Experiment P01 Determination of the equilibrium constant for esterification (Ethanoic acid and Propan-1-ol)

Chemicals:

Glacial ethanoic acid, (density = 1.05 g cm-3, 17.5M), (10 cm3) propan-1-ol, (density = 0.80 g cm-3, 13.33 M), (10 cm3) conc. H2SO4, (1 cm3) standard 0.50 M NaOH, (400 cm3) phenolphthalein indicator, ice.

Apparatus:

Apparatus for refluxing, titration apparatus, 1.0 cm3 pipette. (1) 10.0 cm3 pipette(2)

Principle:

In the presence of conc. H2SO4 and under reflux, ethanoic acid undergoes a reversible reaction with propan-1-ol to form ester and water. As equilibrium is reached, CH3COOH(l)+CH3CH2CH2OH(l) Kc = [CH 3 COOCH 2 CH 2 CH 3 ]eq [ H 2 O]eq [CH 3 COOH ]eq [CH 3 CH 2 CH 2 OH ]eq CH3COOCH2CH2CH3(l)+H2O(l)

By titrating the reaction mixture with standard alkali solution before and after refluxing, the quantity of the acid used, and thus the quantities of the alcohol used as well as of the ester and water formed can be determined. Knowing the quantities or molar concentrations of the species present in the equilibrium mixture, the equilibrium constant, Kc can be calculated.

P.1

Experiment P01 Determination of the equilibrium constant for esterification (Ethanoic acid and Propan-1-ol)
Procedure: a. b. Measure accurately 10.0 cm3 of glacial ethanoic acid and 10.0 cm 3 of propan-1-ol into a clean, dry 100 cm3 distillation flask. Mix thoroughly. Transfer 1.00 cm3 of the mixture by pipette to a 125-conical flask containing about 25 cm 3 distilled water and 2 drops of phenolphthalein indicator solution. Titrate to end point with 0.50 M NaOH. Record this volume. Repeat the titration to obtain an average volume of 0.50 M NaOH used. (Find the original concentration of CH3COOH after mixing) c. Add 8 drops of conc. H2SO4 to (the remainder of) the acid-alcohol solution while continuously swirling the flask. Titrate another 1.00 cm3 sample immediately. Record this volume. The difference between this volume and the one in (b) above represents the volume to be subtracted from subsequent titration to correct for the amount of H2SO4 present. (Find the concentration of H2SO4) d. Add a few boiling chips to the flask, and attach it to a water-cooled reflux condenser. Reflux for 1 hour (first refluxing process). Cool the flask and its contents in an ice bath. Remove 1.00 cm3 sample from the flask for titration with the 0.50 M NaOH (as procedure b). Record the volume needed (and correct it for the H2SO4). (Find the concentration of the remaining CH3COOH) e. Continue refluxing (second refluxing process) for an additional 1/2 hour, cool and titrate another 1.00 cm3 sample. The two titrations should agree to within 0.20 cm3. Otherwise, repeat the second refluxing process. (To ensure the esterification is complete) f. Use the data to calculate the equilibrium constant, Kc, of the esterification reaction.

P.2

Experiment P01 Determination of the equilibrium constant for esterification

Procedure b: (specimen result) Titration Final burette reading (cm3) Initial burette reading (cm3) Volume of NaOH used (cm3) 1(trial) 3.15 23.20 20.05 2 1.10 20.95 19.85 3 2.25 22.20 19.95 4

Average volume of NaOH used (Vb) = 19.90 cm3 --------------------------------------------------------------------------------------------------------------------Procedure c: (specimen result) Titration Final burette reading (cm3) Initial burette reading (cm3) Volume of NaOH used (cm3) 1(trial) 2.15 24.20 22.05 2 1.15 22.90 21.75 3 3.20 24.85 21.65 4

Average volume of NaOH used (Vc) = 21.70 cm3 --------------------------------------------------------------------------------------------------------------------Procedure d: Titration Final burette reading (cm3) Initial burette reading (cm3) Volume of NaOH used (cm3) 1(trial) 2 3 4

Average volume of NaOH used (Vd) = --------------------------------------------------------------------------------------------------------------------Procedure e: Titration Final burette reading (cm3) Initial burette reading (cm3) Volume of NaOH used (cm3) 1(trial) 2 3 4

Average volume of NaOH used (Ve) = N.B. If Vd = Ve, esterification is complete. P.3

Experiment P01 Determination of the equilibrium constant for esterification (Ethanoic acid and Propan-1-ol)
Name: Partner 1 Partner 2 Partner 3 Grade: Given: Concentration of NaOH = Calculation: Conc. of propan-1-ol before mixing = 13.33 mol/dm3 Conc. of ethanoic acid before mixing = 17.50 mol/dm3 13.33 Conc. of propan-1-ol after mixing = = 6.665 (mol/dm3 ) 2 17.50 Conc. of ethanoic acid after mixing = = 8.75 (mol/dm3) 2 In procedure b, average vol. of NaOH used = 19.90 cm3 In procedure c, average vol. of NaOH used = 21.70 cm3 Vol. of NaOH required to neutralize conc.H2SO4 = 21.70 19.90 = 1.8 (cm3) In procedure d (and procedure e), average vol. of NaOH used = Vol. of NaOH required to neutralize ethanoic acid (at equil.) = = Let M be the concentration of CH3COOH at equil. Then M 1 = 1000 - 1.8 cm3 Seat No.: Date:

M= i.e. [CH3COOH] eq = CH3COOH(l)+CH3CH2CH2OH(l) At start At equil. Conc. of CH3COOH consumed = Conc. of propan-1-ol at equil. = [CH3COOCH2CH2CH3]eq = [H2O]eq = Kc = P.4 8.75 6.665 0 CH3COOCH2CH2CH3(l)+H2O(l) 0