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SYNTHESIS AND ANALYSIS OF ASPIRIN LAB ADV COMP 22 From Advanced Chemistry with Vernier, Vernier Software & Technology, 2004 INTRODUCTION Aspirin, the ubiquitous pain reliever, goes by the chemical name acetylsalicylic acid. One of the compounds used in the synthesis of aspirin is salicylic acid, which is itself a pain reliever that was known to many ancient cultures, including the Native Americans who extracted it from willow tree bark. Salicylic acid is extremely bitter tasting, and frequent use can cause severe stomach irritation. The search for a milder form of this pain reliever led to the successful synthesis of acetylsalicylic acid by the German chemist Felix Hoffmann in 1893. Your two primary objectives in this experiment will be to synthesize and analyze aspirin. There is more than one way to synthesize aspirin; in this experiment, you will react acetic anhydride with salicylic acid in the presence of phosphoric acid (which acts as a catalyst). A drawing of the aspirin molecule is shown below. Figure 1 You will conduct two tests of your synthesis to verify that you did indeed make aspirin, and to determine its relative purity. First, you will measure the melting point of a sample of your product. Second, you will use a spectrometer to test the absorbance of your aspirin after it has been “prepped” with an iron solution to give it color. OBJECTIVES In this experiment, you will Synthesize a sample of acetylsalicylic acid (aspirin). Calculate the percent yield of your synthesis. Measure the melting temperature of your aspirin sample. Conduct a spectrophotometric analysis of your aspirin sample. Westminster College SIM T ADV COMP.22-1
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MATERIALS PART I SYNTHESIS MATERIALS 50 mL Erlenmeyer flask Solid salicylic acid two 10 mL graduated cylinders 85% phosphoric acid solution, H 3 PO 4 25 mL graduated cylinder liquid acetic anhydride Büchner funnel, filter, and filter paper distilled water spoon, spatula, or rubber policeman cold distilled water ice bath small rubber band hot plate fume hood plastic Beral pipet or eyedropper balance PART II MELTING TEMPERATURE TEST MATERIALS Vernier computer interface aspirin crystals (from Part I) computer hot plate Temperature Probe mineral oil capillary tubes ring stand, ring, and wire gauze 150 mL beaker or Thiele melting-point tube cork or split stopper mortar and pestle small rubber band glass stirring rod utility clamp PART III COLORIMETER TEST MATERIALS Vernier computer interface olid salicylic acid computer aspirin crystals (from Part I) Vernier Spectrometer or Spec 20 95% ethanol plastic cuvette with lid 0.025 M iron (III) nitrate solution, Fe(NO 3 ) 3 250 mL beaker distilled water 100 mL beaker 100 mL volumetric flask 50 mL graduated cylinder 250 mL volumetric flask PROCEDURE PART I Synthesize Aspirin 1. Obtain and wear goggles. Note: Conduct this reaction in a fume hood or a well- ventilated area of the room. 2. Measure out 2.0 grams of salicylic acid into a 50 mL Erlenmeyer flask.
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This note was uploaded on 11/10/2010 for the course CHE 201 taught by Professor Bong during the Spring '08 term at SUNY Buffalo.

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