A shelf containing several chemicals (Salicylic acid, 4-(4-Hydroxyphenyl)butan-2

Question

A shelf containing several chemicals (Salicylic acid, 4-(4-Hydroxyphenyl)butan-2-one {a.k.a. Raspberry Ketone} and 4-methylaniline) fell and the vials shattered. The white powders are hopelessly mixed in a dustpan. You are promised a big fat raise if you can construct a flowchart that a less qualified chemist will follow to separate the three compounds. You must label what extraction steps are to be taken at each point of the separation and how to isolate each compound again as a solid. To ensure that you get the raise, you will also need to suggest a simple chemical test (not spectral) to test the functional groups present in each compound.

Explanation / Answer

First dissolve mixture in ether (organic layer) then extract with sat NaHCO3 so that salicylic acid will conver sodium salt in aqueous layer by neutralising with diluted HCl we can get pure salicylic acid

then organic layer was extracted with diluted HCl amine will convert as hydrochloride salt will come in

aqueous layer by neutralising with base NaOH we can get pure 4--methylaniline

finally organic layer will be pure 4-(4-Hydroxyphenyl)butan-2-one. so by evaporating ether we can get

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