Lab 8 320L Report

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California State University, Long Beach *

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320L

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Chemistry

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Dec 6, 2023

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Figure 1: Equation and mechanism Ferrocene Acetylferrocene Javier Rios Exp 8 Prep. Of Acylferrocene 1 Acetic Anhydride Phosphoric Acid Acetic Acid

Table 1: Yield results Yield Theoretical 0.237g Percent 42.3 % Actual 0.1 g Table 2: Compounds Information Compound Molecular Weight (g/mol) Melting Point ℃ Density g/mL Appearance Ferrocene (solid) 372.1 172.5 1.228 Solid yellow powder Yellow stain on TLC Acetylferrocene (solid) 228.08 81-83 1.014 Solid orange powder Orange stain on TLC Phosphoric Acid (liquid) 97.99 42.4 1.87 Acetic Anhydride (liquid) 102.09 -73 1.08 Javier Rios Exp 8 Prep. Of Acylferrocene 1

Table 3: TLC Results Name Rf1 Rf2 Rf3 Crude Ferrocene 0.154 0.769 N/A Isolated Ferrocene 0.769 N/A N/A Known Ferrocene 0.769 N/A N/A Recrystallized Ferrocene 0.723 N/A N/A Rf= Solute distance/ Solvent Distance Discussion: For this lab Acetylferrocene was produced by the mixture of Acetic Anhydride, Phosphoric acid, and Ferrocene. The percentage yield as provided in Table 1 was 42.3%, which is a low percentage. Some factors that could have impacted this result are not collecting all the Acetyl-Ferrocene liquid from the column chromatography or some solid evaporated with the solvent right before recrystallization. After collecting the actual mass of the recrystallized Acetylferrocene, a small amount was used to measure the melting point which came out to be (83.1 ℃ -85.2 ℃ ), which is close to the actual substance (82 ℃ -83 ℃ ). The result in TLC shows the crude Ferrocene as impure since it showed two stains in the TLC plate (0.154 color orange, and 0.769 color yellow) this data from Table 3 demonstrates the crude Ferrocene to be a mixture of Ferrocene and Acetylferrocene. The recrystallized Acetylferrocene is a pure substance since it only showed one spot on the TLC plate (0.723 color yellow) and the melting point was close to the actual compound. Questions: Javier Rios Exp 8 Prep. Of Acylferrocene 1

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1) Predict the order of elution of a mixture of triphenylmethanol, biphenyl, benzoic acid, and methyl benzoate from an alumina column. The first substance to elute will be the least polar one since it will be wash off fast with the nonpolar solvent. Knowing this we can find the order in which these substances will be collected by knowing their polarity. The substances will elute in this order, first biphenyl, methyl benzoate, triphenylmethanol, and lastly benzoic acid. 4) Once the chromatographic column has been prepared, why is it important to allow the level of the liquid in the column to drop to the level of the alumina before applying the solution of the compound to be separated? It is important to allow the level of liquid to drop to the level of alumina because the alumina always has to be wet, otherwise it can convert to solid phase and the solution of the compound to be separated won’t be able to enter the alumina. Javier Rios Exp 8 Prep. Of Acylferrocene 1