In cases, where the phases have similar polarity or density, the addition of more solvent can assist the separation. Question 1. 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: Step 2) DCM extraction NOTE: Chromic s method separates the water first to increase the yield. Acid-Base Extraction. Fischer Esterification is the name given to the acid-catalysed reaction between an alkanoic acid (carboxylic acid) and an alkanol (alcohol) (3) . 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. 1. Even if an organic layer should not in theory dissolve very polar components such as acid, acid sometimes "hitches a ride" on polar components that may dissolve in an organic layer, such as small amounts of alcohols or water. The bubbling was even more vigorous when the layers were mixed together. 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. Fortunately, the patient has all the links in the . The presence of water with the product makes the yield inaccurate, and water also must be removed before GC-MS analysis, as water is incompatible with mass-spectrometer detectors. layer is neutralised with NH3 or Na2CO3 and again extracted with ethyl acetate. This can be use as a separation First, add to the mixture NaHCO3. Why is back titration used to determine calcium carbonate? (C2H5)2O + NaOH --> C8H8O2 + H2O. Why is it that sodium iodide can be used as a catalyst for some SN2 reactions? For example, acetic acid has a \(K\) of 0.5 when partitioning between diethyl ether and water, meaning acetic acid favors the aqueous layer only twice as much as the organic layer.\(^4\) The ability of acetic acid and other polar compounds to dissolve in the organic layer of a separatory funnel should not be ignored. The most common drying agents used to remove water from organic solutions are anhydrous sodium sulfate \(\left( \ce{Na_2SO_4} \right)\) and anhydrous magnesium sulfate \(\left( \ce{MgSO_4} \right)\). As trade 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). 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. GMO>yra$!BCTpyjOh"Sl#&NDWLOG_u0_2JAjqjKje Solutions with \(\ce{Na_2SO_4}\) can usually be decanted. this solvent will form two layers in contact with aqueous solutions if it is used in sufficient quantities; this is because the solvent is immiscible in water. Why is bicarbonate important for ocean acidification? How much solvent/solution is used for the extraction? The center is the most concentrated spot, and it's possible a color change may not be seen on the outside where the solution has spread and diluted. Could you maybe elaborate on the reaction conditions before the work up and extraction? Why might a chemist add a buffer to a solution? Why are three layers observed sometimes? A procedural advantage to these drying agents is that their granules are not easily dispersed, allowing for the solutions to be easily decanted (poured). Press J to jump to the feed. 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. . Depending on the chain length, amines might or might not be soluble in water i.e., propylamine is miscible with water (log Kow=0.48), triethylamine displays a limited solubility at room temperature (17 g/100 mL, log Kow=1.44), while tributylamine hardly dissolves at all (0.37 g/100 mL, log Kow=4.60). All rights reserved. This means that solutions of carbonate ion also often bubble during neutralizations. In many cases, centrifugation or gravity filtration works as well. Sodium bicarbonate is also used as an odour neutraliser, cleaning or exfoliating agent, and sometimes as a temporary fire extinguisher. 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. Draw the reaction between acetylsalicylic acid and NaHCO 3 then draw the reaction between that product and HCl. Multiple extractions with smaller quantities are preferred over one extraction with the same quantity of solution/solvent. If the aqueous layer is on the top of a separatory funnel, insert a glass stirring rod into the top layer and touch the wet rod to blue litmus paper. Solid/Liquid - teabag in hot water. . The organic material in the liquid decays, resulting in increased levels of odor. Below are several problems that have been frequently encountered by students in the lab: Why is sodium bicarbonate used for kidney disease? (2017D) answer: BaCl2 (aq) + Na2SO4 (aq) BaSO4 (s) + 2 NaCl (aq) Question 2. A drying agent is swirled with an organic solution to remove trace amounts of water. . copyright 2003-2023 Homework.Study.com. Why does the pancreas secrete bicarbonate? f. The centrifuge tube leaks Hey there! It is the conjugate base of the weak acid {eq}H_2CO_3{/eq}. Using this constant, one can show that extracting a component from a mixture several times with small portions of solvent is more . 4 0 obj This undesirable reaction is called. Get access to this video and our entire Q&A library. 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). The solution of these dissolved compounds is referred to as the extract. Why is an indicator not used in KMnO4 titration? Saturated ionic solutions may be used to decrease the solubility of organic compounds in the aqueous layer, allowing more of a compound to dissolve in the organic layer. Carbonic acid is in equilibrium with the water so there will be protons free for making HCl. . For instance, epoxides hydrolyze to form diols catalyzed by acids and bases. It also increases the pH in the oral cavity and prevents acidophilic bacteria overgrowth. Bicarbonate ion has the formula {eq}HCO_3^-{/eq}. Why is extraction important in organic chemistry? 4 In the hospital, aggressive fluid resuscitation with . samples of the OG mixture to use later. Step 2: Isolation of the ester. In this context it would be wise to label all layers properly in order to be able to identify them correctly later if necessary. Register Yourself for a FREE Demo Class by Top IITians & Medical Experts Today ! Water is cheap, non-hazardous, and works well to remove may impurities found alongside a desired product. Background Extraction is a frequently used technique to selectively transfer a compound of interested from one solvent to another. You will loose some yield, but not much. Anhydrous calcium sulfate \(\left( \ce{CaSO_4} \right)\), can be purchased containing a cobalt compound that is blue when dry and pink when wet (this is then sold under the name Drierite, Figure 4.49c+d). A standard method used for this task is an extraction or often also referred to as washing. 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. NaHCO3 (Sodium Bicarbonate) is mainly prepared by the Solvay Process, which is the reaction of sodium chloride, ammonia, and carbon dioxide in water. Explore the definition and process of solvent extraction and discover a sample problem. This means that solutions of bicarbonate often bubble during a neutralization wash in a separatory funnel. Also, samples intended for GC analysis must be neutral as acidic solutions degrade the polymeric coating of the GC column. g. The separatory funnel leaks Before using the separatory funnel, the user should check if the stopcock plug and the stopcock fit together well. Ketones and aldehydes undergo condensation reactions catalyzed by both, acids and bases. Ethyl acetate was then shaken with brine (Figure 4.44c), and dried with the same quantity of anhydrous \(\ce{MgSO_4}\). \(^5\)When assessing the result of a litmus paper test, look at the center of the drop. The organic solution to be dried must be in an. In fact, some of the dye precipitated in the funnel (Figure 4.47d) as it had such low solubility in both brine and ethyl acetate. The shaking of the mixture increases the surface area, and therefore the apparent vapor pressure of the solvent. Subsequently, an emulsion is formed instead of two distinct layers. This difference in acidity can be exploited to separate carboxylic acids and phenols from each other in an organic layer. As such, it'll react with a NaHCO3,which is a base and become benzoate, which is negatively charged. 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. Instead, gently rocking the separatory funnel back and forth for 2-3 minutes will accomplish sufficient degree of mixing while minimizing the formation of emulsions. Why is a buffer solution added in EDTA titration? The organic layer has only a very faint pink color, signifying that little dye has dissolved. If the target compound was an acid, the extraction with NaOH should be performed first. In order to separate compounds from each other, they are often chemically modified to make them more ionic i.e., convert a carboxylic acid into a carboxylate by adding a base. 6. Small amounts (compared to the overall volume of the layer) should be discarded here. In addition, many extraction processes are exothermic because they involve an acid-base reaction. It helps to regulate and neutralise high acidity levels in the blood. 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If using \(\ce{MgSO_4}\), gravity filter the solution into an appropriately sized round-bottomed flask (Figure 4.53c). Sodium Bicarbonate. HCO3- + H2O = H2CO3 + OH- Since carbonic acid is a weak acid, it remains undissociated. Why is the bicarbonate in blood an effective buffer when its pKa is 6.1, while the pH of the blood is 7.4? Which of the two reagents should be used depends on the other compounds present in the mixture. b) Perform multiple extractions and/or washes to partially purify the desired product. The bulk of the water can often be removed by, shaking or "washing" the organic layer with saturated aqueous sodium chloride (otherwise. A similar observation will be made if a low boiling solvent is used for extraction. In addition, it is preferable to manipulate neutral materials rather than acidic or basic ones, as spills are then less hazardous. Why use sodium bicarbonate in cardiac arrest? Aqueous solutions of saturated sodium bicarbonate \(\left( \ce{NaHCO_3} \right)\) and sodium carbonate \(\left( \ce{Na_2CO_3} \right)\) are basic, and the purpose of these washes is to neutralize an organic layer that may contain trace acidic components. About 5 % of a solute does not change the density of the solution much. Why was NaHCO3 used in the beginning of the extraction, but not at the end? In this way, blue Drierite can be used as a visual indicator for the presence of water.\(^8\). 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. d. Isolation of a neutral species to the solubility.Extraction becomes a very useful tool if you choose a suitable extraction solvent. Practical Aspects of an Extraction What are advantages and disadvantages of using the Soxhlet extraction technique? Extraction Techniques LAB extraction techniques in mixture of water and diethyl ether, which layer will contain an organic compound that has higher solubility Skip to document Ask an Expert If the litmus paper turns pink at all\(^5\), the base wash has not fully neutralized the organic layer, and subsequent base washes are needed. 59 Experimental Procedure 1) Mix isopentyl alcohol (5.4 mL, via burette) and glacial acetic acid (8.5 mL, via graduated . Using sodium bicarbonate ensures that only one acidic compound forms a salt. Be sure to close the jar of drying agent when not in use, as the reagents are hygroscopic. 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. What functional groups are present in carbohydrates? Why is standardization necessary in titration? Thus, the more drying agent that is used, the more compound that may be irrecoverably lost. Which layer should be removed, top or bottom layer? 5% sodium bicarbonate is used in extraction to remove the remaining acid present. Therefore, when the diluted multiple is 5 times (50/10 \u003d 5). In order to separate these compounds from each other, chromatographic techniques are often used, where the compounds are separated based on their different polarities (see Chromatography chapter). Extraction. Removal of a carboxylic acid or mineral acid. All other trademarks and copyrights are the property of their respective owners. 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!). The \(\ce{^1H}\) NMR spectrum of the final product (Figure 4.39b) showed the washes were effective as the acetic acid signal at \(2.097 \: \text{ppm}\) is absent. Why does a volcano erupt with baking soda and vinegar? because a pressure build-up will be observed in the extraction container. These solvents dissolve large quantities of water in comparison to other solvents (Table 4.5). \(^7\)From: Fessenden, Fessenden, Feist, Organic Laboratory Techniques, 3\(^\text{th}\) ed., Brooks-Cole, 2001. Write the balanced chemical equation with the state symbols of the following reaction: Solutions of Barium chloride and Sodium sulphate in water react to give insoluble Barium sulphate and the solution of Sodium chloride. Many liquid-liquid extractions are based on acid-base chemistry. The resulting salts dissolve in water. Drying agents (Figure 4.48) remove trace amounts of water from organic solutions by forming hydrates. Brine works to remove water from an organic layer because it is highly concentrated (since \(\ce{NaCl}\) is so highly water soluble). Why does sodium iodide solution conduct electricity? It is also a gas forming reaction. Why is sodium bicarbonate used in extraction? This will allow to minimize the number of transfer steps required. saturated \(\ce{NaHCO_3}\), \(\ce{NaCl}\), or \(\ce{NH_4Cl}\)). What is N-(2,2,2-Trichloroethyl)carbonyl] Bisnor-(cis)-tilidine's functional group? Why does sodium chloride dissolve in water? Removal of a phenol. Why is sodium bicarbonate used in fire extinguishers? R'OH + H O(O =)CR H3O+ R'O(O =)CR + H 2O Extraction with sodium carbonate solution will remove ANY unreacted acid from the organic phase. Amines are basic and can be converted to ammonium salts using mineral acids i.e., hydrochloric acid. The organic layer is pinker, signifying that more dye has now partitioned toward the organic layer. Why does aluminium have to be extracted by electrolysis? Why is bicarbonate low in diabetic ketoacidosis? Most phenols are weak acids (pKa= ~10) and do not react with sodium bicarbonate, which is a weak base itself (pKa(H2CO3)=6.37, 10.3). Often times the cap is either the wrong cap in the first place or it is not properly placed on the top. Why is smoke produced when propene is burned? Reminder: a mass of the. Jim Davis, MA, RN, EMT-P -. In order to effect the extraction, the two solvents must be immiscible, which means that neither dissolves in the other. A lysis buffer is a buffer solution used for the purpose of breaking open cells for use in molecular biology experiments that analyze the labile macromolecules of the cells (e.g. h. Why is a centrifuge tube, a conical vial or a separatory funnel used for the extraction and not a beaker or test tube? Never dispose of any layer away until you are absolutely sure (=100 %) that you will never need it again. 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. 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). Why do scientists use stirbars in the laboratory? What is the purpose of a . 1. cool sodium bicarbonate solution (part a) & sodium hydroxide solution (part b) by setting the 2 flasks in ice water bath. (@Du//N;#P%$kG}UgRvMSTupKR ?C9\Eyt_TB@4R8T|TvFbA9 Q2B9+rD Give the purpose of washing the organic layer with saturated sodium chloride. What would have happened if 5%. 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. removing impurities from compound of interest. Washing is also used as a step in the recrystallization procedure to remove the impurity containing mother liquor adhering to the crystal surface. Which layer is the aqueous layer? Why wash organic layer with sodium bicarbonate? Write structural formula(condensed) for all the primary , secondary and tertiary haloalkanes An alcohol has the molecular formula C4H10O write the structural formulae of the isomers to show See all questions in Quick Introduction of Structures. Using as little as possible will maximize the yield. If NaHCO 3 is used for extraction, the centrifuge tube has to be vented more frequently. Sodium bicarbonate is an ionic compound of sodium ion and bicarbonate ion. The 4-chloroaniline is separated first by extraction with hydrochloric acid. 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. There is little clumping of the drying agent in this ethyl acetate layer, and fine particles are seen (Figure 4.44d), signifying this layer contained very little water. 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. alcohols, carboxylic acids) can hydrogen-bond with water and increase the likelihood of water dissolving in the organic layer. Pink (wet) Drierite can be dried by spreading it on a watch glass and drying in a \(110^\text{o} \text{C}\) oven overnight. Chlorinated solvents (i.e., dichloromethane, chloroform) exhibit a higher density than water, while ethers, hydrocarbons and many esters possess a lower density than water (see solvent table), thus form the top layer (see solvent table).. One rule that should always be followed when performing a work-up process: In this example, even after filter and rinsing the drying agent with additional solvent, the drying agent remained pink (Figure 4.45c). Problem. The final Sodium Bicarbonate concentration used in the medium depends on the media formulation and the carbon dioxide concentration used in the incubator. 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 Sometimes, the addition of a salt (or salt solution) can also lead to a better phase separation (salting out). \r[(QR\kp'H+yMdC '(\S^.r/XTYDyV 0y@.pk,{=0/G dKq,eLpQNl]O#_p;bHw>unvVII9Qs]pxt/7?|oi{$2 ~savRmA~MEyy`O Why does the sodium potassium pump never run out of sodium or potassium? To demonstrate the effectiveness of a water wash, a Fischer esterification reaction was conducted to produce isoamyl acetate (Figure 4.38). If 5% sodium hydroxide had been used the ester will be hydrolyzed, yielding a carboxylate salt and an alcohol as products. \(\ce{CH_3CH_2OH}\) or \(\ce{CH_3COCH_3}\)). Either way its all in solution so who gives a shit. << /Length 5 0 R /Filter /FlateDecode >> e) Remove the solvent with a rotary evaporator. 4. Extraction is based on solubility characteristics of the organic compound in the solvents being used for the extraction. Why is sulphuric acid used in redox titration? At 2 h after CPR, the brain, heart, and lung were collected and mRNA extraction, followed by cDNA synthesis and real-time PCR were performed. Figure 4.41 shows a strongly acidic organic layer (top) in contact with an aqueous solution of \(10\%\) sodium bicarbonate (bottom). 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. Use Coupon: CART20 and get 20% off on all online Study Material, Complete Your Registration (Step 2 of 2 ), Sit and relax as our customer representative will contact you within 1 business day. The product of reaction (2) is the bicarbonate ion, which can subsequently undergo reaction (1). However, this can change if very concentrated solutions are used (see table in the back of the reader)! #R'OH + HO(O=)CRstackrel(H_3O^+)rightleftharpoonsR'O(O=)CR+H_2O#. In the case of Caffeine extraction from tea e. General Separation Scheme Create an account to follow your favorite communities and start taking part in conversations. For Research Use Only. WE|>t{_[g(qlLo? h~dBSF~x"xoHjN$z_&Sq?$5QyN~.uAoFCh,.1?a1ccEQKWk ~c1/?kqu-vG- pnO_XfhxgC@Nd&rKf\]Ep ^l [4##KCX G3LS0 no=P80Gv-\JGExFJy-T[61Z>2P IqQ.Xk+_a{vLw))efJ_%*S7VCrb_ +nAuV%YuVE&EIMX> JFj)z{iQ8s&"5,k@eU|+~@(C_dJFvhEG\2p:s/]AprC Remove the solvent using a rotary evaporator. Solvent extraction is the process of separating compounds by utilizing their relative solubilities. 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. Why is cobalt-60 used for food irradiation? 3 Kinds of Extraction. If using pellets, the solution should be allowed to sit for a few minutes, then decanted. Extraction is a fundamental technique used to isolate one compound from a mixture. HTR#Ey/?4NWr/dPJG{a%[hde:h>K8ae'?qmg6v Baking soda is a base, with a pH level of around 8, its aqueous solution is slightly basic. Why is the removal of air bubbles necessary before starting titration? 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. 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. Why is saltwater a mixture and not a substance? Why is EDTA used in complexometric titration? If a carboxylic acid (i.e., benzoic acid) was deprotonated using a base or an amine (i.e., lidocaine) was protonated using an acid, it would become more water-soluble because the resulting specie carries a charge. These compounds have to be removed in the process of isolating the pure product. %PDF-1.3 Like many acid/base neutralizations it can be an exothermic process. The conjugate base is a salt and is water soluble; therefore, it is removed from the organic solvent layer . % RC( = O)OH (aq) + N a2CO3(aq) RC( = O)O +N a water soluble +N a+ H CO3 Answer link Strictly speaking, hardly ever all of the solute will be extracted since there is finite distribution coefficient for the compound (see also Extraction II). What is the average pressure on the soles of the feet of a standing 90.0 kg person due to the contact force with the floor? sodium bicarbonate is used. When pouring, leave the solid behind as long as possible (essentially decant the solution, but into the funnel lined with filter paper). With water being so tightly "occupied" in dissolving the ions in these solutions, they are less capable of dissolving organic compounds. What functional groups are found in proteins? does not react with compounds that are sensitive to strong bases or nucleophiles (esters, ketones, aldehydes) because it is a weaker base and a weak nucleophile due to its. resonance stabilization. Water may be produced here; this will not lead to a build up of pressure. 1. transfer ether solution to clean labeled 125 mL Erlenmeyer flask; add anhydrous sodium sulfate until it stops clumping. E>!E?h!I'Xyg6WqfB%t]` B;h_~m3wRq`ja4AM$@0?x/,P:a=93X=v4{g5:YAp[Lkcb-kPl`b. It reacts almost instantaneously to neutralize HCl to produce CO 2 and NaCl. \(\ce{Mg(H_2O)_4^{2+}}\) is somewhat acidic, so is incompatible with highly acid-sensitive groups. As expected, a significant signal for acetic acid is seen at \(2.097 \: \text{ppm}\). We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. However, the solubility of the ammonium salts decreases as the number and size of R-groups increases. Sodium Bicarbonate Sodium bicarbonate is an ionic compound of sodium ion and bicarbonate ion.
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