ESTERIFICATION LAB

Purpose: To synthesize isopentyl acetate Equipment: Microscale kits, stirring hot plates, gas chromatograph Supplies: Safety goggles, isopentyl alcohol, glacial acetic acid, concentrated sulfuric acid, silica gel, Aluminum heating block and collar, 5% aqueous sodium bicarbonate, Pasteur pipets, distilled water, acetone Procedure: 1. Assemble the reflux apparatus according to written and verbal directions. 2. Take a 3.0 mL conical vial with a magnetic spin vane, and add 1.0 mL of isopentyl alcohol using a micropipettor preset to 1.0 mL by the teacher. 3. Add 0.550 mL of glacial acetic acid using a preset micropipettor 4. Add four drops of concentrated sulfuric acid using a dropper 5. Heat the mixture to a boil in a heating block on the hot plate. Stir the mixture with a magnetic stirrer. 6. After the reflux band (the band where the vapors recondense and flow back into the vial) is visible, continue heating under reflux for 20 minutes. Maintain the temperature between 160 degrees C and 180 degrees C. 7. Remove the apparatus from the hot plate and allow the mixture to cool to room temperature. Air cool for a couple of minutes and then use a beaker of water to speed cooling. 8. While waiting for the vial to cool, prepare a 5mL conical vial with 2 mL of 5% aqueous sodium bicarbonate solution (NaHCO3) 9. Use a Pasteur pipet to transfer your solution to the 5 mL conical vial prepared in step 8. Wait for the initial fizzing to subside, and then cap the vial. 10. For this extraction, shake the capped vial and vent additional gas (shake and vent three times), then allow to stand until separate layers are formed. 11. Using a Pasteur pipet, remove the lower, aqueous layer and discard it into a waste collection beaker or sink. 12. Extract again by adding a fresh 2.0 mL portion of 5% NaHCO3 solution to the 5.0 mL conical vial. 13. Again, shake and vent three times, then allow standing until separate layers are formed. 14. Using your Pasteur pipet, again remove the lower aqueous layer and discard it.

15. Dry the organic layer by adding a small amount of anhydrous MgSO4 (this amount varies depending on how much ester you have made). 16. Pre-weigh your clean, dry sample vial with its cap and record its mass. 17. Transfer your sample to the vial using your Pasteur pipet, leaving the drying agent behind. 18. Weigh the sample vial and contents and determine the mass of the ester by subtracting. 19. Clean the 5 mL conical vial by rinsing with distilled water and finally rinsing with acetone. 20. Clean the 3 mL conical vial by rinsing with distilled water and finally rinsing with acetone. 21. Using your dropper, transfer the dry organic layer (containing the ester) into the clean, dry 3 mL conical vial, leaving the dry agent behind. 22. Assemble the distillation apparatus according to written and verbal directions. 23. Add the dry screw-type magnetic spin vane to the ester 24. Begin distillation and continue until only one or two drops of liquid remain in the 3 mL conical vial. 25. During distillation, pre-weigh a sample vial and record its mass. 26. When distillation is complete, transfer your pure banana oil (isopentyl acetate) from the Hickman still to the pre-weighed sample vial using a new Pasteur pipet. 27. Weigh the sample vial and contents and determine the mass of the ester by subtracting. 28. Inject one L of your sample into the gas chromatograph. Identify and label the peaks and their retention times on your print-out. Compare your results with those of the known standards. Complete the data table. Calculations and Questions: 1. Calculate the number of moles of isopentyl alcohol 0.813 g * 1 mol = 9.22 * 10-3 mol 1 mL 88.2 g 2. Calculate the number of moles of acetic acid 1.06 g * 1 mol = 9.70 * 10-3 mol 1 mL 60.1 g 3. Isopentyl alcohol is the limiting reactant. 4. Calculate the theoretical yield.
9.22 * 10-3 mol of alcohol + 9.22 * 10-3 mol of acetic acid 9.22 * 10-3 mol of isopentyl acetate

9.22 * 10-3 mol of isopentyl acetate * 1 mol ester * 71 g ester = 0.654 g of isopentyl acetate 1 mol alcohol 1 mol ester

5. Calculate the percent yield. Mass of product and vial: 1.568 g Mass of vial only: 0.965 g Mass of product: 0.603 g Percent yield: 0.603 g = 0.9220 = 92.20% yield 0.654 g 6. Gas Chromatograph Code: B Known Standards Compound Retention Times Water 0.428 Acetone 1.097 Isopentyl Alcohol 1.868 Isopentyl Acetate 2.242 7. Compound Peak 1 Peak 2 Peak 3 Peak 4 % of Sample 0.166 0.237 0.973 0.756 1.503 7.276 1.967 90.156 Student Sample Peak Retention Times Peak 1 0.166 Peak 2 0.973 Peak 3 1.503 Peak 4 1.967

8. We did not find any acid in our final sample because the acid decomposed and synthesized with the alcohol to produce isopentyl acetate. 9. We did not find any water in our final sample because we did not distill it. 10. We could have reduced the amount of water in our final sample by distilling it. 11. We found isopentyl alcohol in our final sample because we let the sample sit for a day, so a reverse reaction occurred. 12. We could have reduced the amount of alcohol in our final sample by distilling it and taking out the water. 13. The water, acetone, and alcohol peaks should be minimized. The isopentyl acetate peak should be maximized. 14. Our group did not have a high percentage of isopentyl acetate.

15. The sample should be distilled so that would be no water, one setting so that a reverse reaction would not occur.

and done in

Conclusion: From the experiment, the esterification process was put into action. I learned from this lab that esters, which are derivatives of carboxylic acids, are the main components of many odors and flavors of fruits and flowers. In this experiment, the ester isopentyl acetate was synthesized. Isopentyl acetate is what gives bananas its unique scent. In the esterification process, isopentyl alcohol reacts with an acetic acid to produce isopentyl acetate. This is a reversible reaction, so the acid and alcohol reactants and ester products are in equilibrium. In order to result in a higher yield of the ester, Le Chateliers principle (predicts that equilbrium can be driven to the products side by having one of the reactants in excess) was applied on the isopentyl alcohol. Sulfuric acid was used as a catalyst in order to accelerate the rate at which the products formed. The reflux apparatus allowed the experiment to occur. The reacting mixture is refluxed, or heated in a vessel with a water-cooled condenser to prevent loss of volatile material and the reflux band allows the vapors to recondense and flow back into the vial. The heat from the hot place of the apparatus will speed up the reaction. Gas chromatography was needed in order to interpret the results of this lab. The process helps to indicate the masses of the different components of the mixture. The lighter a compound shows, the lighter in mass it is. The peaks should indicate that the ester is heaviest by molar mass, but unfortunately, we produced little ester in our experiment due to unknown variables. A product containing only ester was not possible in this experiment due to a number of factors. We skipped the distillation process, which could have separated the isopentyl acetate even further from the other components of the mixture. In addition, since esterification is a reversible process, it is hard for theoretical yield to be achieved. Hydrolysis, the reverse action, can occur overnight, converting the isopentyl acetate back into isopentyl alcohol.