Acid-base extractions?

Question

when you have two compounds in which the differences in pKa could be used to extract them with different bases, does the stronger acid get deprotonated by the weaker or stronger base?

For example if i have heptanoic acid and 1-heptanol and i add NaOH, wouldnt both of them get deprotonated?

Answer 1

Heptanoic acid is a carboxylic acid and 1-Heptanol is and alcohol (not very acidic at all).

The Heptanoic acid will react with the aqueous Sodium hydroxide, but the 1-Heptanol will not.  Aqueous Sodium hydrogen carbonate would be a better choice.

Since the solubility of the 1-Heptanol in water is small (about 0.1 gram per 100 mL of water at 20 °C) it should be easily separated.