LAB REPORT SHEET-Coumarin

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University of North Florida *

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CHM-2210

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Chemistry

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Feb 20, 2024

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docx

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5

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LAB REPORT SHEET Coumarin synthesis Name (Print): Dalia Elkhatib Partner’s name: Allie Larrimore and Lilly Amsden 2 pts Total points = 76 Data 1. Mass of 4(diethylamino)salicylaldehyde used = 1.00 g 2. Volume of ethyl acetoacetate used = 1.50 mL Mass of ethyl acetate ( use density 1.02g/mL and show work ) = 2 pts (1.02 g/mL) * (1.50 mL) = 1.53 g 3. Drops of piperidine solution used = 8 drops 4. Mass of the watch glass + filter disc = 33.39 g 5. Mass of the watch glass + filter disc + crude laser dye product (3-acetyl-7- (3-acetyl-7- (diethylamino)-2H-chromen-2-one) = 34.09 g Mass of the crude laser dye product 3-acetyl-7-(diethylamino)-2H-chromen-2-one ( show work ) = 0.70 g 2 pts 6. Theoretical yield based on each of the starting materials. 10 pts (Please use two Dimensional Analysis (DA) equations, one for the maximum amount of product obtainable from 4-(diethylamino)salisaldehyde you used and the other from ethyl acetoacetate , then use the lesser of the two to calculate the %Yield. NOTE: You can find two examples of how to calculate theoretical yield and actual % yield uploaded in the Canvas “Miscellaneous
File”. Please study this file; you can use this file as an example for all your synthesis labs. Maximum quantity of product obtainable from 4(diethylamino)salicylaldehyde 1.00 g 4(diethylamino)salic ylaldehyde 1 mol 4(diethylamino)salicyla ldehyde 1 mol 3-acetyl-7- (diethylamino)-2H- chromen-2-one 259.30 g 1 193.24 g 1 mol 4(diethylamino)salicyla ldehyde 1 mol 3-acetyl-7- (diethylamino)-2H- chromen-2-one = 1.34 g Maximum quantity of product obtainable from ethyl acetoacetate 1.53 g ethyl acetoacetate 1 mol ethyl acetoacetate 1 mol 3-acetyl-7- (diethylamino)-2H- chromen-2-one 259.30 g 1 130.14 g 1 mol ethyl acetoacetate 1 mol 3-acetyl-7- (diethylamino)-2H- chromen-2-one = 3.05 g 7. Identity of the Limiting reagent (LR) based on the above two DA equations = 2 pts 4(diethylamino)salicylaldehyde 8. Maximum yield obtainable from the LR = 1.34 g 2 pts %yield of the product obtained: (0.70 g / 1.34 g) x 100% = 52.2% 5 pts 9. Physical state of the coumarin laser dye product ( see video ) = solid, crystal-like 2 pts 10. Color of the coumarin product ( see video ) = yellow 2 pts 11. Literature mp of the product (optional): N/A NA 12. Mp range of the product you synthesized (if determined in class). N/A NA 13. Explain if your determined mp (if determined in class) is significantly different than the literature mp. N/A NA
14. TLC results (attach the two TLC images taken to monitor the progress of reaction) Distance between the baseline and the solvent front = 2.3 cm Distance of the starting material 4(diethylamino)salicylaldehyde from the base line = 2.9 cm R f value of starting material 4(diethylamino)salicylaldehyde . (Show work) = 0.81 cm 2 pts 2.9 cm / 3.6 cm = 0.81 cm Distance of the product (dye laser) from the base line = 2.2 cm R f value of crude laser dye product. (Show work ) = 2.2 cm / 3.6 = 0.61 cm 2 pts Attach TLC with your lab report next week. 5 pts Did the experiment go as planned? 10 pts If not, what were the problems and how did you solve them? Our experiment overall went as planned, although we may not have left the flask in ice water for long enough to maximize the amount of crystals we could have yielded. PLEASE NOTE: Dispose of all chemicals in the appropriately labeled hazard waste containers. Halogenated waste, if any, must be disposed of in its designated container in the specified hood. All glassware must be washed with soapy water, then DI water, and
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finally rinsed with acetone to wash off the organic residue. The clean glassware should be dried and put back into the tray or its original place. Other pieces of equipment (ring stands, clamps, hot plate, stir bars, heating mantels, etc) must be returned to their proper locations. Post-lab questions 1. Write down the overall equation for the reaction you performed (write structural formulas , NOT molecular formulas). 4 pts 2. What is the role of piperidine in the coumarin laser dye analogue synthesis? 2pts Piperidine acts as a weak base catalyst in the coumarin laser dye analogue synthesis. 3. What ‘named’ reaction was used in the coumarin laser dye analogue? 2 pts Knoevenagel reaction 4. Complete the following chemical equation and write down all the resonance structures of the product (must use the specific mechanism that was discussed in class) 4 pts
5. Complete the following equations: 16 pts