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    Saponification

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    Sihanu Subasingha
    This experiment determines the rate of saponification (hydrolysis) of an ester (ethyl acetate) with sodium hydroxide (NaOH). The ester is hydrolyzed to a carboxylic acid (acetic acid) and an alcohol (ethanol). NaOH promotes this hydrolysis by providing the strongly nucleophilic OH- ion. Samples are taken from the reaction mixture at time intervals and titrated with HCl to determine the amount of NaOH remaining and thus the amount of ester hydrolyzed. This allows the rate of the reaction to be determined and analyzed using appropriate rate equations and graphs.

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    Saponification

    Uploaded by

    Sihanu Subasingha
    455 views4 pages
    This experiment determines the rate of saponification (hydrolysis) of an ester (ethyl acetate) with sodium hydroxide (NaOH). The ester is hydrolyzed to a carboxylic acid (acetic acid) and an alcohol (ethanol). NaOH promotes this hydrolysis by providing the strongly nucleophilic OH- ion. Samples are taken from the reaction mixture at time intervals and titrated with HCl to determine the amount of NaOH remaining and thus the amount of ester hydrolyzed. This allows the rate of the reaction to be determined and analyzed using appropriate rate equations and graphs.

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    This experiment determines the rate of saponification (hydrolysis) of an ester (ethyl acetate) with sodium hydroxide (NaOH). The ester is hydrolyzed to a carboxylic acid (acetic acid) and an alcohol (ethanol). NaOH promotes this hydrolysis by providing the strongly nucleophilic OH- ion. Samples are taken from the reaction mixture at time intervals and titrated with HCl to determine the amount of NaOH remaining and thus the amount of ester hydrolyzed. This allows the rate of the reaction to be determined and analyzed using appropriate rate equations and graphs.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as DOCX, PDF, TXT or read online from Scribd
    Download as docx, pdf, or txt
    455 views4 pages

    Saponification

    Uploaded by

    Sihanu Subasingha
    This experiment determines the rate of saponification (hydrolysis) of an ester (ethyl acetate) with sodium hydroxide (NaOH). The ester is hydrolyzed to a carboxylic acid (acetic acid) and an alcohol (ethanol). NaOH promotes this hydrolysis by providing the strongly nucleophilic OH- ion. Samples are taken from the reaction mixture at time intervals and titrated with HCl to determine the amount of NaOH remaining and thus the amount of ester hydrolyzed. This allows the rate of the reaction to be determined and analyzed using appropriate rate equations and graphs.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as DOCX, PDF, TXT or read online from Scribd
    Download as docx, pdf, or txt
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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 + OH> CH3COO+ C2H5OH

    Saponification of ethyl acetate by NaOH is a second order reaction. If a and b represent the initial concentrations of ethyl acetate and NaOH respectively, and x 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

    after integration

    1/(a-x) = kt + c c = 1/a.

    and since x = 0 at t = 0, Therefore 1/(a-x) = kt + (l/a)

    SUMMARY The ester is hydrolyzed to a carboxylic acid and an alcohol or phenol. Under alkaline conditions, of course the carboxylic acid is obtained as its salt, from which it can be liberated by addition of mineral acid. Base promotes hydrolysis of ester by providing the strongly nucleophilic reagent OH-. This reaction is essentially irreversible, since a resonance-stabilized carboxylate anion shows little tendency to react with an alcohol. PROCEDURE 1. Weigh accurately about 1.192 g of Borax and prepare 250 cm3 solution. 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 0.05 M) and find the strength of these solutions. Carry out each titration three times. 2. Pipette 100 cm3 of 0.05M Methyl acetate into one clean dry flask and 100.00 cm3 0.05 M NaOH into another clean dry flask and immerse in the 20oC thermostat for 8 - 10 minutes. 3. CH3COOCH3 + NaOH ---> CH3COOH + CH3OH 4. Label five clean flasks 1, 2, 3, 4, 5 and put 20 cm3 of 0.025 M HCI and 100 cm3 of CO2 free water into each flask. 5. Wash a 20 cm3 pipette and rinse with 0.025 M NaOH, drain and leave ready for withdrawing samples from the reaction mixture. 6. Place flasks 1, 2, 3, 4 and 5 near the thermostat. 7. When ready, pour NaOH into the ester, and back again starting a stopwatch at the mid point of the addition. 8. Mix thoroughly by swirling the solution while keeping in the thermostat.

    9. Withdraw 20 cm3 portions at approximately 2, 5, 8, 12, 16 and 20 min. and put into the prepared flasks containing HCl. Note the time at the mid point of delivery into the flasks. 10. Titrate the excess HCl in each flask with 0.025M NaOH.

    Indicators For borax :HCI titration Methyl orange

    HCl: NaOH titration Phenolphthalein Calculations 1. Calculate the strength of Borax solution. 2. Construct 95% confidence intervals for the concentration of HCl and NaOH solutions. 2. Na2 B4 O7 + 2HCl +5H2 O ----------------------------> 4H3PO3 + 2NaCl 3. Na2 B4 O7 .10H20 + H20 ---------------------- > 4H3 BO3 + 2OH- + 2Na + 4H2 O 4. Na2B4O7 + 2HCl + 5H2O --> 2NaCl + 4H3BO3

    5. 6. 3. Calculate the initial strength of ester and NaOH. 4. Prepare a table containing time/min, and the (a-x)/mol l-1 5. Construct 95% confidence interval for the rate of saponification by using a suitable graph. 6. Check the quality of data using the intercept of the graph. Molecular weight of Borax is 381.2 g. Questions 1. What is the chemical formula of Borax? Na2B4O710H2O 2. Give four reasons to use Borax (instead of anhydrous Na2CO3) for the standardization of a given HCl solution. 3 Write downm n the mechanism of this reaction.

    4. Is your mechanism consistent with kinetics? Explain why ? 7. Why do you want to use CO2 free water for this experiment ?

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