Synthesis Of Nitroacetanilide Lab Report

The purpose of this lab is to investigate the composition of a compound suspected to be Panacetin, a type of pain-killer. Panacetin is typically made up of sucrose, aspirin, and acetaminophen, but the third component in this experiment is unknown. The unknown component is suspected to be a chemical relative of acetaminophen, either acetanilide or phenacetin. Using techniques such as extraction, evaporation, and filtration, the three components will be isolated based on their solubilities and acid-base properties. Then, the percent composition of Panacetin can be deduced based on the masses of the three dried components. The

Data Table 2 shows the results gathered after the purification of 3-nitrochalcone. Since only half of the crude product was used, the theoretical yield for the crystallized product was determined to be 2.1 g. This led to a percent yield of 39%. The melting point of the crystallized product was also determined to be 142℃, which differed slightly from the literature value of 146℃. As a result, the product, 3-nitrochalcone, was not completely pure. It probably contained water and alcohol, because any impurities would have lowered the melting point. Considering the fact that the crude product was not thoroughly dried before purification, water and ethanol were already in the product. Even after crystallization into “pure 3-nitrochalcone”, the product was also not completely dried. The yield should have been much lower than 39%. If the product is not allowed time to dry, not only water, but methanol, which was the solvent that was used to crystallize the crude, would be in the product. Both the crude and crystallized 3-nitrochalcone were analyzed by infrared spectroscopy to test and prove these

Acetic Anhydride and p-Aminophenol were heated in a vial attached to an air condenser to synthesize crude acetaminophen, resulting in 0.097 grams (47.48% yield). The crude acetaminophen was then recrystallized in a solvent of water and methanol over heat resulting in 0.082 grams (39.61% yield) of pure acetaminophen. Melting points of both crude and pure acetaminophen were taken, and found to be 165.9 - 170.9°C and 168.2 - 171.5°C, respectively. The literature melting point of acetaminophen is 169.5 – 171.0°C, indicating that our final product was pure.

The objective of this experiment was to illustrate electrophilic aromatic substitution by synthesizing p-nitroanilide (as well as ortho) from acetanilide by nitration. The para form was separated from the ortho form based on solubility properties using recrystallization techniques.

Chemical synthesis is an imperative technique most relevant to organic chemists. Synthesis employs a succession of chemical reactions by using pre-existing structures to make new and functional ones. A combination of lab techniques could be developed in order to synthesize and attain the desired product. This particular experiment calls for the use for reflux, extraction, recrystallization, infrared spectroscopy, and melting point analysis. The overall objective of this lab is to utilize these steps to synthesize acetaminophen from p-aminophenol and characterize it .

In this experiment, a nucleophilic substitution was performed, where a chloride nucleophile substituted a tertiary hydroxyl group on 2-methyl-2-butanol. In a nucleophilic substitution reaction, an electron rich nucleophile attacks a positively or partially positively charged electrophile, and replaces a leaving group. In this reaction, chloride ions are the nucleophile, the tertiary carbon in 2-methyl-2-butanol is the electrophile, and water is the leaving group. In the mechanism for this reaction, the oxygen from the hydroxyl group of the 2-methyl-2-butanol attacks the hydrogen of the HCl, causing heterolytic cleavage of the HCl, resulting in a chloride ion, and in the oxygen bonding to an extra hydrogen, and becoming positively charged.

Nevertheless, our initial attempts with the reported procedure to isolate the intermediate were proven futile and low yielding due to high reactivity and instability of the intermediate. To circumvent this problem, I revised the synthesis under one-pot reaction condition without the need for the isolation of the intermediate. Activation of the protected guanosine with 1.2 equivalent of the chloroformate and subsequent addition of an excess amount of the tryptamine (4 eqvi) resulted in the coupled product. Isolation and deprotection of the coupled product resulted in the final product with more than 70% yield. Next, we investigated the effect of TrpGc on the activity of hHint1 using a fluorescence assay described previously.3 At a fixed saturating substrate concentration, TrpGc exhibited a dose dependent decrease in the activity of hHint1 with maximum half inhibitory concentration (IC50) values of 25.5 ± 6.0 μM (Fig 1). We next employed isothermal titration calorimetry (ITC) to investigate the nature of non-covalent interactions on the inhibitory activity of Bio-AMS on hHint1. The ITC studies provided an experimental dissociation

Abstract: This procedure demonstrates the nitration of methyl benzoate to prepare methyl m-nitrobenzoate. Methyl benzoate was treated with concentrated Nitric and Sulfuric acid to yield methyl m-nitrobenzoate. The product was then isolated and recrystallized using methanol. This reaction is an example of an electrophilic aromatic substitution reaction, in which the nitro group replaces a proton of the aromatic ring. Following recrystallization, melting point and infrared were used to identify and characterize the product of the reaction.

The purpose of the experiment was to extract acetaminophen from p-aminophenol using a synthesis reaction technique, as shown in Scheme 2. Acetic anhydride was poured into p-aminophenol and used reflux to break down chemical bonds. This was one step process to perform the synthesis. Information about the chemical reaction was provided from the lab manual (Arizona State University, 2017).

An ice bath was prepared in a large beaker and a small cotton ball was obtained. 0.5 g of acetanilide, 0.9 g of NaBr, 3mL of ethanol and 2.5 mL acetic acid was measured and gathered into 50mL beakers. In a fume hood, the measured amounts of acetanilide, NaBr, ethanol and acetic acid were mixed in a 25mL Erlenmeyer flask with a stir bar. The flask was plugged with the cotton ball and placed in an ice bath on top of a stir plate. The stir feature was turned on a medium speed. 7mL of bleach was obtained and was slowly added to the stirring flask in the ice bath. Once all the bleach was added, stirring continued for another 2 minutes and then the flask was removed from the ice bath and left to warm up to room temperature. 0.8mL of saturated sodium thiosulfate solution and 0.5mL of NaOH solution were collected in small beakers. The two solutions were added to the flask at room temperature. The flask was gently stirred. Vacuum filtration was used to remove the crude product. The product was weighed and a melting point was taken. The crude product was placed into a clean 25mL Erlenmeyer flask. A large beaker with 50/50 ethanol/water

Salicylic acid was esterfied using acetic acid and sulfuric acid acting as a catalyst to produce acetylsalicylic acid and acetic acid. The phenol group that will attack the carbonyl carbon of the acetic anhydride is the –OH group that is directly attached to the benzene since it is more basic than the –OH group attached to the carbonyl group. This method of forming acetylsalicylic acid is an esterification reaction. Since this esterification reaction is not spontaneous, sulfuric acid was used as a catalyst to initiate the reaction. Sulfuric acid serves as the acid catalyst since its conjugate base is a strong deprotonating group that is necessary in order for this reaction to be reversible. The need for the strong conjugate base is the reason why other strong acids such as HCl is not used since its conjugate base Cl- is very weak compared to HSO3-. After the reaction was complete some unreacted acetic anhydride and salicylic acid was still be present in

In the second part of the experiment, we will be performing the nitration of Acetanilide. We will first need to form the nitronium ion in situ by the dehydration of the nitric acid. The dehydrating agent for this experiment is sulphuric acid. The nitronium ion is an extremely strong and powerful electrophile which reacts with π–electrons involved with the aromatic ring of

The first step is the process of the diazotization which is converted into an aromatic amine, p-nitroaniline, which combines with sodium nitrite and HCl to form an azide salt. In the second step, diazonium coupling occurs which is an electrophilic aromatic substitution. In the presence of the second aromatic ring along with the azide salt, resorcinol forms. Resorcinol attacks the azide to product the only product possible, azo violet. Only one azo violet dye is produced due to the configuration of the hydroxy groups present on the ortho para directors, so the alcohol groups both point to the exact same carbon.

Instead of approximately 28 mL of water being added, 140 mL of water was added. To correctly identify the compound, it was concentrated with nitrogen while the container was placed in a boiling water bath. After being concentrated enough, the experiment was able to continue. To confirm that the unknown was acetanilide, a comparison of the melting points between the acetanilide, phenacetin and the unknown was performed which led to confirming that the unknown was

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