Daniels organic chemistry 2121 11 february 2014 synthesis of aspirin salicylic acid derivatives, or salicin, are found in the bark of the willow tree in the 5th century b. In the presence of moisture, aspirin may decompose hydrolysis into salicylic acid and acetic acid. Following this recommendation, at least two current general chemistry textbooks make liberal use of organic examples. Practical 3 the preparation and identification of a 2,4dnph derivative.
Diy brick rocket stove cooking without electrical power duration. After germany lost world war i, bayer was forced to give it up as part of the treaty of versailles in 1919. H nmr spectra are obtained using samples dissolved in deuterated solvents or ccl use. This agent exhibits analgesic, antipyretic, and anticoagulant properties. The synthesis of aspirin chemistry standard level lab report data collection and processing and conclusion and evaluation date. If you will be calculating actual and theoretical yield, be sure to record how much salicylic acid you actually measured add 6 ml of acetic anhydride and 58 drops of 85% phosphoric acid to the flask. The synthesis and analysis of aspirin mariam elmagbri department of chemistry, american university, washington, d. Sulphuric acid is added and heated for a short period to complete reaction. Remove all the liquid from the crystals by pressing with a clean stopper or cork. Prostaglandins were found to be responsible for pain and blood clotting. The book provides an exhaustive list of organic compounds, methods of its identification. The preparation of aspirin core practical 10a stage 1. Aspirin synthesis tap water was heated on a steam bath in a 250 ml beaker. It is aimed at post16 chemistry and science students and their teachers.
Using familiar a level chemistry, you will produce aspirin using an esterification reaction with ethanoic anhydride. Place a 250 cm3 beaker, halffilled with water, on top of a tripod and gauze. E29 preparation of aspirin acetylsalicylic acid and thin. H nmr and c nmr spectra and chemical shift data from the chemistry data booklet to suggest possible structures or part structures for molecules. Aspirin is synthesized through the reaction of salicylic acid with acetyl anhydride.
When you see that prostaglandins induce inflammation, pain, and fever, what comes to mind but aspirin. Errors affecting the purity of aspirin during the preparation of aspirin aspirin. Synthesis of aspirin aspirin or acetyl salicylic acid asa is a derivative of salicylic acid, which is used as a pain reliever for various body ailments such as head ache. Acetylsalicylic acid, also known as aspirin, is one of the most widely used medications to reduce fever and is also used as a pain killer.
Acetylsalicylic acid binds to and acetylates serine residues in cyclooxygenases, resulting in decreased synthesis of prostaglandin, platelet aggregation, and inflammation. The third part of the book tells the story of aspirin s renaissance in the second half of the 20th century. The letter a stands for acetyl, spir is derived from the plant known as spiraea ulmaria meadowsweet, which yields salicin, and in was a common suffix used for drugs at the time of the first stable synthesis. Thinlayer chromatography tlc is an important technique in organic chemistry. Preparation and recrystallisation of aspirin 1796 words. Practical work in reformed alevel biology, chemistry and physics. Reviewing over a century of aspirin research and use, aspirin and related drugs provides a comprehensive source of information on the history, chemistry, absorption in the body, therapeutic effects, toxicology, elimination, and future uses of aspirin. Preparation and recrystallisation of aspirin contents page synopsis iii 1 introduction 1 1. Aspirin is one of the most commonly used drugs in the world, so why not bring chemistry out of the text books, and synthesise aspirin in the undergraduate chemistry laboratory at reading university. Since acetic acid is very soluble in water, it is easily separated from the aspirin product. Tlc can be used to assess the course of a reaction, to assess the purity of a sample and also to. Pdf this aim of this experiment focuses on the synthesis of pure aspirin.
Aspirin is a drug that is usually used to relieve minor aches and pain and other medical uses such as antiinflammatory medication. Top 5 examiners report feedback top 5 easy fixes you can make to improve your grade. An ester is a compound that is formed when an acid reacts with an alcohol, oh group. The aspirin isolated in this step is the crude product. This reaction is the reverse of the synthesis reaction. The aspirin product is not very soluble in water so the aspirin product will precipitate when water is added. Aspirin was first isolated by felix hoffmann, a chemist with the german company bayer in. Aspirin determination a level chemistry making aspirin synthesis of benzoic acid.
H 2 so 4 use a dropper, h 2 so 4 is highly corrosive and swirl the flask gently until the salicylic acid dissolves heat the flask gently on the steam bath for at least 10 minutes. Pure acetyl salicylic acid aspirin synthesis chemistry ch3 o ch3 o o acetic. Results at the end of the experiment, the result gotten should be a result of 40 60 % yield and a melting point that is around the theoretical melting point of aspirin. The industrial advantages of ethanoic anhydride over ethanoyl chloride in the manufacture of the drug aspirin. Pdf preparing a pure aspirin acetylsalicylic acid researchgate.
By calculating the theoretical yield based on the original amount of salicylic acid, one could determine the actual yield percentage of. Organic synthesis of aspirin abstract the purpose of this experiment is to synthesize a common organic product called acetylsalicylic acid aspirin, and to become familiar with the optimum conditions needed for successful yields. A history of aspirin infographic pharmaceutical journal. Synthesis of aspirin lab report and analysis odinity. Synthesis of aspirin experiment chemistry libretexts. Make sure that the resulting solution is acidic blue litmus paper and that the aspirin has completely precipitated out. With an intention to serve the students at the graduate and postgraduate level. For preparation of aspirin, acetic anhydride is added to the measured amount of salicylic acid. You can also buy a copy of this book via the royal society of chemistry online shop for. 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.
Wm3 investigating the chemistry of the oh group in various environments wm4 interpretation of the mass spectrum of salicylic acid wm5. Aspirin background also known as acetylsalicylic acid abbreviated asa, is a salicylate drug. Store the aspirin in the desicooler and determine the percent yield of the synthesis by taking the actual yield and dividing it by the theoretical yield, determined from the original amount of salicylic acid used. Filter the solid by suction and wash the crystals 3x with 5 ml of cold water each. Preparation and recrystallisation of aspirin biology essay. Outline the method for the preparation of aspirin using 2hydroxybenzenecarboxylic acid with ethanoic anhydride 1 add to 50cm3 pear shaped flask the two substances followed by a few drops of a phosphoric acid catalyst and swirl to mix. The temperature of an alcohol thermometer was equilibrated in a beaker. To determine which of four catalysts yields the fastest reaction rate in the acetylation of salicylic acid 1 to form acetylsalicylic acid 2. The book is organised in two main sections a series of student activities and a guide. Aspirin blocks an enzyme called cyclooxygenase, cox1 and cox2, which is involved with the ring closure and addition of oxygen to arachidonic acid converting to prostaglandins. Highlighting the historical evolution of the salicylates and the commercial development of. The preparation of aspirin practical 5 the preparation of ethyl ethanoate practical 6 using thin layer chromatography to separate the pigments in chlorophyll. The purpose of this experiment was to make aspirin via esterification, and to determine the percent yield we as a lab group made.
Aspirin, also known as acetylsalicylic acid, has a chemical formula of c9h8o4. Analytical, transition metals, electrochemistry and organic nirtrogen chemistry. Sp11 1021 synthesis of aspirin and oil of wintergreen. Acetylsalicylic acid commonly known as aspirin is the most widely used drug in the world today. In june 1971 nature published a seminal paper by john vane and priscilla piper, inhibition of prostaglandin synthesis as a mechanism of action for aspirin. Charlie archer, the oratory school, reading, 2008 aspirin is one of the most commonly used drugs in the world, so why not bring chemistry out of the text books, and synthesise aspirin in the undergraduate chemistry laboratory at reading university. Austin peay state university department of chemistry chem 1121 synthesis of aspirin and oil of wintergreen revision f8 page 3 of 7 procedure synthesis of aspirin 1. Aspirin, one of the first drugs to come into common usage, is still mostly the widely used in the world approximately 35,000 metric tonnes are produced and consumed annually, enough to make over 100 billion standard aspirin tablets every year. Clamp a 50 cm3 roundbottomed flask so that it is partially submerged in the. Synthesise aspirin from 2hydroxybenzoic acid objectives to perform and explain the reactions of acid anhydrides to synthesise aspirin from 2hydroxybenzoic acid safety perform the experiment in a wellventilated room. The preparation of aspirin, the recrystallisation of aspirin and the melting point determination of aspirin. Synthesis of aspirin a general chemistry experiment john olmsted iii department of chemistry and biochemistry, california state university, fullerton, fullerton, ca 92834 cc c hc cc h c h h o o o r1 r2 reactive sites common core compound oil of wintergreen salicylic acid aspirin r1 ch3 ch3 h h r2 h h c o. The synthesis of aspirin from wintergreen oil a green two step synthesis of aspirin. E29 preparation of aspirin acetylsalicylic acid and thinlayer chromatography of analgesic drugs the task to prepare a pharmaceutical compound and test its purity.
Aspirin is follows aspirin through its birth ancient sumer andor egypt using willow bark as medicinal treatment, childhood purification, chemical synthesis, adolescence the race for monopoly and profit, adulthood most popular drug on the planet, midlife crisis advent of new drugs such as tylenol and ibuprofen, and its sudden discovery that there is life after middle. Practical 4 the preparation of aspirin practical 5 the preparation of ethyl ethanoate practical 6 using thin layer chromatography to separate the. Practical 6 using thin layer chromatography to separate the pigments in chlorophyll. Aspirin is an orally administered nonsteroidal antiinflammatory agent.
Synthesis and characterization of aspirin purpose the purpose of this lab was to synthesize aspirin and measure the synthesized aspirin s purity. The main procedures are preparation of aspirin, recrystallisation of aspirin and lastly determining the melting point of the aspirin. 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 starting material, for this synthesis, is 2hydroxybenzoic acid salicylic acid. To verify the identity of the aspirin, completely dissolve. Synthesizing aspirin and oil of wintergreen purpose in this experiment, you will synthesize acetylsalicylic acid, commonly known as aspirin, and methyl salicylate, oil of wintergreen, from salicylic acid. The knowledge organiser includes the method and apparatus diagrams and goes into more depth about filtration under reduced pressure, recrystallisation and reflux. You will be able to see how two very different organic compounds can be made from the same common starting material. Edexcel asa level chemistry student book 1 answers.