0.3 g of aspirin was weighed by difference and dissolved in 5 mL of methanol in an Erlenmeyer flask for each trial. Because the range of peaks matches (table 2.3), with the aromatic hydrocarbon peaks, this range must represent the hydrogen atoms present in the benzene ring, and by process of elimination, the final peak at 9.1 PPM must be the remaining hydrogen in the alcohol in the structure of salicylic acid. %��������� Because the NMR spectrum of the synthesized aspirin sample does not have a peak at 11.0 PPM, it can be concluded that there is no leftover acetic acid in the final product. 1) Calculate The Theoretical Yield Of Aspirin… The proposed laboratory is a hybrid of both classic (synthesis of aspirin, TLC analysis, 1H, 13C NMR and IR spectra) and new (molecular modeling) chemistry elements. IR Spectral … %PDF-1.3 CDCl3, used later for spectroscopy, is also a toxic chemical. Acetic anhydride reacts with Salicylic acid to yield the ester (aspirin). The crystals were then washed three times with the vacuum using 5 mL amounts of DI water. The aspirin will be characterized by three methods: melting point analysis, Fourier transform infrared spectroscopy (FTIR), … While the mixture in the flask cooled, a vacuum filtration system was created, and once crystallization occurred, the mixture was poured through the system so as to pull the liquid in the mixture through to the flask, leaving white, powdery crystals on the filter paper. The moles of aspirin used was calculated and incorporated into a calculation of the average concentration of NaOH (mol/L) using the second and third trial amounts of NaOH. The final product of synthesized aspirin contained no starting materials and its molecular weight was relatively close to that of pure aspirin, thus it was almost entirely pure. Caution – acetic anhydride, salicylic acid, and phosphoric acid are all toxic chemicals and should not come into contact with the skin. Spectral analysis plays an important role in the production of aspirin. Record the mass of the aspirin tablet. Thus, the synthesized aspirin was close to the identity of commercial aspirin, but not exactly, so it can be concluded that the synthesized aspirin was not entirely pure. In order to determine the purity of the aspirin, it must be characterized through various techniques based on an understanding of the energy of the system on the microscopic and atomic scale. Most students know about aspirin, a pain-relieving compound, and they gain knowledge about the role of chemistry in real-life applications from its synthesis. The theoretical yield for aspirin synthesis … The electronic spectra, percentage metal analysis … Write The Balanced Equation For This Reaction Showing The Structures Of The Reactants And Products. This leaves a peak at 9.1 PPM and a range of peaks from 6.7 to 8.1 PPM. Medicine Analysis – Synthesising Aspirin results After recrystallisation differences between the crude and purified aspirin were noted. The two starting materials in the aspirin synthesis reaction were acetic anhydride and salicylic acid. Utilizing 2.545 grams of salicylic acid and mixing it with 5mL of acetic anhydride, 6.051 grams of aspirin (acetylsalicylic acid) was obtained. Do not lose this container or its contents, you will use them later. To do this, place an arbitrary amount of the substance to be … These trials’ pink solution were light, while the first trial’s pink solution was too dark, and resulted in a smaller concentration of NaOH. SYNTHESIS OF ASPIRIN (acetylsalicylic acid) Place 2.0 g (0.015 mole) of salicylic acid in a 125-mL Erlenmeyer flask. H 2 SO 4 … The end point reading of NaOH was recorded. Part of NCSSM CORE collection: This video shows the synthesis of aspirin. The table below lists IR standards from several IR spectra of functional group chemicals: There are several things to be taken away from the collected data in regards to the purity of the synthesized aspirin sample. NSF CCLI Project Page 1 EXPERIMENT Aspirin: Synthesis and NMR Analysis Introduction: When salicylic acid reacts with acetic anhydride in the presence of an acid catalyst, acetylsalicylic acid, or aspirin, is … The synthesis of aspirin … The table below lists NMR standards from several NMR spectra of functional group chemicals: NMR peak for functional groups (PPM range). synthesize and analyze aspirin by the esterification of salicylic acid to aspirin using acetic anhydride. Synthesis of Aspirin … From these two analyses, it can be concluded that no reactants remain in the final product aspirin, and that the functional groups present in the synthesized aspirin NMR spectrum are CH3 and aromatic hydrocarbon (benzene). Each spectrometer yields further results regarding the purity of the aspirin. After 15 minutes of maintained heat, the flask was removed from the water and 2 mL of DI water was added, producing an aromatic vapor. First, an average molecular weight of 1.7 x 102 g/mol was derived from titrations (table 2.2). Titration was then performed in three trials, each by adding NaOH to the mixture in the flask until the mixture turned light pink and maintained this color for 15 seconds. The spectrum attained from IR spectroscopy is below: Figure 2.2 The IR spectrum of synthesized aspirin displays two peaks in the 1650 cm(^-1) to 1850 cm(^-1) range at 1679.70 cm(^-1) and at 1749.46 cm(^-1). The synthesis of this reaction obtained a percent yield of 98.19%. Additionally, based on the IR spectra of the starting materials in the reaction, it is further conclusive that they are not present in the final product, and that the peaks on the IR spectrum of synthesized aspirin show functional groups ester and carboxylic acid in the final structure. The starting reading of NaOH was recorded. Thus, the peak at 1679.70 cm-1 represents a carboxylic acid. Qualitative analysis of the Pure Aspirin Synthesized The pure Aspirin prepared was characterized qualitatively by physical constants, ferric chloride test, esterification and IR spectroscopic studies. In the following experiment, Aspirin was synthesized and analyzed in a laboratory setting in order to recognize the chemical process behind a common drug like aspirin and to relate it to the conceptual study of organic chemistry. To summarize, both spectrometers give significant evidence suggesting the purity of the synthesized aspirin product. Add 5 mL (0.05 mole) of acetic anhydride, followed by 5 drops of conc. The experiment differs in three ways from traditional aspirin synthesis experiments for general chemistry. Determine The Purity Of Your Product By Measuring The Melting Point. earlier paper described our ferrioxalate synthesis experiment (4). The Beer-Lambert law and two (FT-IR) permits continuous monitoring of the spectral chemometric approaches, partial least squares (PLS) baseline and simultaneous analysis of different compo- and … All three synthesized aspirin titrations yielded a light pink color for 15 seconds, thus each trial was successful and used in calculations. Although other testing methods are available, spectrophotometers offer the most versatile options in pharmaceutical testing and monitoring. Therefore, the second peak from acetic acid pertains to the hydrogen the carboxylic acid, at 11.0 PPM. Learn vocabulary, terms, and more with flashcards, games, and other study tools. Question: Synthesis Of Aspirin Lab 1) In Part 1 Of This Experiment , You Will Synthesize Aspirin A) Salicylic Acid Reacts With Acetic Acid To Produce Aspirin And Water. The solution was then inserted into an Anasazi 60 MHz FT-Nuclear Magnetic Resonance Spectrometer and the spectrum was printed. Overall, the purpose of this lab, to synthesis aspirin and prove its purity using organic functional groups, was accomplished successfully. The trial results of the commercial aspirin titrations are listed below: As mentioned in the experimental section, the first trial was not used in the final calculation of the average NaOH concentration. During IR spectroscopy, a pinhead sample of aspirin was placed on the diamond ATR plate of a Nicolet iS10 Infrared Spectrometer and the spectrum was printed. NMR was the first to be tested: a glass NMR tube was filled with the aspirin sample to a height of approximately 0.5 cm and 0.6 mL of CDCl3 was added in order to avoid large protein peaks. It is possible to perform aspirin synthesis in a … • Take a small amount of the aspirin … In this experiment aspirin, also known as acetylsalicylic acid, was synthesized from salicylic acid and … To begin the experiment, 2.00 g of salicylic acid (formula weight of 138.12 g/mol), 5.0 mL of acetic anhydride (density of 1.082 g/mL), and 5 drops of phosphoric acid were mixed in a 150mL Erlenmeyer flask, which was then placed in a beaker containing de-ionized (DI) water heated to 75°C on a hot plate. This simple and effective form of laboratory testing provides valuable data that is required for maintaining the quality and purity of this widely used pharmaceutical. After the vapor dissipated, a second volume of DI water, 20 mL, was added. This gas was acetic acid; an end product in the aspirin synthesis reaction, thus the NMR spectrum of acetic acid was analyzed. Aspirin is a drug that is usually used to relieve minor aches and pain and other medical uses such as anti-inflammatory medication. Many different laboratory techniques are used in the synthesis of Aspirin. The proposed laboratory is a hybrid of both classic (synthesis of aspirin, TLC analysis, 1 H, 13 C NMR and IR spectra) and new (molecular modeling) chemistry elements. Aspirin is a drug that is usually used to relieve minor aches and pain and other medical uses such as anti-inflammatory medication. To finish the experiment, three titration trials were performed using the synthesized aspirin. << /Length 4 0 R /Filter /FlateDecode >> A useful synthesis of acetylsalicylic acid was developed in 1893, patented in 1899, marketed under the trade name of “aspirin” by the Bayer Company in Germany. We suggest a simple and safe method for the synthesis of aspirin and its analysis … IR spectra display the wavenumbers at which reference compounds are transmitted. Next, NaOH was used to titrate commercial aspirin tablets – one tablet of aspirin, weighing 325 mg, was dissolved in methanol, and then 10 mL of DI water and 4 drops of phenolphthalein (indicator) were added. Aspirin, acetylsalicylic acid, is a familiar drug, used for relieving cold and flu symptoms, fevers, and general aches and pains in the body, and, as made clear by its chemical formula, contains salicin – a chemical found in willow bark. I would like to acknowledge a few people who helped make this scientific paper better than it would have been: Kevin Braun, for supplying the materials of the experiment, assisting with the experiment, teaching NMR and IR spectroscopy, and reviewing the results of the experiment; *****, for assisting me with the interpretation of the NMR and IR spectra; ******, for assisting me with the IR worksheet assignment, experimental calculations, and proofreading; ********, for assisting me with the NMR worksheet assignment; and ******, for proofreading this paper. The final mixture, a clear, colorless liquid, was stirred occasionally and the temperature of the water was monitored. 5.11.6 use volumetric analysis to determine the concentration of aspirin in solution (link with Section 5.3); 5.11.7 recall the synthesis of aspirin from salicylic acid using ethanoic anhydride and reasons for … Excess anhydride reacts with water produced in esterification, which shifts the equilibrium in the forward direction and … After aspirin synthesis was complete, the aspirin was analyzed using both IR and NMR spectrometers in order to determine the hydrogen atoms and organic functional groups present in the synthesized aspirin and to verify the overall identity of the aspirin. Before humans had the luxury of pain relievers and pharmaceutical drugs, many relied on the curing effects of willow tree bark, which was either chewed or boiled and used to relieve fevers and inflammation. This reaction is represented visually below: Figure 1.1 Aspirin synthesis: chemical reaction involving salicylic acid and acetic anhydride as reactants and aspirin and acetic acid as products. Aspirin is an ester that has high molecular weight and it not soluble in water hence the solid can be separated by crystallization process. Question: Organic Chemistry I: Synthesis Of Aspirin PURPOSE OF THE EXPERIMENT Synthesize Acetylsalicylic Acid. The Synthesis of Aspirin 1. When cold water was added, a by- product of acetic acid had formed … DI water and four drops of phenolphthalein were added, and the same process of titration was used. Day 1: Synthesis of Aspirin Lab Introduction: The Day 1 Aspirin Analysis PowerPoint Presentation (available for download) is an introduction to the lab experiment based on students having the lab … The remaining peak value from the synthesized aspirin is 1679.70 cm-1, which corresponds with values in both the ketone and carboxylic acid sections of table 2.4. Place approximately 200 mL of water into a 400 mL beaker and allow to warm to 70°C on a hot plate Further Analysis When was aspirin first synthesized, by whom, and for … After aspirin synthesis was complete, the aspirin was analyzed using both IR and NMR spectrometers in order to determine the hydrogen atoms and organic functional groups present in the synthesized aspirin and to verify the overall identity of the aspirin. This week you will use NMR, IR, and melting point to characterize your product. We suggest a simple and safe method for the synthesis … By using acetic acid’s spectrum as a reference for salicylic acid, it is known that the peak at 10.3 PPM is probably the hydrogen belonging to the carboxylic acid in the structure. This is accomplished by dissolving the acid in warm ethyl alcohol, adding cold water, and then allowing it to recrystallize in an ice bath. By matching the synthesized aspirin peak at 1749.46 cm-1 to the peak values in table 2.4, it is evident that this peak represents the ester in the structure of aspirin. The aspirin is allowed to dry, weighed, and then the percent yield is … Aspirin Synthesis and Analysis Revised: 12/13/14 • Crush an aspirin tablet and place in a labeled, pre-weighed vial or test tube. Because the synthesized aspirin spectrum does not have a peak at 9.1 PPM to represent alcohol or, as mentioned previously, at 10.3 PPM to represent carboxylic acid, the synthesized aspirin has no leftover salicylic acid present.
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