Synthesis of Aspirin and Various Flavoring Esters Omran Azimi 4/21/14 Lab Partners:

Purpose: To synthesize various esters and note their odors and synthesize aspirin using the same esterification reaction. Safety: Make sure to tie your hair back, wear closed toed shoes, wear an apron and goggles, and be careful with handling acetic anhydride and phosphoric acid because it can burn and irate skin, nose and eyes. Hypothesis: If I use the esterification reaction then I will be able to synthesize aspirin successfully If I synthesize various esters then I will be able to record the odor of the ester I have produced. Procedure: 1. Set up a hot-water bath using a 600-mL beaker and a hot plate. Heat up the water to approx 75 oC and try to keep it around that temperature by adjusting the hot plate or adding a little cold water occasionally as needed. 2. Weigh out approximately 2 g of salicylic acid; record mass. Transfer the acid quantitatively (this means don't spill any!) to a small (50 mL) erlenmeyer flask. 3. Measure out 5.00 mL of acetic anhydride from the buret into the flask. Run the liquid into the flask so that it washes down any crystals of acid that might be clinging to the sides of the flask.. (CAUTION: Acetic anhydride is a corrosive liquid that can burn and irritate skin, nose, and eyes). 4. Add five drops of concentrated (85%) phosphoric acid. (CAUTION--Like all concentrated acids, this acid can cause serious skin/eye damage!) This acid will act as a catalyst in the reaction. 5. Clamp the flask so that the reaction mixture is immersed in the hot water bath. Stir the mixture occasionally with a stirring rod over about 15 minutes. After this time, the reaction should be complete. 6. Cautiously add about 2 mL of water to the flask to decompose any unreacted acetic anhydride into acetic acid. (There will be some hot acetic acid vapors given off as a result of this reaction; it may smell strongly like vinegar). 7. After a few minutes (when the mixture has stopped giving off vapors), remove the flask from the water bath. Add about 20 mL of distilled water to the mixture; a white solid should begin to crystallize out from the mixture. This is crude (impure) aspirin. Dump out the hot water from the bath and refill the beaker with ice water. Clamp the flask in the ice bath to hasten

crystallization and increase the yield of the aspirin product. If crystals are slow to appear, you may need to take a stirring rod and scratch it around the inside of the flask to coax the crystals to form. Leave the flask in the ice bath for five minutes. 8. Set up a Buchner funnel that is equipped for suction filtration. Collect the crude (unpurified) aspirin by filtering the reaction mixture through the funnel using suction filtration. Turn off the suction; then pour 5-10 mL of ice-cold distilled water over the crystals. Then turn on the suction to remove this wash water. Repeat this washing process with another 5-10 mL portion of icecold distilled water. Draw air through the funnel for several minutes; this will help dry the crystals. Then disconnect the suction. You may discard the filtrate liquid down the sink. 9. The instructor will designate a place to let the aspirin dry overnight. Carefully lift the edge of the filter paper in the funnel, and slide it (hopefully with the aspirin crystals adhering to it!) onto a larger piece of filter paper marked with your initials. 10. After your crude aspirin has air-dried for at least 24 hours, record its mass. In your lab report, you will also calculate and report your percent yield of crude aspirin. PART B a. Prepare a hot water bath by filling a 600-mL beaker half-full of warm water and placing it on a hot plate. Heat the water until the temperature reaches about 70 oC, and then try to keep the water temperature between 65-75 oC throughout the experiment by adjusting the hot plate control as needed or adding a little cold water occasionally. b. To a clean, dry test tube, combine the required quantities of the desired alcohol and carboxylic acid (see table below). Mix well by rapping the bottom of the test tube with a finger. c. Add 5 drops of concentrated sulfuric acid to the test tube. (CAUTION!) Mix again. d. Heat the test tube in the hot water for 5-10 minutes. Remove and let cool in a test tube rack. Then cautiously smell and record the odor of the ester you have produced. e. Pour the contents of the test tube into the waste beaker located in the fume hood. Then wash the test tube thoroughly with soap and water, and dry it.

ESTERS TO PREPARE: Following the procedure above, react the following. (You can measure out the liquids in the hood, using a calibrated plastic pipet).

DATA TABLES # 1 2 methanol (3 mL)

Alcohol

Carboxylic Acid 1 g salicylic acid 2 mL ethanoic (acetic) acid

isopentyl alcohol (2 mL) (formal name is 3-methyl-1-butanol)

3 4

1-octanol (2 mL) ethanol (2 mL)

2 ml ethanoic (acetic) acid 2 mL pentanoic acid (Caution--foul odor)