grignard reaction malachite green

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grignard reaction malachite green

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For example: The product is then hydrolyzed (reacted with water) in the presence of a dilute acid. The procedure is a modification of a normal Grignard reaction. Malachite green appears green, so it must absorb red light at 605-700 nm. The Grignard reagent is a type of organometallic reagent,. stream The greener approach reduces the use of undesirable ethers, and avoids the use of hexanes, and magnesium. R = alkyl / aryl / alkenyl / allyl group. 0000008950 00000 n The colour of the compound appears to be unaffected by the anions. For example: \[ CH_3CH_2MgBr + H_2O \rightarrow CH_3CH_3 + Mg(OH)Br\]. The reaction with formaldehyde leads to a primary alcohol. A nucleophile is a species that attacks positive (or slightly positive) centers in other molecules or ions. Grignard reagents react rapidly with acidic hydrogen atoms in molecules such as alcohols and water to produce alkanes. 0000055890 00000 n Regioselective Halogen-Metal Exchange Reaction of 3-Substituted 1,2-Dibromo Grignard Reagent Preparation and Reaction: READ THIS HANDOUT CAREFULLY! 2 0 obj Grignard Reagents - Sigma-Aldrich Malachite Green - Meaning, Properties, Uses, Preparation and FAQs - VEDANTU You could ring the changes on the product by. Malachite green is formed by treating the same Grignard reagent with methylbenzoate. The alcohol formed is: So this time the final product has one CH3 group and one hydrogen attached: A secondary alcohol has two alkyl groups (the same or different) attached to the carbon with the -OH group on it. Pharmaceutical syntheses featuring the Grignard reaction. Lett., 2019, 21, 7851-7856. The Barbier-Grignard-type arylation of aldehydes using - Nature Crystal Violet (2), whereas addition to methyl benzoate followed by acid hydrolysis could lead to the dye Malachite Green (3). S. T. Handy, J. Org. It has been used as an effective compound to control external fungal, bacterial, and protozoan infections of fish, and successfully used as a treatment to control fish saprolegniosis and as a prophylactic treatment to protect fish eggs from infection (Ali et al., 2015). 0000056072 00000 n Grignard reaction between p-dimethylaminophenylmagnesium bromide and diethylcarbonate. Copper is already in a higher oxidation state (+2) so it can't reduce hydronium to hydrogen. No, pure malachite $\ce {Cu2CO3 (OH)2}$ usually doesn't produce hydrogen because it is a copper carbonate. Both procedures involve preparing a Grignard reagent from 4-bromo-N,N-dimethylaniline and reacting it with an ester (methyl benzoate to make Malachite Green or ethyl carbonate to make Crystal Violet). The iodine will react with those sites and the magnesium iodide formed will dissolve away and that consequently exposes more Mg (O) on the surface. You could obviously get a different primary alcohol if you started from a different Grignard reagent. X = Cl / Br / I. On3O&@##t(Pr- CHEM. 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The Grignard reagent first reacted with the methyl benzoate substrate and . A Grignard reagent has a formula \(\ce{RMgX}\) where \(\ce{X}\) is a halogen, and \(\ce{R}\) is an alkyl or aryl (based on a benzene ring) group. Aryl Grignards are more easily prepared from Aryl x\tG!P*AZ!f|G m+Eb^R|!p[c 0000009113 00000 n Experimental procedure lab write up for grignard reaction. S. Usami, T. Suzuki, K. Mano, K. Tanaka III, Y. Hashimoto, N. Morita, O. Tamura, Synlett, 2019, It will reach a point where the alkyl halide you're using can take over and accelerate the process. { Grignard_and_Organolithium_Reagents : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Grignard_Reagents : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Preparation_of_Aldehydes_and_Ketones : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Synthesis_of_Aldehydes_and_Ketones : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()" }, { Nomenclature_of_Aldehydes_and_Ketones : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Properties_of_Aldehydes_and_Ketones : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Reactivity_of_Aldehydes_and_Ketones : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()", Synthesis_of_Aldehydes_and_Ketones : "property get [Map MindTouch.Deki.Logic.ExtensionProcessorQueryProvider+<>c__DisplayClass228_0.b__1]()" }, [ "article:topic", "authorname:clarkj", "showtoc:no", "license:ccbync", "licenseversion:40" ], https://chem.libretexts.org/@app/auth/3/login?returnto=https%3A%2F%2Fchem.libretexts.org%2FBookshelves%2FOrganic_Chemistry%2FSupplemental_Modules_(Organic_Chemistry)%2FAldehydes_and_Ketones%2FSynthesis_of_Aldehydes_and_Ketones%2FGrignard_Reagents, \( \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}}}\) \( \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash{#1}}} \)\(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\) \(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\)\(\newcommand{\AA}{\unicode[.8,0]{x212B}}\), to small bits of magnesium in a flask containing, (commonly called diethyl ether or just "ether"). Both involve preparing a Grignard reagent from 4-bromo-N,N-dimethylaniline and reacting it with anester (methyl benzoate to make Malachite Green or diethyl carbonate to make Crystal Violet). 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Malachite green | C23H25ClN2 - PubChem In our lab, we combines magnesium and 4-Bromo-, N,N-dimethyl-Aniline with bromobenzene and, reacted to methyl benzoate to obtain malachite green. 0 0 Comments The amounts are: 0.802 g magnesium, MW: 24.305 5.004 g p -bromo- N,N -dimethylaniline , MW: 200.08 g/mol For the purposes of this page, we shall take R to be an alkyl group. The molecular weight of the compound which can be calculated from the molecular formula is 364.911 g/mol. 0000005380 00000 n Summary. However, it is still highly desirable . stream Carbonyl compounds contain the C=O double bond. 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. EES 150 Lesson 3 Continental Drift A Century-old Debate, BUS 225 Module One Assignment: Critical Thinking Kimberly-Clark Decision, 1-2 Short Answer Cultural Objects and Their Culture, Module One Short Answer - Information Literacy, Ejemplo de Dictamen Limpio o Sin Salvedades, Sample solutions Solution Notebook 1 CSE6040, Answer KEY Build AN ATOM uywqyyewoiqy ieoyqi eywoiq yoie, 46 modelo de carta de renuncia voluntaria, Leadership class , week 3 executive summary, I am doing my essay on the Ted Talk titaled How One Photo Captured a Humanitie Crisis https, School-Plan - School Plan of San Juan Integrated School, SEC-502-RS-Dispositions Self-Assessment Survey T3 (1), Techniques DE Separation ET Analyse EN Biochimi 1, Organic Chemistry Ii Laboratory (CHEM 310). Conversion of Imines into C,N-Dimagnesiated Compounds and Trapping with Grignard Reagents - Chemistry LibreTexts Grignard Reagents to Carboxylate Anions Preparation of Grignard reagent. The Grignard reagent is formed by the reaction of an alkyl or aryl halide with magnesium metal via a radical mechanism. The two wires shown in the figure carry currents of I - ITProSpt Dry carbon dioxide is bubbled through a solution of the Grignard reagent in ethoxyethane, made as described above. Chem. The usually quoted equation is (without the red bits): Almost all sources quote the formation of a basic halide such as Mg(OH)Br as the other product of the reaction. General Properties of Malachite Green The structure of malachite green is given as follows: I m a g e w i l l b e u p l o a d e d s o o n The Grignard reaction is a useful tool for the formation of carbon-carbon bonds in organic synthesis. Upon reaction of Mg metal with an alkyl halide in dry ether gives the respective Grignard reagent. How does malachite react with acid? - Chemistry Stack Exchange Calculate the net magnetic field at a point midway between the wires. 0000031790 00000 n 0000008012 00000 n ( a) Strict anhydrous conditions for the Barbier-Grignard-type reaction. The Barbier reaction is an organic reaction between an alkyl halide and a carbonyl group as an electrophilic substrate in the presence of aluminium, zinc, indium, tin or its salts. 4) Practice questions. Chem., 2019, A primary alcohol has only one alkyl group attached to the carbon atom with the -OH group on it. %^OtJ1HgqTv1PZe!Om^Y03;>81sW;e&p 6 The Reaction (shown for methyl benzoate) 4-bromo-N,N-dimethylaniline . Crystal Violet (Gentian Violet) and Malachite Green are two of the best known of the triarylmethane dyes. Experimental Procedure Grignard Reaction (Malachite Green), Copyright 2023 StudeerSnel B.V., Keizersgracht 424, 1016 GC Amsterdam, KVK: 56829787, BTW: NL852321363B01, Experimental Procedure: Formation of Malachite Gree, Magnesium (0.080 g, 3.3 mmol) was grinded with a mortar and pestle and added to 4-bromo-, N,N-dimethylaniline (0.500 g, 2.499 mmol), and iodine (one crystal) in a 5-mL, mL) was added to the round bottom flask and magnetically stirred with a stir ba, generated heat that bubbled the ether and changed the solution to a turbid and grass-green color, that lasted 25 sec, before becoming clear and olive-gray, was magnetically stirred and refluxed using a water bath at 35.0 C for 30 min with an appa, (0.10 mL, 0.81 mmol) and diethyl ether (0.50 mL) was added that altered the appearance to a, and solution became olive/vomit colored. By accepting all cookies, you agree to our use of cookies to deliver and maintain our services and site, improve the quality of Reddit, personalize Reddit content and advertising, and measure the effectiveness of advertising. 2002, 63-64. It is much easier to understand what is going on by looking closely at the general case (using "R" groups rather than specific groups) - and then slotting in the various real groups as and when you need to. [1] [2] This reaction is important for the formation of carbon-carbon bonds. Recall that you studied the reactivity of a series of C-X bonds in Chapter 5. (1) In this reaction, the so-called Grignard reagent, an organomagnesium species RMgX where R is an organic residue and X is a halogen (usually Cl or Br), promotes the addition of its organic residue to an electrophilic substrate. Iodine "activates" magnesium so it can form a Grignard reagens. A colorful grignard reaction - ProQuest [3] [4] The reaction of an organic halide with . : an American History (Eric Foner). How do you Deprotect trityl group? ]{| Nk &nVzYBz@++cs|"YjM8gZRFEY L&ih vgrjR+ne=L6/tAilF:6]d&VZoZ *geB2}AslzGRt4Ui `ML~%L2&n61a0c&"fnh?_]4M; Oi(J4r=*d%t|OJkN# , u)7AP;R5O5zoLwKss|$xV5>lW|F-"@ The right reaction is the following: $$\ce {Cu2CO3 (OH)2 +2H2SO4 -> 2CuSO4 + CO2 ^ + 3H2O}$$. Addition of the Grignard reagent to methyl benzoate, followed by. The Grignard reagent is represented as R-Mg-X, where. The flask is fitted with a. reagent are carried out with the mixture produced from this reaction. A typical Grignard reagent might be CH 3 CH 2 MgBr. Grignard Reagents: Preparation, Mechanism and Reactions - Collegedunia In aquaculture, it is often used as an anti-fungal for eggs in hatcheries, in spite of growing concern regarding . Conclusion In the experiment malachite green dye was A greener approach to a traditional Grignard Reaction has been implemented by Dr. Abby OConnor at the College of New Jersey (TCNJ). Lett., 2007, Use of iodine in making Grignard reagent? : r/chemhelp Grignard Reaction with Alcohol, Ketone, & Aldehyde - Study.com 0000006254 00000 n Introduction The Grignard reaction is an extremely valuable reaction in organic chemistry because it allows for the formation of carbon-carbon bonds. Grignard Reaction Mechanisms | Real Time Monitoring in Batch or Flow Grignard Synthesis Lab Report - 654 Words | Studymode For example: If both of the R groups are alkyl groups, the compounds are called ketones. Grignard's reaction mechanism explains the addition of alkyl/vinyl/aryl magnesium halides to any carbonyl group in an aldehyde/ketone. A carboxylic acid is produced with one more carbon than the original Grignard reagent. Procedure Making the Grignard reagent (whole class) 1. 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The Grignard reaction is an organic reaction used to produce a variety of products through the reaction of an organomagnesium compound, also known as an electrophilic "Grignard reagent," followed by an acidic reaction. 4 0 obj Lett., 2005, 7, 573-576. 0000055613 00000 n 0000011756 00000 n The Grignard reaction is my go-to for chain elongation in orgo 2 synthesis. teacher harriet voice shawne jackson; least stressful physician assistant specialties; grandma's marathon elevation gain; describe key elements of partnership working with external organisations History & Uses: First made in 1877, Malachite Green has been used primarily as a dye for fabrics, leather, and paper. Meredith's course. << /Length 5 0 R /Filter /FlateDecode >> The simplest ones have the form: R and R' can be the same or different, and can be an alkyl group or hydrogen. status page at https://status.libretexts.org, changing the nature of the Grignard reagent - which would change the CH, changing the nature of the aldehyde - which would change the CH, changing the nature of the ketone - which would change the CH. Malachite Green | Properties, Uses, Side Effects & Application in Beyond Benign You can't separate it out in any way. Continuous Flow One of the R groups is hydrogen and the other CH3. 0000002065 00000 n Functionalized Aryl- and Heteroarylmagnesium Compounds from Organic Bromides We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. Reaction usually in Et 2 O or THF followed by H 3 O + work-up Reaction type: Nucleophilic Addition. By rejecting non-essential cookies, Reddit may still use certain cookies to ensure the proper functionality of our platform. A colorful grignard reaction. Skeletal system diagrams - unlabelled, 16. However, if there are traces of metallic . Grignard reagents are made by adding the halogenoalkane to small bits of magnesium in a flask containing ethoxyethane (commonly called diethyl ether or just "ether"). Carbonation of Grignard Reagents, RMgX, by CO 2. The alkyl groups can be any combination of same or different. Snieckus, 0000055409 00000 n The carbon-oxygen double bond is also highly polar with a significant amount of positive charge on the carbon atom. 0000064706 00000 n Solution was transferred to a 50-mL, in an ice bath for 2 min before hydrochloric acid (0.5 M, 0.30 mL) was added, which af, malachite green (0.90 mL, pH 4) as a turbid, dark blue/green solution: UV, Business Law: Text and Cases (Kenneth W. Clarkson; Roger LeRoy Miller; Frank B. Grignard reagents react with water to produce alkanes. The Grignard Reaction is the addition of an organomagnesium halide (Grignard reagent) to a ketone or aldehyde, to form a tertiary or secondary alcohol, respectively. EN. Grignard Reagent Reactions - PowerPoint PPT Presentation . Grignard reaction - Wikipedia 0000002969 00000 n % That leaves the carbon atom with a slight negative charge. Ku'g>yS(Av{Z%F>5 XG)mXG=\Z{:?8+zR} Y 0gZA(_RY3 D""& &M4.a8IEX)iq7[ AO The Application of a Continuous Grignard Reaction in the Preparation of organic chemistry 2. mgchit02. Grignard reagents react with carbon dioxide in two stages. PDF Manual - Grignard Dyes - Organic Chemistry at CU Boulder The Grignard reaction (pronounced Grin-yard) involves an R-Mg-X, a carbon chain bound to a magnesium halide, typically used to form alcohols by attacking carbonyls such as in aldehydes or ketones. 0000007105 00000 n %PDF-1.4 U( & 3Y8LYLwCStSx5mkXUl.o![5E>P#p@E|_6}U4N|=o Y+19_. The reaction was discovered by the French chemist Victor Grignard. General Reaction between Grignards and carbonyls, Reaction between Grignard reagents and methanal, Reaction between Grignards and other aldehydes, The reaction between Grignard reagents and ketones. A tertiary alcohol has three alkyl groups attached to the carbon with the -OH attached. Reddit and its partners use cookies and similar technologies to provide you with a better experience. Malachite green diethylcarbonate methybenzoate Mg HCl HCl Procedure: Complete the synthesis and purification of para-nitroaniline in Week 6. 0000003347 00000 n Download Lesson CS_Greener_Grignard.pdf The Grignard Reaction Mechanism | Study.com 2-Methyltetrahydrofuran (2-MeTHF), which can be derived from renewable resources, had at least an equal if not a superior overall process most Conventionally, the preformed organometal reagent (organolithium or organomagensium) reacts with carbonyl under air and. : an American History (Eric Foner), 14. To ensure optimization and safety of Grignard reactions in research, development and production, in situ monitoring and understanding reaction heat flow is important. P.O. The two wires shown in the figure carry currents of I = 5.37 A in opposite directions and are separated by a distance of d 0 = 8.78 cm. How to make trityl chloride? Explained by Sharing Culture The Grignard reagent can therefore serve as a nucleophile because of the attraction between the slight negativeness of the carbon atom in the Grignard reagent and the positiveness of the carbon in the carbonyl compound. Typically, you would add dilute sulfuric acid or dilute hydrochloric acid to the solution formed by the reaction with the CO2. Mechanochemical Grignard Reactions with Gaseous CO2 and Sodium Methyl Grignard Reaction - ChemConnections. In the first stage, the Grignard reagent adds across the carbon-oxygen double bond: Dilute acid is then added to this to hydrolyse it. reagent and the positiveness of the carbon in the carbonyl compound. 0000064445 00000 n - The role of the HCl in the reaction (protonation of the alkoxide ion and reaction with excess Mg/Grignard reagent) - Draw the mechanism of Grignard Synthesis of Malachite Green. 0000078049 00000 n One-Pot Access to 1-Azaspirocyclic Framework ]XC 5kj6 *&]T oDq20)JE8\zwCPJYn>\H>\kol&. {NgCPcQ}08HWYZ8=UU2 ^ q~;B}16^w1bx/#z "sWjs5VT\TMJ\exoX.>]jl4d` }KRa\/y[B7~E)h]}~ VbI W l@[9}@az7A[r3:k*]{Axm_O_ N|IVPD8Df[Z?>^=BljsVm`] \q^E*(g7st?C-@[W3f 5(grs8s$Mu;l@[aXH]@E=dmAg;L.'[r4i|>vDT@1 1?OKrn&]jF)#YIo&l=7!Gc#~MJ0fH F@=jqs 9.>+iy*R^4y$hwj,)-u-tn_6$O`I+P:L%Jt>3_E\LWs_s=\HN{x.(0ulG,?;hV !s~UKvW1BcS}wh{|?F4"e_w benzaldehyde solubility in hexane Methanal is the simplest possible aldehyde. 3) Reactions of Grignard reagent. Grignard Reagents - Preparation, Reactions & Organometallic Reagents That is actually misleading because these compounds react with dilute acids. % Solved Draw the mechanism of Grignard Synthesis of Malachite | Chegg.com (PDF) MODULE 1: DYE SYNTHESIS & DYEING | GAMING X - Academia.edu The reaction is similar to the Grignard reaction but the crucial difference is that the Barbier reaction is a One-pot synthesis whereas a Grignard reagent is . The reaction of Grignard reagents with O-alkyl S-pyridin-2-yl Lab Analysis of Malachite Green from Grignard Reaction 2002, 1115-1120. 9, 1335-1337. Legal. Malachite green | C23H25ClN2 | CID 11294 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities . In addition to being a topical antiseptic, Crystal Violet is especially well . In methanal, both R groups are hydrogen. This is the third video in the sequence: Part 1 (preparation for the reaction). . It is also used as a biological stain. 0000010821 00000 n Dry carbon dioxide is bubbled through a solution of the. Grignard reactions are performed using a Grignard reagent, which is typically a alkyl-, aryl- or vinyl- organomagnesium halide compound. 0000002227 00000 n PDF Part 1: Grignard Synthesis of Triphenylmethane Dyes Crystal Violet and The anions have no effect on the color. Grignard Reaction - Organic Chemistry P. Cali, M. Begtrup, Synthesis, trailer <]>> startxref 0 %%EOF 70 0 obj<>stream OneClass: Grignard Synthesis of malachite GreenFind the theoretical Grignard Lab Report - Name: Mohammad Sazid Hassan Partner's Name: Daniel, Nguyen, Maurice and Jason - StuDocu name: mohammad sazid hassan name: daniel, nguyen, maurice and jason title of experiment: grignard reaction formation of malachite green date: 10 february, 2016 Sign inRegister Sign inRegister Home My Library Courses 0000050305 00000 n Org. 0000069390 00000 n Wang, L. Zhang, X. Again, think about how that relates to the general case. Meredith's course. This MUST be read before entering the laboratory in addition to Chapter 19. . So I'm hoping you all can figure out what's missing. 0000002726 00000 n A Colorful Grignard Reaction: Preparation of the - ResearchGate Grignard Reaction Mechanism - Reaction Contributors & Important Reactions In English, please? PDF CHEM-333: Experiment 10: Grignard Reagent Preparation and Reaction: )uh9z ogG6$'\G`B&Y,l The greener approach reduces the use of undesirable ethers, and avoids the use of hexanes, and magnesium. 17 0 obj <> endobj xref 17 54 0000000016 00000 n The Grignard reaction is a reaction in organic chemistry that uses the Grignard reagent to form new carbon-carbon bonds. malachite; grignard; pear; ribbon; stir; spectrum; concentration; reagent; chemconnections . vmnwPV\-Tm 937x| Wg/R;*]*YySot3\_^BbMsjO357r2g H|hju 8un!zv kGC>=`Z;8C"\[UF.A@1&f \=_v ic!U:uoe H\dgqQu1j#)gf |SP.)b( E?yonvdr?8/k#@5RKDA,)R. 84, 11823-11838. Grignard reagent and its reactions as a nucleophile - OCT-Student Hub! 1) Preparation. Cookie Notice 0.85 g of methyl benzoate in a small test tube, to make Malachite Green To dry the glassware, rinse the condenser and flask with a few mL of anhydrous THF (discard into waste solvent). A. Deichert, L. Kapeniak, R. Lee, J. Harris, P. G. Jessop, V. Hydrogenation Reactions. This specific triarylmethane produces a vivid crystal violet color when dyed. tqH:8&>,fi(Mv1uQj7LwG[ J7t-!w03O.G% b7Qmj+F6%,g) >W=wBQ OK;bYy,#9l~x3eK(RuHh$C[eN8Y|)Iam@#&^EMqn1drs})W.UAyZ1\G*,L$#.>E{FG aE__a7Qs @9:n@P0,/CR3&MeL,nI.

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