Step 1: Performing the Esterification Reaction
1. [Plug a hot plate or a sand bath and turn the dial to medium setting. Allow the temperature to stabilize at 125±5
°C, while getting reagents ready for the reaction].
2. Weigh 1.0 mL of glacial acetic acid in a 5 mL long neck round bottom flask and add to it 0.5 mL of i-pentyl
alcohol. Swirl the mixture.
3. Add 0.025 g of Dowex50x2-100 ion exchange resin, 5 drops of conc. H2SO4, and a magnetic bar or an acid-
resistant (black) boiling chip. Note 1: It is recommended to use
4. Assemble the apparatus as shown in Fig 3. a magnetic stirrer (if available) to
mix the solution, otherwise some
5. Gently reflux (boil) the reaction mixture for 75 minutes (Note 1).
knocking and popping may occur
during reflux due to uneven
Step 2: Isolation of Product heating.
1. Turn off the sand bath and remove the apparatus.
2. Cool the reaction flask to room temperature in cold water-bath.
3. Using a clean glass Pasteur pipette, transfer the solution from the flask (leaving the resin) into a centrifuging
tube. Note 2: You may see substantial
4. Add 1 mL of cold 5% NaHCO3 solution in two portions (Note 2); carefully flick the foaming due evolution of CO2, vent
the tube frequently by opening the
tube after each addition until bubbles evolution is no longer vigorous. cap.
5. Cap the tube and shake it well for 1 minutes or until no more bubble are seen.
6. Remove the cap off the tube and allow the two layers to separate.
7. Pull out the lower aqueous layer using the same glass Pasteur pipette and place it into a beaker labeled
"Aqueous wash".
8. Add another 1 mL of cold 5% NaHCO3 solution to the organic layer in the centrifuging tube, cap the tube and
shake it for 1 minute.
9. Uncap the tube and allow the two layers to separate.
10. Use the same Pasteur pipette to transfer the lower aqueous layer to the "Aqueous wash" beaker.
11. Add 1 mL of cold water to the remaining organic layer in the centrifuging tube, cap the tube and shake it briefly.
12. Uncap the tube and allow the two layers to separate.
13. Use the same Pasteur pipette, transfer the lower aqueous layer to the "Aqueous wash" beaker.
14. To the remaining oil in the centrifuging tube, add 0.1 g of anhydrous Na2SO4 drying agent, mix for 1 minute
(add additional Na2SO4 if necessary, until the drying agent does not clump).
15. Use a dry/clean Pasteur pipette transfer the liquid from the centrifuging tube into a dry/clean long neck round
bottom flask (make sure not to transfer any of the drying agent with it).
16. Add a boiling chip and assemble the distillation apparatus as shown in Fig 4.
17. Carefully distill the product, collect the fraction that distills at 130-145 °C into a tared/clean glass vial.
18. Measure the weight of the product and calculate the percentage yield of the reaction.