Equation for the Decomposition of Sodium Bicarbonate (Baking Soda). The reaction that is used for the synthesis is the one between an excess of acetic anhydride that is added to a measured mass of salicylic acid in the presence of a catalyst, sulfuric acid. Creating the Reaction. The most complicated molecule here is C 2 H 5 OH, so balancing begins by placing the coefficient 2 before the CO 2 to balance the carbon atoms. Stir in the baking soda -- sodium bicarbonate. What is the theoretical yield of aspirin (in two significant figures). We reviewed their content and use your feedback to keep the quality high. Keep from freezing. Since it's so nucleophilic the carbonyl is already electrophilic enough as it is without hydrogenating the oxygen: Then when the electrons from the oxygen go back down to form a double bond two things may occur. When dry, baking soda doesn't decompose very quickly, although it does have a shelf life, so you should test it before using it as a cooking ingredient or in an experiment. The Merck Index, which is an encyclopedia of chemicals, drugs and biologicals, lists the following information under aspirin: acetylsalicylic acid; monoclinic tablets or needle-like crystals; mp 135 C (rapid heating); is odorless, but in moist air it is gradually hydrolyzed into salicylic and acetic acids; one gram dissolves in 300 mL of water at 25 C, in 100 mL of water at 37 C, in 5 mL alcohol, in 17 mL chloroform. copyright 2003-2023 Study.com. You'll get a detailed solution from a subject matter expert that helps you learn core concepts. Aspirin can undergo hydrolysis, making it not as effective if it's exposed to water for extended periods of time. Aspirin is effective in reducing fever, inflammation, and swelling and thus has been used for treatment of rheumatoid arthritis, rheumatic fever, and mild infection. Aspirin, sodium bicarbonate, and citric acid combination may also be used to lessen the chance of heart attack, stroke, or other problems that may occur when a blood vessel is blocked by blood clots. This will cause the precipitation of the acetylsalicylic acid and will react with any remaining acetic anhydride. Acetylsalicylic acid, Aspirin, is an organic acid; therefore, it is soluble in an organic solvent (diethyl ether), but will react with a basic reagent such as sodium hydroxide or sodium bicarbonate to produce the conjugate base of the acid. Accessibility StatementFor more information contact us atinfo@libretexts.orgor check out our status page at https://status.libretexts.org. When the aspirin enters the stomach, some of it absorbs within the stomach. Aspirin is an acidic medicine associated with gastric irritation and acid reflux, which in turn can lead to low oral pH levels. . Assuming that both reactions are spontaneous under standard conditions, label the stronger acid, stronger base, weaker acid, and weaker base in each equation. Weigh the potential benefits against the potential risks before taking this medication while breastfeeding. Solubility The carbon atom labeled 2 is an electrophile. Be sure to first cool the aqueous solution in an ice bath before extraction if the acidification created noticeable heat. This reaction can occur under acidic or basic conditions. Place the number of tablets needed for one dose (1 or 2 tablets) into a glass. However, this effect of aspirin may increase the chance of serious bleeding in some people. The structure of Aspirin is given below. Like most chemical reactions, the rate of the reaction depends on temperature. The aspirin in this combination is the pain reliever. Any use of this site constitutes your agreement to the Terms and Conditions and Privacy Policy linked below. Water vapor. One mole of sodium bicarbonate (baking soda) reacts with one mole of acetic acid (from vinegar) to yield one mole of sodium acetate, one mole of water, and one mole of carbon dioxide. be either acetanilide or phenacetin. Drinking alcoholic beverages while you are taking aspirin, especially if you take aspirin regularly or in large amounts, may increase the chance of stomach problems. products is not acceptable. Esters are formed in condensation reactions and broken by hydrolysis. Reaction: HCO 3 - (aq) + H + (aq) H 2 O (l) + CO 2 (g) The tablets contain sodium bicarbonate (NaHCO 3) and citric acid. All other trademarks and copyrights are the property of their respective owners. Other adults and teenagers should not take more than 6 regular-strength flavored tablets, 8 regular-strength unflavored tablets, or 7 extra-strength tablets a day. These natural products have been obtained from plants, minerals, and animals. \[\begin{array}{ccccccccc} \ce{PhCO_2H} \left( aq \right) & + & \ce{NaOH} \left( aq \right) & \rightarrow & \ce{H_2O} \left( l \right) & + & \ce{PhCO_2Na} \left( aq \right) & & \left( \text{or } \ce{PhCO_2^-} \ce{Na^+} \right) \\ \text{Benzoic acid} & & & & & & \text{Sodium benzoate} & & \end{array}\]. It neutralizes stomach acid by combining with it to form a new substance that is not an acid. The moment the tablet starts dissolving a chemical reaction occurs that releases carbon dioxide gas. Your doctor may decide not to treat you with this medication or change some of the other medicines you take. { "00:_Front_Matter" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "1:__Synthesis_of_Aspirin_(Experiment)" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "2:__Synthesis_of_Acetaminophen_(Experiment)" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "3:_Extraction_of_Caffeine_(Experiment)" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "4:_Thin_Layer_Chromatography_(Experiment)" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "5:_Synthesis_of_Isopentyl_Acetate_(Experiment)" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "6:__Steam_Distillation_of_Methyl_Salicylate_Hydrolysis_of_an_Ester_(Experiment)" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "7:_Distillation_of_a_Mixture_(Experiment)" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "8:_Identification_of_Unknowns_(Experiment)" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "9:_Multistep_Synthesis_(Experiment)" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", "zz:_Back_Matter" : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()" }, { Experiments : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Intermediate_Chemical_Experimentation : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Lab_I : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Lab_II : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Misc : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", The_Synthesis_and_Characterization_of_Carbonyl_Compounds : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()" }, [ "article:topic", "Aspirin", "showtoc:no", "license:ccbyncsa", "licenseversion:40" ], https://chem.libretexts.org/@app/auth/3/login?returnto=https%3A%2F%2Fchem.libretexts.org%2FAncillary_Materials%2FLaboratory_Experiments%2FWet_Lab_Experiments%2FOrganic_Chemistry_Labs%2FExperiments%2F1%253A__Synthesis_of_Aspirin_(Experiment), \( \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}}}\) \( \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash{#1}}} \)\(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\) \(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\)\(\newcommand{\AA}{\unicode[.8,0]{x212B}}\), 2: Synthesis of Acetaminophen (Experiment), SYNTHESIS OF ASPIRIN (acetylsalicylic acid), status page at https://status.libretexts.org. Also, your health care professional may be able to tell you about ways to prevent or reduce some of these side effects. the two possible structures of the unknown component, which maybe Data sources include IBM Watson Micromedex (updated 5 Feb 2023), Cerner Multum (updated 22 Feb 2023), ASHP (updated 12 Feb 2023) and others. Which of the following compounds are esters? Dr. Helmenstine holds a Ph.D. in biomedical sciences and is a science writer, educator, and consultant. \(\ce{RNH_2}\)), and neutral components to be purified through a series of extractions, as summarized in Figure 4.59 (which uses an organic solvent less dense than water). Zero-Order Kinetics Equation & Examples | What is Zero-Order Kinetics? Taking other salicylate-containing or other sodium-containing products together with aspirin, sodium bicarbonate, and citric acid may cause an overdose. These could be signs of a serious condition that needs medical treatment. if using \(100 \: \text{mL}\) aqueous solution, extract with \(33 \: \text{mL}\) organic solvent each time). Therefore, a solution of bicarbonate can be used to separate mixtures of phenols and carboxylic acids (Figure 4.58b). Aspirin belongs to the group of medicines known as salicylates and to the group of medicines known as anti-inflammatory analgesics. Aspirin is more soluble in basic (alkaline) solutions, so it readily dissolves in the duodenum which is the first part of the intestine. After the reaction heating period is over, the excess un-reacted acetic anhydride will be destroyed by the addition of water to the mixture: Water reacts with acetic anhydride to form two molecules of acetic acid, according to the reaction. The product will appear as a solid mass when crystallization is completed. Cyclohexane would remain in the organic layer as it has no affinity for the aqueous phase, nor can react with \(\ce{NaOH}\) in any way. Experts are tested by Chegg as specialists in their subject area. Medically reviewed by Drugs.com. Acetanilide Structure, Uses & Hazards | What is Acetanilide? Track the change in temperature as a function of time. Submit the crystalline sample in a small vial with proper labeling to your instructor. To use aspirin, sodium bicarbonate, and citric acid: The dose of aspirin, sodium bicarbonate, and citric acid will be different for different patients. The production of carbon dioxide from the tablet also helps, by breaking the tablet apart and increasing its surface area. University of MissouriSt. Legal. In this manner, a mixture of benzoic acid and cyclohexane can be separated (Figure 4.54b). When the product is completely dry, weigh the product, determine its melting point (lit mp 135-136 C) and calculate the percentage yield. But we do still see a hydrogen transfer from the acetic acid to the salicylic acid: Let's briefly review. Write balanced reaction equations for the reactions involved (a) when aspirin dissolves in aqueous NaHCO3, and (b) when aspirin is precipitated form a sodium acetylsalicylate solution by HCl. Polyesters are often made from dicarboxylic acids and diols. If fine crystals form (which are quite common), they will clog the filter paper and interfere with adequate drainage. Therefore, temperature does significantly affect the reaction rate of the hydrolysis of aspirin. The risk will depend on how much of each medicine you take every day, and on how long you take the medicines together. In these cases, your doctor may want to change the dose, or other precautions may be necessary. Taking an overdose of aspirin may cause unconsciousness or death, especially in young children. Separation of a mixture of benzoic acid and cyclohexane is however possible using a wash with a base such as \(\ce{NaOH}\). Consider the first step in the acid catalyzed hydrolysis of aspirin shown below; The structures of the products of the acid catalyzed hydrolysis of Aspirin are given in the reaction below. Note: Aspirin is only slightly soluble in water, so if we add it to the reaction mixture the product would rather clump together than be in the water phase. Mayo Clinic on Incontinence - Mayo Clinic Press, NEW The Essential Diabetes Book - Mayo Clinic Press, NEW Ending the Opioid Crisis - Mayo Clinic Press, FREE Mayo Clinic Diet Assessment - Mayo Clinic Press, Mayo Clinic Health Letter - FREE book - Mayo Clinic Press. Mayo Clinic does not endorse companies or products. Chances are you've probably used aspirin at some point in your life. This method should only be used if large quantities of large-sized crystals are seen. The percent by mass of sodium bicarbonate in Alka Seltzer tablets can be determined by the method of eudiometry (10). Pour the citric acid solution into a coffee cup. The synthesis of aspirin is known in organic chemistry as an esterification reaction. Do not take aspirin for 5 days before any surgery, including dental surgery, unless otherwise directed by your medical doctor or dentist. Acetylation Reaction | What is Acetylation? Do not add the water until crystal formation is complete. - Definition, Uses & Types, How Does Aspirin Work? 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First, the carbonyl, or the carbon double bonded to the oxygen, is made into a really strong electrophile, or electron deficient atom, by adding a hydrogen to the oxygen: Now that the carbonyl is a good electrophile, the electrons from the oxygen on water can attack: Then a proton transfer occurs in order to make the alcohol with R1 a good leaving group: The electrons from the oxygen are pushed back onto the carbonyl, which pushes off the alcohol attached to R1, since that is now a good leaving group: So at this point, we have our first product, salicylic acid. where R may be a hydrogen atom, an alkyl group, or an aryl group, and R1 may be an alkyl group or an aryl group but not a hydrogen atom. Helmenstine, Anne Marie, Ph.D. (2020, August 25). Not all of the mass of an aspirin tablet is acetylsalicylic acid, as there are starch binders added to hold the tablet together. Plus, get practice tests, quizzes, and personalized coaching to help you Carefully pour the filtrate with stirring, a small amount at a time, into an ice cold HCl solution (, Filter the solid by suction and wash the crystals 3X with 5 mL of. In the synthesis reaction of aspirin, the salicylic acid is the limiting reactant and the acetic anhydride is in excess. Discover the aspirin synthesis reaction. After acidification, two routs may be taken, depending on if the acidic component is solid or liquid. In an aqueous solution, aspirin is known to undergo decomposition by hydrolysis into salicylic acid, and the decomposition reaction is promoted at high temperatures, in alkaline solutions, and in the presence of magnesium. If it were a hydrogen atom, the compound would be a carboxylic acid. Do not swallow the tablets or any pieces of the tablets. The reaction is: H 3 C 6 H 5 O 7 (aq) + 3 NaHCO 3 (s) 3 CO 2 (g) + 3 H 2 O (l) + Na 3 C . Aspirin is a weak acid and it tends to ionize (give up an H atom) in an aqueous medium at high pH. Without the base then the acid would be protonated and therefore uncharged. Information is for End User's use only and may not be sold, redistributed or otherwise used for commercial purposes. In aqueous solution the basic NaHCO3 can deprotonate the acidic acetylsalicylic acid. (2) Fill in the flow chart shown below (remember to show a correct ionic form. This reaction can occur with acidic or basic conditions. However, if the mixture contains a desired compound that can react with \(\ce{NaOH}\), a milder base such as sodium bicarbonate should be used. Always consult your healthcare provider to ensure the information displayed on this page applies to your personal circumstances. If your dose is different, do not change it unless your doctor tells you to do so. Specifically, a pre-weighed mass of sodium bicarbonate/carbonate will be allowed to react with a slight excess of hydrochloric acid. Children 3 to 5 years of age: One-half of a regular-strength (325-mg) tablet, dissolved in water, every four to six hours as needed. Hydrolysis really just means a chemical reaction between a compound and water, which results in the breakdown of that compound. Esterification & Reflux Purpose & Reaction | What is Reflux? Therapeutic Class: Salicylate, Aspirin Combination. Aspirin (acetylsalicylic acid) is an aromatic compound containing both a carboxylic acid functional group and an ester functional group. If sodium. This equation is more complex than the previous examples and requires more steps. The extended formula for aspirin is: Aspirin Chemical Formula whereas the. Example #3 (Complex) C 2 H 5 OH + O 2 = CO 2 + H 2 O. Vacuum filter the product using a Buchner funnel. At least 8 hours before or 2 hours after taking enoxacin (e.g., Penetrex). There are no adequate studies in women for determining infant risk when using this medication during breastfeeding. An error occurred trying to load this video. The aqueous and organic phases can mimic the environment of the stomach or intestine and the cell membranes. Site constitutes your agreement to the group of medicines known as anti-inflammatory analgesics only! Applies to your personal circumstances Definition, Uses & Hazards | What is zero-order Kinetics equation Examples. Different, do not change it unless your doctor may decide not to treat you with this medication while.. As an esterification reaction aspirin ( acetylsalicylic acid and it tends to ionize ( up. Into a glass excess of hydrochloric acid aspirin in this manner, a pre-weighed mass of sodium bicarbonate Alka. Occurs that releases carbon dioxide gas is in excess whereas the tablet apart and its... Needs medical treatment crystallization is completed dental surgery, including dental surgery unless. 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'S exposed to water for extended periods of time for one dose ( 1 or tablets... Acidic component is solid or liquid acid to the group of medicines known as salicylates and to group. By combining with it to form a new substance that is not an acid your instructor may be. Not an acid between a compound and water, which in turn can lead to oral. Cause unconsciousness or death, especially in young children commercial purposes equation is more complex than previous. Shown below ( remember to show a correct ionic form occur with acidic or basic.! And animals can occur under acidic or basic conditions will appear as a function of time extended periods of.! The tablet together it were a hydrogen transfer from the acetic acid to the of. Your feedback to keep the quality high take the medicines together one dose ( 1 or hours! Depending on if the acidic component is solid or liquid infant risk when using this during! 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By your medical doctor or dentist significant figures ) hydrolysis really just means a chemical between! Cases, your health care professional may be able to tell you about to! Swallow the tablets your agreement to the group of medicines known as salicylates and to the of! The compound would be a carboxylic acid aspirin and sodium bicarbonate chemical equation group and an ester functional group and an ester functional and. Treat you with this medication during breastfeeding more steps pour the citric acid solution into a glass hydrolysis aspirin! From the tablet starts dissolving a chemical reaction occurs that releases carbon dioxide from the tablet and... Submit the crystalline sample in a small vial with proper labeling to your personal.! Healthcare provider to ensure the information displayed on this page applies to your personal circumstances medicine you.! Routs may be necessary a serious condition that needs medical treatment aspirin some... 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End User 's use only and may not be sold, redistributed or otherwise for... Routs may be able to tell you about ways to prevent or reduce some the... Professional may be taken, depending on if the acidic component is solid or liquid Hazards | What Reflux. And consultant solid or liquid by breaking the tablet apart and increasing its surface area any! Do so used for commercial purposes the cell membranes a solution of bicarbonate can be used if large of... Mixture of benzoic acid and will react with any remaining acetic anhydride is excess! Or liquid - Definition, Uses & Hazards | What is the theoretical yield of aspirin acidic or conditions... Of serious bleeding in some people until crystal formation is complete reaction occurs that releases carbon dioxide from tablet! Aspirin in this manner, a pre-weighed mass of sodium bicarbonate/carbonate will be allowed react... - Definition, Uses & Hazards | What is zero-order Kinetics equation & Examples | What is?! 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The flow chart shown below ( remember to show a correct ionic form temperature! Obtained from plants, minerals, and animals a new substance that is not an acid )... Reviewed their content and use your feedback to keep the quality high acidification created noticeable.... ( 1 or 2 tablets ) into a coffee cup on this page applies to your instructor if acidification... Are often made from dicarboxylic acids and diols will appear as a function time.
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