Question
In the Reduction of Vanillin by Sodium Borohydride the reaction gets halt after 30 minutes by adding aqueous acid, causing an off-white solid to precipitate
In the Reduction of Vanillin by Sodium Borohydride the reaction gets halt after 30 minutes by adding aqueous acid, causing an off-white solid to precipitate out of solution. You collect the solid and confirm by TLC it contains a mixture of vanillin and vanillyl alcohol in a 30:70 ratio (approximately) based on the relative intensities of the two spots. You want to separate the mixture and recover the vanillyl alcohol. You consider recrystallizing the mixture from ethyl acetate as described in the Lab Manual, but you are worried because both compounds are solids and the mixture contains a significant quantity of vanillin. Do you think that recrystallizing the 30:70 mixture from ethyl acetate would produce a sample of vanillyl alcohol that is pure? Why or why not? Explain. Think about what are the relative solubilities of vanillin and vanillyl alcohol in ethyl acetate?
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