An etheral solution contains benzoic acid, 9-fluorenone, abd ethyl 4-aminobenzoate. Why would benzoic acid and 9-fluorenone not be extracted from this etheral solution by aqueous HCl ?
Fluorenone is neutral and benzoic acid is acidic; neither is soluble in an acid solution as compared to ether.
Benzoic acid and 9-fluorenone would not be extracted from the etheral solution by aqueous HCl due to their different acid-base properties. To understand why, let's first take a look at their structures:
1. Benzoic acid (C6H5COOH): It is a carboxylic acid, meaning it contains a -COOH functional group. This functional group can readily donate a proton (H+) and acts as an acid.
2. 9-fluorenone (C13H8O): It is a ketone, characterized by the presence of a carbonyl group (C=O). Ketones, unlike carboxylic acids, do not have a hydrogen attached to the carbonyl carbon that can be easily ionized.
Now, let's consider the properties of the solvent and the acid used:
1. Etheral solution: Ether is a nonpolar solvent. It is primarily used for dissolving organic compounds that are nonpolar or weakly polar.
2. Aqueous HCl: Hydrochloric acid (HCl) is a strong acid that dissociates completely in water to produce H+ ions. Hence, it is important to consider the water component in this solution.
When benzoic acid is introduced into a solution of water, it will readily donate a proton to water, resulting in the formation of hydronium ions (H3O+), and the benzoate anion (C6H5COO-). Since HCl is also a strong acid, it offers a high concentration of H+ ions in the aqueous solution. The presence of a large number of H+ ions in the aqueous HCl solution can effectively protonate the benzoate anion, leading to the reformation of benzoic acid.
However, in the nonpolar etheral solution, there is a lack of water molecules required for the protonation process to occur. As a result, benzoic acid remains in its neutral form (C6H5COOH) and does not readily interact with the HCl present in the aqueous phase.
Similarly, 9-fluorenone, being a ketone, does not have an easily ionizable hydrogen atom. Consequently, it does not react with the H+ ions provided by the aqueous HCl solution.
Therefore, benzoic acid and 9-fluorenone would not be extracted from the etheral solution by aqueous HCl due to the differences in their acid-base properties and the absence of water in the nonpolar etheral phase.