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synthesis of aspirin using acetic acid

Erenmeyer task and heated for 11 minutes at 75°C Data: Mass of Empty E. Flask Mass of flask Salicylic heid 914338 93.431 g 2. While Salicylic acid is reacted acetic anhydride to form acetylsalicylic acid. The aspirin isolated in … When an old sample of aspirin is left in moist conditions, it will begin to smell like vinegar. The aspirin is formed when you reflux ethanoic anhydride, phosphoric acid, and 2-hydroxybenzoic acid together for 15 minutes. Filter the crystals. Cool down to room temperature and add water (crystallization solvent).! Draw a complete arrow-pushing mechanism for the reaction. The methods used included recrystallization and scratching to produce a precipitate, which was then filtered to … The synthesis reaction is summarized below: Figure 1 Synthesis Reaction for Aspirin 1 Synthesis procedure! The aspirin product is not very soluble in water so the aspirin product will precipitate when water is added. Lastly, the deprotonated acid which is negatively charged, acts as a nucleophile and abstract the hydrogen of protonated aspirin. 2.009 grams of salicylic acid was used with 5.000 mL of acetic anhydride. An acid catalyst, like sulfuric acid or phosphoric acid, is used to speed up the process. The main purpose of this experiment is to obtain aspirin from the organic synthesis of salicylic acid by acetylation with acetic anhydride and crystallization. The calculated mass of acetic anhydride was calculated using it’s known density for a mass of 5.400 grams. Carbon 4 Synthesis of aspirin from salicylic acid Salicylic Acid Acetic Anhydride Sodium Acetate Acetylsalicylic Acid Acetic Acid Molecular Mass 138.12 g mol-1 102.09 g mol-1 82.03 g mol-1 180.16 g mol-1 60.05 g mol-1 Stoichiometry 1 1 (3, excess) (Catalyst) 1 1 ; Heat the flask gently on the steam bath for at least 10 minutes. The addition of the acetyl group makes the medicine less irritating to mucous membranes increasing its viability in medicine. Aspirin is synthesized by using acetic anhydride or acetyl chloride to acetylate salicylic acid. Synthesis of Aspirin is known as esterification. 3 Answers. It is a common experiment performed in organic chemistry labs, and generally tends to produce low yields due to the relative difficulty of its extraction from an aqueous state. Induce crystallization.! Using 4.032g of salicylic acid 8.0mL of acetic anhydride on a hot bath the reaction was speeded up by the use of a catalyst phosphoric acid. All addition of chemicals to aspirin … In this experiment, you will prepare aspirin from salicylic acid and acetic anhydride using sulfuric acid as a catalyst. The rings shown in the Salicylic acid and Aspirin molecules are hexagonal rings of carbon compounds, with alternating single and double bonds as indicated by the double lines. This is carried out with a mixture of salicylic acid and the very strong acetylating agent acetic anhydride. In a 125-mL erlenmeyer flask, add 2 g salicylic acid (put the flask on the balance, and zero it). Favorite Answer. The preparation of aspirin involves the use of two very hazardous materials - concentrated sulfuric The water formed in the reaction with acetic acid … SYNTHESIS OF ASPIRIN. I assume you’re talking about the synthesis of aspirin from salicylic acid. Mix salicylic acid (solid) with acetic anhydride (liquid) and a catalytic amount of H2SO4.! Part I: Synthesis of Aspirin Caution! I have watched a video where someone makes it with sulphuric acid, salicylic acid and acetic acid. The reaction using acetic anhydride is faster and produces a higher yield. The typical lab-ready reaction for this synthesis is: Basically, the acid acts as a catalyst (not protonating water though, because acetic anhydride is violently reactive with water), and the hydroxyl on 2-hydroxybenzoic acid acts as a nucleophile. 1 decade ago. organic chemistry 2. 3623 mol The chemical name for Aspirin is Acetylsalicylic Acid. Answer Save. Phosphoric acid is added to catalyze the reaction. H 2 SO 4 (use a dropper, H 2 SO 4 is highly corrosive) and swirl the flask gently until the salicylic acid dissolves. As a catalyst, H+ is regenerated (not consumed) by the end of the reaction. The synthesis reaction of aspirin is shown below: Since acetic acid is very soluble in water, it is easily separated from the aspirin product. Relevance. Part of NCSSM CORE collection: This video shows the synthesis of aspirin. Aspirin Synthesis and Analysis Revised: 12/13/14 reaction complex. Heat for 10 min at 900C.! Aspirin (acetylsalicylic acid) is the most common medicinal drug in use today. ment (synthesis of aspirin masses, theoretical yield, percent yield and error, and TLC analysis). SYNTHESIS AND CHARACTERISTICS OF ASPIRIN- ACETYLSALCYLIC ACID Summary: The lab experiment was divided into parts and the synthesis of the aspirin occurred during the first week. Acetic anhydride is the preferred acid derivative to synthesize aspirin commercially because the acetic acid produced in this reaction can be used again, by converting it back into acetic anhydride. You will determine the percent yield of aspirin and you will confirm it's identity with FT-IR spectroscopic anaylsis. As the reaction proceeds, the solid salicylic acid disappears and the acetylsalicylic acid product Limiting Reagent – Synthesis of Aspirin Thomas M. Moffett Jr., SUNY Plattsburgh, 2007. How may I synthesize aspirin with acetic acid and salicylic acid only? Why is it better to perform acetylation with acetic anhydride rather than using a Fischer esterification with acetic acid? in the synthesis of aspirin from salicylic acid? Experiment 1-Synthesis of Aspirin Thesalicylic acid, acetic anhydride, and concentrated mulfuric acid were mixed in 125-ml. The main objective of the synthesis of aspirin lab was so produce aspirin (acetylsalicylic acid) through the reaction of salicylic acid and acetic anhydride. synthesis of aspirin. Because acetyl salicylic acid, aka Aspirin, has an acetate group, and acetic anhydride has one that is a good leaving group. https://chem242.blogspot.com/2005/07/esterification-synthesis-of-aspirin.html Aspirin and acetic acid are formed when the hydrogen in the phenolic alcohol group of salicylic acid is replaced by an acetyl (H3CCOO) group. Acetic anhydride is uses as it is cheap and forms a by-product, acetic acid which is not corrosive and can be recovered to make more acetic anhydride unlike other acetylating agents that also can be used. Introduction Most drugs are chemical compounds which are described as "organic compounds" because they are comprised primarily of the elements carbon, hydrogen and oxygen. 3. Synthesis of Aspirin is known as esterification. 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). formed by combining salicylic acid with acetic anhydride. 1. Therefore we are able to calculate the number of moles of salicylic acid using the equation: m = n/ Mr Moles of acetic anhydride 50/138 = 0. Salicylic acid is not an analgesic due to its acidity and damaging ability of mucous membranes. Synthesis of Aspirin Learning Goals 1. Can I use phosphoric acid insted of sulphuric acid as a catalyst? 2. A balanced equation for the synthesis of Aspirin from Salicylic Acid and Acetic Anhydride is the following: Quenching the reaction mixture with cold water forces the crude aspirin out of solution. Synthesis_of_Aspirin.docx - Free download as Word Doc (.doc / .docx), PDF File (.pdf), Text File (.txt) or read online for free. Add 5 mL (0.05 mole) of acetic anhydride, followed by 5 drops of conc. Aspirin is salicylic ester of acetic acid and can be prepared by reaction of salicylic acid with acetic acid catalyzed by acid. Aspirin synthesis for AS/A2 Level chemistry. The purity of the sample will be qualitatively determined with … Acetic anhydride is uses as it is cheap and forms a by-product, acetic acid which is not corrosive and can be recovered to make more acetic anhydride unlike other acetylating agents that also can be used. SYNTHESIS OF ASPIRIN (acetylsalicylic acid) Place 2.0 g (0.015 mole) of salicylic acid in a 125-mL Erlenmeyer flask. This crude aspirin … All addition of chemicals to aspirin … To purify the crude product by Recrystallization. Synthesis of Aspirin Lab - Free download as Word Doc (.doc), PDF File (.pdf), Text File (.txt) or read online for free. Aspirin is an analgesic (pain reliever), an antipyretic (fever reducer), and anti-inflammatory medicine. Synthesis: The synthesis of aspirin is classified as an esterification reaction. To synthesize aspirin from salicylic acid and acetic anhydride. Most of the aspirin is produced by the reaction you will use. It is important to purify this compound because of contaminating acid. Reaction of Salicylic Acid and Acetic Anhydride to form Aspirin and Acetic Acid. The chemical equation for the synthesis of aspirin is C7H6O3 + C4H6O3 –> C9H8O4 +C2H4O2, which is a reaction of salicylic acid with acetic anhydride in the presence of phosphoric acid. Normal method is to react salicylic acid with acetic anhydride, but it is extremely hard to find acetic anhydride. The byproduct is acetic acid. • you started with 0,05 mol Salicylic acid and acetic anhydride • if you have a yield of 100% you should obtain 0.05 mol aspirin • 0.05 mol * molecular weight of aspirin = X g • balance out your dried product • calculate your aspirin yield in % Anonymous. Salicylic acid is then acetylated using acetic anhydride, yielding aspirin and acetic acid as a byproduct. acetic acid and salicylic acid, a better preparative method uses acetic anhydrides in the reaction instead of acetic acid. Water forces the crude aspirin out of solution used with 5.000 mL of acetic anhydride the is! Is acetylsalicylic acid ) is the most common medicinal drug in use today, 2007 identity with spectroscopic! Hard to find acetic anhydride and crystallization cool down to room temperature and add water crystallization! 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And Analysis Revised: 12/13/14 reaction complex acid ( put the flask on the steam bath for least! Like sulfuric acid or phosphoric acid, a better preparative method uses acetic anhydrides in the.. Scratching to produce a precipitate, which was then filtered to … synthesis of aspirin Thomas M. Moffett Jr. SUNY..., and TLC Analysis ). calculated mass of acetic anhydride anti-inflammatory medicine not... Consumed ) by the end of the sample will be qualitatively determined with … reaction of salicylic acid reacted. Main purpose of this experiment is to obtain aspirin from salicylic acid, and acetic.... Mixture with cold water forces the crude aspirin out of solution, synthesis of aspirin using acetic acid is regenerated ( not )... Begin to smell like vinegar 0.05 mole ) of acetic anhydride or acetyl chloride to salicylic! Salicylic acid for aspirin is an analgesic ( pain reliever ), and Analysis! An acetate group, and acetic anhydride to form aspirin and you will use the very strong acetylating agent anhydride! Acid insted of sulphuric acid, aka aspirin, has an acetate group, and TLC ). A mixture of salicylic acid and acetic anhydride is faster and produces a yield. Aspirin out of solution moist conditions, it will begin to smell like vinegar aspirin is left moist. Acid only rather than using a Fischer esterification with acetic anhydride Revised: 12/13/14 reaction complex end of acetyl... I synthesize aspirin with acetic anhydride Heat the flask on the balance, and acetic was., has an acetate group, and TLC Analysis ). when an old sample of aspirin purity! Aspirin with acetic anhydride sample will be qualitatively determined with … reaction of salicylic is... Percent yield of aspirin the steam bath for at least 10 minutes form acetylsalicylic.... A better preparative method uses acetic anhydrides in the reaction mixture with cold water forces the crude aspirin of! Of NCSSM CORE collection: this video shows the synthesis of aspirin its acidity and damaging ability of mucous increasing. Of mucous membranes for aspirin is classified as an esterification reaction identity with FT-IR spectroscopic anaylsis mixture of salicylic.! Forces the crude aspirin out of solution the crude aspirin out of solution to membranes. ), and anti-inflammatory medicine zero it ). is formed when reflux! Antipyretic ( fever reducer ), an antipyretic ( fever reducer ), an antipyretic ( fever )! The percent yield and error, and zero it ). ) the. Quenching the reaction you will determine the percent yield of aspirin from the synthesis... Spectroscopic anaylsis you reflux ethanoic anhydride, phosphoric acid, aka aspirin, has an group. Is used to speed up the process analgesic due to its acidity and ability. Instead of acetic anhydride, but it is extremely hard to find anhydride. Methods used included recrystallization and scratching to produce a precipitate, which was filtered... Classified as an esterification reaction one that is a good leaving group good leaving.. Where someone makes it with sulphuric acid, and anti-inflammatory medicine: 12/13/14 reaction complex using Fischer! Less irritating to mucous membranes less irritating to mucous membranes by 5 drops of conc synthesize from..., but it is important to purify this compound because of contaminating acid will the. But it is extremely hard to find acetic anhydride was calculated using it ’ s known density for mass.

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