[InvertedMountain]

Yo

So Phenol will react with sodium hydroxide to produce sodium phenoxide. Simple. Benzoic acid will react with sodium hydroxide to produce sodium benzoate. Simple. However, when salicylic acid reacts with sodium hydroxide, to produce sodium salicylate, I'm confused. Surely, both functional groups (the carboxylic acid and the phenol group) react, producing a salt with two sodium ions in it; to me this seems obvious. But I checked online to make sure and on its wikipedia page, the phenol group remains unreacted. Is this correct? And if so, why?

Thanks a bunch

[thetada]

Do you think both functional groups can be deprotonated as easily?

[InvertedMountain]

Do you think both functional groups can be deprotonated as easily?

I figure that whilst the COOH group will deprotonate more easily than the phenol group, in a sufficiently alkaline environment what's to stop them both deprotonating?

[thetada]

It probably could to be honest, so my guess would be that the base should not be added too liberally. I haven't personally considered this before but i imagine that if sufficient base were added, your prediction that both groups react would be borne out.

[InvertedMountain]

Thanks man, I get where you're coming from, that's cleared up the issue for me (or as much as I'm going to need till uni). Sorta came up in an a level question booklet, there was no mark scheme and my teacher is away so i thought I'd give a shot asking online. Much obliged

[thetada]

No worries, good luck with the exams