Nathaniel Cheung Chem 12A Experiment 12 TLC Analysis of Analgesic Drugs Objective: To use thin layer chromatography to differentiate

and determine the identity of given samples. MSDS: Compound MSDS skin contact (irritant), of eye contact Acetaminophen (irritant), of ingestion, of inhalation skin contact (irritant), of eye contact Aspirin (irritant). skin contact (irritant), of eye contact Caffeine (irritant), of ingestion, of inhalation Ibuprofen Very hazardous in case of ingestion, of inhalation Extremely hazardous in case of ingestion. Very hazardous in case of eye contact (irritant), of inhalation. Hazardous in case of ingestion. Slightly hazardous in case of skin contact (irritant)

Salicylamide Naproxen

Procedure: 1. Prepare 12 capillary micropipettes to spot plates. 2. Obtain 2 TLC Plate and draw very gently with a lead pencil a line 1 cm from the bottom and 4 dots along the line in 1 cm intervals. 3. On the first plate, starting from left to right, spot acetaminophen, then aspirin, salicylamide, and unknown. Keep spots as small as possible 4. Obtain a 16 ounce wide mouth, screw cap jar and prepare the development chamber by wetting filter paper and placing in the jar. Fill chamber with solvent to below the line (.5-.7 cm) 5. Place second plate (with dots of Ibuprofen, Naproxin, Caffeine, and Unknown) with the same setup. 6. When solvent has risen to a level of .5 cm, remove plate and mark position of solvent with a lead pencil. 7. When plate has dried, observe under an UV lamp and outline all observed spots 8. Note any differences in behavior between the spotted substances. 9. Obtain half a tablet of analgesics and crush well with a spatula. 10. Transfer each crushed half tablet into a test tube 11. Mix 15 mL of ethanol and 15 mL of methylene chloride and mix 5 mL of solution into crushed sample 12. Heat gently for a few minutes on a steam bath or sand bath at 100 degrees Celsius. 13. Then repeat steps 1-8 with the solution.

Nathaniel Cheung Chem 12A 14. Place the three plates in a jar containing a few iodine crystals, cap the jar, and warm gently until spots appear. 15. Note which spots become visible and note their relative colors.

Nathaniel Cheung Chem 12A Experiment 12 TLC Analysis of Analgesic Drugs Objective: To use thin layer chromatography to differentiate and determine the identity of given samples. Reaction: No chemical reaction took place during this lab Data: See attached sheet

Discussion: Our unknown #01 is aspirin. This is obvious due to two reasons. First is that the Rf value of our unknown matches with aspirin. The second reason is that like our known sample of aspirin, our unknown has two spots that traveled up on the TLC plate compared to the one spot on every other known sample.

Questions: 1.What happens if the spots are made too large when preparing a TLC plate for development? The spots will run into each other because they are too large and it will be impossible to differentiate between different spots.
2. What happens if the spots are made too small when preparing a TLC plate for development? While it is preferable to make them as small as possible, there is a point when they are too small and impossible to actually see the dot on the TLC plate and read how far it has moved 3. Why must the spots be above the level of the development solvent in the developing chamber? If the spots are below the level of the development solvent in the developing chamber, the compounds would not move up the TLC plate. They would instead take the path of least resistance and flow into the solvent and would not travel up TLC plate. 4. What would happen if the spotting line and positions were marked on the plate with a ball-point pen? The ink in the ballpoint pen is nonpolar and would move up along with the solvent making it impossible to see the mark because the ink would spread over the TLC plate and cover the compounds mark 5. Is it possible to distinguish two spots that have the same Rf value but represent different compounds? Give two different methods. Yes it is possible. One method is to use the Iodine analysis. Some compounds under Iodine gas would change colors and darken. An unknown that darkens the same amount as a known compound would be one way to tell the identity of a compound. Another way to identify a compound is to mix the unknown with the known sample and then dot the TLC plate. If the unknown and known do not separate into two dots, then the unknown is the known sample. If they separate into two dots, then your unknown is definitely not the known sample.

Nathaniel Cheung Chem 12A

6. Name some advantages of using acetaminophen (Tylenol) instead of aspirin as an analgesic. Aspirin could be potentially dangerous due to its side effects as a blood thinner compared to acetaminophen which has relatively very little side effects.

Conclusion: During this lab, we learned that TLC analysis is a great way to differentiate between different compounds by comparing our unknowns Rf values to known substances Rf values.