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orgolab2 - The solution was heated for approximately 30...

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Flora Vo 10 February 2008 Kimberly Stewart Experiment V: A Wittig Reaction – Preparation of a para -methoxycinnamic Acid The 10 mL Erlenmeyer flask with a stirring bar and two test tubes were heated in a drying oven for 10 minutes. Approximately 2 mL of sodium methoxide was added to the Erlenmeyer flask and the solution was stirred and stopped with a septum. The triethylphosphonacetate was massed, at 0.580 g, in the first test tube. The methoxide solution was slowly added dropwise, and the mixture was stirred for 5 minutes at room temperature. Then the flask was cooled in an ice bath and stirred simultaneously. The p-anisaldehyde was massed, at 0.349 g, in the second test tube. This was added dropwise in the ylide solution. The solution was allowed to warm to room temperature and stirred for 15 min. Approximately 4 mL of 5% sodium hydroxide was added to the reaction solution using the Thermowell heater.
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Unformatted text preview: The solution was heated for approximately 30 minutes, and additional NaOH was added because the entire solution crystallized within the first 5 minutes. When solution volume had reached 4 mL, the solution was then cooled to room temperature and transferred to an Erlenmeyer flask. Water was added to dissolve the crystals, but the abundance of crystals had required its filtration from the solution. The acid, 10% H2SO4, was added drop wise, but the final pH was too high, at 2. The crude product was filter and recrystallized from ethanol-water. The melting point of the alcohol and the percent yield was determined. Write-up Questions 1. asdf 2. Sodium methoxide was stored under nitrogen in the buret to avoid water exposure. NaOCH 3 is very sensitive to water, and exposure will inhibit its function as a base catalyst. Water and NaOCH 3 also react to make methanol and NaOH. 3....
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