Expt 3: Reduction of Vanillin with Sodium Borohydride to ...
first be deprotonated with the strong base sodium hydroxide in order for it to dissolve. Phenols (pKa = 10) are considerably more acidic than ordinary alcohols (pKa = 16-18) because the conjugate base (called a phenolate) is resonance stabilized. Since sodium hydroxide is the conjugate base of water (pK a = 15.7), the deprotonation of vanillin will
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