[webguy54]

Q: Are the following compounds more soluble in an aqueous solution of 0.1M NaOH or 0.1M HCL?

Pyridine ion (pKa ~ 5)
B-Naphthol (pKa ~ 10)
N-Acetylyrosine methyl ester (pKa ~ 10)

I'm confused on how the acid or base effects the dissociable proton of each compound.  Is it correct to go by the rule of "like dissolves like?"

[Yggdrasil]

Draw out the protonated and deprotonated forms of each compound.  Which form will be more soluble in water?