Amber Patel Organic Chemistry Lab Section 004 1/29/2014 Crystallization Purpose: To purify an impure crystalline solid by performing

crystallization Reagents: a) Test compounds: Resorcinol, Anthracene, Benzoic acid, 4-Amino-1naphalenesulfonic acid, and sodium salt. b) Unknown melting point (Unknown No: - 11) Compound Benzophenone Maleic anhydride 4-Nitrotoluene Naphthalene Acetanilide Benzoic acid Urea Salicyclic acid Sulfanilamide Succinic acid 3,5-Dinitrobenzoic acid p-Terphenyl Melting Point 49-51 52-54 54-56 80-82 113.5-114 121.5-122 132.5-133 158.5-159 165-166 184.5-185 205-211 210-211

Procedure: 1) Solubility test Take the solid to be tested and transfer 10mg of solid into a reaction tube and add about 0.25mL of solvent with the help of a pipette. Stir the reaction tube with help of a rod or swirl. If readily soluble at 22C then add a few drops of water and see if it precipitates. If solid precipitates heat the mixture to produce a saturated solution and let it stand to note the characteristics of crystal formed. If the

substance failed to dissolve at 22C heat the tube and see if a solution occurs. If it readily dissolves it is soluble in hot solvent if it does not dissolve add further drops of solvent and check if it dissolves. If a solute dissolves cool the tube, reheat, and cool again to note the type of crystals that appear. Use ethanol, methanol, toluene and hexanes as solvents. Use Resorcinol, Anthracene, Benzoic acid and sodium salt as solutes. 2) Decolorizing a solution with decolorizing charcoal To a reaction tube add 1mL of methylene blue dye that has a concentration of 10mg per 100mL of water. To the same test tube add 10 to 12 pieces of decolorizing charcoal and observe for 1-2 minutes. Heat the test tube to boiling and then observe color from time to time. If color is removed then you see a clean solution on top of charcoal if not removed add more charcoal pellets to the solution. 3) Recrystallization of Benzoic acid from water and a solvent pair Dissolve 50mg of Benzoic acid in minimum volume of methanol and add water to the solution slowly. Continue to drop water until cloudiness appears in the hot solution. Stop heating the solution and allow it to cool at 22C for a while and then transfer to ice bucket. Collect the crystals and compare the crystals with those in solvents such as methanol and ethanol. 4) Purification of an unknown Two grams of unknown 11 was added to an Erlenmeyer flask. To the same Erlenmeyer flask hexane was added as a solvent. The solution was then heated to higher temperatures and the unknown was dissolved in the solvent. Charcoal was added to the same solution to remove the impurities present. The Erlenmeyer flask was heated and left standing until the solution was decolorized and a clear solution was present. The solution was then filtered to remove the charcoal and the solution was then heated to evaporate excess hexane. When crystals appeared the flask was removed and allowed to cool. The solution was then vacuum filtered with help of a Buchner funnel to dry the crystals that appeared. Collect the crystals and weigh them to check yield. Then check the melting point of the crystals and compare to unknown chart to find the compound. Clean Up: All liquid waste should be placed in the waste in the organic solvent waste container. The filter paper and charcoal should be disposed in nonhazardous waste container. All solid waste should be disposed in organic solids waste container.

Data: Solubility Tests Compound Ethanol Dissolved at room and high temperature No Methanol Dissolved at room and high temperature. No Toluene Dissolved at high temperature Dissolved at high temperature Dissolved at high temperature Hexane

Resorcinol Anthracene

No No

Benzoic Acid

Dissolved at high temperature partially

Dissolved at high temperature partially Dissolved at high temperature

No

4 amino 1 Dissolved at nepthalenesulfonic high temperature

No

No

Unknown # 11 Melting Point 112.8C-113.7C Possible compound Acetanilide Percent Yield .42/2 = 21%

Observation and Conclusion In the first part of the experiment the compounds were tested with different solvents to see which solvents were good and which were bad. In the first part we were trying to check whether like dissolves like. In the first part of the experiment we had resorcinol that dissolved in ethanol and methanol at room temperature. By doing that we realized that ethanol and methanol were bad solvents for dissolving resorcinol as using both would make it hard to easily remove resorcinol by cooling. We also noticed that toluene was a good solvent for resorcinol which means it was a good solvent. The dissolving was counterintuitive as toluene is non-polar while resorcinol is slightly polar suggesting like does not always dissolve like. There was a similar case with benzoic acid, which is also polar and dissolved in toluene. The dissolving of anthracene and toluene supported the hypothesis like dissolves like. The first part of the experiment helped because it showed that like dissolves like is not always true and a good solvent is one that dissolves solute at

high temperatures so that it can be easily removed by recrystallization at lower temperature. In the second part of the experiment after adding charcoal to test tube a dark blue color was noticed in the liquid. The solution was then heated with time the dark blue color slowly disappeared as the charcoal was attracting the impurities in the methylene blue dye. After the solution had settled a clean layer was present at the top and a layer of charcoal was present at the bottom. In the third part of the experiment when benzoic acid was put into water it was seen that the crystals that were formed were long needle like but when the benzoic acid was dissolved in methanol the crystals shape had changed into small crystals. The change in shape meant that methanol had caused a disruption in the shape of the crystals. It was also seen that methanol was a bad solvent for crystallization of Benzoic acid as it formed a cloudy mixture than clear and thus reacted with the solute. For the last part of the experiment all the three parts were redone with an unknown. The unknown dissolved in hexane as suggested by the instructor. The solution though did not look clear after solute dissolved in hexane because there were yellow and brown impurities in the solution. After charcoal was added and the procedure was decolorizing was followed a clear solution was obtained at the top and was filtered. The solution was then heated to saturate and remove excess hexanes. When crystals appeared it was vacuum dried and weighed to find a twenty percent yield of crystals. The crystals were long flat needle like structure. The melting point of the crystals was then found to be 112.8C-113.7C, which compared with Acetanilide. I then looked up the shape of Acetanilide and saw it was polar, while hexanes were non-polar this again suggested that two different polarity substances could dissolve in one another at high temperatures. In the fourth part the low yield could be due to many errors in the experiment. Some of them include recrystallization of some crystals on charcoal when left stagnant, overheating the clear solution when saturating it, and loss of crystals while transferring from Buchner funnel to watch glass.