Organic Chemistry 333L, section 03M LaboratoryPost-LabChemical ExtractionBy: Cameron Kahn14 January 2019TA: James Collie1 | P a g eObservations: In the chemical extraction experiment, he/she took four (4) test tubes and added a liquid solution to each one. During the experiment, the test tubes changed colors. Below is a table and the colorchanges that were observed.Test Tube ColorsTest Tube Before mixing After mixing Final productA Clear liquidClear liquid with white piecesWhite powder crystalsB Orange/brownBrown orange on top cream white on bottomVery light orange whiteC Light orange yellowOrange with MgSO4 clusterSeparated into test tube DD Liquid orange/white Solid orange/whiteCrystal yellowish/light brownishThe starting ternary compound, a light brown and white powder mixture, was added to a large test tube. Next, ether was added and a distinctive odor smell was noted and white pieces were seen. When hydrochloric acid was added to the test tube, bubbles and precipitate formed. Finally, when adding magnesium sulfate, lumps of magnesium sulfate observed on the bottom of the test tube. See the extraction flow diagram for a visual reference of the process for the experiment (both diagrams came from George Handy’s lab manual and I do not take credit for making them).2 | P a g eResults:The initial mass of the ternary mixture was 1.030 grams (g). The Mass of benzoic acid recorded minus the filter paper was 0.277 g. The melting point of benzoic acid recorded was 121.4˚C and percentage composition was 26.89%. The mass of 2-naphthol minus the filter paper was 0.125 g. The melting point of 2-naphthol record was 95.30˚C and percentage composition 12.14%. The 3 | P a g eMass of naphthalene minus the mass of the test tube was recorded to be 0.324 g. The melting point of naphthalene record was 71.1˚C and the percent composition was 31.46%. The total final mass of the ternary mixture was 0.726 g. Therefore, the percent recovery of the ternary mixture was 70.49%.Calculations:ChemicalsMass with filter paper – Mass of filter paper = ProductBenzoic Acid 0.465g – 0.188g = 0.277g2-Naphtol 0.311g – 0.186g = 0.125gNaphthalene 8.304g – 7.98g = 0.324g Mass of test tubeTotal Mass(final)Benzoic Acid+2-Naphtol+Naphthalene = Ternary Mixture 0.277g+ 0.125g + 0.324g =0.726gChemicalsPercent Recovery ¿Final Mass∈GramsInitial Mass∈Grams * 100%Ternary Mixture0.7261.030∗100 %=70.49 % Conclusion:The results for this experiment vary due to the use of the separation funnel. In order to get the bottom layer out without contaminating the solution some part or the bottom remained in the separation funnel. Then to remove the finally bit of the bottom layer in the separation funnel some part of the top layer had to be removed with the bottom. Also, product was lost when transferring from test tube to separation funnel and back into another test tube. The mass of benzoic acid and 2-naphthol was lost during suction filtration. Due to the loss of products, the 4 | P a g eChemicalsPercent Compositions ¿Element Mass∈GramsCompound Mass∈Grams * 100%Benzoic Acid0.2770.726∗100 %=26.89 %2-Naphthol0.1250.726∗100 %=12.14 %Naphthalene0.3240.726∗100 %=31.46 %percent composition for each compound ended up to be low. Also due to the loss of product during the experiment, the percent recovery of the ternary mixture was 70.49%. Besides the general steps and use of the apparatus for a chemical extraction, the experiment also taught one to be careful with the transfer of compounds/aqueous solutions. The IR analysis does not fully support the experiment and its findings. The IR spectroscopy machine malfunctioned and there were fingerprints detected that screwed up the readings.IR analysis: **Readings most likely contain errors due to machine malfunction**Sample A (Benzoic acid)Sample B (2-naphthol)5 | P a g eAcid chlorides 1770cm-1-CH2 bending vibrations 1250cm-1Fingerprint region 700cm-1Sample D (naphthalene)References:1. Handy, Dr. George. Ali, Salman. Experiments in Organic Chemistry Fall 2013 – 2014, (University of South Carolina Department of Chemistry and Biochemistry)6 | P a g e1250cm-1 Fingerprint region1735cm-1 indicates esterFingerprint region 700cm-11100-1750cm-1 (error in machine)—no definitive indications4000-2500cm-1 (error in machine)—no definitive indications Fingerprint region 700cm-12. "Extraction in Theory and Practice (Part I)." Extraction in Theory and Practice (Part I). University of California, Los Angeles, 23 June 2003. Web. 22 Sept. 2013.7 | P a g