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Preparation of Acetanilide
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Recommended: Preparation of Acetanilide
Introduction: Acetanilide (chemical formula C8H9NO) is an important chemical which has a wide variety of uses in many different substances. It is commonly used in the manufacturing of colored dyes and fabrics, and as a reagent in the production of rubber. Acetanilide is also incredibly valuable because of its use in pharmaceuticals. It is a main building block in the synthesis of penicillin, which is an important antibiotic used to treat a variety of bacterial infections such as syphilis; pneumonia, meningitis, gonorrhoea, scarlet fever and many more. In the late 1800’s it was discovered Acetanilide had painkiller properties and it was packaged and sold under the name Antifebrin. However, it was quickly discovered that this substance was quite …show more content…
The final melting point of the product within a range is then used to determine the overall purity of the solid obtained. The actual yield of Acetanilide was also compared to the theoretical yield, determining the % of product formed. When the reagents (Aniline and Acetic anhydride) were initially added to the flask, the crude product of acetanilide started to form, along will a small number of impurities. As the compounds were mixed the solution turned a pale-yellow color, with white crystals of acetanilide forming in the solution as the reaction proceeded. As the solution began to heat up the crystals dissolved because the energy (as heat) was being added to the molecules of liquid causing separation between the pure Acetanilide and impurities in solution. The charcoal was then added to bond to the impurities in the solution, separating them from the Acetanilide, and ensuring they would not recrystalized as the solution was cooled. The solution was then left to return to room temperature, and the acetanilide became purified pure crystals, while the impurities remained in the solution and were filtered out. The final product was flaky white crystals of
In a small reaction tube, the tetraphenylcyclopentadienone (0.110 g, 0.28 mmol) was added into the dimethyl acetylene dicarboxylate (0.1 mL) and nitrobenzene (1 mL) along with a boiling stick. The color of the mixed solution was purple. The solution was then heated to reflux until it turned into a tan color. After the color change has occurred, ethanol (3 mL) was stirred into the small reaction tube. After that, the small reaction tube was placed in an ice bath until the solid was formed at the bottom of the tube. Then, the solution with the precipitate was filtered through vacuum filtration and washed with ethanol. The precipitate then was dried and weighed. The final product was dimethyl tertraphenylpthalate (0.086 g, 0.172mmol, 61.42%).
The purpose of the Unknown White Compound Lab was to identify the unknown compound by performing several experiments. Conducting a solubility test, flame test, pH paper test, ion test, pH probe test, conductivity probe test, and synthesizing the compound will accurately identified the unknown compound. In order to narrow down the possible compounds, the solubility test was used to determine that the compound was soluble in water. Next, the flame test was used to compare the unknown compound to other known compounds such as potassium chloride, sodium chloride, and calcium carbonate. The flame test concluded that the cation in the unknown compound was potassium. Following, pH paper was used to determine the compound to be neutral and slightly
Extraction is a separation method that is often used in the laboratory to separate one or more components from a mixture. Sucrose was separated at the beginning because it is the most immiscible and it’s strongly insoluble. Next Acetylsalicylic Acid was separated which left Acetanilide alone. Variety steps could have led to errors occurring. For example the step of separation, when dichloromethane layer was supposed to be drained out, it could be possible some aqueous layer was drained with it. Which could make the end result not as accurate. Also errors could have occurred if possibly some dichloromethane was not drained out. Both way could interfere with end result of figuring the amount of each component in the mixture. The solids percentage were 22.1% more than the original. That suggests that solids weren’t separated completely which clarifies the reason the melting points that were recorded were a slightly lower than the actual component’s melting point. The melting point for Acetylsalicylic Acid is 136 C but that range that was recorded during the experiment was around 105 C to 118 C. The melting points were slightly lower than the literature value. Sucrose was the purest among all component due to its higher melting point which follows the chemical rule that the higher the melting point the more pure the component
For this experiment we have to use physical methods to separate the reaction mixture from the liquid. The physical methods that were used are filtration and evaporation. Filtration is the separation of a solid from a liquid by passing the liquid through a porous material, such as filter paper. Evaporation is when you place the residue and the damp filter paper into a drying oven to draw moisture from it by heating it and leaving only the dry solid portion behind (Lab Guide pg. 33.).
Triphenylmethyl Bromide. A 400 mL beaker was filled with hot water from the tap. Acetic acid (4 mL) and solid triphenylmethanol (0.199 g, 0.764 mmol) were added to a reaction tube, with 33% hydrobromic acid solution (0.6 mL) being added dropwise via syringe. The compound in the tube then took on a light yellow color. The tube was then placed in the beaker and heated for 5 minutes. After the allotted time, the tube was removed from the hot water bath and allowed to cool to room temperature. In the meantime, an ice bath was made utilizing the 600 mL plastic beaker, which the tube was then placed in for 10 minutes. The compound was then vacuum filtered with the crystals rinsed with water and a small amount of hexane. The crude product was then weighed and recrystallized with hexane to form fine white crystals, which was triphenylmethyl bromide (0.105 g, 0.325 mmol, 42.5%). A Beilstein test was conducted, and the crystals produced a green to greenish-blue flame.
Since, the expected weight was 50.63 mg the percent yield is 59.3%. A TLC was conducted on this final product and a faint spot of 4-tert-butylcyclohexanone still appeared in lane 3 of the plate; meaning the reaction did not fully go to completion. The Rf values were 0.444, 0.156, and 0.111, where the lowest value is the trans isomer and the highest value is the ketone. This affected the IR spectrum conducted by having a carbonyl group peak at 1715 cm-1 which should not be present if all the product was 4-tert-butylcyclohexanol. However, the IR spectrum still showed peaks at 3292 cm-1 (hydroxyl group), 2939 cm-1 (sp2 carbon bonded to hydrogen) and 2859 cm-1 (sp3 carbon bonded to hydrogen) which support the presence of the alcohol. The accepted melting point of 4-tert-butylcyclohexanol is in the range of 62 – 70˙C (Lab Manual). The two melting point measurements using the Mel-Temp® machine gave ranges of 57 – 61˙C and 58 – 62˙C, which is not exact due to some 4-tert-butylcyclohexanone being present that has a low melting point of around 47 – 50˙C
In a separate beaker, acetone (0.587 mL, 8 mmol) and benzaldehyde (1.63 mL, 16 mmol) were charged with a stir bar and stirred on a magnetic stirrer. The beaker mixture was slowly added to the Erlenmeyer flask and stirred at room temperature for 30 minutes. Every 10 minutes, a small amount of the reaction mixture was spotted on a TLC plate, with an eluent mixture of ethyl acetate (2 mL) and hexanes (8 mL), to monitor the decrease in benzaldehyde via a UV light. When the reaction was complete, it was chilled in an ice bath until the product precipitated, which was then vacuum filtrated. The filter cake was washed with ice-cold 95% ethanol (2 x 10 mL) and 4% acetic acid in 95% ethanol (10 mL). The solid was fluffed and vacuum filtrated for about 15 minutes. The 0.688 g (2.9 mmol, 36.8%, 111.3-112.8 °C) product was analyzed via FTIR and 1H NMR spectroscopies, and the melting point was obtained via
Mixed melting point was used to confirm the identity of the product. The smaller the range, the more pure the substance. When the two substances are mixed; the melting point should be the same melting range as the as the melting range obtained after filtering. If the mixed melting point is lower one taken from the crystals, then the two substances are different.
Aspirin has grown so much in popularity that about 35,000 metric tons of it is produced and consumed each year to meet the consumer’s demand. 35,000 metric tons is equivalent to 100 billion standard aspirin tablets (10). That many tablets means that the market for aspirin is very good. Today, Aspirin is known as the leading non-prescription medicine of all time. It is the most common pill taken for pain, inflammation and fever. It has grown all over the world, being made available in eighty countries (9). It would not be surprising if one day, all the countries would have aspirin available to them.
In the late 1800’s it was discovered that papa-amino-phenol, could reduce fever, but the drug was too toxic to use. A less toxic extract called phenacetin was later found to be just as effective but also had pain-relieving properties. In 1949, it was learned that phenacetin was metabolized into an active but also less toxic drug, acetaminophen. Since then, acetaminophen has been sold under many over the counter brand names, most popular being Tylenol.
The esterification procedure was performed first. To begin the lab, the heating mantle was set at the 6 setting, and the hot plate heat was turned on to low. In a round bottom flask, 6.1 g of benzoic acid and 21 mL of MeOH were added into the flask. Once this was added to the flask, 2 mL of sulfuric acid was added and poured carefully down the side of the flask. It was noted that after the addition of the sulfuric acid there was heat production in the flask. The contents were swirled and a boiling chip was added into the flask. The flask was connected to the hood by a clamp. Water was then ran through the condenser and connected to the round bottom flask to begin refluxing the contents in the flask. The mixture was gently heated at reflux for one hour.
The conical vial was placed in a small beaker and allowed to cool to room temperature. The mixture was Cooled thoroughly in an ice bath for 15-20 minutes and crystals collected by vacuum filtration on a Hirsch funnel. The vial was rinsed with about 5 mL of ice water and transferred into to the Hirsch funnel and again washed with two additional 5mL portions of ice water. Crystals were dried for 5-10 minutes by allowing air to be drawn through them while they remained on the Hirsch funnel. The product was transferred to a watch glass plate and allow the crystals to dry in air. Crude acetaminophen product was weighed and set aside a small sample for a melting point determination and a color comparison after the next step. Calculation of the percentage yield of crude acetaminophen (MW = 151.2). was done and recorded in the lab notebook.
The observed melting point for the purified acetanilide was 113.2 °C – 115.4 °C. In the end, the chosen solvent was water as the compound was completely dissolved in it while being heated but recrystallized once placed in an ice bath. Overall, the product was pure with the analytical data. The expected melting point is 114.3 °C.
Analysis of Aspirin Tablets Aim --- To discover the percentage of acetylsalicylic acid in a sample of aspirin tablets. ----------------------------------------------------------------- In order to do this, the amount of moles that react with the sodium hydroxide must be known. This is achieved by using the method of back titration.
Discovery and Development of Penicillin. (2014, April 4). Retrieved from American Chemical Society International Historic Chemical Landmarks: https://www.acs.org/content/acs/en/education/whatischemistry/landmarks/flemingpenicillin.html