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. …show more content…
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 …show more content…
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
The last goal was to determine the percent yield of a product formed during a reaction with the unknown compound. Experimental Design The first day of lab consisted of various preliminary tests that helped identify the unknown compound.
Anthracene-9,10-bismethylmalonate (ADMA), Orange G and polystyrene (PS, Mw = 192,000 g/mol) were purchased from Sigma-Aldrich. Acetic acid (glacial), tetrahydrofuran (THF) and dimethylformamide (DMF) were purchased from Saarchem, while Rose Bengal was purchased from Fluka. Water collected from milli-Q water (Millipore corp., Bedford, MA, USA) was used for the preparation of all aqueous solutions. All solvents were dried prior to use using molecular sieves. BODIPY 1 was synthesized using the method described previously described (Fig. 1) [16].
Percent yield = (mass of actual yield )/(mass of theorethical yield) ×100% ≐(1.22 grams)/(0.7066 grams) × 100% ≐
This report presents how to optimize experiment and equipment to obtain highest percent yield possible. Percent yield is the percent ratio of actual yield to the theoretical yield. % yield= (Actual yield)/(Theoretical yield)×100% Where the actual yield is the amount of product actually produced in a chemical reaction in grams, theoretical yield is the amount of product obtained from the stoichiometry or balanced equation using the limiting reactant to determine the product. Units for both actual and theoretical yield need to be the same (moles of grams) (”Percent Yield Definition and Formula”, 2018).
With the data collected from this chemical reaction percentage yield of the precipitate can be calculated to determine the effects of impurities in the reactants on percentage yield. PRE-LAB QUESTIONS 1. What is the balanced chemical equation for the reaction in this investigation? 2. Which reactant is considered impure in this investigation?
However, after refluxing for a while, yellow precipitates begin to form near the top of the flask. It was assumed that the remaining starting material was concentrated from a decrease volume to reappeared in solution. Nevertheless, this may have been a sign of contamination that will negatively affect the entire reaction. This observation later resulted in a yellowish
Next, the oxygen is protonated from the 3-nitrobenzaldehyde, which is then followed by an elimination reaction where this acts as a leaving group. The product is the trans-alkene present in the product. After the reaction was completed, purification of the product was conducted using semi-microscale recrystallization.
TLC was used to identify the actual unknown product as well as other products/reactants present in the filtered solution. The procedure was conducted by placing a TLC plate in a developing chamber that is filled with a small amount of solvent. The solvent cannot be too polar because it will cause spotted compounds on the TLC plate to rise up too fast, while a very non-polar solvent will not allow the spots to move. The polarity of the spots also determines how far it moves on the plate; non-polar spots are higher than polar ones. After spots on the TLC form, the Rf values are calculated and used to analyze the similarity of the compounds.
The mechanism for this reaction is a nucleophilic acyl substitution reaction. In the synthesis, the nucleophile is the methoxide ion, which is a strong nucleophile generated from methanol and potassium hydroxide base. The methoxide nucleophile then attacked the C =O group. Additionally, since the reaction is reversible, an excess of methoxide or methanol is used to favor the product.
The objective of the experiment completed was to form the product 9,10-dihydroanthracene-9,10-α,β-succinic anhydride from anthracene and maleic anhydride. The reaction that took place is named a Diels-Alder reaction, defined as an addition reaction in which a diene unites with a double or triple bond of an unsaturated compound to form a 6-membered-ring. The following reactions below depict the ways in which dienes and dienophiles join to form products. Anthracene functioned as a diene and maleic anhydride functioned as the dienophile. Xylene was used as a solvent that provided a quicker way of reaction between the two starting materials.
In the synthesized Friedel-Craft acylation reaction mechanism, anisole (methoxybenzene) is the nucleophile. The double bond on the nucleophile attacks the electrophile acetyl. The acetyl compound is then bound to the anisole in the para position, which created the product p-methoxyacetophenone. Since anisole is an activator (electron donor), the acetyl could have bound in either the ortho or para position (or in the meta position, but it is not as likely). However, the reason that acetyl was not bound in the ortho position was because the para position demonstrated the least amount of steric hindrance.
Finding percent yield: actual yield/theoretical x 100% Finding percent yield: 2.55/3 x 100% = 86.667 % Finding the amount of iron filings in a 250 mL beaker. Percent of
To analyze the acetanilide product of the reaction, 1H NMR and IR were used. Results, Discussions, and Conclusions In this experiment, acetanilide was synthesized via nucleophilic acyl substitution from both acetic anhydride and aniline. During this reaction, aniline acts as the nucleophile and acyl (CH3CO-) group from acetic anhydride acts as the electrophile.
Procedure :- A) Fischer Esterification 's Procedure ( Direct esterification of a carboxylic acid with an alcohol ):- 1- Choose any pair of these caboxylic acids and alcohols . When using excess alcohol, a molar ratio 4:1 is used in the procedure. 2- Mix 0.48 mol methanol with 0.12 mol butyric acid in a dry round bottom flask .
So the actual yield of alum was 66.2013 g - 51.8004 g = 14.4009 g of alum actually yielded. After plugging in all the calculated values into the percent yield