Experiment 3: Separation and Identification of Organic UnknownsIn this experiment a mixture of an acidic, basic, and neutral compound was separated using extraction techniques. By dissolving the mixture in various aqueous and organic solvents, separating the solvents based on their densities, and then cooling each solvent separately, we end up with three different precipitates. These precipitates were then identified based on which solvent they dissolved in, the melting point range of each precipitate, and their corresponding IR spectrum. Our job was to identify the compounds in unknown mixture #5.After adding acid to the basic aqueous solution and cooling it, we were left with a white, "fluffy" precipitate. Because it dissolved in the basic aqueous solution, we were able to conclude that this is our acidic compound. Based on the same principle, our basic compound was collected from the acidic aqueous solution after we added in base and cooled the solution. This basic precipitate was a chalky, yellow powder. Finally, we obtained a yellow precipitate with a crystal-like consistency as our neutral compound. This time, we separated it from the solvent by heating the organic solution until the solvent evaporated (rather than cooling it and using vacuum filtration).We recovered 227mg of our acidic compound, 247mg of our basic compound, and177mg of our neutral compound from our original 750mg of mixture. Assuming that we had an even amount of each compound in our unknown mixture, we had a 90.8% recovery, a 98.8% recovery, and a 70.8% recovery for our compounds, respectively. The lower percent recovery for our neutral compound is most likely due to the organic solution going through more processes (meaning more opportunities to lose product) and,because the organic solution was always the upper layer in our separatory funnel, some ofthe neutral compound may have ended up in the aqueous solutions.We determined the melting point range for our acidic compound to be 146-149°C.For our basic compound, we determined the melting point range to be 98-101°C. Lastly, we got a melting point range of 78-80°C for our neutral compound. With our experimental melting point ranges, the melting point ranges of possible compounds, and the IR spectra of each compound, we were able to determine the identity of each compound. We recognized our acidic compound to be 3-chlorobenzoic acid, our basic compound to be 3-nitroaniline, and our neutral compound to be 9-fluorenone.The IR spectrum for our acidic compound did not produce many peaks which did not give us any subtle differences in which to differentiate between substances. Instead, we used the IR spectrum to determine that the product was significantly impure, thereforewe expect the melting point to vary by more than just one degree. For the basic and neutral compounds, we were able to produce much more helpful IR spectrums. The fact that our experimental melting point ranges were a reasonable range from only one possible compound aided in identifying the compounds.Despite our IR spectrum for our acidic compound being of little help, this lab was rather successful because our melting point ranges were so helpful. In any case, possible sources of error may include: having IR spectrums heavily influenced by water vapor or carbon dioxide, the inevitable impurity of the final compounds, or having trace amounts of some of the other 2 compounds present in the final precipitate.Compound: 3-Chlorobenzoic acid 9-Fluorenone 3-NitroanilineExperimental M.P.R. 146-149°C 78-80°C 98-101°CLiterature M.P.R. 153-157°C 80-83°C