Question

A mixture of 3 substances that include, Anthracene, Aniline, and Toulic acid is supplied. You are asked to outline an experimental strategy for separating these three substances from the mixture. Assume all substances are soluble in ether. Explain your rationale.

Answer 1

One way to do this is separating these in separating funnel.

A mixture of these 3 are taken in ether solution. When sodium bicarbonate solution is added to these mixture and shaken well in separating funnel, two layers will be formed. One is aqueous layer which will contain the sodium salt of toluic acid and organic layer which will have the mixture of aniline and anthracene.

Collect the aqueous layer and add conc HCl. Toluic acid will be precipitated out.

Next dil HCl is added to the mixture of aniline and anthracene and shaken well in separating funnel. Thus aqueous layer will be separated out which will contain the ammonium salt of aniline. Thus when conc NaOH is added to this aqueous medium, aniline will be regenerated as gelatinous ppt.

Next ether will be having just the anthracene. Thus these three will be separated out.