O-Vanillin Lab Report

The purpose of this experiment is to perform a two step reductive amination using o-vanillin with p-toluidine to synthesize an imine derivative. In this experiment, 0.386 g of o-vanillin and 0.276 g of p-toluidine were mixed into an Erlenmeyer flask. The o-vanillin turned from a green powder to orange layer as it mixed with p-toludine, which was originally a white solid. Ethanol was added as a solvent for this reaction. Sodium borohydride was added in slow portion as the reducing agent, dissolving the precipitate into a yellowish lime solution. Glacial acetic acid and acetic anhydride were added to the mixture while refluxing, which converted the lime colored solution into a clear mixture. The flask was cooled in an ice bath and the solution
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As seen in table 1, the theoretical yield was .712 g of C_17 H_19 NO_3. The % yield of this experiment was 7.51 % of C_17 H_19 NO_3. . This low yield can be explained from a poor recrystallization technique combined with potential contamination. Throughout the experiment, the mixture changed color from green, orange, to yellowish lime, and eventually clear. These color changes indicate a chemical change, which show that a reaction had occurred. In the first step when o-vanillin and p-toludine, imine was formed. The color change from green to orange suggests that imine appears as orange colored. In the second step, the addition of sodium borohydride reduced the imine into another derivative, which was yellowish lime color. The solution turned clear when acids and anhydrides was added, which indicated the precipitate were dissolved. However, after refluxing for a while, yellow precipitates begin to form near the top of the flask. It was assumed that the remaining starting material was concentrated from a decrease volume to reappeared in solution. Nevertheless, this may have been a sign of contamination that will negatively affect the entire reaction. This observation later resulted in a yellowish