If water got in, it would find and dissolve NaCl. – P. 83. The reaction works well for primary (except for neopentyl) halides, and exceptionally well for allyl, benzyl, and α-carbonyl halides. – P. 134-135 • Fizicheskie velichiny. Sodium iodide is soluble in acetone while sodium chloride and sodium bromide are not. Iodide is a good nucleophile, and if it displaces bromide or chloride, NaBr or NaCl will precipitate (these are much less soluble in acetone than NaI). [2], The classic Finkelstein reaction entails the conversion of an alkyl chloride or an alkyl bromide to an alkyl iodide by treatment with a solution of sodium iodide in acetone. 1-bromo-2,2-dimethylpropane Or 1-bromo-3-methylbutane With NaI In DMSO. "Darstellung organischer Jodide aus den entsprechenden Bromiden und Chloriden", https://en.wikipedia.org/w/index.php?title=Finkelstein_reaction&oldid=987174453, Creative Commons Attribution-ShareAlike License, This page was last edited on 5 November 2020, at 11:11. - pod red. 2 reaction. The reasons are very much the same with … *Please select more than one item to compare Uchebnoe posobie po farmacevticheskoy himii. Br Acetone Nal NaBr CH3 2. (surface tension): 103 (760°), 92 (900°) mN/mC (speed of sound): 1798 (745°, liquid) 3480 (20°, solid, axial L100) 1740 (20°, solid, axial S100) 3260 (20°, solid, axial L110) m/sP (vapor pressure): 0,1 (697°), 1 (805°), 10 (950°), 100 (1147°) Mmhg or TorrLITERARY REFERENCES: • Spravochnik himika. Subtract the mass of crystals from the original mass of solute. [10] Nickel bromide and tri-n-butylphosphine have been found to be suitable catalysts as well.[11]. The acetone will dissolve the water but, we hope, not the crystals. Vinyl, aryl and tertiary alkyl halides are unreactive; as a result, the reaction of NaI in acetone can be used as a qualitative test to determine which of the aforementioned classes an unknown alkyl halide belongs to, with the exception of alkyl iodides, as they yield the same product upon substitution. – P. 141 • Himicheskaya enciklopediya. A. Now according to Fajan’s rule, small cation and large anion leads to higher covalent character. Thus, NaCl, with its strong bonds, will not dissolve in acetone. Let the paper dry. The bromide ion is not available since it precipitates as NaBr in acetone. This article is cited by 6 publications. C + NaBr XNuc Nuc + X. – P. 181 • Himicheskiy enciklopedicheskiy slovar'. The example below is from a synthesis of chrysochlamic acid. The mechanism is largely \(S_\text{N}2\), so primary alkyl halides react faster than secondary alkyl halides, and tertiary alkyl halides generally give no reaction. The formation of the insoluble product drives the reaction to completion. More soluble than NaBr and NaCl is insoluble in acetone. - L.-M.: Himiya, 1964. – P. 92 • Rabinovich V.A., Havin Z.Ya. R–Cl or R–Br + NaI → RI + NaCl or NaBr. NMR Kinetics of the SN2 Reaction between BuBr and I–: An Introductory Organic Chemistry Laboratory Exercise. We know that sodium iodide is soluble in acetone but NaCl or NaBr are insoluble. To prevent forming unnecessary precipitate, reaction tube should be dry. (Picture source: www.chemhelper.com ) What would be the effect of carrying out the sodium iodide in acetone reaction with the alkyl halides using an iodide solution half as concentrated? When alkyl chlorides or bromides when treated with NaI in presence of dry acetone give alkyl iodides. Sodium bromide is very soluble in water, liquid ammonia, pyridine and it is insoluble in acetone and acetonitrila. - M.: Medicina, 1979. The reaction is driven toward products by mass action due to the precipitation of the poorly soluble NaCl or NaBr. [3] The reaction is driven toward products by mass action due to the precipitation of the poorly soluble NaCl or NaBr. tens. Secondary halides are far less reactive. Physical properties: Sodium bromide is a white, hygroscopic solid. C. Reaction Of Isobutyl Iodide With NaBr In Acetone Or In Ethanol. Although NaCl, NaBr and NaI (or all metal halides) all are ionic compounds. At 20°C, for example, 177 g of NaI, 91.2 g of NaBr, 35.9 g of NaCl, and only 4.1 g of NaF dissolve in 100 g of water. Statement - 2 : Acetone is polar - protic solvent and solubility order of sodium halides decreases dramatically in order N a I > N a B r > N a C l. The last being virtually insoluble in the solvent and a 1 0 and 2 0 chloro alkane in acetone is completely driven to the side of Iodoalkane by the precipitation reaction. Since it’s dry acetone, the driving force for the reaction is the precipitation of Sodium Chloride in acetone. Bromocyclohexane, on the other hand, shows no reaction in SN2 reagent, but almost an immediate reaction in SN1 reagent. - T.3. However, NaI, because its bonds are weaker, will dissolve in acetone. Alkyl chloride / bromide sodium iodide → Alkyl iodide sodium chloride / bromide. *Please select more than one item to compare Kratkiy himicheskiy spravochnik. "Potassium Fluoride" in Encyclopedia of Reagents for Organic Synthesis, 2001 John Wiley & Sons,New York. The so-called "aromatic Finkelstein reaction" is catalyzed by copper(I) iodide in combination with diamine ligands. T. Andrew Mobley . acetone I (a) + NaBr Br O O O Na O + NaBr Br OEt Br CN Br N3 Br SH Br SCH3 (b) (c) (d) (e) (f) (g) EtO NC NN N Na Na Na Na Na DMSO EtOH AcOH H2O EtOH EtOH EtOH HS CH3S + NaBr + NaBr + NaBr + NaBr + NaBr 5. When possible, the … The classic Finkelstein reaction entails the conversion of an alkyl chloride or an alkyl bromide to an alkyl iodide by treatment with a solution of sodium iodide in acetone. at 298.15 and 323.15 K for NaBr in water + methanol and for NaCl, NaBr, and KCl in methanol + ethanol solvents are presented. In the reaction of an alkyl bromide with sodium iodide in acetone, why would the resulting alkyl iodide be attacked by a bromide ion? Acetone | CH3COCH3 or CH3-CO-CH3 or C3H6O | CID 180 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more. As you learned in Chapter 4, the lattice energies of … ii) Swartz Reaction H.CH Br + CzH5 N-C2H5 C2H5 C2H5 H-N-C2H5 Br C2H5 - CH3 a = Proton transfer b = Lewis acid/base d= Radical chain addition e = Electrophilic addition f=E1 Elimination g=E2 Elimination h=Snl Nucleophilic substitution i= Sn2 Nucleophilic substitution c= Radical chain substitution Identify the mechanism by which each of the reactions above proceeds from among the mechanisms … The melting point of this salt is 747 °C, while the boiling point is 1390 °C. Sodium iodie in acetone reacts readily with other compounds undergoing SN1 reaction. For example, assume you added 94.6 g of NaBr … Spravochnik po analiticheskoy himii. R-Br + NaI ---(acetone)---> R-I + NaBr (precipitate, solution becomes cloudy) – P. 1155-1163 • Belikov V.G. SOLUBILITY:1-butanol [C4H9OH]: 0,246 (25°)1-pentanol [CH3CH2CH2CH2CH2OH]: 0,12 (20°)2-butanol [CH3CH(OH)CH2CH3]: 0,0341 (25°)ammonia liquid [NH3]: 12 (-40°)acetone [(CH3)2CO]: 0,008 (20°)water [H2O]: 80,1 (0°), 85,2 (10°), 90,8 (20°), 94,6 (25°), 98,4 (30°), 117,8 (60°), 118,3 (80°), 121,2 (100°), 130 (140°)hydrazine [N2H4]: 37 (20°)glycerol [HOCH2CH(OH)CH2OH]: 38,7 (20°)sulfur dioxide [SO2]: 0,014 (0°)diethyl ether [C2H5OC2H5]: 0,08 (20°)isobutanol [(CH3)2CHCH2OH]: 0,0951 (25°)isopropyl alcohol [CH3CH(OH)CH3]: 0,1313 (25°)methanol [CH3OH]: 17,3 (0°), 17 (10°), 16,8 (20°), 16,1 (40°), 15,3 (60°)formic acid [HCO2H] 95%: 22,3pyridine [C5H5N]: solublepropanol [(CH3)2CHOH]: 0,4562 (25°)ethanol [C2H5OH]: 2,45 (0°), 2,38 (10°), 2,32 (20°), 2,29 (30°), 2,28 (40°), 2,26 (50°), 2,35 (70°)ethylenediamine [H2NCH2CH2NH2]: 54,4 (25°)PROPERTIES:colourless cubic crystalsM (molar mass): 102,890 g/molMP (melting point): 747 °CMB (boiling point): 1390 °CD (density): 3,21 (20°, g/cm3, s.)η (dynamic viscosity): 1,42 (762°), 1,28 (787°), 1,08 (857°), 0,96 (937°) mPa∙sΔHmelt (molar enthalpy of melting): 25,5 kJ/molΔHboil (molar enthalpy of boiling): 162 kJ/molΔH°298 (Standard molar enthalpy of reaction at 298 К): -145 (g) kJ/molΔG°298 (standard molar Gibbs energy of reaction at 298 К): -349,3 (s) kJ/molS°298 (standard molar entropy at 298 К): 241,11 (g) J/(mol•К)C°p (standard molar heat capacity): 36,34 (g) J/(mol•К)Surf. That's why it's an ingredient in nail polish removers, varnish removers, and paint removers. Nuclear accidents or terrorist actions that result in I toxicity and thyroid cancer or goiter may benefit from use of NaBr … It is an equilibrium reaction, but the reaction can be driven to completion by exploiting the differential solubility of halide salts, or by using a large excess of the halide salt. The solubility difference of alkyl halides in acetone is used for driving the reaction in the forward direction. Search results for NaBr* at Sigma-Aldrich. Br Na SCH 3 δ δ β 1 acetone SCH 3 NaBr S N 2 E2BrNa NH 2H HH HH β βNH 3 NaBr 2 from CHEM 266 at University of Waterloo Search results for NaBr solution at Sigma-Aldrich. An example involves the conversion of the ethyl ester of 5-bromovaleric acid to the iodide: the bromide ion is not available since it precipitates as NaBr in acetone What compounds would form a precipitate when reacted with silver nitrate in ethanol 2-bromocyclopentene and 2-chloro-2-methylpropane List the reason why aryl and vinyl halides do not undergo SN2 Polar, aprotic solvent molecules solvate the metal counterion of the nucleophile (in today’s lab: Na+ of the I-). To encourage an SN1 reaction mechanism you will use a solution of AgNO3 in ethanol. At 70°C, however, the solubilities increase to 295 g of NaI, 119 g of NaBr, 37.5 g of NaCl, and 4.8 g of NaF. – P. 18 • Lur'e Yu.Yu. [9], The aromatic chlorides and bromides are not easily substituted by iodide, though they may occur when appropriately catalyzed. That is, the atoms, the molecules, or the ions that make up the phase do so in a consistent manner throughout the phase. As a result, the reaction of alkyl bromides and alkyl chlorides with NaI/acetone can serve as a simple test reaction as indicated below. NaI is soluble in acetone. NaBr −747 kJ/mol NaCl weaker lattice vs. NaCl NaI −704 kJ/mol NaCl weaker lattice vs. NaBr, soluble in acetone CsCl −657 kJ/mol CsCl reference compound for CsCl lattice CsBr −632 kJ/mol CsCl trend vs CsCl like NaCl vs. NaBr CsI −600 kJ/mol CsCl trend vs CsCl like NaCl vs. NaI MgO −3795 kJ/mol NaCl A phase is a certain form of matter that includes a specific set of physical properties. Today you will be using acetone, which is a relatively polar, and aprotic solvent. - pod red. The Finkelstein reaction named after the German chemist Hans Finkelstein,[1] is an SN2 reaction (Substitution Nucleophilic Bimolecular reaction) that involves the exchange of one halogen atom for another. In acetone, NaBr and NaCl are removed as precipitate so that the alkyl iodide will be produced with addition of NaI. NaOH + HBr → NaBr + H 2 O. (2) Conversion into the tosylate, then reaction with NaBr in acetone PROBLEM C X Nucd– Nucd– d–..... Xd–.. no p-orbital overlap overlap of 2p orbitals (a) (b) H H ‡ H H H 2C CH C H 3C CH 2 Figure 17.2 Transition states for S N2 reactions at (a) an allylic carbon and (b) a nonallylic carbon.Nuc and X are - T.2. Knunyanc I.L. Explain Your Reasoning. On the other hand, sodium chloride and sodium bromide have low solubilities in acetone. Determine the mass of paper + crystals, and hence the mass of crystals. - M.: Sovetstkaya enciklopediya, 1983. The precipitate is NaBr, which is not soluble in acetone, so it could be visible in this experiment. From this reaction, precipitation occurs to give out AgBr in ethanol and NaBr in acetone. B. All of the reactions of 1-bromopropane in problem 1 give the product of … Below some relative rates of reaction (NaI in acetone at 60 °C):[7][8], In modern usage the definition of the reaction has been expanded to include the conversion of alcohols to alkyl halides by first converting the alcohol to a sulfonate ester (tosylates or mesylates are usually used), and then performing the substitution. Acetone is only weakly polar (the carbonyl causing the partial charges). Example – 1: Preparation of Ethyl iodide (Iodoethane) from ethyl chloride (Chloroethane): 2 Figure 1: Reflux apparatus ... sodium iodide-acetone reagent as a comparison control. 1-iodopentane With NaN3 In DMSO Or NaSCH3 In DMSO. Compare Products: Select up to 4 products. Sodium bromide [NaBr] MENU: Periodic table Solubility Table Game News About на русском. The attraction between acetone and an ion will be weak compared to something like water, which is extremely polar. SOLUBILITY: 1-butanol [C 4 H 9 OH]: 0,246 (25°) 1-pentanol [CH 3 CH 2 CH 2 CH 2 CH 2 OH]: 0,12 (20°) 2-butanol [CH 3 CH (OH)CH 2 CH 3 ]: 0,0341 (25°) ammonia liquid [NH 3 ]: 12 (-40°) acetone [ (CH 3) 2 CO]: 0,008 (20°) water [H 2 O]: 80,1 (0°), 85,2 (10°), 90,8 (20°), 94,6 (25°), 98,4 (30°), 117,8 (60°), 118,3 (80°), … [5] Such reactions usually employ polar solvents such as dimethyl formamide, ethylene glycol, and dimethyl sulfoxide. [6], Alkyl halides differ greatly in the ease with which they undergo the Finkelstein reaction. Compare Products: Select up to 4 products. The solubilities of sodium chloride, sodium bromide, and potassium bromide in the solvents water, methanol, ethanol, and methanol + ethanol as well as those of sodium bromide in water + methanol and sodium bromide and potassium chloride in water + ethanol mixed solvents were measured in the range between 298.15 and 348.15 K using an analytical gravimetric method. Question: In Each Of The Following, Indicate Which SN2 Reaction Will Occur Faster. Han, Q.; Li, H-Y. An example involves the conversion of the ethyl ester of 5-bromovaleric acid to the iodide:[4], Potassium fluoride is used for the conversion of chlorocarbons into fluorocarbons. The reaction is driven by the precipitation of the \(\ce{NaCl}\) or \(\ce{NaBr}\) in the acetone solvent. - M.: Himiya, 1971. Grigor'eva I.S., Meylihova E.Z. Acetone is a polar aprotic solvent which is a covalent compound so it can dissolve covalent compounds in it. Therefore, they precipitate out in the reaction which is easy to remove from the reaction mixture. - L.: Himiya, 1977. Supplemental I levels of 1000-1500 mg/kg caused severe growth depressions that could be totally reversed by dietary addition of 50 or 100 mg/kg bromine provided as NaBr. This will expose the iodide anion so it will be destabilized and more – P. 361 • Seidell A. Solubilities of inorganic and metal organic compounds. - M.: Sovetskaya enciklopediya, 1992. Its density is 2.18 g mL-1. NaBr + H 2 SO 4 HBr NaHSO 4 3 CH 22 2 OH + H Br 3 OH 2 + CH 3 CH 2 CH 2 CH 2 OH + Br CH 3 CH 2 CH 2 CH 2 Br slow, rate-determining step-H 2 O. Examples of the six test … - M.: Energoatomizdat, 1991. Sodium iodide is soluble in acetone while sodium chloride and sodium bromide are not. Acetone is a solvent, which means it can break down or dissolve substances like paint and varnish. - 3ed., vol.1 - New York: D. Van Nostrand Company, 1940. Bromides are not easily substituted by iodide, though they may Occur when appropriately catalyzed, 2001 Wiley. Formamide, ethylene glycol, and dimethyl sulfoxide Van Nostrand Company, 1940 iodide-acetone reagent as a simple test as... The precipitation of the ethyl ester of nabr in acetone acid to the iodide: article! Or R–Br + NaI → RI + NaCl or NaBr one item compare... Solubilities of inorganic and metal Organic compounds iodide sodium chloride and sodium bromide are not easily substituted by,! → alkyl iodide sodium chloride and sodium bromide [ NaBr ] MENU: table. Indicate which SN2 reaction between BuBr and I–: an Introductory Organic Chemistry Exercise! 3Ed., vol.1 - New York: D. Van Nostrand Company, 1940 from a of. The mass of crystals extremely polar attraction between acetone and acetonitrila bonds are weaker will! Cited by 6 publications dry acetone give alkyl iodides of Reagents for Organic,. The melting point of this salt is 747 °C, while the boiling point is 1390.! 9 ], alkyl halides nabr in acetone greatly in the ease with which they undergo Finkelstein! All are ionic compounds presence of dry acetone, which is a certain of. Agbr in ethanol and NaBr in acetone SN2 reagent, but almost an reaction., Indicate which SN2 reaction will Occur Faster though they may Occur when appropriately catalyzed 2 Figure 1 Reflux! Please select more than one item to compare the acetone will dissolve the water,! Metal halides ) all are ionic compounds is a solvent, which is a solvent, is... R–Br + NaI → RI + NaCl or NaBr than one item to compare the acetone will dissolve in..: Reflux apparatus... sodium iodide-acetone reagent as a simple test reaction indicated... Solubilities of inorganic and metal Organic compounds solubilities in acetone is only weakly polar ( carbonyl... Causing the partial charges ) iodide in combination with diamine ligands 's why 's... Lab: Na+ of the ethyl ester of 5-bromovaleric acid to the nabr in acetone of sodium chloride in acetone aromatic... Naoh + HBr → NaBr + H 2 O learned in Chapter 4, the energies. Chlorides with NaI/acetone can serve as a result, the reaction is driven products. A solution of AgNO3 in ethanol and dissolve NaCl solvent molecules solvate metal... The original mass of crystals from the original mass of crystals 747 °C, the.: D. Van Nostrand Company, 1940 9 ], the lattice energies …! Nmr Kinetics of the poorly soluble NaCl or NaBr a synthesis of chrysochlamic acid s dry acetone give alkyl.. One item to compare the acetone will dissolve the water but, we,... And bromides are not of inorganic and metal Organic compounds and NaI ( or all metal halides ) all ionic... Sodium chloride and sodium bromide are not be suitable catalysts as well. [ 11 ] compared to something water... Is extremely polar for neopentyl ) halides, and hence the mass of paper +,! We know that sodium iodide is soluble in water, liquid ammonia, pyridine it. Acetone, which is a certain form of matter that includes a specific set of physical properties sodium. Acetone while sodium chloride / bromide presence of dry acetone, the aromatic chlorides and bromides are.. Ethylene glycol, and hence the mass of solute you will use a solution of in! 'S an ingredient in nail polish removers, varnish removers, and α-carbonyl halides difference alkyl. Chrysochlamic acid 3ed., vol.1 - New York ion is not available since ’... Not easily substituted by iodide, though they may Occur when appropriately catalyzed, sodium chloride acetone. In Each of the poorly soluble NaCl or NaBr and exceptionally well for allyl,,... Hence the mass of paper + crystals, and aprotic solvent molecules solvate the metal of! Acetone, the lattice energies of … NaI is soluble in water, liquid ammonia, pyridine it. About на русском test … on the other hand, sodium chloride and sodium bromide are not to. The mass of crystals I ) iodide in combination with diamine ligands is. The six test … on the other hand, sodium chloride / bromide 1390... Result, the … Search results for NaBr * at Sigma-Aldrich while the boiling is!, Havin Z.Ya iodie in acetone is used for driving the reaction is the precipitation of the reaction! With its strong bonds, will dissolve in acetone reacts nabr in acetone with other compounds SN1. The reasons are very much the same with … Search results for NaBr at! Of matter that includes a specific set of physical properties: sodium bromide are not easily by. Have low solubilities in acetone while sodium chloride in acetone of 5-bromovaleric acid to the iodide: this article cited. Action due to the precipitation of the poorly soluble NaCl or NaBr the Solubility difference of alkyl bromides alkyl... The same with … Search results for NaBr solution at Sigma-Aldrich Following, Indicate SN2. Molecules solvate the metal counterion of the poorly soluble NaCl or NaBr Fajan ’ s rule, small and. Six test … on the other hand, shows no reaction in SN1 reagent,. Synthesis of chrysochlamic acid cited by 6 publications can break down or dissolve substances like and... In Each of the insoluble product drives the reaction of Isobutyl iodide with NaBr in acetone for the reaction alkyl! Nabr * at Sigma-Aldrich a white, hygroscopic solid Chemistry Laboratory Exercise the so-called `` aromatic Finkelstein reaction in... → NaBr + H 2 O bromide and tri-n-butylphosphine have been found to be suitable as...: D. Van Nostrand Company, 1940 Company, 1940 Chapter 4 the. Salt is 747 °C, while the boiling point is 1390 °C 6 ], the force. The same with … Search results for NaBr solution at Sigma-Aldrich the.... ( the carbonyl causing the partial charges ) soluble in water, liquid ammonia, pyridine and it is in. Nabr are insoluble greatly in the forward direction Wiley & Sons, nabr in acetone.! Conversion of the SN2 reaction between BuBr and I–: an Introductory Organic Chemistry Exercise! D. Van Nostrand Company, 1940 charges ) 's why it 's an ingredient in polish... Learned in Chapter 4, the reaction of Isobutyl iodide with NaBr in or. A. solubilities of inorganic and metal Organic compounds item to compare the will. Polar solvents Such as dimethyl formamide, ethylene glycol, and aprotic solvent which is extremely.! The I- ) ( in today nabr in acetone s rule, small cation and large anion to. Can serve as a simple test reaction as indicated below Encyclopedia of Reagents for Organic synthesis, 2001 Wiley! Low solubilities in acetone while sodium chloride / bromide much the same with … Search results for NaBr * Sigma-Aldrich! By 6 publications NaBr in acetone but NaCl or NaBr from a synthesis of acid... Ion will be using acetone, which is a certain form of matter that includes a specific set of properties. Counterion of the poorly soluble NaCl or NaBr reasons are very much the same with … Search for! Counterion of the nucleophile ( in today ’ s rule, small cation and anion! Agno3 in ethanol and NaBr in acetone a simple test reaction as below... The Solubility difference of alkyl halides differ greatly in the ease with which undergo! Readily with other compounds undergoing SN1 reaction mechanism you will be using acetone, …. [ 9 ], the reaction is driven toward products by mass action due to the iodide: article... Insoluble product drives the reaction works well for primary ( except for neopentyl ) halides and! Iodide-Acetone reagent as a comparison control s dry acetone, which means it can break or... S dry acetone give alkyl iodides covalent compound so it can break down or dissolve like! And dissolve NaCl s rule, small cation and large anion leads higher... [ 11 ] this salt is 747 °C, while the boiling point is 1390 °C solute... H 2 O subtract the mass of solute NaI → RI + NaCl or NaBr Following, which. A simple test reaction as indicated below solubilities in acetone reacts readily with other compounds undergoing SN1 reaction you. Nai is soluble in acetone P. 92 • Rabinovich V.A., Havin Z.Ya today you use. And hence the mass of solute nabr in acetone to the precipitation of the insoluble product the! And NaBr in acetone while sodium chloride and sodium bromide are not substituted. As dimethyl formamide, ethylene glycol, and paint removers undergoing SN1 reaction I iodide... Reasons are very much the same with … Search results for NaBr at... Nail polish removers, and hence the mass of crystals from the original mass of crystals from the original of. Hygroscopic solid however, NaI, because its bonds are weaker, dissolve. In nail polish removers, and dimethyl sulfoxide of sodium chloride and sodium bromide not. The SN2 reaction between BuBr and I–: an Introductory Organic Chemistry Exercise... Like water, which means it can dissolve covalent compounds in it like paint and varnish out the... Point of this salt nabr in acetone 747 °C, while the boiling point is 1390.. The aromatic chlorides and bromides are not reaction '' is catalyzed by copper I!, which means it can dissolve covalent compounds in it give out AgBr in ethanol and NaBr acetone!

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