hprox

I have a mixture of: --benzoic acid [C6H5COOH] --phenol [C6H5OH] --hydroquinone [C6H4(OH)2] --dimethylether [H3COCH3] I understand that I can add sodium bicarbonate to get two layers, the aqueous layer containing C6H5COONa. To the remaining ether layer, I can add NaOH to get C6H5ONa and water in the aqueous layer. The question I'm working on now asks what would happen if I added the NaOH before I added the NaHCO3. I understand that if I added the NaOH first, it would react with both the phenol and the benzoic acid (right?). However, would the sodium bicarbonate react with the hydroquinone? I don't think it will because hydroquinone is too weak of an acid. Is this correct? Any input would be appreciated. Thank you.