O Chem Lab

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University of California, Berkeley *

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3AL

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Chemistry

Date

Feb 20, 2024

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pdf

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2

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1 Chem 3AL, Fall 2022 Lab H. Pre-lab document for Experiment #9 (What do you take for pain?) (5 pts) 1.Draw the structures of (S)-naproxen as well as (S)-sodium naproxen. Calculate the molecular weight for each of the molecules and write it below each structure. 2. Calculate the maximum number of milligrams of (S)-naproxen that could be isolated from one pill of Aleve (see the annotated lab lecture notes for information). O HOM ** - Na . -* O E Imos Na-Naprox H-Naprox x - X 220mg Na-Naprox x Ig NaNaP 252 249 Na-Naprox I mol Na-Naprox 230 . 76 g H-Naprox - MoTH-Naprop-x omg H-Na prox = 200 . 829 my of (S) - Naproxen - 19 H- Naprox
2 5. Here is a start to your flow-chart to put into your lab notebook. Fill in the boxes and label the different states/phases/conditions (like tablet and paper towel, or organic and aqueous) following mixing with water and centrifugation. Tablet paper towel Pulverize, transfer to pre-weighed test tube Binder Blue Coating (OpaDry) Swirl with 0.5mL EtOH, wipe off tablet "Na-Naprox" 3. Aleve contains sodium naproxen, a pro-drug. When it hits the stomach, it is converted to the active compound, naproxen. Draw the structure of (S) sodium naproxen again ("Na-Naprox" abbreviation), show an arrow - pushing mechanism where it reacts with H-Cl (stomach acid), to create naproxen and chloride. 4. Using solubility data found in the lab text, explain why ethanol, and not water, is used to remove the blue OpaDry coating from the pill. Add 1 mL H 2 O, heat, centrifuge, separate Add 0.5 mL H 2 O, heat, centrifuge, separate 1 pill of Aleve + + Add H 2 SO 4 , centrifuge, separate Supernatent Solid Where is H-Naprox? Add ice-water, centrifuge, separate Solid Recrystallize( Co-solvent) -- S O- i + H - c ** O Nag Na c I O -- E - > Hom - E you need to use ethanol bl Na-Naproxen is not very soluble in ethanol and the opadry coating is . Therefore you are able to separate the 2 substances , room temp Iwarm Na-Naproxen is much more soluble in water so if you used water while OpaDry is soluble in water you would not be able to separate the I compounds because they world both dissolve . Na-Naprox + binder blue coating Copadry) Na-Naprox + binder Na-Naprox binder Nat HSOy- H-Naproxen H-Naproxen H-Naproxen
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