synthesis of aspirin mechanism with sulfuric acid

Clamp a side-arm flask to the ring stand, and connect a piece of rubber tubing to the side-arm. Substituting Lewis structures for molecular formulas in chemical reactions provides more information. 0000005241 00000 n After refluxing, the resulting solution smelled quite strongly of wintergreen which indicates that the experiment was successful. Synthesis procedure! Add 8.5 ml acetic anhydride and 3-4 drops of concentrated sulphuric acid to the flask carefully and mix thoroughly. The sulfuric acid came from hardware-store drain cleaner which contained some impurities and was also not as concentrated as I would have liked. 0000001819 00000 n This reaction uses an excess of acetic anhydride, sulfuric acid as a catalyst, and heat to push the equilibrium toward the products. Practical Organic Chemistry by Frederick George Mann and Bernard Charles Saunders Published by Longan Inc., Fourth Edition; Page No. Quenching with water will leave both acid products in their protonated form. It is recommended for arthritis and related arthritic conditions, myocardial infarction prophylaxis. Recrystallize from boiling water along with small quantities of methylated spirit. Our starting material is aspirin (acetylsalicylic acid). Get a piece of filter paper that fits in the funnel, and place it flat in the funnel. 0000010832 00000 n Put a Büchner funnel with a rubber stopper in the flask. 0000009838 00000 n 0000008237 00000 n This hydrolysis reaction can be accomplished through either acid or base catalysis. Reactions: Procedure and Results: Aspirin Synthesis Tap water was heated on a steam bath in a 250 mL beaker.The temperature of an alcohol thermometer was equilibrated in a beaker of room temperature tap water. Synthesis of aspirin from salicylic acid using acetic anhydride. This procedure will use starting materials that can be found at a supermarket including aspirin, antifreeze, and drain cleaner. Weigh 6 gs of salicylic acid and transfer it to a clean and dry 250 ml conical flask. 0000003024 00000 n Bacterial growth curve cultivation of anaerobs. Principle: Synthesis of aspirin from salicylic acid occurs by acetylation process in acidic medium. 0000006303 00000 n The synthesis is broken down into two parts: hydrolysis of the aspirin and esterification. This reaction uses an excess of acetic anhydride, sulfuric acid as a catalyst, and heat to push the equilibrium toward the products. Principle: Synthesis of aspirin from salicylic acid occurs by acetylation process in acidic medium. Vogel’s text book of Practical Organic Chemistry, Page No. 0000000868 00000 n Salicylic acid interacts with acetic anhydride in presence of few drops of concentrated sulphuric acid to produce aspirin and a molecule of acetic acid. 76 0 obj << /Linearized 1 /O 78 /H [ 923 371 ] /L 191664 /E 11064 /N 22 /T 190026 >> endobj xref 76 26 0000000016 00000 n The second step is a standard Fisher esterification. The final solution had a brown-orange tint which is the result of contamination since methyl salicylate should be a colorless oil. In the first step, water is used to break the ester bond. 0000009008 00000 n Purpose: To determine which of four catalysts yields the fastest reaction rate in the acetylation of salicylic acid (1) to form acetylsalicylic acid (2). ment (synthesis of aspirin masses, theoretical yield, percent yield and error, and TLC analysis). 0000001504 00000 n trailer << /Size 102 /Info 75 0 R /Root 77 0 R /Prev 190016 /ID[<2d4afc2c761e351bf9150f76bbe78a83><2d4afc2c761e351bf9150f76bbe78a83>] >> startxref 0 %%EOF 77 0 obj << /Type /Catalog /Pages 72 0 R >> endobj 100 0 obj << /S 298 /Filter /FlateDecode /Length 101 0 R >> stream 0000001841 00000 n 0000004204 00000 n This reaction is a series of electrophilic aromatic substitutions,... Production of alcohol from sugarcane Punit Tripathi, Vectors in Gene Cloning Plasmids Yogita Salgar, Bacterial growth curve cultivation of anaerobs Suman Kumar Mekap, Neuro Humoral Transmission Suman Kumar Mekap, Principles & Mechanism of Drug Action Suman Kumar Mekap. The reaction that is used for the synthesis is shown below. In this experiment, you will prepare aspirin from salicylic acid and acetic anhydride using sulfuric acid as a catalyst. If I acquire additional glassware in the future, I will perform a distillation to purify the results. 0000004183 00000 n 0000000923 00000 n Water is added to quench the reaction, destroy the excess acetic anhydride, and cause crude aspirin to crystallize. This removes the acetate from the aspirin. Dry the synthesized product in an oven at 90 °C and calculate the yield. Click here to subscribe: Get great contents delivered straight to your inbox, just a click away, Subscribe Now, Synthesis of sulphanilamide from acetanilide, Synthesis of 9, 10-dihydroanthracene-9, 10-endo-α, β-succinic anhydride from anthracene, Synthesis of p-aminophenol from nitrobenzene, Synthesis of chalcone from benzaldehyde and acetophenone, Synthesis dihydroxytriptycene of from anthracene and p-benzoquinone, Synthesis of fluorescein from resorcinol and phthalic anhydride. 0000005262 00000 n 110. H���Mn�8��9�N����,� s��L�;�Ff�j��������]U���wv?�]���_?���ܯ�X��eO�U���_�}Br��|} ��v�[�ͭ��Ŧ���vCK�}]��)�tl��]���kW Induce crystallization.! 0000007424 00000 n Use: 0000008987 00000 n 136-137 °C.). In this reaction, the –OH on the salicylic acid acts as the alcohol and the acetic anhydride acts like a carboxylic acid. It reduces the risk of transient ischemic attacks in men. The reaction that is used for the synthesis is shown below. This hydrolysis reaction can be accomplished through either acid or base catalysis. After synthesis and analysis, it will be deter-mined if the crude and recrystallized samples were composed solely of either salicylic acid, acetylsalicylic acid, or a combination of both (3). Methyl salicylate is an organic ester responsible for the minty smell of wintergreen. Filter the crude product on a Buchner funnel using suction, wash with cold water. Aim: To prepare aspirin from salicylic acid. In practice, I decided to perform the reaction in a single flask and use concentrated sulfuric acid to complete both steps at the same time. The acid serves to protonate one double bonded oxygen on the acetic anhydride this makes the reaction with the salicylic acid faster. Subscribe our Telegram channel for regular updates. (The product is obtained as colourless crystals, yield 11 g and m.p.

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