Question

ORGANIC LAB: Separating a Mixture of two Unknowns, different acidity
I have a mixture of two unknowns, both solids, in my Organic Chemistry lab. I have to separate them, then find out what each compound is. The only thing I really have that I can go by is that they have different acidities, each is either an acid (weak or strong), a base, or a neutral, and one can't be what the other is.

I found a separation technique that starts by adding a weak base (NaHCO3) to the two unknowns (dissolved in an organic solvent) as the first step to extract a strong acid, if it's present. But when I added NaHCO3 to my separatory funnel I got a white ppt and didn't know what that meant and if I can use that? That must mean I have an acid as one of my unknowns... I can't separate it in the sep funnel, but maybe I can vacuum filter it? Can I use that ppt? Another thing I noticed was that when I was doing the solubility tests, both my unknowns dissolved in NaOH, but they formed two layers. There was nothing else in that test tube- only my unknowns and 6M NaOH. One is an acid? How do I extract it? I am not worried about their identification later, but have problems separating them.

Here are my solubilities:
In H2O: both are soluble
In sodium bicarbonate: both are soluble
In 6M NaOH: It took a little while (at first it looked like about half of the mixture of unknowns was soluble), but both dissolved and there were two layers that formed. A transparent/yellow layer on bottom and brown layer on top.
In 10M HCl: At first about half dissolved, but after heating all dissolved

Answer 1

First point of separation analysis is solubility in water if it is soluble in water then we don't do the solubility in basic and acidic water. Because it will be soluble in acidic as well as basic water.

I think you have not done properly solubility technique.

You have to check the solubility of the unknown mixture in ether or organic solvent.