Introduction
Widely used all over the world, organic compounds, drugs, are constructed through the pharmaceutical method of organic synthesis. The most common drug is acetylsalicylic acid, known commonly as Aspirin.
C_7 H_6 O_3 (s)+C_4 H_6 O_3 (aq)→C_9 H_8 O_4 (s)+C_2 H_4 O_2 (aq)
In this experiment, Aspirin, along with acetic acid, was a product of the chemical reaction between salicylic acid and acetic anhydride – as shown by the chemical formula above. The product, acetylsalicylic acid, shows three structural features: an aromatic ring, a carboxylic group, and an ester group (as shown by the diagram below)1:
Procedure1
As in the Chemistry 101 Lab Manual, pages 75 to 77. No changes to the procedure were made.
Data and results
Table 1: reagents used.
Reagent MW
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Reagent MW
(g/mol) Amount used
(g) Moles used
Salicylic acid 138.12 0.1101 7.914 x 10
Acetic acid 60.05 0.27 4.5 x 10
Table 2: yield of product, Aspirin
Substance Weight (g)
Aspirin in vial 0.0958
Aspirin residue on filtration disc 0.0011 TOTAL Asprin yield 0.0969
Yield percentage of Asprin 68.0%
Table 3: Observations on the activity of Aspirin
Test Tube Content of Test Tube Observations made
#1 10 mg salicylic acid 1 drop 1% FeCl¬3 solution 1 ml water Solution turned purple, remained clear No odor detected Solution fizzed and bubbled
#2 10 mg Aspirin 5 drops 0.1M HCl Later added 5 drops 0.1M NaOH solution Solution turned light yellow, remained clear No odor detected
#3 10 mg Aspirin 5 drops 0.1M NaOH Later added 5 drops 0.1M HCL solution Solution turned light pink, remained
Next, aspirin was extracted from the filtrate. When the filtrate was first mixed with the sodium hydroxide and inverted a couple times, an organic layer formed underneath an aqueous layer in the separatory funnel. Dichloromethane was present in the organic layer because it has a higher density than sodium hydroxide, therefore, it’s in the bottom layer. Aspirin reacts with bases like sodium hydroxide, and it forms the salt sodium acetylsalicylate. The polar salt molecules migrate from the organic layer, where they are insoluble, to the aqueous layer, where they are soluble. After the two layers were separated into two different containers, the aqueous layer, which contained sodium acetylsalicylate, was mixed with hydrochloric acid. A white, cloudy precipitate formed, which was a purer form of the salt. The HCl
Both Aspirin and the Unknown are soluble in dichloromethane, due to their non-polar characteristics. To separate the two components, sodium bicarbonate was added (see figure 3). Sodium bicarbonate reacted with aspirin and converted it to a salt, also forming water and carbon dioxide. It was observed that the solution "fizzed" when this reaction took place, showing the release of carbon dioxide. The newly formed salt then traveled to an aqueous layer where it was soluble, while the unknown remained in the dichloromethane layer. The two layers were then separated. To collect an aspirin solid, the combination of the addition of HCl and the process of vacuum filtration helped to break down the salt and form a solid. Then the solid was placed in the Fisher Scientific Biotemp Oven to dry it to a constant mass of 0.091 g, 32.97% of the total composition. The
I measured out 3grams of Panacetin and then mixed it with CH2Cl2. Then after the filtration I was left with sucrose isolated, and then a substance containing aspirin and
8 test tubes were then labelled A-H, 1ml of DCPIP was added to each of the test tubes. 2ml of NaHCO3 was added tubes A through G.
And finally into test tube 3, I pipetted 1.0 ml turnip extract and 4.0 ml of water. The contents of test tube 1 was poured into a spectrometer tube and labeled it “B” for blank. “B” tube was now inserted it into the spectrometer. An adjustment to the control knob was made to zero the absorbance reading on the spectrometer since one cannot continue the experiment if the spectrometer is not zeroed. A combination of two people and a stop watch was now needed to not only record the time of the reaction, but to mix the reagents in a precise and accurate manner. As my partner recorded the time, I quickly poured tube 3 into tube 2. I then poured tube 2 into the experiment spectrometer tube labeled “E” and inserted it into the spectrometer. A partner then recorded the absorbance reading for every 20 seconds for a total of 120 seconds. After the experiment, a brown color in the tube should be observed to indicate the reaction was carried out. Using sterile techniques, any excess liquid left was disposed
Aspirin is one of the most consumed painkillers created up to this date due to its reliability and low expense. It is often used to relieve minor aches and pains, reduce fever and as an anti-inflammatory medication. Due to its wide range of uses, the demand for this pharmaceutical is very high. As a result, manufacturers who produce this drug must be efficient in order to reduce the time taken to produce this drug and produce the in very high quantities.
The mixture was heated at 120°C using an aluminum block and was stirred gently. After all of the solid dissolved, it was heated for 20 additional minutes to ensure the reaction was complete.
Aspirin crystals were collected via vacuum filtration with a Hirsch funnel. Then, aspirin crystals were weighted to calculate percent yield and saved to perform TLC
Dispense .5 mL water into the already weighed conical vial, replace cap and face insert on its down side.
Atoms are the basic units of matter and all life is based on them. Life on earth is based on the element carbon. It is a highly versatile atom able to form four covalent bonds with itself or other atoms such as hydrogen and water. Atoms combine to form molecules and those that are carbon based are referred to as organic molecules. Organic molecules occur in four different types in living cells; carbohydrates, lipids, proteins and nucleic acids. They are also known as hydrocarbons due to the presence of both hydrogen and carbon. Carbohydrates are made up of carbon, hydrogen and oxygen in the ratio 1:2:1. They are important sources of energy and are classified in three main groups; monosaccharides, disaccharides and polysaccharides.
The filter paper, holding the aspirin crystals, was removed from the funnel and was left to dry before being weighed. Once the aspirin crystals were weighed, the theoretical yield and the percent yield of the experiment were calculated. The procedure was repeated once more using the same steps.
The goal of this experiment was to synthesize aspirin. In this experiment aspirin, also known as acetylsalicylic acid, was synthesized from salicylic acid and acetic anhydride. In the reaction the hydroxyl group on the benzene ring in salicylic acid reacted with acetic anhydride to form an ester functional 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. After the reaction was complete some unreacted acetic anhydride and salicylic acid was still be present in the solution as well as some sulfuric acid, aspirin, and acetic acid. Crystallization, which uses the principle of
In this current time, a good number of people have only seen Salicin as a pill, so this paper stands to show how salicin developed from a leaf to a pill. There were numerous people from different countries and centuries involved in the development of Salicin. The person who formatted salicin in its present form is Felix Hoffman. Felix Hoffman kept Salicin in the pill form it had already been in, except he somewhat improved it. Felix Hoffman’s Salicin was enhanced due to the fact that the positive effects outweighed the negative ones. Before Hoffman, there was Charles Frederic Gerhardt. Gerhardt made Aspirin by deactivating salicylic acid and mixing sodium salicylate and acetyl chloride. Gerhardt, was not the first person to formulate Salicin into an acid, but he was the last. There was a version of Salicin that was an acid before Gerhardt’s. The needle acid form was developed by Raffaele Piria. In this form Piria would divide the salicin and eventually turn it into an acid. Earlier, a scientist named Henri Leroux, found a way to obtain Salicin from the willow tree bark. Preceding him though, is Johann Buchhner. Buchhner, first made salicin into an acid, in addition to naming it. Finally,
Mix panacetin with CH2 Cl2 and you will get a solid which is sucrose and you’ll get a filtrate of aspirin and an unknown substance. Then you will extract the aspirin with NaHCO3 to get an organic layer and a water layer. The bottom layer for us was the organic layer, while the top layer was the water layer.
3.0g of salicylic acid was weighed then 3.0mL of acetic anhydride and 6 drops of 85% H3PO4 were added to it. The mixture was warmed over a water bath for 5 minutes while stirring. After warming, 20 drops of distilled water was slowly added. 15mL of water was added then the solution was heated until it became clear. It was allowed to cool and was placed in an ice bath until the solution becomes cloudy. Using pre-weighed filter paper, the mixture was filtered and was allowed to dry in the filter paper.