Examples Of Acylation Of Ferrocene Formal Lab Report

Acylation of Ferrocene – Formal Lab Report
Trey Worcester
Organic II Laboratory
March 10th, 20223

Introduction The acylation of ferrocene is classified as a Friedel-Crafts acylation reaction. The Friedel-Crafts acylation is an example of an electrophilic aromatic substitution and adds an acyl group to the aromatic ring within ferrocene’s structure [2]. The structure of ferrocene consists of a central iron atom bonded to two cyclopentadienyl groups. The structure of ferrocene can be viewed in Figure 1.

Figure 1: Ferrocene Structure.
In an electrophilic aromatic substitution, an electrophile replaces a proton with an electrophile [3]. The electrophile is the acylium cation. The acylation of ferrocene reaction can be viewed in Figure 2.

Column chromatography utilizes a stationary phase, in this case silica gel, to separate out different substances based on their absorptions [1]. Substances with different absorptions will move down the column at different rates. The rate at which they move is determined by their polarity. Very polar substances move through the column slower whereas less polar substances move much faster [1]. During the purification process, two distinctly colored bands pass through the column. The dark red band represents the purified 4-toluoylferrocene and was collected. However, the yellow band was unreacted ferrocene and was

Percentage yield is used to measure the amount of product produced (actual yield) and compare it to the theoretical yield calculated. The calculation of theoretical yield can be seen below in Figure 4.
Theoretical Yield: 0.001376 mol x (304.0 g/mol)/(1 mol) = 0.3064 g
Figure 4: The calculation of theoretical yield. The actual yield of this experiment was measured to be 0.1805 g of 4-toluoylferrocene. Using this number as well as the theoretical yield, the percentage yield was calculated and can be seen below in Figure 5.
% Yield: (0.1805 g)/(0.3064 g) x 100 = 58.92%
Figure 5: The calculations of the percent yield. The percentage yield was calculated to be 58.92% and this represents that a portion of the reactants were lost during the experiment due to a small spill or improper collection of the product during the purification process. Next, the spectrum of the product was obtained. The IR spectrum for 4-toluoylferrocene can be seen below in Figure 6.

Figure 6: 4-toluoylferrocene IR