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18 Nov 2019
Lab #6: Friedel-crafts Acylation of Ferrocene Wade chapter 17(reactionsef aromatiecompounds: zubrick chapter (column chromatography) Objectives To execute a Friedel-Crafts acylation on an aromatic ring To become proficient using the technique ofeolumn chromatography Background Friedel-Crafts alkylation and acylation reactions are powerful tools for substituting aromatic reactions. the absence of strong activating groups, powerful Lewis acid such as AICb must be used. However, activated aromatic compounds will undergo substitution under much milder conditions. Ferrocene, acommon organometallic compound, is highly activated and undergoes acylation readily using a milder Bronsted-Lowry acid catalyst. In fact, ferrocene is so reactive that a diacetyl derivative usually Fe Fee H3PO4 major product Figure 1. Acylation of ferrocene. acylation reaction iscomplete, unreacted ferrocene starting material and diacetylferrocene will be removed using column chromatography. Column chromatography allows for the separation of materials based on their relative solubility (mobile phase) and attractions to a packed solid column (stationary Table 1. Physical properties. compound molar mass Lmp ferrocene 186.04 acetic anhydride 02.09 monoacetylferrocene 228.08 82 C 247.09 126 C Experimental Procedure: 1. Chemical reaction Weigh 200 mg of ferrocene into a conical vial and add in 2 mL of acetic anhydride. Attach an air condenser and heat gently in a warm water bath while stirring until the ferrocene is dissolved. Once dissolved, allow the solution to cool and disconnect the condenser so that you may carefully add 10 drops of phosphoric acid. Reattach the condenser and stir the reaction while heating in a hot water bath at approximately 100 C for 10 minutes.
Lab #6: Friedel-crafts Acylation of Ferrocene Wade chapter 17(reactionsef aromatiecompounds: zubrick chapter (column chromatography) Objectives To execute a Friedel-Crafts acylation on an aromatic ring To become proficient using the technique ofeolumn chromatography Background Friedel-Crafts alkylation and acylation reactions are powerful tools for substituting aromatic reactions. the absence of strong activating groups, powerful Lewis acid such as AICb must be used. However, activated aromatic compounds will undergo substitution under much milder conditions. Ferrocene, acommon organometallic compound, is highly activated and undergoes acylation readily using a milder Bronsted-Lowry acid catalyst. In fact, ferrocene is so reactive that a diacetyl derivative usually Fe Fee H3PO4 major product Figure 1. Acylation of ferrocene. acylation reaction iscomplete, unreacted ferrocene starting material and diacetylferrocene will be removed using column chromatography. Column chromatography allows for the separation of materials based on their relative solubility (mobile phase) and attractions to a packed solid column (stationary Table 1. Physical properties. compound molar mass Lmp ferrocene 186.04 acetic anhydride 02.09 monoacetylferrocene 228.08 82 C 247.09 126 C Experimental Procedure: 1. Chemical reaction Weigh 200 mg of ferrocene into a conical vial and add in 2 mL of acetic anhydride. Attach an air condenser and heat gently in a warm water bath while stirring until the ferrocene is dissolved. Once dissolved, allow the solution to cool and disconnect the condenser so that you may carefully add 10 drops of phosphoric acid. Reattach the condenser and stir the reaction while heating in a hot water bath at approximately 100 C for 10 minutes.
Jamar FerryLv2
1 Jun 2019