You will loose some yield, but not much. have a stronger attraction to water than to organic solvents. O A Because NaHCO3 deprotonates 3-chlorobenzoic acid and NaOH does not O B Because NaOH deprotonates both 3-chlorobenzoic acid and 2-naphthol 0 C Because NaHCO3 deprotonates both 3-chlorobenzoic acid and This problem has been solved! %PDF-1.3 Get access to this video and our entire Q&A library. Ethanol, methanol, tetrahydrofuran (THF) and acetone are usually not suitable for extraction because they are completely miscible with most aqueous solutions. Washing is also used as a step in the recrystallization procedure to remove the impurity containing mother liquor adhering to the crystal surface. Additionally, solutes dissolved in an organic layer with polar functional groups (e.g. Why is a conical flask used in titration? . For instance, if the target compound was the base in the system, the extraction with HCl should be performed first. Let's consider two frequently encountered Remove the finger on the pipette to allow a sample of the aqueous layer to enter the pipette through capillary action (Figure 4.42b). First inspect the solution to see if it's homogenous, or if there is a second layer of liquid (typically a puddle on the bottom). Predict the results you would expect if the following treatments were performed on four-cell embryos of each of these two species (assuming these manipulations could actually be performed): a. In this particular case K saccharin is a large number because saccharin is more soluble in ether than water while K salt is a small number because salt is slightly soluble in ether. Carbonic acid is in equilibrium with the water so there will be protons free for making HCl. The mixture is dissolved in ether and mixed thoroughly with aqueous sodium bicarbonate (weaker base). The bottom layer is always removed first independently if this is the one of interest or not because it is much easier to do. Figure 4.47 shows how brine affects the partitioning of red food dye in ethyl acetate and aqueous solutions. Summary. The reason sodium carbonate is added to the tea is because the tannins are acidic and sodium carbonate is a base, so when sodium carbonate is added to the tea water mixture, the acids are . Figure 4.44 shows a qualitative difference in the amount of water present in an organic layer with and without the use of a brine wash. Ethyl acetate was shaken with water (Figure 4.44a), then dried with a portion of anhydrous \(\ce{MgSO_4}\). I'm just spitballing but that was my initial guess when I saw this. The most important point to keep in mind throughout the entire extraction process is which layer contains the product. Acid-Base Extraction. Bicarbonate ion has the formula HCO 3 H C O. Use ACS format. Quickly removes most water, and can hold a lot for its mass (\(0.15\)-\(0.75 \: \text{g}\) water per \(\text{g}\) desiccant).\(^9\) Is a fine powder, so must be gravity filtered. This undesirable reaction is called saponification. When utilizing extraction solvents for liquid-liquid extraction, two solvents must be used; one is usually water or water-based, and the other an organic solvent. The density is determined by the major component of a layer which is usually the solvent. Thus, diethyl ether and ethyl acetate, which are both less dense than the dilute solutions that are usually used for extraction, form the top layer, while dichloromethane and chloroform form the bottom layer (currently both of them are not used in Chem 30BL or Chem30CL due to safety concerns!). Draw the reaction between acetylsalicylic acid and NaHCO 3 then draw the reaction between that product and HCl. Why does the pancreas secrete bicarbonate? e. General Separation Scheme The method is based on the extraction of phosphate from the soil by 0.5 N sodium bicarbonate solution adjusted to pH 8.5. Sodium carbonate is used for body processes or reactions. \(\ce{Mg(H_2O)_4^{2+}}\) is somewhat acidic, so is incompatible with highly acid-sensitive groups. For neutral organic compounds, we often add Why does sodium bicarbonate raise blood pH? Figure 4.47d shows the brine layer containing the dye after shaking with a portion of ethyl acetate. Most neutral compounds cannot be converted into salts without changing their chemical nature. the solution was swirled with white anhydrous \(\ce{MgSO_4}\), and the drying agent turned pink as it adsorbed the red food dye compound (Figure 4.45a). What is the purpose of a . hydroxide base does not produce CO2 like the bicarbonate base does; no CO2 is being generated here when the hydroxide base is added to the ether soln. Why is NaHCO3 used in extraction? This difference in acidity can be exploited to separate carboxylic acids and phenols from each other in an organic layer. The container should be vented immediately before the pressure build-up can cause an explosion, an ejection of the stopper on the top or excessive spillage upon opening. In addition, many extraction processes are exothermic because they involve an acid-base reaction. 2. It is not uncommon that a small amount of one layer ends up on top of the other. The solution of these dissolved compounds is referred to as the extract. Why does a volcano erupt with baking soda and vinegar? 11.2. Experiment 1 - Determination of Physical Prop, Experiment 2 - Infrared Spectroscopy: Liquid, Experiment 3 - Simple Miniscale & Microscale, Experiment 4 - Steam Distillation & Isolation, Experiment 15 - Hydrogenation of Castor Oil, Experiment 13 - Synthesis of Ethanol by Ferme, Julie S Snyder, Linda Lilley, Shelly Collins, Winningham's Critical Thinking Cases in Nursing, Overview of Neuroscience Part 3 (SUBDIVISIONS. \(\ce{CH_3CH_2OH}\) or \(\ce{CH_3COCH_3}\)). Solvent extraction is the process of separating compounds by utilizing their relative solubilities. Cite advantages and disadvantages of using the following drying agents: a) sodium sulfate b) magnesium sulfate c) sodium carbonate d) potassium carbonate. so to. The resulting salts dissolve in water. The LibreTexts libraries arePowered by NICE CXone Expertand are supported by the Department of Education Open Textbook Pilot Project, the UC Davis Office of the Provost, the UC Davis Library, the California State University Affordable Learning Solutions Program, and Merlot. Before using the separatory funnel, the user should check if the stopcock plug and the stopcock fit together well. because CO2 is released during the procedure. From this point of view, a solvent with higher density than water would be preferential, especially when very small quantities are used. What functional groups are found in proteins? The organic layer is pinker, signifying that more dye has now partitioned toward the organic layer. The conical shape of these pieces of equipment makes it easier to collect the solution on the bottom using a Pasteur pipette because of the smaller interface. Multiple extractions with smaller quantities are preferred over one extraction with the same quantity of solution/solvent. In order to remove an acidic compound from a mixture, a base like NaOH or NaHCO3 is used. Sodium bicarbonate is also used as an odour neutraliser, cleaning or exfoliating agent, and sometimes as a temporary fire extinguisher. Often times the cap is either the wrong cap in the first place or it is not properly placed on the top. The shaking of the mixture increases the surface area, and therefore the apparent vapor pressure of the solvent. Add a small portion of drying agent to the flask,the size of one pea for macroscale work (Figure 4.51b), and swirl the solution (Figure 4.51c). Solvents like dichloromethane (=methylene chloride in older literature), chloroform, diethyl ether, or ethyl ester will form two layers in contact with aqueous solutions if they are used in sufficient quantities. western blot for protein, or for DNA extraction).Most lysis buffers contain buffering salts (e.g. Give the purpose of washing the organic layer with saturated sodium chloride. However, this can change if very concentrated solutions are used (see table in the back of the reader)! Strictly speaking, the two operations are targeting different parts in the mixture: while the extraction removes the target compound from an impure matrix, the washing removes impurities from the target compound i.e., water by extraction with saturated sodium chloride solution. Figure 4.47b shows the water layer containing the dye after shaking with a portion of ethyl acetate. Water may be produced here; this will not lead to a build up of pressure. Formulated as 75 g per liter of water, Gibco Sodium Bicarbonate, 7.5% Solution is perfect for supplementing dry powder medium during reconstitution. In this way, blue Drierite can be used as a visual indicator for the presence of water.\(^8\). When the goal of an experiment is to conduct a reaction and isolate the product, the general sequence of events is shown in Table 4.4. Ammonium salts from primary amines are much more soluble in water than salts from tertiary amines due the increased ability to form hydrogen bonds [(H3NEt)Cl: 280 g/100 g H2O, (H2NEt2)Cl: 232 g/100 g H2O, (HNEt3)Cl: 137 g/100 g H2O (all at 25 oC)]. About 5 % of a solute does not change the density of the solution much. 59 Experimental Procedure 1) Mix isopentyl alcohol (5.4 mL, via burette) and glacial acetic acid (8.5 mL, via graduated . However, they do react with a strong base like NaOH. Additionally, ionic solutions have high dielectric constants, making them less compatible with organic compounds. 1. transfer ether solution to clean labeled 125 mL Erlenmeyer flask; add anhydrous sodium sulfate until it stops clumping. Keep in mind that it is always easier to recover the product from a different layer in a beaker than from the waste container or the sink. When it is known, through experience, that some mixtures may form emulsions, vigorous shaking should be avoided. Why does the sodium potassium pump never run out of sodium or potassium? Why is sulphuric acid used in redox titration? such as sodium hydroxide or sodium bicarbonate to produce the conjugate base of the acid. Part D) Isolating p-Toluic Acid and p-tert-Butylphenol. Why is extraction important in organic chemistry? Why is the removal of air bubbles necessary before starting titration? The aq. 1. add 10-15 mL of 0.5 M NaHCO3 to the ether solution; shake funnel & allow layers to separate. Press J to jump to the feed. In this experiment you will use extraction techniques to separate a mixture of an organic acid, a base, and a neutral compound. Since the carboxylic acids that are used in Chem 30BL are solids, using them in excess would produce a heterogeneous reaction mixture. 1. (C2H5)2O + NaOH --> C8H8O2 + H2O. sodium hydroxide had been used? . What is the purpose of using washing buffer during RNA extraction? 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Also, samples intended for GC analysis must be neutral as acidic solutions degrade the polymeric coating of the GC column. With a finger placed atop the glass pipette again, remove the pipette from the separatory funnel. Which sequence is the most efficient highly depends on the target molecule. Enumerate some of the common drying agents and identify how each can be, Commonly used drying agents in organic laboratories are calcium chloride (CaCl, All four of them readily form hydrates at low, The efficiency of a drying agent (measured by intensity, capacity and velocity) can. don't want), we perform an "extraction". What is N-(2,2,2-Trichloroethyl)carbonyl] Bisnor-(cis)-tilidine's functional group? Reminder: a mass of the. 2. The reaction affords carbon dioxide (CO2), which is a gas at ambient temperature. The sodium bicarbonate wash in this example was necessary (and discussed in the next section) because a water wash alone may not fully remove the acetic acid. An organic layer is always treated with a drying agent after having been exposed to water in a separatory funnel (step c) in Table 4.4). Addition of more anhydrous \(\ce{MgSO_4}\) made the drying agent pinker (Figure 4.45b), as more dye was removed from solution. All rights reserved. Process of removing a compound of interest from a solution or solid mixture. If using anhydrous \(\ce{Na_2SO_4}\), allow the solution to sit for at least 5 minutes before declaring the solution dry, as this reagent takes time to work. The bubbling was even more vigorous when the layers were mixed together. The CO2 is visible as bubbles; as the pressure from the CO2 builds up, gas and some of the liquid is pushed up and out. Bicarbonate ion has the formula {eq}HCO_3^-{/eq}. ago Posted by WackyGlory b. The purpose of washing the organic layer with saturated sodium chloride is to remove the . c. Removal of an amine 5Q. After the extraction, the phenol can be recovered by adding a mineral acid to the basic extract. The most common wash in separatory funnels is probably water. Thus, additional precautions (i.e., frequent venting) have to be taken to prevent any accidents resulting from the pressure build up in the extraction vessel. What would have happened if 5% NaOH had been used? By. Background Extraction is a frequently used technique to selectively transfer a compound of interested from one solvent to another. In many cases, centrifugation or gravity filtration works as well. 8.4.1.7 Sodium bicarbonate Sodium bicarbonate (NaHCO3) does not have any direct antibacterial effect but it has a cleansing action by loosening debris and dissolving mucus. With water being so tightly "occupied" in dissolving the ions in these solutions, they are less capable of dissolving organic compounds. Fortunately, the patient has all the links in the . anhydrous sodium sulfate, magnesium sulfate, or calcium chloride), these reagents at best remove only small amounts of water. j. Whatever remains in the organic layer is not of interest anymore afterwards, unless one of the other compounds has to be isolated from this layer as well. Sodium bicarbonate is an ionic compound of sodium ion and bicarbonate ion. An acidic solution turns blue litmus paper pink (or red), while a neutral or basic solution gives blue litmus paper only a darkened "wet" appearance (Figure 4.42d). If using a fine powder, the solution must be gravity filtered and drying agent rinsed. Its slight alkalinity makes it useful in treating gastric or urinary . Esters are synthesized from either organic or inorganic acids through a process called esterification.2 In this reaction, a carboxylic acid (RCOOH) and an alcohol (R'OH) mix in the presence of a strong acid catalyst to form a neutral, water-insoluble ester (RCOO'R) that gives off a pleasant smell.3 The following is an example of this reaction: Why is back titration used to determine calcium carbonate? Hey there! layer is neutralised with NH3 or Na2CO3 and again extracted with ethyl acetate. When the solution is dry, separate the drying agent from the solution: If using \(\ce{Na_2SO_4}\), \(\ce{CaCl_2}\) pellets, or \(\ce{CaSO_4}\) rocks, carefully decant the solution into an appropriately sized round-bottomed flask (Figure 4.53b), being sure to fill the flask no more than halfway. \(^5\)When assessing the result of a litmus paper test, look at the center of the drop. Register Yourself for a FREE Demo Class by Top IITians & Medical Experts Today ! It is not possible to test the pH of an organic solution directly, however it is possible to test the pH of an aqueous solution that the organic solution has been in contact with. After the reaction is complete, you will remove the excess acetic acid and sulfuric acid from the reaction mixture by extraction with sodium hydrogen carbonate. 4 0 obj In some cases, a careful draining of the existing lower layer can also be helpful because it pushed the bubbles together in the smaller part of the extraction vessel. How much solvent/solution is used for the extraction? c. The cells from two different four-celled embryos are fused together to make an eight-celled embryo. For an organic compound, it is relatively safe to assume that it will dissolve better in the organic layer than in most aqueous solutions unless it has been converted to an ionic specie, which makes it more water-soluble. Why use methyl orange instead of phenolphthalein as a pH indicator. The large clumps of drying agent in Figure 4.44b indicate that this ethyl acetate layer is still noticeably wet. Why is aqueous NaHCO3 used for separation of benzoic acid from methyl benzoate? \(^7\)From: Fessenden, Fessenden, Feist, Organic Laboratory Techniques, 3\(^\text{th}\) ed., Brooks-Cole, 2001. Benzoic acid is, well, an acid. Plz answer me. Identify one cation and one anion in the given unknown salt m1 by performing dry tests. This constant depends on the solvent used, the solute itself, and temperature. The dye has obviously partitioned toward the aqueous layer, which is consistent with its very polar structure (Figure 4.46). Why is EDTA used in complexometric titration? Why does sodium create an explosion when reacted with water? e. Why does the extraction container (vial, centrifuge tube, separatory funnel) make funny noises? Brine works to remove water from an organic layer because it is highly concentrated (since \(\ce{NaCl}\) is so highly water soluble). Washing. the polar dye molecules are much less soluble in the brine solution than in pure water (they have been "salted out"). A wet organic solution can be cloudy, and a dry one is always clear. The initial product of reaction (1) is carbonic acid \(\left( \ce{H_2CO_3} \right)\), which is in equilibrium with water and carbon dioxide gas. - prepare 2 m.p. Ca (OH)2 + CO2 CaCO3 + H2O This highly depends on the quantity of a compound that has to be removed. The organic solvents that require a brine wash before exposure to a solid drying agent are diethyl ether and ethyl acetate. greatly vary from one solvent to the other. 1. cool sodium bicarbonate solution (part a) & sodium hydroxide solution (part b) by setting the 2 flasks in ice water bath. : r/OrganicChemistry r/OrganicChemistry 10 mo. This often leads to the formation of emulsions. If the litmus paper turns pink at all, the base wash has not fully neutralized the organic layer, and subsequent base washes are needed. Why is sodium bicarbonate used in fire extinguishers? Early C. elegans embryos display mosaic determination, whereas early mouse embryos exhibit regulative determination. We are not going to do that in order to decrease the complexity of the method. Why might a chemist add a buffer to a solution? copyright 2003-2023 Homework.Study.com. known as brine). If the target compound was an acid, the extraction with NaOH should be performed first. Anhydrous magnesium sulfate \(\left( \ce{MgSO_4} \right)\) is a fine, loose powder (Figure 4.49a), but its hydrate is clumpy and often clings to the glass (Figure 4.49b). d. How do we know that we are done extracting? Add another portion of drying agent and swirl. Why is phenolphthalein an appropriate indicator for titration? In order to separate a carboxylic acid compound from the rest of the organic substances, a solution of sodium bicarbonate is added during extraction. Our experts can answer your tough homework and study questions. the possible sources of error may have occurred when: one was emptying the solution in the clean beaker while filtering the acetanilide solution, some of the solution may have been wasted because it remained in the filtered flask. Question 1. However, in some cases it is possible to accomplish a phase separation by the addition of large amounts of a salt (salting out). An extraction can be carried out in macro-scale or in micro-scale. However, it is most common for desiccators and drying tubes to use \(\ce{CaSO_4}\) or \(\ce{CaCl_2}\) (Figure 4.50), as they can be easily manipulated in their pellet or rock forms. Why is sodium bicarbonate used for kidney disease? It can be difficult to completely remove a water layer by pipette, so leaving a tiny bit is acceptable. It reacts almost instantaneously to neutralize HCl to produce CO 2 and NaCl. 75% (4 ratings) for this solution. Why is bicarbonate important for ocean acidification? The organic material in the liquid decays, resulting in increased levels of odor. The purpose of washing the organic layer with saturated sodium chloride is to remove. If the aqueous layer is on the bottom of the separatory funnel, test an "aliquot" of the aqueous layer (or tiny sample) on litmus paper through the following method: In some experiments, an organic layer may be washed with brine, which is a saturated solution of \(\ce{NaCl} \left( aq \right)\). What should I start learning after learning the basics of alkanes, alkenes, and alkynes? What are advantages and disadvantages of using the Soxhlet extraction technique? In cases, where the phases have similar polarity or density, the addition of more solvent can assist the separation. Why is bicarbonate low in diabetic ketoacidosis? It helps to regulate and neutralise high acidity levels in the blood. Give the purpose of washing the organic layer with saturated sodium chloride. Drying agents are anhydrous inorganic materials that favorably form "hydrates", which incorporate water molecules into their solid lattice structure (for example, \(\ce{Na_2SO_4} \cdot 7 \ce{H_2O}\)). They utilize a mixture of powerful ingredients to strengthen enamel, prevent cavities, replenish calcium, reduce plaque, and prevent gingivitis in the best ways advances in science have discovered over the last 100 or more years. The work-up refers to methods aimed at purifying the material, and most commonly occur in a separatory funnel. A bit of liquid should remain in the pipette tip, an aliquot of the bottom layer (Figure 4.42c). All while providing a more pleasant taste than a bitter powder. ~85F?$_2hc?jv>9 XO}.. Beets in poor conditions start to 'juice', creating a large amount of high organic content liquid. Another drawback to \(\ce{MgSO_4}\) is that all fine powders heavily adsorb product on their surface (which is why they must be rinsed with solvent after filtration), and sometimes more granular drying agents are used to minimize the loss of product by adsorption. Why do sodium channels open and close more quickly than potassium channels? Many organic solvents dissolve a significant portion of water (Table 4.6) that must be removed before rotary evaporation, or else water will be found in the concentrated product. Fischer Esterification is the name given to the acid-catalysed reaction between an alkanoic acid (carboxylic acid) and an alkanol (alcohol) (3) . \(^8\)Blue Drierite is expensive, so is commonly used by mixing it together with white Drierite (\(\ce{CaSO_4}\) without the cobalt indicator). The product shows a low purity (75%). Why was the caution in question #3a not as important when adding the hydroxide base to the ether solution? The four cells of the embryo are separated from each other and allowed to develop. What is the goals / purpose of the gravimetric analysis of chloride salt lab? We receieved your request, Stay Tuned as we are going to contact you within 1 Hour. This undesirable reaction is called. Sodium bicarbonate is widely available in the form of baking soda and combination products. Why do scientists use stirbars in the laboratory? The only time that you can really be sure about it is if you isolated the final product in a reasonable yield, and it has been identified as the correct compound by melting point, infrared spectrum, etc. How can I draw the following amines: butan-1-amine, pentan-2-amine, propan-1,2-diamine? But Baking soda (NaHCO 3 ) can act as acid as well as a base, Because of its bicarbonate anion (HCO 3-) amphoteric activity. Why is aqueous NaHCO3 used for separation of 'x' gm of a compound A3B2C5 contains 'y' gm of A atoms Using above information Match the following, WHAT IS THE VALUE OF THE elementary STATE OF AN ELEMENT. Transcribed Image Text: Mixture dissolved in organic solvent: dichloromethane benzoic acid 2-naphthol 1,4-dimethoxybenzene Extract with 25 mL of 10% NaHCO3 (3 times) organic layer aqueous layer = NaHCO3 extract separate Na* HO + 2-phthol 1,4-dimethoxybenzend sodium benzoate Extract with 25 mL of 10% NaOH (3 times) Place on ice Add HCl until As a general rule, multiple extractions with small quantities of solvent or solution are more efficient than one extraction using the same amount of solvent (see below). Safety note: To prevent excess pressure form being generated by the release of carbon dioxide gas into a separatory funnel during neutralization, the layers should be gently swirled together before placement of the stopper. R You can use extraction to separate a substance selectively from a mixture, or to remove unwanted impurities from a solution.In the practical use, usually one phase is a water or water - based (aqueous) solution and the other an organic In such an event, the mixture can be stirred slowly with a glass rod to bring the small droplets together a little faster, which ultimately leads to the formation of a new layer. Why is bicarbonate buffer system important? c. Why do the layers not separate? R. W. et al. The task of getting a clean phase separation will be more difficult if the liquids are spread out over a large, flat or curved surface. Why was NaOH not used prior to NaHCO3? This is because NaHCO3 will deprotonate only the benzoic acid , allowing it to go into the aqueous layer while the phenol is left behind in the organic layer. The following are common materials that can be removed with a water wash: unconsumed acid or base, many ionic salts, and compounds that can hydrogen bond with water (have an oxygen or nitrogen atom) and are relatively small (e.g. . Your paramedic crew responds to a cardiac arrest in a large shopping complex. Answer: It is important to use aqueous NaHCO3 and not NaOH. Why is bicarbonate the most important buffer? % Synthesis or preparation of esters in the laboratory involves 3 steps: Step 1: Synthesis of the ester. What are the advantages and disadvantages of Soxhlet extraction? It's important to know that when a compound is "water soluble" it does not necessarily mean it is "organic insoluble", a common misconception that arises from the "like dissolves like" principle. By easy I mean there are no caustic solutions and . saturated \(\ce{NaHCO_3}\), \(\ce{NaCl}\), or \(\ce{NH_4Cl}\)). Why is an indicator not used in KMnO4 titration? b) Perform multiple extractions and/or washes to partially purify the desired product. The ether layer is then NaHco3 allows us to just ionize the acid; any base would deprotonate the stronger acid, it's more about not also deprotonating the phenol. It is also a gas forming reaction. In many situations drying agents are interchangeable (see Table 4.8 for a survey of drying agents). Mixing with a stirring rod or gentle shaking usually takes care of this problem. After separation of the organic and the aqueous layer, the amine can be recovered by addition of a strong base like NaOH or KOH to the acidic extract i.e., lidocaine synthesis. varieties are used, the small-leaved China plant (C. sinensis sinensis) and the large-leaved Assam plant (C. sinensis assamica). This method estimates the relative bioavailability of inorganic ortho-phosphate (PO4-P) in soils with neutral to alkaline pH. Explain why sodium chloride, which is a nasal spray ingredient, can decongest a stuffed nose. In addition, the salt could be used to neutralize your organic layer. Extraction involves dissolving a compound or compounds either (1) from a solid into a solvent or (2) . These solvents dissolve large quantities of water in comparison to other solvents (Table 4.5). To demonstrate the effectiveness of a water wash, a Fischer esterification reaction was conducted to produce isoamyl acetate (Figure 4.38). 6. The sodium salt that forms is ionic, highly polarized and soluble in water. The target compound can subsequently be recovered by adding a mineral acid to the basic extract i.e., benzoic acid in the Grignard experiment in Chem 30CL. because a pressure build-up will be observed in the extraction container. Each foot has a surface area of 0.020. \(\ce{CaCl_2}\) value is quoted for the formation of \(\ce{CaCl_2} \cdot 2 \ce{H_2O}\). HCO3- + H2O = H2CO3 + OH- Since carbonic acid is a weak acid, it remains undissociated. What happens chemically when quick lime is added to water? Mechanism for reaction of tert-Butyl alcohol with hydrochloric acid (HCl) During the extraction, saturated aqueous sodium chloride and saturated aqueous sodium bicarbonate were used in washing the organic layer .
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