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Lab procedure for separating compounds

I will be given 3 compounds in a mixture, which must be separated and varified by melt point. I will have 1 of each of the following sets (either Benzoic or Salicylic Acid),(either 2-Naphthol or Phenol)(either Biphenyl or Naphthalene). I have been told I can do this using a seperatory funnel for an extraction. The resulting separated componets must be pure solids to be melt-point tested.The following reagents are availible to me: 5%Aqueous NaOH 5%Aqueous HCl, 5%Aqueous NaHCO3, Sat.Aqueous NaCl brine, NaHCO3, NaOH,concentrated HCL(12M), Ethyl Acetate, Acetone, ethanol, Hexanes, Silica TLC Plates, Reference samples of compounds, Ice, Anhydrous CaCl2, Anhydrous MgSO4. I can also use a rotovap, mel-temp.

Solution Preview

For this seperation you must try and learn a little about the acid base chemistry of these organic molecules. Also, you must know a little about the theory of the solubility of compounds. The acid base chemistry we can deal with in a bit, but the overall theory of solubility is quite simple, "like dissolves like". This means that if you have two phases, the state of the dissolved compound will tell you which phase it is in. Organic solvents are of course made up of organic molecules, and all the bonding in the organic solvent molecules are covalent. That leads to a phase that has no dipole moments, nor charges. Aqueous phase, is of course based on water, is quite the opposite. Water has an overall dipole moment, so water will dissolve anything that can either hold a charge, or that has a dipole ...

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