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Could you use NaOH to separate acetylsalicylic acid (aspirin) and acetaminophen (Tylenol) by acidbase extraction? Briefly...

Could you use NaOH to separate acetylsalicylic acid (aspirin) and acetaminophen (Tylenol) by acidbase extraction? Briefly justify your answer

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Answer #1

NaOH cannot be used to separate acetylsalicylic acid (aspirin) and acetaminophen (Tylenol) by acid-base extraction. this is because acetylsalicylic acid and acetaminophen contain acidic hydrogens ( acetylsalicylic acid contains carboxylic acid hydrogen while acetaminophen contains phenolic hydrogen) which will be abstracted by the NaOH to give sodium salt of acetylsalicylic acid and acetaminophen. The sodium salt of both these compounds will be soluble in the aqueous layer and therefore cannot be separated.

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