Orgo 1 Report 9.docx - Experiment A2b Bromination...

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Experiment A2 b : Bromination of (E)-Stilbene: meso-Stilbene Dibromide Objective: The purpose of this lab is to determine and review the stereospecificity of the addition of molecular bromine to an alkene. We will also synthesize the second intermediate in the b series of sequential reactions by carrying out the bromination of (E)-stilbene to obtain meso-stilbene dibromide. We will also use liquid extractions, pipets, crystallization, and Hirsch funnels. Experimental Procedure: The procedure was followed as described in Mayo, pages 483-487, with the modifications listed in the posted Blackboard document. Additional modifications to the procedure included the following: 1. The reaction was run on a 1/6 times scale 2. A 10 mL round-bottomed flask was used 3. Water-jacketed reflux condenser was used 4. Use cold methanol instead of cold water 5. Don’t wash product in acetone; but rather let product dry in Hirsch funnel 6. Chemical tests will be omitted Reaction Scheme: Data and Results:
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Compound Molecular Formula Molecular Weight (g/mol) Amount mmol MP ( o C) BP ( o C) Density (g/mL) (E)-Stilbene C 14 H 12 180.25 102 mg 0.566 122-124 Glacial Acetic Acid C 2 H 4 O 2 60.0 2.00 mL 118 1.049 Pyridinium Bromide Perbromide C 5 H 6 NBr 3 319.83 203 mg 0.635 205 Meso- Stilbene Dibromide C 14 H 12 Br 340.05 156 mg Yield 192 mg TY 0.565 243- 245 Observations: My initial solution turned yellow
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