orgo2lab8 - Experiment 7: Friedal Crafts Acylation of...

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Experiment 7: Friedal Crafts Acylation of Ferrocene Objective : The objective of this experiment was to perform a Friedel Crafts acylation of ferrocene and isolate the crude product. In order to confirm the identity of the compound produced, IR spectroscopy was employed. Finally, TLC was used to identify how many impurities were present and column was used for purification. Table of Pertinent Physical Properties Substance (include Structure) M.F. M.W, (g/mol) B.P. °C M.P. °C Grams moles mL Weight % Molarity Reactant and Main Reagent(s) 1)Ferrocene C 10 H 10 Fe 186.04 - 174 0.3 0.0016 - - - 2) Acetic Anhydride C 4 H 6 O 3 102.1 139.8 - - - 3 - - 3) Phosphoric acid H 3 PO 4 98.0 158 - ? ? - 85 - 4) Sodium hydroxide NaOH 39.997 - - - - 5 - 6M 5) Hexane C 6 H 14 86.18 - −95 - - - - - 6) Ethyl acetate C 4 H 8 O 2 88.105 - −83.6 - - - - - 7) dichloromethane CH 2 Cl 2 84.93 - 96.7 - - - - - Product 8) Acetylferrocene C 12 H 12 FeO 228.1 - 83 ° * 1 - - - - - Overall Reaction Chemicals Uses Acetic Anhydride Introduction of acetyl groups in organic synthesis Phosphoric Acid Acid catalyst Sodium Hydroxide Neutralizes the acetic anhydride Hexane Nonpolar solvent used in column chromatography Ethyl Acetate The second part of the solvent system Dichloromethane Dissolves product
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CH 3 COCCH 3 O O Fe 85% H 3 PO 4 Fe O CH 3 Major Product Procedure A 50-mL Erlenmeyer flask with 0.3 g ferrocene and 3 mL acetic anhydride was charged. 85% phosphoric acid was slowly added drop wise with swirling, until about 10 drops were added. The mixture was heated on the steam bath for 5 min. After five minutes on the steam bath, the mixture was poured from the flask into a 100 mL beaker containing 15 g cracked ice. The reaction flask was rinsed with about 5 mL of cold water and ice water solution in the beaker was added to it. The acetic anhydride and excess phosphoric acid was neutralized to litmus by adding 5 mL of 6M aqueous sodium hydroxide solution followed by careful dropwise addition of additional 6M aqueous sodium hydroxide solution. Addition of excess base was avoided. Subsequent to neutralization, the mixture was allowed to stand in an ice-water bath for about 10 minutes. The product was suction filtered and washed twice with 10 mL portions of ice- cold water. The crude product was transferred to a pre-weighed watch glass and allowed to air dry. For the TLC portion of the experiment, the following procedure was employed: A
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orgo2lab8 - Experiment 7: Friedal Crafts Acylation of...

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