If mistakenly extracted the ether sol't 1st w/ NaOH sol't & w/ NaHCO3, y upon acid. of the NaHCO3 no crystals?

Question

If you mistakenly extracted the ether solution 1st w/ NaOH and then w/ NaHCO3. Why are no crystals produced upon acidification of the NaHCO3 layer? What product will be obtained if H2O was evaporated from the NaOh layer prior to acidifying the layer?

Answer 1

The extraction of ether with a basic solution is usually to remove acidic compounds. Any organic acid that was dissolved in the ether would be extracted into the NaOH solution and would not be in the ether to be extracted by the NaHCO3 solution which was used next.

If the water was evaporated from the NaOH solution you would get the sodium salt of the organic acid, contaminated with excess NaOH.