Pre-Lab Exercises Lab 11: Drug Chemistry

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1 Pre-Lab Exercises Lab 11: Drug Chemistry Name Date Section 1. Describe how a non-steroidal anti-inflammatory drug (NSAID) reduces pain and inflammation. 2. The active ingredient in an aspirin tablet is acetylsalicylic acid (ASA). Draw its structure. 3. What are at least 3 of the negative side-effects of taking NSAIDs on a regular basis? 4. How does a buffered aspirin help prevent stomach irritation? 5. Why does modern aspirin contain acetylsalicylic acid rather than regular salicylic acid? Page 1 of 6

2 Chemistry 100 Lab 11: Drug Chemistry DISCUSSION The last time you had a headache, maybe you reached for an analgesic a substance that relieves pain. Aspirin is probably the oldest pain reliever we know, and it s the most widely used drug in the world. Aspirin is one of a group of drugs called non-steroidal anti-inflammatory drugs (NSAIDs), which also includes ibuprofen, acetaminophen, naproxen and ketoprofen. Aspirin was originally extracted from willow bark back in ancient Greece. Centuries later, in 1827, chemists finally identified the active ingredient in aspirin as salicin, a derivative of salicylic acid. The first commercial aspirin containing acetylsalicylic acid was produced by the German company Bayer in 1899, and the world has been popping aspirins ever since. Today, we still use acetylsalicylic acid (formula C 9H 8O 4) which is a derivative of the original salicylic acid. The active ingredient in modern aspirin, acetylsalicylic acid (ASA), is only part of what you swallow each time you take an aspirin. There are inert binders that hold the tablet together and sometimes a buffered coating to help the drug be more gentle on your stomach. How much of the active ingredient is contained in each tablet? We will find out, and compare our calculations with what is printed on the label. To do this, we ll be performing titrations. A titration is a process in which a base (often NaOH) is added to an acid (in this case, ASA) that contains a ph indicator (in this case, phenolphthalein). The indicator we ll be using is colorless in the presence of an acid and turns pink in the presence of a base. As you slowly add the base to the acid, they react together until all the acid has been reacted. One additional drop of base will turn the solution basic and the indicator will turn pink. We will then use some simple stoichiometric calculations to determine how much ASA was present in the solution. Titration Using Aspirin PROCEDURES 1. Obtain an aspirin and weigh it. Record the mass to 2 decimal places. 2. Using a mortar and pestle, grind the tablet into a fine powder. 3. Add 20mL of isopropyl alcohol (rubbing alcohol) to your mortar to dissolve all the aspirin powder. Stir with the pestle and continue to grind until you have a very fine suspension of aspirin in the alcohol. 4. Test the ph using a test strip and record the ph. 5. Pour your solution from the mortar into a flask. Be careful not to spill any! Add a little more isopropyl alcohol to the mortar, swirl around and add to flask (this will hopefully get all the aspirin into the flask so none is left in the mortar). 6. Add 2 drops of phenolphthalein indicator to your solution in the flask. 7. Obtain a buret in a clamp. Open the stopcock (valve) at the bottom and allow the distilled water to drain out. Pour a little of the NaOH solution into the buret and allow it to drip out the bottom (this is called a wash and it removes any water still in the buret). Do this at least twice. Close the stopcock. 8. Fill the buret with approximately 10 ml of the NaOH solution. 9. Open the stopcock at the bottom of the buret to allow the NaOH to begin dripping into the aspirin solution. You don t have to count the number of drops because we ll be using volume readings from the buret. After each drop of NaOH, swirl the flask gently to make sure the 2 solutions mix. You may see a faint pinkish color directly after a drop of NaOH hits the aspirin solution, but as you swirl it the solution will go clear again. Page 2 of 6

3 10. Continue one drop at a time of NaOH into the aspirin solution until ONE DROP makes the solution turn pink and stay pink. Close the stopcock immediately and stop the NaOH dripping. Don t go past this point or your calculations will not come out correctly. 11. Determine the volume of NaOH used (read the meniscus in the buret). Record the volume to 2 decimal places. 12. Pour the contents of your flask down the sink and rinse the flask with distilled water. 13. Repeat steps 1-12 twice more for a total of 3 trials. The second and third trials will go faster because you can let your NaOH flow more quickly until you get fairly close to the volume you expect, then slow to one drop at a time. 14. Once you have finished your 3 trials and have reasonable data, pour any NaOH left in your buret down the sink. Wash the buret several times with distilled water, then close the stopcock and fill the buret to the top with distilled water. Put a rubber stopper in the top of the buret. 15. Average the mass of your 3 aspirin tablets (in grams) and record it in the table. 16. Average the volume of NaOH used in your 3 trials (in ml) and record it in the table. 17. Convert the average volume from ml into liters and record it in the table. Remember, 1 L = 1000 ml. Comparison of Generic and Name-brand Aspirin 1. Obtain a name-brand aspirin and grind it using the mortar and pestle, as you did in the previous section. 2. Add 20mL of isopropyl alcohol (rubbing alcohol) to your mortar to dissolve all the aspirin powder. Stir with the pestle and continue to grind until you have a very fine suspension of aspirin in the alcohol. 3. Test the ph using a test strip and record the ph. Page 3 of 6

4 Lab Station Check Out # Titrations Using Aspirin REPORT Name Lab Partner Date Section Mass of aspirin tablet Trial 1 Trial 2 Trial 3 ph of aspirin solution Volume of NaOH used Average mass of aspirin tablet (g) Average volume of NaOH used (ml) Average volume of NaOH used (L) Comparison of Generic and Name-brand Aspirin ph of aspirin solution Calculations 1. Calculate the molar mass of acetylsalicylic acid. Use 2 decimal places on all the atomic masses and in your answer, but be sure to round correctly. Don t forget units! Molar mass of acetylsalicylic acid: 2. Calculate the molar mass of NaOH. Use 2 decimal places on all the atomic masses and in your answer, but be sure to round correctly. Don t forget units! Molar mass of NaOH: Page 4 of 6

5 3. The NaOH concentration is given in molarity (M), which means moles / Liter. Calculate the average number of moles of NaOH used in your titrations using the following calculation. Record your answer to 5 decimal places. moles NaOH x volume of NaOH used (in Liters) = moles of NaOH 1 Liter Moles of NaOH used in the aspirin titrations: 4. When the acid (ASA) and the base (NaOH) combine, 1 mole of acid reacts with 1 mole of base. Therefore, the numbers you calculated in question 3 also represent moles of ASA. Moles of ASA in the aspirin titrations: 5. Now, using the molar mass of ASA that you calculated in question 1 and the moles of ASA in question 4, calculate the grams of ASA according to the following formula: g ASA x mole ASA = g ASA 1 mol ASA Grams of ASA in the aspirin (3 decimal places): 6. Now convert the grams you calculated in the last question into milligrams. Remember that 1 g = 1000 mg. Milligrams of ASA in the aspirin (3 decimal places): Page 5 of 6

6 7. How close did your calculations come to the actual value recorded on the aspirin bottle? To find out, calculate a percent error. The accepted value will be the mg of aspirin recorded on the bottle, and the measured value will be the mg you calculated in the previous question. A value of 5% or less is great! percent error accepted value measured accepted value value 100% Percent error (1 decimal place): Post-Lab Analysis 1. What might be some sources of error in this experiment? In other words, what might make your data come out differently than the label on the aspirin bottle, and differently between each of your trials? 2. How does the ph of the generic aspirin compare to the name-brand aspirin? 3. Some people consider genuine Bayer aspirin to be superior to store-brand aspirin because it s the original. Compare a bottle of genuine Bayer aspirin to the store-brand aspirin. What similarities and differences are there? Can you hypothesize about whether a store-brand aspirin should work as well as the name brand, based on the label? Page 6 of 6

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