Hydrolysis of Acetylsalicylic Acid

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LAB REPORT: Hydrolysis of Acetylsalicylic Acid PURPOSE: The purpose of this lab is to become familiar with the identification of ester, carboxylic acid and alcohol functional groups, to understand that formation and hydrolysis of esters are equilibrium processes, to understand how ester hydrolysis yields carboxylic acid and alcohol products, and to understand what a sympathetic ink is and how such inks are visualized. PROCEDURE: 1. Crushed two 325mg aspirin tablets into powder; placed the powder in a 50 or 100mL beaker; added 2 grams of sodium carbonate; then measured and added 20mL of water. 2. Stirred the mixture occasionally; covered it with plastic wrap and allowed to stand overnight in a safe place undisturbed to hydrolyze the aspirin to salicylic acid; noticed the odor of acetic acid in the beaker the following morning. 3. Prepared a developing solution by dissolving 1 gram of iron (II) sulfate heptahydrate into 60mL of white vinegar; stirred until fully dissolved; cloudy green solution resulted. 4. Added 2-3mL of liquid household bleach solution and stirred; solution turned orange. 5. Dipped cotton swab into the salicylic acid hydrolysis solution and wrote a message on a blank piece of flat, white paper and allowed it to dry. 6. Laid the dried message paper on several layers of paper towels for the visualization step to keep the developer solution from soaking on the work surface and surrounding materials. 7. Developed the dried invisible message by dipping a clean cotton swab into the orange developing solution and used it to paint over the message. Questions A. Identify the functional groups in methylsalicylate, acetylsalicylic acid and salicylic acid: The functional groups in methylsalicylate are ester, alcohol & phenol groups. The functional groups in acetylsalicylic acid are carboxylic

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