After a reaction is completed, the solution often times does not only contain the desired product, but also undesired byproducts of the reaction, unreacted starting material(s) and the catalyst (if it was used). Experiment 8 - Extraction pg. Why is sulphur dioxide used by winemakers? Many. Why is baking soda and vinegar endothermic? Why is the bicarbonate in blood an effective buffer when its pKa is 6.1, while the pH of the blood is 7.4? Sodium bicarbonate is found in our body and is an important element. Dean, Lange's Handbook of Chemistry, 15\(^\text{th}\) ed., McGraw-Hill, 1999, Sect. Why do sodium channels open and close more quickly than potassium channels? Why is back titration used to determine calcium carbonate? Sodium hydroxide is usually easier to handle because it does not evolve carbon dioxide as a byproduct. Why is sodium bicarbonate used in extraction? c. The cells from two different four-celled embryos are fused together to make an eight-celled embryo. \(^9\)Grams water per gram of desiccant values are from: J. Why does sodium bicarbonate raise blood pressure? ago Posted by WackyGlory 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. This technique selectively dissolves one or more compounds into an appropriate solvent. 1. 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. Problem. Strictly speaking, hardly ever all of the solute will be extracted since there is finite distribution coefficient for the compound (see also Extraction II). This pressure build-up can cause an explosion; an ejection of the stopper on the top/excessive spillage upon opening may occur. \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 Liquid-liquid extraction also known as solvent extraction is a common method in separating liquids inn virtue of their relative solubility in different solvents (polar and non-polar solvents).. . Product Use. Sodium hydrosulfide is used as an activator of cobalt-nickel minerals in copper tailings. Ethyl acetate was then shaken with brine (Figure 4.44c), and dried with the same quantity of anhydrous \(\ce{MgSO_4}\). Why use sodium bicarbonate in cardiac arrest? Why is sodium bicarbonate added to water? Extraction is one of the more common procedures in organic chemistry, and it's often performed to remove an organic solvent from water. . Water has a particular density and naphthalene, as well as benzoic acid, are insoluble in water. saturated \(\ce{NaHCO_3}\), \(\ce{NaCl}\), or \(\ce{NH_4Cl}\)). After the layers settle, they are separated and placed into different tubes. 5Q. However, if compounds were present that are sensitive towards strong bases or nucleophiles (i.e., esters, ketones, aldehydes, etc. 4 In the hospital, aggressive fluid resuscitation with . 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. Be sure to close the jar of drying agent when not in use, as the reagents are hygroscopic. As was discussed in the previous section, NaOH can be used to convert a carboxylic acid into its more water-soluble ionic carboxylate form. The most common wash in separatory funnels is probably water. Why are hematoxylin and eosin staining used in histopathology? . the gross of the water from the organic layer. Why was it important to be careful when adding the bicarbonate base to the ether solution when extracting the toluic acid? You will use sulfuric acid to catalyze the reaction. Introduction Extraction is a widely used method for the separation of a substance from a mixture. On a large scale, it is prepared by passing carbon dioxide gas through calcium hydroxide (slaked lime). Liquid/Liquid. The organic layer has only a very faint pink color, signifying that little dye has dissolved. For instance, epoxides hydrolyze to form diols catalyzed by acids and bases. Cannot dry diethyl ether well unless a brine wash was used. Why was NaHCO3 used in the beginning of the extraction, but not at the end? Since the carboxylic acids that are used in Chem 30BL are solids, using them in excess would produce a heterogeneous reaction mixture. Baking soda (NaHCO 3) is basic salt. This constant depends on the solvent used, the solute itself, and temperature. What functional groups are found in the structure of melatonin? What is the goals / purpose of the gravimetric analysis of chloride salt lab? . The resulting salts dissolve in water. The reason of using $\ce {NaHCO3}$ is the reaction: $$\ce {HCO3- + OH- <=> CO3^2- + H2O}$$ First, near all hydroxide is converted to carbonate, and then an excess of bicarbonate shifts $\mathrm {pH}$ below 10. 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 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. We are not going to do that in order to decrease the complexity of the method. 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. 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. At the CERN particle accelerator in Geneva, Switzerland, protons are accelerated to a speed of 0.999999972c0.999999972 c0.999999972c. Quickly removes water, but needs large quantities as it holds little water per gram. Extraction is based on solubility characteristics of the organic compound in the solvents being used for the extraction. This is because the concentrated salt solution wants to become more dilute and because salts. For Research Use Only. Cite advantages and disadvantages of using the following drying agents: a) sodium sulfate b) magnesium sulfate c) sodium carbonate d) potassium carbonate. 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 Solid/Liquid - teabag in hot water. Why don't antiseptics kill 100% of germs? The sodium salt that forms is ionic, highly polarized and soluble in water. Explanation: You have performed the condensation. With a finger placed atop the glass pipette again, remove the pipette from the separatory funnel. Why is phenolphthalein an appropriate indicator for titration? \(^4\)A. Seidell, Solubilities of Inorganic and Organic Substances, D. Van Nostrand Company, 1907. Why is bicarbonate the most important buffer? 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 Additionally, ionic solutions have high dielectric constants, making them less compatible with organic compounds. If a desired product can hydrogen bond with water and is relatively small, it may be difficult to keep it in the organic layer when partitioning with an aqueous phase (\(K\) will be <1). Multiple extractions with smaller quantities are preferred over one extraction with the same quantity of solution/solvent. 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). Synthesis or preparation of esters in the laboratory involves 3 steps: Step 1: Synthesis of the ester. Course Hero is not sponsored or endorsed by any college or university. Sodium Bicarbonate Sodium bicarbonate is an ionic compound of sodium ion and bicarbonate ion. In this way, blue Drierite can be used as a visual indicator for the presence of water.\(^8\). 1. add 10-15 mL of 0.5 M NaHCO3 to the ether solution; shake funnel & allow layers to separate. The \(\ce{^1H}\) NMR spectrum in Figure 4.39a was taken of the reaction mixture immediately after ceasing heating and before the work-up. By easy I mean there are no caustic solutions and . This strategy saves steps, resources and time, and most of all, greatly reduces waste. Any ECG signs of hyperkalemia warrant treatment with calcium chloride, beta agonist (albuterol), insulin/glucose and sodium bicarbonate. f. The centrifuge tube leaks The conjugate base is a salt and is water soluble; therefore, it is removed from the organic solvent layer . The main purpose of the water wash was to remove the majority of the catalytic sulfuric acid and the excess acetic acid, while the sodium bicarbonate wash neutralized the rest. 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). Absorbs water as well as methanol and ethanol. Additionally, solutes dissolved in an organic layer with polar functional groups (e.g. Commonly used solvents like ethyl acetate (8.1 %), diethyl ether (6.9 %), dichloromethane (1.3 %) and chloroform (0.8 %) dissolved up to 10 % in water. Either way its all in solution so who gives a shit. Hybrids of these two varieties are also grown. Figure 4.41 shows a strongly acidic organic layer (top) in contact with an aqueous solution of \(10\%\) sodium bicarbonate (bottom). Why should KMnO4 be added slowly in a titration? You will loose some yield, but not much. Sodium bicarbonate is an ionic compound of sodium ion and bicarbonate ion. If 5% sodium hydroxide had been used the ester will be hydrolyzed, yielding a carboxylate salt and an alcohol as products. Solutions are added to the funnel to either extract or wash the mixture, with the goal of isolating the product from excess reagents, catalysts, side products, solvents, or compounds formed from side reactions. 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 \(\ce{MgSO_4}\). The organic layer is pinker, signifying that more dye has now partitioned toward the organic layer. Hey there! b. The large clumps of drying agent in Figure 4.44b indicate that this ethyl acetate layer is still noticeably wet. Fischer Esterification is the name given to the acid-catalysed reaction between an alkanoic acid (carboxylic acid) and an alkanol (alcohol) (3) . In this extraction step, NaHCO3 was added to neutralize the acid so that the neutralized acid would go into the organic phase. 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. The mixture is dissolved in ether and mixed thoroughly with aqueous sodium bicarbonate (weaker base). Which layer should be removed, top or bottom layer? Why is eriochrome black T used in complexometric titration? Why is the removal of air bubbles necessary before starting titration? 2. 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. If a second layer is noticed, this is probably water and the majority of it should be pipetted out before continuing on (Figure 4.51a). Why does a volcano erupt with baking soda and vinegar? The leaves may be fermented or left unfermented. Note that amides are usually not basic enough to undergo the same protonation (pKa of conjugate acid: ~ -0.5). They should be vented directly after inversion, and more frequently than usual. We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. c) Remove trace water with a drying agent. i. GMO>yra$!BCTpyjOh"Sl#&NDWLOG_u0_2JAjqjKje The most useful drying agents indicate when they have completely absorbed all of the water from the solution. Step-by-step solution. Remove the finger on the pipette to allow a sample of the aqueous layer to enter the pipette through capillary action (Figure 4.42b). 4. The following reactions occur between bicarbonate ion (1), carbonate ion (2) and acid \(\left( \ce{H^+} \right)\) during a wash: \[\ce{HCO_3^-} \left( aq \right) + \ce{H^+} \left( aq \right) \rightarrow \ce{H_2CO_3} \left( aq \right) \rightleftharpoons \ce{H_2O} \left( l \right) + \ce{CO_2} \left( g \right) \tag{1}\], \[\ce{CO_3^{2-}} \left( aq \right) + \ce{H^+} \left( aq \right) \rightarrow \ce{HCO_3^-} \left( aq \right) \tag{2}\]. Although the organic layer should always be later exposed to a drying agent (e.g. Why is a buffer solution added in EDTA titration? Water also dissolves in organic solvents: ethyl acetate (3 %), diethyl ether (1.4 %), dichloromethane (0.25 %) and chloroform (0.056 %). After the extraction, the phenol can be recovered by adding a mineral acid to the basic extract. wOYfczfg}> In this experiment you will use extraction techniques to separate a mixture of an organic acid, a base, and a neutral compound. 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. 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. 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. R. W. et al. 1. If NaHCO 3 is used for extraction, the centrifuge tube has to be vented more frequently. western blot for protein, or for DNA extraction).Most lysis buffers contain buffering salts (e.g. Students also viewed NaHco3 allows us to just ionize the acid; any base would deprotonate the stronger acid, it's more about not also deprotonating the phenol. 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. Why is bicarbonate of soda used to bake a cake? Discover how to use our sodium bicarbonate in a pancake recipe. Sodium Bicarbonate | NaHCO3 or CHNaO3 | CID 516892 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological . Benzoic acid is, well, an acid. d. How do we know that we are done extracting? layer contains quarternary ammonium ions. Water is cheap, non-hazardous, and works well to remove may impurities found alongside a desired product. 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. Touch the aliquot to blue litmus paper and observe the color (Figure 4.42d). Why is an indicator not used in KMnO4 titration? Why is an acidic medium required in a redox titration? 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. varieties are used, the small-leaved China plant (C. sinensis sinensis) and the large-leaved Assam plant (C. sinensis assamica). << /Length 5 0 R /Filter /FlateDecode >> Also, samples intended for GC analysis must be neutral as acidic solutions degrade the polymeric coating of the GC column. About 5 % of a solute does not change the density of the solution much. g. The separatory funnel leaks 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. It involves the removal of a component of a mixture by contact with a second phase. 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. A key step in this sequence comes immediately after the reaction is complete, and is called the reaction "work-up" (step b) in Table 4.4). 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. Drying agents must be used with even relatively nonpolar organic solvents that do not theoretically dissolve much water, as water may cling to the sides of the separatory funnel and inadvertently travel with the organic layer while draining. The organic solvents that require a brine wash before exposure to a solid drying agent are diethyl ether and ethyl acetate. This undesirable reaction is called saponification. To test whether a base wash with \(\ce{NaHCO_3}\) or \(\ce{Na_2CO_3}\) was effective at removing all the acid from an organic layer, it is helpful to test the pH. If the total percent recovery is unusually low or unusually high, briefly explain the possible sources of error that might've occurred. Add another portion of drying agent and swirl. Most solutions are relatively diluted (~5 %) and their density is not much different from that of water (i.e., 5 % HCl: 1.02 g/cm3, 5 % NaOH: 1.055 g/cm3). Many chemists consider \(\ce{MgSO_4}\) the "go-to" drying agent as it works quickly, holds a lot of water for its mass, and the hydrates are noticeably chunkier compared to the anhydrous form, making it easy to see when you've added enough. This can be use as a separation First, add to the mixture NaHCO3. This can pose a serious problem when using low boiling solvents i.e., diethyl ether, dichloromethane, etc. Accessibility StatementFor more information contact us atinfo@libretexts.orgor check out our status page at https://status.libretexts.org. 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. With a finger placed atop a glass pipette, insert the pipette into the separatory funnel so the tip is positioned in the bottom aqueous layer (Figure 4.42a). Which sequence is the most efficient highly depends on the target molecule. 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. Drying agents (Figure 4.48) remove trace amounts of water from organic solutions by forming hydrates. Therefore a uncharged acidic compound dissolved in diethyl ether can be converted to a salt and . Why is cobalt-60 used for food irradiation? Create an account to follow your favorite communities and start taking part in conversations. What do I use when to extract? greatly vary from one solvent to the other. Early C. elegans embryos display mosaic determination, whereas early mouse embryos exhibit regulative determination. Why use methyl orange instead of phenolphthalein as a pH indicator. It is important to neutralize any organic solvent that was exposed to an acidic or basic solution as trace acid or base may cause undesired reactions to occur when the solutions are concentrated. In this reaction, an excess of acetic acid is used to drive the reaction through Le Chatelier's principle, and the acetic acid had to be removed from the product during the purification process. What would have happened if 5%. It is not appropriate for soils which are mild to strongly acidic (pH <6.5). Can hold a lot of water for its mass (\(1.25 \: \text{g}\) water per \(\text{g}\) desiccant), but may leave small amounts of water remaining. 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). Why potassium is more reactive than sodium. 1 6. Many of these neutral compounds tend to react in undesired ways i.e., esters undergo hydrolysis upon contact with strong bases or strong acids. The reaction affords carbon dioxide (CO2), which is a gas at ambient temperature. Most neutral compounds cannot be converted into salts without changing their chemical nature. Figure 3 shows the mechanism for the synthesis of tert-Butyl chloride from tert-Butyl alcohol using hydrochloric acid. 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 \(\left( \ce{MgSO_4} \right)\). A solution is nearing dryness when fine particles are noticed that don't cling to other particles (Figure 4.52a+c) or to the glass when swirled (Figure 4.53a). 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. It helps to regulate and neutralise high acidity levels in the blood. around the world. Why does sodium bicarbonate raise blood pH? Why is sodium bicarbonate used in fire extinguishers? What happens chemically when quick lime is added to water? Since most of the extractions are performed using aqueous solutions (i.e., 5 % NaOH, 5 % HCl), the miscibility of the solvent with water is a crucial point as well as the compatibility of the reagent with the compounds and the solvent of the solution to be extracted. 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. stream 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! Plz answer me. Identify one cation and one anion in the given unknown salt m1 by performing dry tests. Other solvents such as alcohols increase the solubility of water in organic layers significantly because they are miscible with both phases and act as a mediator. Step 3: Purification of the ester. 4 0 obj Why is acid alcohol used as a decolorizing agent? Figure 4.47d shows the brine layer containing the dye after shaking with a portion of ethyl acetate. The bulk of the water can often be removed by, shaking or "washing" the organic layer with saturated aqueous sodium chloride (otherwise. Epinephrine and sodium bicarbonate . This means that solutions of bicarbonate often bubble during a neutralization wash in a separatory funnel. The 2-naphthol was extracted from the organic layer by adding 20mL of cold 10% aqueous sodium hydroxide solution to the 125mL separatory funnel. Why can you add distilled water to the titration flask? - Solid Inorganic: excess anhydrous sodium sulfate. A commonly used method of separating a mixture of organic compounds is known as liquid-liquid extraction. We receieved your request, Stay Tuned as we are going to contact you within 1 Hour. It is not uncommon that a small amount of one layer ends up on top of the other. Why is saltwater a mixture and not a substance? A procedural advantage to these drying agents is that their granules are not easily dispersed, allowing for the solutions to be easily decanted (poured). The final Sodium Bicarbonate concentration used in the medium depends on the media formulation and the carbon dioxide concentration used in the incubator. Solid can slow drainage in the filter paper. ~85F?$_2hc?jv>9 XO}.. \(\ce{CH_3CH_2OH}\) or \(\ce{CH_3COCH_3}\)). Acid-Base Extraction. Step 2: Isolation of the ester. 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. The ether layer is then The organic solution to be dried must be in an. As such, it'll react with a NaHCO3,which is a base and become benzoate, which is negatively charged. 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!). 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? Remove the solvent using a rotary evaporator. Why does the pancreas secrete bicarbonate? In order to effect the extraction, the two solvents must be immiscible, which means that neither dissolves in the other. Solid-liquid and liquid-liquid extractions are commonly performed by batch and continuous processes. Using sodium bicarbonate ensures that only one acidic compound forms a salt. Why does vinegar have to be diluted before titration? These solvents dissolve large quantities of water in comparison to other solvents (Table 4.5). A drawback to using \(\ce{MgSO_4}\) is that it is a fine powder, and so the solutions must be subsequently filtered to remove the drying agent. Water can potentially remove water-soluble impurities from an organic layer, as long as they are present in quantities that do not exceed their water solubility. to the solubility.Extraction becomes a very useful tool if you choose a suitable extraction solvent. Micro-scale extractions can be performed in a conical vial or a centrifuge tube depending on the quantities. Brine works to remove water from an organic layer because it is highly concentrated (since \(\ce{NaCl}\) is so highly water soluble). How much solvent/solution is used for the extraction? Why is sodium bicarbonate used in extraction? stream This difference in acidity can be exploited to separate carboxylic acids and phenols from each other in an organic layer. Let's consider two frequently encountered - prepare 2 m.p. If using \(\ce{MgSO_4}\), gravity filter the solution into an appropriately sized round-bottomed flask (Figure 4.53c). Why was the caution in question #3a not as important when adding the hydroxide base to the ether solution? Sodium bicarbonate is a salt that breaks down to form sodium and bicarbonate in water. The organic material in the liquid decays, resulting in increased levels of odor. The four cells of the embryo are separated from each other and allowed to develop. A wet organic solution can be cloudy, and a dry one is always clear. NaHCO3 (Sodium Bicarbonate) is mainly prepared by the Solvay Process, which is the reaction of sodium chloride, ammonia, and carbon dioxide in water. Process of removing a compound of interest from a solution or solid mixture.
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