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An unknown mixture is given to a student in 442 lab. The student uses the flow chart below to seperate the compounds. After first extraction step with solution X, compound A was isolated and a FTIR spectrum of the compound A was taken. Some functional tests were applied to the mixture containing B, C and D compounds. According to the results, the mixture gives a brown- black color with Cerric ammonium nitrate reagent. The mixture gives a green color with Jones reagent. lodine test result of this mixture shows a color change from purple to tan. Silver nitrate test of this mixture results in a white precipitate. The mixture gives a red-brown solution with Br2/CC14. Compound B was seperated in the second extraction. However, C and D mixture cannot be seperated by extraction, so TLC study was performed for C,D mixture to understand whether column chromatography can be used as a seperation technique or not. According to these given information, please define each compound (A-D) and the solution used in the extraction steps (X-Y)?
a Unknown mixture (A,B,C,D) X Aqueous Phase, A Organic Phase B,C,D Aqueous Phase, B Organic Phase, C, D C D OH FTIR Spectrum of A 3276 H HCI 2735 2933 The "NH₂ NaOH 1462 N. NaHCO, H₂O