Answer :

It is possible to separate the aspirin and caffeine in the filtrate by extracting either with an acid, which will remove the caffeine as a salt that is soluble in water or with a base, which will remove the aspirin as a salt that is soluble in water.

Since acetylsalicylic acid, the active ingredient in aspirin, is an organic acid, it is soluble in organic solvents but will react with a basic reagent to form the conjugate base of the acid. Examples of such reagents are sodium hydroxide or sodium bicarbonate.

While somewhat insoluble in water, aspirin is soluble in dichloromethane. In order to create the salt sodium acetylsalicylate, which is soluble in water but insoluble in dichloromethane, sodium hydroxide must be used to remove the acidic hydrogen from aspirin.

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