Final answer:
The solubility of deprotonated carboxylic acid derivatives in water is due to their ability to form hydrogen bonds with the solvent. The solubility in ethers is lower because ethers are less polar and do not provide as effective hydrogen bonding.
Step-by-step explanation:
Rationalizing Solubility in Different Solvents
The solubility of deprotonated carboxylic acid derivatives in different solvents can be explained by examining specific intermolecular interactions between the solute and the solvent. In the case of water, a highly polar solvent, the solubility is greatly influenced by the molecule's ability to form hydrogen bonds with the water molecules due to the polar C=O and O-H bonds present. These interactions include hydrogen bonding and dipole-dipole interactions alongside London dispersion forces. Carboxylic acids show great solubility in water due to these strong interactions.
Conversely, in the case of ether, which is a relatively nonpolar solvent, the solubility of deprotonated carboxylic acid derivatives is considerably lower. This is because ethers lack the hydroxyl group that contributes to hydrogen bonding, making their ability to dissolve polar substances like carboxylic acids less effective. Ethers have an oxygen atom, though, which allows them to engage in some hydrogen bonding with water, but generally, the solubility of compounds similar in structure to ethers, like alcohols, is reduced in less polar solvents.