separation schemes flow chart

Question

I'm trying to do a separation scheme that separates benzophenone, 3-methylaniline, and salicyclic acid but I have no clue what to use, please help

Answer 1

The separation of these compounds takes advantage of the solubility and acid/base properties of the noted compounds.  I can give you some ideas, but you need to confirm what solvents you have available in order to actually give specifics for your assignment.  First, benzophenone is an ketone which has minimal acid/base reactivity with the solvents we use in organic lab.  3-methylaniline is a base and could therefore be reacted with an acid produce an insoluble salt.  Salicylic acid on the other hand is an acid, and could be reacted with a base something like sodium hydroxide to form its salt.

 

Here's an outlined idea to get you started:

• Dissolve the mixture in ether
• Add sodium bicarbonate solution
• ether layer will have neutral compound and acidic compound
• aqueous layer (sodium bicarbonate) will have basic compound
• Separate the layer 
• To the ether layer that now only has neutral and acidic compounds, add sodium hydroxide
• ether layer will have neutral compound
• aqueous layer (sodium hydroxide) will have acidic compound
• Separate the layers

• ether layer will have neutral compound and acidic compound
• aqueous layer (sodium bicarbonate) will have basic compound
• Separate the layer