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Lab 8 - M Farrell Matt Farrell Lab 8 The Wittig Reaction...

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M. Farrell Matt Farrell November 10, 2006 Lab 8: The Wittig Reaction with Chemiluminescence Purpose: The purpose of this lab is to perform and become proficient in the Wittig reaction. This will be done by thin layer chromatography and a filtration vacuum. After using the Wittig reaction and forming a product, with this product chemiluminescence is created with the addition of other chemicals. Background: The Wittig reaction is either an aldehyde or a ketone that is treated with a phosphorous ylide (phosphorane) to produce an olefin. The phosphorane is typically treated with a phosphonium salt and a base. The key step in the Wittig reaction is the formation of the oxaphosphetane, which is known as the cyclic intermediate in the reaction. Wittig reactions give primarily Z olefins, but sometimes E olefins can be produced. Phosphine Phosphonium salt Page 1 of 6
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M. Farrell Mechanism for the Wittig Reaction: Mechanism for the Chemiluminescence: Page 2 of 6
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M. Farrell Procedure: Part A: 1. In a 25 mL Erlenmeyer flask place a small stir bar, 0.5 grams (0.00242 moles) of 9-anthraldehyde, 0.87 grams (0.00223 moles) of benzyltriphenlyphosphonium chloride. 2. Observation- When adding 0.5 grams of anthraldehyde, 0.87 grams of benzyltriphenylphosphonium chloride, and 6 mL of DMF the solution is a powder, mustard yellow color.
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