CER Labs 2-3 Figure 1. Friedel-Crafts Acylation. Claim: An acetyl group was efficiently introduced to ferrocene by Friedel-Crafts Acylation (Figure 1). We isolated our crude yield while comparing 2 purification techniques: column chromatography and recrystallization. TLC, NMR, and IR spectroscopy were used throughout the process to identify ferrocene and acetylferrocene in addition to evaluating the levels of purity. Evidence: The objective of our experiments was to prepare acetylferrocene from ferrocene. The overall reaction was carried out using 6.1 equivalents of liquid acetic anhydride to 1.8 equivalents of phosphoric acid and concluded with an aqueous workup with NaOH. The initial reaction mixture containing ferrocene, acetic anhydride, and phosphate acid was mixed on a hot stir plate. During this period, reflux was observed, and the mixture appeared dark brown in color. To quench the reaction, the reaction mixture was transferred onto ice. NaOH was slowly added into the mixture, which resulted in acetic acid byproduct from the acetic anhydride reactant/solvent. This resulted in a clumpy and dark mixture. During …show more content…
The 1:1 hexane to ethyl acetate solvent resulted in the best separation because it not only showed extra spots that the other solvent mixtures did not have, but also the 4 spots were relatively dispersed with Rf values at 0.77, 0.56, 0.27, and 0.10 (Figure 2). Missing spots were also noted on the hexane only TLC plate. The orange eluent was ultimately chosen as our major product because it had significantly different TLC results than the 3 yellow eluents with the same Rf of 0.23 (Figure 3). The percent yield for this purification method was 248% and the extrapolated percent purified yield was around 135 %, which are both erroneously high. These high percent yield may be due to extra water weight or not fully evaporated
After 28 minutes, the mixture stopped boiling, and approximately 4.5 ml of bromobenzene was added drop by drop in the mixture, and color of the mixture was turned light brown orange. Then, the phenylmagnesium bromide was cooled in ice bath for a few minutes, and 10 ml of anhydrous diethyl ether was added in the mixture by using the syringe. After that, approximately 2.3 ml of methyl benzoate was added to the reaction, and it was added slowly slowly because the reaction was exothermic which needed to be cool in order to maintain a gentle reflux. Once all the methyl benzoate solution was added, the heating mantle was removed from the reaction flask and was cooled to the room temperature. During the reaction, a milky white salt began to precipitate, and the reaction flask was swirled for ten minutes until most of the reaction became visibly subdivided.
This addition aids in controlling the reproducibility and retention. Separation of the mixture via RP-HPLC can be done using continuous gradient or stepwise to move out the sample components. For every separation, the ideal gradient and volume must be
Benzyne Formation and the Diels-Alder Reaction Preparation of 1,2,3,4 Tetraphenylnaphthalene Aubree Edwards Purpose: 1,2,3,4-tetraphenylnaphthalene is prepared by first producing benzyne via the unstable diazonium salt. Then tetraphenylcyclopentadienone and benzyne undergo a diels-alder reaction to create 1,2,3,4-tetraphenylnaphthalene. Reactions: Procedure: The reaction mixture was created. Tetraphenylcyclopentadienone (0.1197g, 0.3113 mmol) a black solid powder, anthranilic acid ( 0.0482g, 0.3516 mmol) a yellowish sand, and 1,2-dimethoxyethane (1.2 ml) was added to a 5-ml conical vial.
Lab Report 5: Acetylsalicylic Acid (Aspirin) Synthesis Name: Divya Mehta Student #: 139006548 Date Conducted: November 19th 2014 Date Submitted: November 26th 2014 Partner’s Name: Kirsten Matthews Lab Section: Wednesday 2:30 L9 IAs Name: Brittany Doerr Procedure: For the procedure, see lab manual (CH110 Lab Manual, Fall 2014) pages 96-98. Wilfrid Laurier University Chemistry Department. Fall 2014. Acetylsalicylic Acid (Aspirin) Synthesis.
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
The purpose of this experiment was to learn about metal hydride reduction reactions. Therefore, the sodium borohydride reduction of the ketone, 9-fluorenone was performed to yield the secondary alcohol, 9-fluorenol. Reduction of an organic molecule usually corresponds to decreasing its oxygen content or increasing its hydrogen content. In order to achieve such a chemical change, sodium borohydride (NaBH4) is used as a reducing agent. There are other metal hydrides used in the reduction of carbonyl groups such as lithium aluminum hydride (LiAlH4).
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.
It is understood the mechanism is acid-catalyzed where protons coordinate with the carbonyl oxygen to make the carbonyl carbon more electropositive for nucleophilic attack (Scheme 1). In the experimental procedure all reactants were added together, this is inefficient as the protons can coordinate with either trans-cinnamic acid or methanol. Coordination with methanol is unnecessary as it reduces its nucleophilicity and makes less protons available to coordinate with the carboxylic acid. To improve
In acetanilide, the lone pair of the nitrogen is delocalized into the
Generally speaking, Friedel-Craft acylation could be useful in a practical application such as industrial chemistry. Using this reaction mechanism can create plastic, synthetic rubber and ethylbenzene, which can eventually lead to polystyrene (Chemical Technology). This reaction can also synthesize high-octane gasoline, commonly referred to as “premium gas.” Therefore, the products generated from Friedel-Crafts acylation are significant because they are used in everyday