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A careless student, Will Bobble, misread the label on a bottle of 10 M sodium hydroxide and used it (rather than 1 M NaOH) to dissolve his vanillin. Then he stored the solution and left the lab early to catch a ride home. During the next lab period, he added NaBH4 and finished the experiment. Although his product was a white solid, it melted over a broad temperature range that was much lower than the melting point of vanillyl alcohol. His instructor suggested washing the product with dilute sodium bicarbonate; when he did so, about half of the product dissolved and the remainder melted at 115 degrees C. Explain what happened and write an equation for the reaction.

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