The lab experiment was divided into parts and the synthesis of the aspirin occurred during the first week. IR spectra display the wavenumbers at which reference compounds are transmitted. A clean and dry watch glass is measured together with a filter paper and the weight is measured and recorded. 1 Introduction 1 Indus. 101 115 31 90% on oxygen 2 L/min via nasal cannula 170/96 4 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. Once solid dissolved, weigh the watch glass and filter paper, use the filter paper to carry out suction filtration, place crystals on watch glass, weigh the dried crystal and calculate the weight of the aspirin. From this experiment, I have learnt how to carry out suction filtration in the right way and to be cautious at all time when handling chemicals and so on. To summarize, both spectrometers give significant evidence suggesting the purity of the synthesized aspirin product. Overall, the purpose of this lab, to synthesis aspirin and prove its purity using organic functional groups, was accomplished successfully. Aspirin is an ester that has high molecular weight and it not soluble in water hence the solid can be separated by crystallization process. A small mass of one of four different unknown solid compounds was added to each tube. The crystals were then washed three times with the vacuum using 5 mL amounts of DI water. 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 melting point of pure acetylsalicylic acid is 135 ˚C1. Page 2 of 5 Warning: The aspirin you are making is relatively impure and should not be taken internally. PREPARATION OF ASPIRIN AND ACETAMINOPHEN. 4.4 Appearance 4 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. Figure 2. This allowed a chemical reaction to take, place and made acetylsalicylic acid to form. Then, determine the melting point of aspirin using necessary apparatus. A small melting point range close to the standard of acetylsalicylic acid would suggest a high purity sample, meaning the recrystallization process was effective. I hypothesize that salicylic acid will react with acetic anhydride to produce acetylsalicylic acid (aspirin), Synthesis of Acetaminophen
and they were labeled #1 – 4. 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. Starch is present in aspiring tablets to bind the medicine together. This might have affected the results. would consist of a lot of water. To do this I used acetic, acid and phosphoric acid. Next, 3.00 g of salicylic acid were weighed into a 100 mL beaker, which was then covered with a watch glass.
Application to the synthesis (generation) of acetylsalicylic acid (aspirin) 3. The percent yield was about 76.7% whereas the temperature range is between 134.2 to 136.1 ÌŠÌŠC. The purification technique of recrystallization is very effective, as long as the temperature is lowered slowly enough that very pure crystals are formed. There are several things to be taken away from the collected data in regards to the purity of 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. 4.1 Mass 4 The purpose of this lab was to synthesize aspirin, determine the theoretical yield, compare the percent yield to the theoretical yield and test the purity of aspirin by adding Iron (III) chloride to the product. To develop basic procedures in organic chemistry for the synthesis of aspirin 4. Felix Hoffmann, a German chemist, produced a stable form of acetylsalicylic acid, more commonly known as aspirin; in 1897. Synthesis of Aspirin is known as esterification. Hypothesis:
In this lab, for recrystallization, the solution was allowed to cool to room temperature very slowly, but was then plunged rapidly into ice water. If you need assistance with writing your essay, our professional essay writing service is here to help! Secondly, once we have dissolved and during the second round suction filtration in attempt to obtain the pure aspirin, we forgot to use 2 filter papers but instead use only one on the Buchner funnel. Unknown compound D was determined to be pure salicylic acid because it had, qualitatively, the darkest, strongest purple color, as can be seen from Table 3. Monitoring the rate of a reaction via temperature change is not the most accurate method of measuring reaction rate because it is so indirect. 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.
After I added these two chemicals to the salicylic acid I placed the new solution in a boiling water bath for 5-10minutes. 24th May 2018 This is why pyridine increases the rate of reaction more so than the acetate ion. the market today is Ibuprofen which This increases propensity for nucleophilic attack and leaving group bond cleavage several times rather than just one. To finish the experiment, three titration trials were performed using the synthesized aspirin. Part I. Synthesis and Characterization of Aspirin 2.009 grams of salicylic acid was used with 5.000 mL of acetic anhydride. Hence this might have affected the percent yield too. We then cooled this substance so a precipitate. These two qualitative tests could be improved by making them quantitative tests. The mass of pure acetylsalicylic acid was determined and recorded and the percent yield of the reaction was calculated, Table 2. you may know as Motrin or Advil. Caution – acetic anhydride, salicylic acid, and phosphoric acid are all toxic chemicals and should not come into contact with the skin. This might explain the large data spread. Esterification is a chemical reaction used for making esters. Hence, due to the pressure, the filter paper tore and our crude product entered the filter flask that was containing the impurities and other liquid. T.A.’s: Long Pu
This mixture was generated a total of three times, so as to have three separate flasks with identical mixtures for three trials. Fumehood is a local ventilation device that is designed to limit exposure to hazardous or noxious fumes, vapours and dust. From simple essay plans, through to full dissertations, you can guarantee we have a service perfectly matched to your needs. Unknown compound C was the only unknown that underwent a color change when treated with iodine solution, meaning compound C was determined to be ground aspirin tablet even though there was some concentration of phenol present. .It is also useful in organic chemistry for the test of alcohols and carboxylic acid. However, the low percent yield can also mean that the reactant has not reacted completely or the reaction is not complete. The elapsed time was noted and recorded. The table below lists NMR standards from several NMR spectra of functional group chemicals: NMR peak for functional groups (PPM range). Salicylic acid and acetic anhydride have heats of solvation in water, so aqueous catalyst would change the reaction’s rate of temperature change relative to the non-aqueous catalyst even if the catalysts were equally effective. The contents of each tube and 50 mL distilled water were then added to a 125 mL Erlenmeyer flask. Introduce general concept of organic molecules and reaction 2. Synthesis of Aspirin … 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. 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. Am. 6mL of acetic anhydride is added to the salicylic acid to the flask in the fumehood. A fume hood is a large piece of equipment five enclosed sides of a work area, the bottom of which is most commonly located at a standing work height. Name Professor Chem 111 Date Experiment 19 Aspirin Synthesis and Analysis Discussion: In this experiment I made acetylsalicylic acid from salicylic acid. Protect the product and experiment from undesired reactions. This procedure was repeated using pyridine (5 drops), boron trifluoride etherate (5 drops), then concentrated sulfuric acid (5 drops) as the catalyst. Aspirin is a drug that is usually used to relieve minor aches and pain and other medical uses such as anti-inflammatory medication. Acetic acid has a peak at 1704.69 cm-1 and salicylic acid has a peak at 1652.36 cm-1. Iodide ions infiltrate the helical chain of long starch molecules, turning the solution dark purple/black in the presence of amylose2. The general mechanism for catalysation by a base, like the acetate ion or pyridine, is shown in Figure 2. The produced (PhO)2Fe(II) species is a dark purple color, the presence of which indicates the presence of phenol functional groups in an unknown compound. Percent yield is the amount of substance we have obtained in total in the experiment. The experimental yield percentage is different from the theoretical percentage is because there is loss of product often occurring during the isolation and purification steps. Therefore, the second peak from acetic acid pertains to the hydrogen the carboxylic acid, at 11.0 PPM. This would reduce yield and shift equilibrium toward the reverse reaction.
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