A stereotypic Wittig Reaction Experiment

A stereotypic Wittig Reaction Experiment - Name Joseph...

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Name: Joseph Youkhanna CHM2230 : Section 11 Title: A Stereospecific Wittig Reaction Date: January 31 st , 2007 Purpose: The purpose of this experiment is to convert an aldehyde to an alkene using a phosphorus ylide. After isolating the product, and recrystallization, we get a moderate high yield of trans isomer exclusively. The geometry of the double bond will be saturated by ¹H NMR. Table of Reagents: Reagent Name Molecular Weight Mol used 0.5g of 9-anthraldehyde 207.26 g/mol 2.4 x 10^-3 0.95g of benzyltriphenylphosphonium 388.89 g/mol 2.4 x 10^-3 12.50 mL of methylene chloride 84.73 g/mol 2.0 x 10^-1 1.25 mL of 50% NaOH 40 g/mol 6.7 x 10^-2 5 mL of H2O 18.02 g/mol 2.8 x 10^-1 5 mL 2-propanol 60.09 g/mol 6.5 x 10^-2 Anhydrous sodium sulfate 142.05 g/mol NA (not measured) Magnetic stir bar Product Data: Trans-9-(2-phenylethenyl) anthracene Melting Point: 131-132ºC Molecular Weight: 280.41 g/mol Balanced Equation(s):
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Mechanisms (Reaction Scheme): Procedure: -As per lab manual (no changes) Results and Observations: →I placed a magnetic stir bar in a flask →I added 0.5g of 9-anthraldehyde, 0.95g of benzyltriphenylphosphonium, and 5 mL of methylene chloride into the flask →I placed the flask on the stir plate, and stirred the mixture vigorously (turn the stir plate on high) →Then I slowly added 2-3 drops of NaOH every 5-10 minutes (for a 30 minute period) →The mixture turned a dark-yellowish color →I added 5 mL of H20, and 5 mL of methylene chloride to the mixture →I proceeded to set up the separatory funnel to remove the organic layer →I shook up the separatory funnel before each titration of the organic layer into a clean flask →After my first titration, the mixture color turned from dark yellow to lime green →The weight of my rounded bottom flask was 38.186g
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