synthesis and spectral analysis of aspirin

1) Calculate The Theoretical Yield Of Aspirin… Determine The Purity Of Your Product By Measuring The Melting Point. 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. To summarize, both spectrometers give significant evidence suggesting the purity of the synthesized aspirin product. 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. Acetic anhydride reacts with Salicylic acid to yield the ester (aspirin). 2 0 obj The experiment differs in three ways from traditional aspirin synthesis experiments for general chemistry. SYNTHESIS OF ASPIRIN (acetylsalicylic acid) Place 2.0 g (0.015 mole) of salicylic acid in a 125-mL Erlenmeyer flask. Thus, the average concentration of NaOH was 5.0 x 10-2 mol/L. After the crystals were completely dry, the beaker was weighed a second time, including the crystals, in order to obtain the actual yield of synthesized aspirin: 2.1 g. This value was used, along with the theoretical yield value, to calculate the percent yield of the synthesized aspirin: 81%. The trial results of the synthesized aspirin titrations are listed below: By combining all three molecular weights, the average molecular weight was 1.7 x 102 g/mol. 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. Part of NCSSM CORE collection: This video shows 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). The aspirin will be characterized by three methods: melting point analysis, Fourier transform infrared spectroscopy (FTIR), … This week you will use NMR, IR, and melting point to characterize your product. Learn vocabulary, terms, and more with flashcards, games, and other study tools. Synthesis of Aspirin … 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. The synthesis of this reaction obtained a percent yield of 98.19%. Caution – acetic anhydride, salicylic acid, and phosphoric acid are all toxic chemicals and should not come into contact with the skin. 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 … 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 … IR spectra display the wavenumbers at which reference compounds are transmitted. Synthesis of Aspirin … These trials’ pink solution were light, while the first trial’s pink solution was too dark, and resulted in a smaller concentration of NaOH. 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. NMR spectra reflect the presence of hydrogen atoms, or protons, in a substance. Analysis of Aspirin GOALS: This is the second of two weeks related to aspirin. Record the mass of the aspirin tablet. Scheme 1: Synthesis of Aspirin O O H O O O O Na + Na + O H O H O O O O Na + MW = 152.15 MF = C 8 H 8 O 3 d = 1.18 g/ml pKa = 9.8 MW = 159.10 MF = C 7 H 4 O 3 Na 2 MW = 138.12 MF = C 7 H 6 O 3 MP = … It is known from the NMR spectrum of acetone, which is a reference compound with only one type of hydrogen (that belonging to CH3), that the peak at 2 PPM in the acetic acid spectrum pertains to CH3 (table 2.3). This paper describes the first of our organic synthesis experiments, the synthesis, purification, and qualitative spec-troscopic characterization of aspirin. 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 … DI water and four drops of phenolphthalein were added, and the same process of titration was used. To do this, place an arbitrary amount of the substance to be … First, an average molecular weight of 1.7 x 102 g/mol was derived from titrations (table 2.2). H 2 SO 4 … Aspirin is a drug that is usually used to relieve minor aches and pain and other medical uses such as anti-inflammatory medication. This is accomplished by dissolving the acid in warm ethyl alcohol, adding cold water, and then allowing it to recrystallize in an ice bath. The first of these that is used is the procedure of weighing by difference. The molecular weight of commercial aspirin is 180.1574 g/mol, approximately 10 g/mol higher than that of the synthesized aspirin. 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. The synthesized aspirin was also used in two different types of spectroscopy: NMR and IR. Excess anhydride reacts with water produced in esterification, which shifts the equilibrium in the forward direction and … 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. The flask was then scratched on the bottom and placed in an ice bath to encourage crystallization. This value, compared with the molecular weight of commercial aspirin, C9H8O4, will demonstrate the difference in purity. The spectrum attained from NMR spectroscopy of synthesized aspirin is below: Figure 2.1 The NMR spectrum of synthesized aspirin displays a peak 2.4 PPM and a range of peaks from 7 PPM to 8.3 PPM. However, looking at the structure of synthesized aspirin, the remaining component that has not been identified but is present in the structure is carboxylic acid. All three synthesized aspirin titrations yielded a light pink color for 15 seconds, thus each trial was successful and used in calculations. Looking again at the starting materials of the aspirin synthesis reaction, acetic acid and salicylic acid, each compound has one peak in the 1650 to 1850 cm-1 range on their IR spectra. INTRODUCTION: Recall that last week you did the reaction shown to prepare aspirin… The two peaks in the 1650 to 1850 cm-1 range in the synthesized aspirin IR spectrum (figure 2.2) are at 1679.70 cm-1 and 1749.46 cm-1. 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. After the vapor dissipated, a second volume of DI water, 20 mL, was added. 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. The theoretical yield for aspirin synthesis … 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. earlier paper described our ferrioxalate synthesis experiment (4). Because neither of these values matches with those values on the acetic acid and salicylic acid IR spectra, it can be concluded that neither of the starting materials are present in the synthesized aspirin sample. First, based on the NMR spectra of the starting materials in the aspirin synthesis reactions, it is conclusive that there are no starting materials present in the final product, and that the peaks on the NMR spectrum of synthesized aspirin show the hydrogen atoms in CH3 and aromatic hydrocarbon in the final structure. The solution was then inserted into an Anasazi 60 MHz FT-Nuclear Magnetic Resonance Spectrometer and the spectrum was printed. 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. 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. 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). Spectral analysis plays an important role in the production of aspirin. 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. When cold water was added, a by- product of acetic acid had formed … Aspirin, also referred to as acetylsalicylic acid, is one of the most common synthetic medications found on the market today.1 Wh… Add 5 mL (0.05 mole) of acetic anhydride, followed by 5 drops of conc. 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. 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. 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. Each spectrometer yields further results regarding the purity of the aspirin. Medicine Analysis – Synthesising Aspirin results After recrystallisation differences between the crude and purified aspirin were noted. 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. Utilizing 2.545 grams of salicylic acid and mixing it with 5mL of acetic anhydride, 6.051 grams of aspirin (acetylsalicylic acid) was obtained. Write The Balanced Equation For This Reaction Showing The Structures Of The Reactants And Products. The two starting materials in the aspirin synthesis reaction were acetic anhydride and salicylic acid. This gas was acetic acid; an end product in the aspirin synthesis reaction, thus the NMR spectrum of acetic acid was analyzed. 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. 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. We suggest a simple and safe method for the synthesis of aspirin and its analysis … 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 mixture was generated a total of three times, so as to have three separate flasks with identical mixtures for three trials. 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. Aspirin Synthesis and Analysis Revised: 12/13/14 • Crush an aspirin tablet and place in a labeled, pre-weighed vial or test tube. The Synthesis of Aspirin 1. 0.3 g of aspirin was weighed by difference and dissolved in 5 mL of methanol in an Erlenmeyer flask for each trial. Last week you made and purified aspirin. A 50 mL burette was then washed with one 5 mL portion of NaOH, then filled to near the 0 mark of the burette with NaOH. The initial step of the experimental process was the synthesis of Aspirin, which required the reaction of salicylic acid, acetic anhydride, and phosphoric acid to produce aspirin and acetic acid. Aspirin is a drug that is usually used to relieve minor aches and pain and other medical uses such as anti-inflammatory medication. 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. Aspirin (acetylsalicylic acid) is a pain-relieving compound familiar to virtually all students. The impure (crude) aspirin was powered and fluffy with small clumps and was slightly yellow in colour whereas the pure aspirin … Acetic acid has a peak at 1704.69 cm-1 and salicylic acid has a peak at 1652.36 cm-1. CDCl3, used later for spectroscopy, is also a toxic chemical. IR Spectral … Aspirin is an ester that has high molecular weight and it not soluble in water hence the solid can be separated by crystallization process. The electronic spectra, percentage metal analysis … %��������� The synthesis of aspirin … 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 name aspirin was invented by the … The starting reading of NaOH was recorded. The final mixture, a clear, colorless liquid, was stirred occasionally and the temperature of the water was monitored. Although other testing methods are available, spectrophotometers offer the most versatile options in pharmaceutical testing and monitoring. We suggest a simple and safe method for the synthesis … Many different laboratory techniques are used in the synthesis of Aspirin. It is possible to perform aspirin synthesis in a … 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. << /Length 4 0 R /Filter /FlateDecode >> Synthesis of Aspirin Lab Report The goal of this experiment was to synthesize aspirin. 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. 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. It is designed to be performed early rather than late; it starts from a naturally occurring material and requires two steps rather than one; and it utilizes FTIR spectroscopy to distinguish among oil of wintergreen starting material, salicylic acid intermediate, and aspirin product. Aspirin (acetylsalicylic acid) was synthesized by reacting salicylic acid and acetic anhydride with the aid of phosphoric acid as a catalyst. Some metal(II) complexes of the mixed drugs-Aspirin and Vitamin B2 (Riboflavin) were synthesized and characterized by melting point, conductance, percentage metal measurements, as well as infrared and electronic spectroscopies. Aspirin is an ester that has high molecular weight and it not soluble in water hence the solid can be separated by crystallization process. 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. Overall, the purpose of this lab, to synthesis aspirin and prove its purity using organic functional groups, was accomplished successfully. synthesize and analyze aspirin by the esterification of salicylic acid to aspirin using acetic anhydride. 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 end point reading of NaOH was recorded. In this experiment aspirin, also known as acetylsalicylic acid, was synthesized from salicylic acid and … Do not lose this container or its contents, you will use them later. To finish the experiment, three titration trials were performed using the synthesized aspirin. The aspirin is allowed to dry, weighed, and then the percent yield is … The crystals were then washed three times with the vacuum using 5 mL amounts of DI water. 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. This leaves a peak at 9.1 PPM and a range of peaks from 6.7 to 8.1 PPM. Salicylic acid was a white, chalky powder; acetic anhydride a clear, colorless liquid; and phosphoric acid a clear, yellow-tinted liquid. As shown in the above reaction, phosphoric acid, H3PO4 acts as a catalyst in the initial mixture of the reactants in order to speed up the reaction. 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. %PDF-1.3 Therefore, the second peak from acetic acid pertains to the hydrogen the carboxylic acid, at 11.0 PPM. Thus, the peak at 1679.70 cm-1 represents a carboxylic acid. 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). 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. 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 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. stream Lastly, the crystals were scraped into a labeled, pre-weighed beaker and placed in a 40°C oven for 46 hours to dry. 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. Start studying Experiment 34: Synthesis and Spectral Analysis of Aspirin. 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. Question: Organic Chemistry I: Synthesis Of Aspirin PURPOSE OF THE EXPERIMENT Synthesize Acetylsalicylic Acid. xڽ}M��q�=E�f`+�?�@�#�5�DI/�����A��Y��׫��+�:=��`%3�naz��2#=<<����*�jB^���1Z�WWV|��n�������?��]��뷫�������+�����ߙ��.�w?Q��ê�P�����r>�l�qi��R�����c;��m��_~&N�`F��O��u|�Ϗݕ`��_y�_q��3��+a��x|ez���A(��A�Y^�^1OW�%O'�Ȯ��=73_����d����^O�z���W���a���w����nq�N��b����������Ǖ[�iE^���'���qm+lÜw��Gw���%��j��.8뎞��J��͇�Z�F���J,G�zqE����Jp���?�W�?Z�z%�p��劉q�>���w�k4����1�v�y��Ă3�է�[��[�X�����>��O���9���PP�P�8H'���!\¾��W�"���㜽. 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 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. 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