at the bottom to of the condenser to collect the ester

00222-091 9. 10. 11. 12. Place the Bunsen burner below the round bottom flask to start heating the mixture Heat the mixture till the temperature reaches 50C. Continue heating mixture for a long period of time, approximately 45 minutes. Measure the amount of ester produced at the end of the time period.

May 2010

Prepare a new solution with a different carboxylic acid with a longer carbon chain such as propanoic acid, butanoic acid, pentanoic acid, etc. Prepare a solution of concentration 1moldm-3 for each of these acids and use 100cm3 of the solution prepared. React the acid with the exactly 100cm3, add 20cm3 of sulphuric acid as the catalyst and allow the reaction mixture to react for the same period of time. Record the results in table in the format given below. Number of carbon atoms in Acid 2-ethnoic 3-propanoic 4-butanoic 5-pentanoic Amount of ester formed (cm3)

Uncertainty analysis
Uncertainy in preparation of Solution Apparatus Measuring Cylinder Balance Instrumental Uncertainty 0.5 0.01 Percentage error (0.5/150)*100 = 0.33% (0.01/9)*100 = 0.11%

Total = 0.44%

00222-091 Uncertainty of esterification reaction Apparatus Measuring Cylinder Uncertainty of Thermometer Instrumental Uncertainty 0.5 0.5

May 2010

Percentage Error 2*(0.5/150)*100 = 0.66% (0.5/50)*100 = 1%

Total = 1.66%