Chromatographic Separation of Fluorene and Fluorenone Abstract: A mixture of Fluorene (1) and Fluorenone (2) was separated by column chromatography. Chemical Equation: Fluorene (1) Fluorenone (2) Mp 114C mp 83C MW 166.22 MW 180.21 Introduction: Column chromatography was invented by Tswett in 1906 so that his study of the chemistry of chlorophyll could be facilitated. Tswett made significant advances in the method and demonstrated its applicability to the separation
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conversion of fluorene to Fluorenone. In order to achieve the goal of the experiment fluorene was oxidized to Fluorenone. The hydroxide ions from the sodium hydroxide in the presence of Stark’s catalyst would be able to de-protonate the acidic fluorene protons. This would result in the formation of a carbanion which attacks the oxygen from the air resulting in the formation of a hydroperoxide and eventually a ketone (after removal of water). Since the goal was to have a mixture of 50% fluorene conversion
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other. If multiple spots were present for a compound‚ give Rf value for each component and state if the component was major or minor. | 100% hexane | 25% EtOAc in hexane | 10% EtOAc in hexane | Fluorene | 0.34 cm | 0.94 cm | 0.67 cm | 9 - fluorenol | 0.00 cm | 0.49 cm | 0.05 cm | 9 - fluorenone | 0.00 cm | 0.69 cm | 0.21 cm | 2. Explain how Rf values were generally affected by polarity of the solvent/eluent systems. As part of your answer‚ rank the solvent/eluent systems in order of decreasing
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Discussion: In this experiment a ketone‚ 9-fluorenone is reduced to and alcohol. The are two possible ways by which this reduction can occur. One is by a catalytic hydrogenation‚ this uses a catalyst such as palladium or nickel‚ hydrogen gas‚ and heat/pressure. This can reduced an alkane to alkene. This catalytic process is preferred in industrial practices because the cost is low in the long run and more importantly there is little to no waste expense. However‚ hydrogen gas is dangerous due to
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solvent front (cm)) Toluene: Rf=2 cm/3.8 cm=0.53 (Fluorenone) Rf=1.1 cm/3.8 cm=0.29 (Fluorene) Hexane: Rf=1.8 cm/2.2 cm=0.82 (Fluorene) Rf=0 cm/2.2 cm=0 (Fluorene Table 1: Experimental IR peaks compared to literature IR peaks for fluorenone Functional group Experimental peak (cm-1) Literature peak (cm-1) C-H 3010.5 3013 C=O 1715.2 1715 C=C 1599.6 1600 Table 2: Experimental IR peaks compared to literature IR peaks for fluorene Functional group Experimental peak (cm−1) Literature
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3418-2 March 3‚ 2011 Theoretical Background- The fluorene and fluorenone mixture was separated by first dissolving the mixture in heptane. Since “like dissolves like”‚ fluorene dissolves with the non-polar heptane and the polar fluorenone dissolves in the polar ethyl acetate solvent. This phenomenon was illustrated in class before the experiment‚ when it was pointed out why water will not dissolve fluorene‚ fluorenone‚ or transstilbene as readily as a nonpolar solvent such as heptane
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Density Grams Moles Acetone Flammable‚ Irritant 58.08 g mol−1 0.791 g cm−3 2.0 g 0.0344 Hexane Flammable‚ Irritant‚ Dangerous to Environment 86.18 g mol−1 .6548 g mL−1 9.0 g 0.1044 Fluorene Very toxic to aquatic life with long lasting effects 166.223 g/mol 1.202 g/mL 0.3 g 0.00180 Fluorenone Irritant 180.20 g mol−1 1.13 g/cm3 0.3 g 0.00166 Alumina none 101.96 g mol−1 .95–4.1 g/cm3 1.25g 0.01225 Nitrogen (g) Nitrogen is nontoxic‚ but may cause suffocation by displacing
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This technique is important in organic chemistry because certain experiments may require the separation of compounds in solution to be used for chemical synthesis and/or analysis of a particular desired product by isolating it. Fluorene is to be separated from 9-fluorenone using the technique of column chromatography. The success of separation and purity is determined with analyzation technique thin layer chromatography and measuring the melting temperatures. The theory of column chromatography is
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Introduction: The purpose of this lab was to separate and purify a compound. This was achieved using techniques that allowed the extraction of the acid‚ the isolation of the neutral compound and the melting point classification of the neutral compound to test the purity of the sample. Chemical Reactions: HA + OH- A- + H2O R-COOH + OH- R-COO- + H2O Organic Acid Insoluble in H2O Conjugate base Soluble in H2O Procedure: A 0.170g sample consisting of a mixture of 0.110g
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Theoretical Ratio | Obs. Ratio | Obs.m.p. | Physical Appearance | Ethyl 4-aminobenzoate | .233g | .2093 | 89% | 30% | 20% | 89 ° C | Off white appearance; powdery | Benzoic Acid | .233g | .243 | 104% | 30% | 20% | 125 ° C | Clear crystals | 9-fluorenone | .311g | .623 | 200% | 40% | 60% | 82 ° C | Yellow‚ filmy‚flakes | Discussion: Based on the results‚ the most accurate extraction achieved was the first compound‚ ethyl 4-aminobenzoate. With an 89% actual yield of the compound‚ a 3rd or 4th
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