LAB REPORT SHEET_Dehydydrobromination of CinnAcid dibromide

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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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LAB REPORT SHEET Dehydrobromination of cinnamic acid dibromide Name (Print):… Dalia Elkhatib ………………………….. Partner’s name:… Allie Larrimore and Lilly Amsden ………………………. Total Points = 78 Data 1. Mass of 2,3-dibromo-3-phenylpropanoic acid (cinnamic acid dibromide) used = 2.00 g 2. Volume of 25% KOH solution used = 4.00 mL from a 25% (w/v) solution of KOH solution Mass of pure KOH used (show work) = 4 pts (25 x 4 mL) / 100 = 1.00 g Mass of the watch glass + filter paper = 33.40 g Mass of the watch glass + filter paper + product (3-phenylpropynoic acid) = 33.68 g Mass of the crude product (3-phenylpropynoic acid; show work) = 2 pts 33.68 g – 33.40 g = 0.28 g Melting point of cinnamic acid dibromide: 5 pts 3. 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 the cinnamic acid dibromide you used and the other from 25% KOH (w/v) , 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. LIMITING REAGENT Dimensional Analysis Maximum amount of product possible from cinnamic acid dibromide 2.00 g cinnamic acid dibromide 1 mol cinnamic acid dibromide 1 mol product 150.17 g 1 211.05 g 1 mol cinnamic acid dibromide 1 mol product = 1.42 g Maximum amount of product possible from 25% KOH w/v (i.e., this solution was made by dissolving 25 grams KOH in enough methanol to make 100 mL of solution 1.00 g KOH 1 mol KOH 1 mol product 150.17 g 1 56.11 g 1 mol KOH 1 mol product = 2.67 g 4. Identity of the Limiting reagent (LR) based on the above two DA equations = Cinnamic acid dibromide 2 pts 5. Max mass of the product obtainable on the basis of LR = 1.42 g 2 pts %yield of the product obtained (show work): (0.28 g / 1.42 g) x 100% = 19.7 % 5 pts 6. Physical state of the product ( see video ) = Solid 2 pts 7. Color of the product ( see video ) = White and yellow 2 pts Characterization of the product: 1. Have two test tubes labelled A and B each containing 1 mL of DCM. 2. To test tube A, add about half of your product. 3. To test tube B, add about half about 50 mg of your starting material product.
4. Add 2-3 drops of 2% solution of bromine in DCM (provided in the main hood). Note the color. 8. Color of the solution in test tube A (containing the product) = N/A 2 pts 9. Color of the solution in test tube B (containing cinnamic acid dibromide) = N/A 2 pts Quiz guidelines Overall equation for the double dehydrobromination; Mechanism of double dehydrobromination across a double bond. Reaction of bromine with a triple bond. Did the experiment go as planned? 10 pts If not, what were the problems and how did you solve them? Overall, the experiment went as planned, except in the beginning, we had to add extra cinnamic acid dibromide from the hood as not enough had been collected from the previous lab. 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 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 with proper stereochemistry- indicate if the product is racemic, or optically active). 4 pts
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2. What product is formed when your reaction product (3-phenylpropynoic acid) is brominated with: a. One equivalent of 2% bromine in DCM solvent? Write down the relevant chemical equation (write only structural formulas and its IUPAC name ). 4 pts b. Two equivalents of 2% bromine in DCM solvent? Write down the relevant chemical equation (write only structural formulas and its IUPAC name ). 4 pts 3. What is the first - the very first and rapid reaction - when you added KOH to the solution of cinnamic acid dibromide at room temp in methanol? Write the relevant chemical equation (write only structural formulas ). 4 pts
4. What compound could the “yellow colored (nice smelling!) by-product on the crude crystals be due to after you evaporated most of the methanol during the product formation? Write its structural formula of that by-product . 2 pts Hyacinth 5. What is the % yield of the product diphenylacetylene in the following reaction when 2.0 g of the reactant 1,2-dibromodiphenylethane were evaporated with 5.0 mL of 25% KOH (w/v) solution to obtain 0.80 g of product? ( NOTE: Make sure you write two complete DA equations to determine the Limiting Reagent ) 12 pts 2.0 g dibromodiphenylethan e 1 mol dibromodiphenylethan e 1 mol diphenylacetylene 178.24 g 1 340.05 g 1 mol dibromodiphenylethan e 1 mol diphenylacetylen e = 1.0 g 5.0 mL KOH 2.04 g 1 mol KOH 1 mol diphenylacetylene 178.24 g 1 1 mL 56.106 g 1 mol KOH 1 mol diphenylacetylene = 32.4 g (0.80 g / 1.0 g) x 100% = 80% ============================================================================== TL IMAGE: Optional for 10% extra credit: +7