Reissert - Amy Linkous CHEM 2556 CRN 91653 Reissert...

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Unformatted text preview: Amy Linkous 12/9/09 CHEM 2556: CRN: 91653 Reissert Objective : To create three different products from the Reissert compound using 1) a base with no electrophile present; 2) alkylation; and 3) reaction with an aldehyde and identify said products. Reaction Scheme: Procedure : Reaction 1: Base 0.78 g of the Reissert compound was dissolved in 15 mL dry DMF with stirring. 0.14 g NaH was added and the solution was stirred for at least 30 minutes, noting the color of the solution before, during and after addition of the NaH. The reaction mixture was poured into a flask with 75 mL of ice and water and stirred, after which the solid precipitate was collected by vacuum filtration. If no precipitate formed, the mixture was extracted three times with dichloromethane, washed three times with water, dried over sodium sulfate and placed on the rotary evaporator to remove the solvent. The product was recrystallized from hexane and a melting point measurement, NMR spectrum and MS spectrum were obtained. Reaction 2: Alkylation 0.78 g of the Reissert compound was dissolved in 15 mL dry DMF with stirring. After it was fully dissolved, 0.4 mL 2-methyl-1bromopropane (isobutyl bromide) and 0.14 g NaH was added and the solution was stirred for at least 30 minutes, noting the color of the solution before, during and after addition of the NaH. The reaction mixture was poured into a flask with 75 mL during and after addition of the NaH....
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This note was uploaded on 02/22/2010 for the course CHEM 2556 at Virginia Tech.

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Reissert - Amy Linkous CHEM 2556 CRN 91653 Reissert...

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