[big]

Aniline, C₆H₅NH₂, does not dissolve well in water. which reagent could be used to increase its aqueous solubility?

A) 1 M HCl
B) 1 M NaOH
C) diethyl ether
D) toluene

i realize it probably won't be diethyl ether because diethyl ether's non polar. And is it not NaOH because NaOH is a base and aniline is more like a base than an acid? So how do you know whether it will be HCl, which would act like an acid and react with the aniline, or toluene, which is similar to aniline in that both have a benzene ring?

Also, as an additional note, why isn't aniline soluble in water? Doesn't aniline have the NH2, which can hydrogen bond?

[opti384]

It will probably be HCl. The reason why it can't be toluene is that the question focuses on "increasing its aqueous solubility." Also, the reason why aniline does not dissolve well is because of its benzene ring.