if you are careful. aspirin is strongly acidic and tylenol is weakly acidic. if you split the difference between the two, you can deprotonate aspirin without deprotonating tylenol. more specifically, if you use NaOH to raise the pH of a solution to approximately 7 or 8, you could effectively deprotonate all of the aspirin, making it water soluble, while leaving the tylenol protonated and not very water soluble. if the pH goes above 10, you will deprotonate the tylenol and make them both water soluble. HOPE THIS HELPED :)
