Benzoin is acidic, 4-aminoacetophenone is basic and 1,4-dibromobenzene is neutral.
Dissolve mixture of these three in dichloromethane. To this add aqueous NaOH, benzoin form sodium salt and go in aqueous solution. Separate the aqueous layer and add HCl, benzoin get precipitate out.
To dichloromethane layer left add HCl, 4-aminoacetophenone form salt and go in aqueous layer. Separate both layers and add NaOH to aqueous layer, 4-aminoacetophenone precipitate out.
Evaporate the dichloromethane and we get 1,4-dibromobenzene.
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Separation scheme for 4-aminoacetophenone- 50%
1,2,3,4- tetrachlorobenzene- 40%
1,4 dibromobenzene & experiment
4-aminoacetophenone-50% 1,2,3,4- tetrachlorobenzene-40% 1,4 dibromobenzene
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