The strongly polar, hydrogen-bonding properties of water make it an excellent solvent for ionic (charged) species. By contrast, nonionized, nonpolar organic molecules, such as benzene, are relatively insoluble in water. In principle, the aqueous solubility of any organic acid or base can be increased by converting the molecules to charged species. For example, the solubility of benzoic acid in water is low. The addition of sodium bicarbonate to a mixture of water and benzoic acid raises the pH and deprotonates the benzoic acid to form benzoate ion, which is quite soluble in water?

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Pyridinium  ion is more soluble in 0.1 M HCL (aqueous solution) and this is because the Pyridine ion reacts with NaOH  and after the reaction it comes out neutral.

N-acetyltyrosine methyl ester is more soluble in 0.1 M HCL while

B-napthol is more soluble in 0.1 M NaOH because it forms phenoxide ion

Explanation:

Pyridine ion is more soluble in 0.1 M HCL (aqueous solution) and this is because the Pyridine ion reacts with NaOH  and after the reaction it comes out neutral.

N-acetyltyrosine methyl ester is more soluble in 0.1 M HCL while

B-napthol is more soluble in 0.1 M NaOH because it forms phenoxide ion

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