Which compound remains in the ether layer when separating 2-chlorobenzoic acid and 4-Bromophenol?

When separating 2-chlorobenzoic acid and 4-bromophenol using extraction techniques, the properties of these compounds must be considered, particularly their acid-base behavior and solubility in different solvents, such as ether and water.

4-Bromophenol is a phenolic compound that can donate a proton because of the hydroxyl (-OH) group, making it slightly acidic. However, it is significantly less acidic than carboxylic acids like 2-chlorobenzoic acid. Consequently, when the mixture is treated with a base such as sodium bicarbonate, 2-chlorobenzoic acid will react to form its sodium salt, which is water-soluble, while 4-bromophenol remains unreacted and therefore stays in the ether layer.

In contrast, sodium bicarbonate itself does not remain in either organic or aqueous layers since it's a salt that dissolves in water, forming bicarbonate ions. Water will not remain in the ether layer, as it is a separate phase, and 2-chlorobenzoic acid, after reacting with sodium bicarbonate, will shift to the aqueous layer as well, leaving 4-bromophenol in the ether layer for easy extraction.

This understanding