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Suppose you are performing an extraction procedure with a carboxylic acid, like a benzoic or toluic acid. Which layer should contain the carboxylic acid in a two-layer mixture of water and an organic solvent, like diethyl ether?

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Answer:

diethyl ether

Explanation:

Benzoic acid and toluic acid are more soluble in organic solvents than in water. Even though many carboxylic acids with a short alkyl chain are soluble in water due to hydrogen bonding, aromatic carboxylic acids are only slightly soluble in water.

However, when converted to benzoates, these species are now more soluble in water than in organic solvents.