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DETERMINATION OF RATE OF SAPONIFICATION OF AN ESTER WITH NaOH

Apparatus: Burettes Pipettes Thermostat Stop watch Titration flasks 2 Stoppered bottles 8 Solutions: NaOH (0.05M) NaOH (0.025M) HCl (0.025M) CH3COOC2 H5 (0.05M) CO2 free water Powder: Borax Theory Saponification is the process by which an ester is hydrolyzed in an alkaline solution to give an alcohol and conjugate base. CH3COOC2 H5 + OH²²²²²²> CH3COO+ C2H5OH

Saponification of ethyl acetate by NaOH is a second order reaction. If ³a´ and ³b¶¶ represent the initial concentrations of ethyl acetate and NaOH respectively, and ³x¶¶ denotes the number of moles per liter which react in time t, then the velocity of the reaction is expressed by the equation: dx /dt =k (a-x) (b-x) If the two substances are present in equal concentrations i.e. a = b, the rate equation becomes, dx /dt = k (a-x)2 dx /(a-x)2 = k dt

3. Under alkaline conditions. Label five clean flasks 1. 3. When ready. Carry out each titration three times. 2. 2. 4 and 5 near the thermostat. Weigh accurately about 1. This reaction is essentially irreversible. pour NaOH into the ester. 5. 7. 8. Mix thoroughly by swirling the solution while keeping in the thermostat.05M Methyl acetate into one clean dry flask and 100.025 M NaOH. Place flasks 1. PROCEDURE 1.025 M HCI and 100 cm3 of CO2 free water into each flask. 2. Wash a 20 cm3 pipette and rinse with 0. Take 10 cm3 portion and titrate with the given HCl solution and then titrate 20 cm3 portion of HCl solution with NaOH solution (approximately 0.025 M and 0. 4.192 g of Borax and prepare 250 cm3 solution. drain and leave ready for withdrawing samples from the reaction mixture. 5 and put 20 cm3 of 0. 6.05 M) and find the strength of these solutions.05 M NaOH into another clean dry flask and immerse in the 20oC thermostat for 8 . Pipette 100 cm3 of 0. CH3COOCH3 + NaOH ---> CH3COOH + CH3OH 4. of course the carboxylic acid is obtained as its salt. Therefore 1/(a-x) = kt + (l/a) SUMMARY The ester is hydrolyzed to a carboxylic acid and an alcohol or phenol. .after integration 1/(a-x) = kt + c c = 1/a. from which it can be liberated by addition of mineral acid. since a resonance-stabilized carboxylate anion shows little tendency to react with an alcohol. and back again starting a stopwatch at the mid point of the addition. 3.10 minutes.00 cm3 0. Base promotes hydrolysis of ester by providing the strongly nucleophilic reagent OH-. and since x = 0 at t = 0.

+ 2Na + 4H2 O 4. 2. and the (a-x)/mol l-1 5. 12. Withdraw 20 cm3 portions at approximately 2. Indicators For borax :HCI titration Methyl orange HCl: NaOH titration Phenolphthalein Calculations 1. Prepare a table containing time/min.> 4H3 BO3 + 2OH. Note the time at the mid point of delivery into the flasks. 4. Calculate the initial strength of ester and NaOH. . 3 Write downm n the mechanism of this reaction.2 g. What is the chemical formula of Borax? Na2B4O7·10H2O 2. 10. 16 and 20 min. Give four reasons to use Borax (instead of anhydrous Na2CO3) for the standardization of a given HCl solution. Na2 B4 O7 + 2HCl +5H2 O ----------------------------> 4H3PO3 + 2NaCl 3.025M NaOH. 2. Questions 1.9. 5. and put into the prepared flasks containing HCl. Molecular weight of Borax is 381. Na2B4O7 + 2HCl + 5H2O --> 2NaCl + 4H3BO3 5. 8. Na2 B4 O7 . 6. Calculate the strength of Borax solution. Construct 95% confidence intervals for the concentration of HCl and NaOH solutions. Titrate the excess HCl in each flask with 0. Construct 95% confidence interval for the rate of saponification by using a suitable graph. 3. Check the quality of data using the intercept of the graph.10H20 + H20 ---------------------. 6.

Why do you want to use CO2 free water for this experiment ? . Is your mechanism consistent with kinetics? Explain why ? 7.4.