Question: The solvent diethyl ether can be mixed with water but only by shaking the two liquids together. After the shaking is stopped, the liquids separate

The solvent diethyl ether can be mixed with water but only by shaking the two liquids together. After the shaking is stopped, the liquids separate into two layers, much like oil and vinegar. The free-base form of the alkaloid caffeine is readily soluble in diethyl ether but not in water. Suggest what might happen to the caffeine of a caffeinated beverage if the beverage was first made alkaline with sodium hydroxide and then shaken with some diethyl ether.

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