Organic Chemistry Lab I Report Experiment titles: Recrystallization of acetanilide One-base extraction Distillation of cyclohexane Outline of experiment: For

the recrystallization of acetanilide experiment, we begin the experiment with a sample of impure acetanilide crystals. These crystals are placed in a test tube and were allowed to dissolve in water over flameless heat. The test tube is then allowed to cool in a beaker, and several minutes later is allowed to cool in an ice-water bath. It is in the icewater bath that the crystals reformed after stirring the sample for a bit, which is suggested in the manual if crystals failed to form. Vacuum filtration is then applied, and a Buchner funnel was used. We then carefully transfer the acetanilide crystals to a watchglass to dry for one week. For the one-base extraction experiment, we begin with a mixture of naphthalene and benzoic acid. Diethyl ether is added to this mixture in order to separate the aqueous layer from the organic layer. We then extract the aqueous layer while leaving the organic layer in the tube and allow to dry out using crystals of sodium sulfate (Na2SO4). These crystals are then transferred to a watchglass to dry. The naphthalene is weighed by subtraction. We measure the aqueous layer by adding hydrochloric acid (HCl) to it until the litmus paper (originally blue) turn red and crystals began to form. They are cooled in an ice-bath in a filter by vacuum filtration. We then transfer the crystals to a watchglass to dry for a week. For the distillation of cyclohexane experiment, we beginn with a sample of impure cyclohexane. The sample is distilled with a microscale apparatus over flameless heat. As the sample begins to boil, vapor is produced and condensed into a separate part of the apparatus. We record the amount of cyclohexane that is distilled. We also recor the amount of cyclohexane that is distilled, and the temperature at which the cyclohexane distilled. Purpose of experiment: The purpose of the recrystallization experiement was to become familiar with the technique of purifying an impure sample, as well as to become familiar with vacuum filtration. The purpose of the one-base extraction was to observe the separation of organic and aqueous layers, while applying the proper technique of identifying and extracting the appropriate layer. The purpose of distillation is to separate compounds based on boiling point differences.

Data tables: Recrystallization Mass of acetanilide (g) .107 g Volume of H2O (mL) 3.5 mL Mass of acetanilide recovered (g) .10 g Melting point % recovery range (Celsius) 100-105 9.35%

Sample calculations:

One-base extraction Mass of benzoic Volume of acid/naphthalene diethyl ether mixture (g) added (mL) Volume of 2.5M NaOH added (mL) Mass of Naphalene remaining after evaporation of ether .100 g Melting point (Celsius)

.203 g Amount of HCl added to aqueous layer 1 drop

2 mL Mass of Benzoic acid crystals recovered (mg) .025 mg

0.5 mL Melting point of benzoic acid crystals (Celsius) 115-119

83-86

Sample calculations:

Distillation Volume of cyclohexane added (mL) 2.0 Temperature during distillation (Celsius) 80 Boiling point (Celsius) 80

Summary of procedures: Recrystallization: Add 100 mg of impure acetanilide and 1 mL of water to a small test tube, and then heat the test tube by adding about 2 cm of sand to a 50 mL beaker. Place the beaker with the sand on a hot plate. Then hold the test tube with a test tube holder while heating. Add water until the acetanilide dissolves completely (it should only take 4 mL of water to do this). It is important to remember to not add the water too slowly, because water is constantly lost while heating. The test tube should be about half full when the acetanilide has dissolved. Decolorizing carbon is not necessary, because If there are any insoluble impurities, simply decant the hot liquid into another test tube, leaving the insoluble impurities in the original test tube. Allow the test tube to cool until crystals begin to form in the solution. After crystals appear in the test tube, cool the test tube in an ice-water bath to induce further crystallization. Filter the crystals using vacuum filtration with the Hirsch funnel and a small filtering flask. Then place the crystals on a piece of filter paper and leave them on a watchglass to dry, at which time the melting point of the dry crystals can be taken. Extraction: Begin by adding 2 grams of naphthalene & benzoic acid mixture with 2 mL of diethyl ether and 0.5 mL of cold 2.5M NaOH. Add this to a vial, cap and shake slowly, and unscrew the cap of the vial to release pressure. Recap and shake again. Unscrew the cap once again to relieve pressure. At this point, two layers should form: an organic layer, and an aqueous layer. Extract the aqueous layer (at the bottom of the vial) and leave the organic layer in the vial. Add crystals of Na2SO4 , and then transfer the organic layer to a watchglass and place the watchglass over a steam cone to allow it to dry completely. Then determine the weight of the naphthalene by subtraction. Next, take the aqueous layer and neutralize by adding HCl, and add a piece of blue litmus paper in the tube. Continue adding HCl until the litmus paper turns red. Crystals should start to form in the solution. Cool the solution in an ice-bath and apply vacuum filtration. Place the crystals on the watchglass to dry until the following week. Distillation of cyclohexane: Begin by setting up the Hickman stillhead with a condenser and conical vial. Then transfer 2mL of impure cyclohexane (containing a non-volatile dye) to a 5mL conical vial. Place the distillation apparatus over flameless heating, and make sure the instructor checks the apparatus before heating the sample. Record the bath temperature. Stop heating the sample when approximately 3mL of the original solution remains. Using a pipet, transfer the distillate to a labeled screwcap vial. Observations: Recrystallization: We noticed that the acetanilide dissolved quickly. However, the crystallization took a bit longer and only began after placing the test tube in an ice-bath, and stirring the sample after allowing it to cool in the bath for a few minutes.] Extraction: Once we added the diethyl ether to the vial of the benzoic acid/naphthalene mixture to the vial and shook it, there was a very clear distinction between the aqueous (bottom) layer of benzoic acid and the organic (top) layer of naphthalene.

Distillation: I experienced a temporary difficulty with this experiment, as the distillate boils really quickly, more than I had anticipated, so I had to turn down the flameless heating in order to control the boiling, and was done quickly enough so that evaporation of the distillate did not occur. Results: For the recrystallization and extraction experiments, we were able to crystallize our samples as directed and the melting points were taken. The melting point range recorded for my sample of acetanilide was 100-105 degrees Celsius, with a 9.35% recovery. This low recovery could be due to an error on my part when measuring reagents. The melting point recorded for my sample of naphthalene was 83-86 degrees Celsius. The melting point recorded for my sample of benzoic acid was 115-119 degrees Celsius. For the distillation of cyclohexane experiment, the temperature of the boiling water, and the boiling point of the cyclohexane, was 80 degrees Celsius. I experienced some difficulty during the heating process, because I did not expect the sample to boil so violently and suddenly, and I was required to remove the apparatus from the heating source for a few moments to calm the boiling a bit. After I did this, the sample resumed boiling normally. Calculations: See data table for all sample calculations.

Post-Lab Questions
Pages 112-113 23. (a) If more solvent is used than necessary, there would not be as much solute recovered. (b) If the crystals were not rinsed out with cold water, impurities would be present in the mixture. (c) If the crystals were rinsed with a hot solvent, then some of the crystals may melt and the amount of crystals recovered would decrease. (d) Only small quantities of decolorized carbon should be used, otherwise some of the solute being measured may be absorbed by the carbon. (e) You would have impure crystals because the solute and impurities were not completely dissolved in the solution. (f) If you place the hot test tube directly into the ice-bath, small crystals will form and absorb impurities. 30. You seldom see high-boiling solvents used as recrystallization solvents because a high-boiling solvent will prevent the sample from dissolving, and the impurities couldnt be extracted from the original sample. An effective solvent is one where it is able to dissolve the sample at high temperature so as to free the impurities, but weak enough so that some of the sample is able to crystallize after cooling.

3. You should never heat a closed system because the increasing pressure from the vapors inside the system will cause the glassware to explode. This rule applies to distillation because we are using a Hickman stillhead, and the top part of this apparatus must be open so that there will not be a dangerous increase in vapor pressure.