Why are a few drops of trimethylamine added to the reaction (step 6) in this lab
ID: 1051525 • Letter: W
Question
Why are a few drops of trimethylamine added to the reaction (step 6) in this lab procedure?
Obtain a 25 mL round bottom flask and place 5.0 g of methyl-alpha-D-glucopyranoside into the flask. Clamp the flask in the fume hood above a magnetic stirrer and place a magnetic stir bar into the flask Dissolve the solid in 10 mL of tetrahydrofuran and add 7.0 mL of benzaldehyde dimethyl acetal and 0.10 g of 10-camphorsulfonic acid. Equip the flask with a reflux condenser and heat at reflux for 30 mins. After 30 minutes, take a TLC (3:7 hexanes: ethyl acetate) to monitor the progress of your reaction. Visualize your TLC using a methanolic solution of sulphuric acid (10& H_2SO_4 in methanol). Using tweezers, dip the TLC plate into the solution, allow it to dry, and heat the plate. Due to the equilibrium of this reaction, there will always be a small amount (5%) of starting material remaining in solution. If the reaction is complete, continue with the experimental procedure. If not, allow the reaction to reflux for another 30 minutes. Cool the reaction to room temperature and add a few drops of trimethylamine. Transfer the contents of the flask into a sepratory funnel and dilute with 50 mL of ethyl acetate Wash the organic layer with 3 times 15 mL distilled waterExplanation / Answer
The addition of triethyl amine is to get rid off the acid that is present in the reaction mixture. The addition would form the ammonium salt that is soluble in water and therefore would come into the organic layer. The acid could be the result of hydrolysis of benzaldehyde to benzoic acid and camphorsulfonic acid
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