[rory1984]

How would you separate a mixture of benzoic acid, phenol, and naphthalene? Benzoic acid (pKa = 4.2), phenol (pKa = 10) and naphthalene (pKa is too high for chemically active extraction to be practical) are soluble in organic solvents like methylene chloride or ether, but insoluble in water. A mixture of the three compounds can be separated by a chemically active extraction using two different bases, sodium hydroxide and sodium bicarbonate (NaHCO3). Prepare a flowchart. Write out a series of equations for the acid-base reactions between each of the acids and each of the bases so that you can determine the correct order of steps in your flowchart. Note that naphthalene is neither acidic nor basic enough to participate in a chemically active extraction. You will also need to consider the fact that when bicarbonate ion (HCO3−) accepts a proton, it becomes carbonic acid (H2CO3, pKa 6.4); carbonic acid decomposes immediately to carbon dioxide and water. Recall also that the pKa of water is 15.7.PLEASE HELP ME WITH THIS PROBLEM NEED A FLOW CART 


this is what I came up with:
Then, in a seperating funnel, add an (Aqueous) solution of sodium hydroxide. The Phenol, and benzoic acid, as acids, will react with the base to form phenolate and benzenoate ions, which will dissolve into the water layer. Collect this layer, and re-precipitate the organic molecules by adding concentrated Hydrochloric acid. The phenol and Benzoic acid can be seperated via their varying solubilities, (8.3g/100ml vs 0.34g/100ml. respectively) by heating the mixture in water to dissolve the phenol, and then filtering of the (practically) insoluble benzoic acid. The solution can then be acidified (with HCl) to return the phenol.

 Now add a solution of hydrochloric acid to the seperating funnel, which (as before) will react with the basic anniline dossilving it into the water. Collect the aqueous layer and re-precipitate the anniline with excess sodium hydroxide.finally boil off the remaining organic solvent to obtain the napthalene, which was left untouched by all the acids and bases

[Arkcon]

Try to make some attempt to begin to solve this problem yourself.  I don't know why bicarbonate is inserted in the middle of your paragraph, perhaps you should try to separate the different parts of your question for your own benefit, as well as ours.  You've mentioned twice that a flowchart is needed, and that was clear enough, you'll have to draw one out, along with possible acid-base reactions for each component.