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Sodium amide

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	Topics Sodium amide Topic Home Sodium amide, commonly called sodamide, is the chemical compoundFacts About Chemical compound A chemical compound is a chemical substance consisting of two or more different chemically bonded chemical elements, with a ... with the formulaChemical formula A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compoun... NaNH₂. This solid, which is dangerously reactive toward water, is white when pure, but commercial samples are typically gray due to the presence of small quantities of metallic iron from the manufacturing process. Such impurities do not usually affect the utility of the reagentReagent A reagent or reactant is any substance used in a chemical reaction.... . NaNH₂ has been widely employed as a strong base in organic synthesisOrganic synthesis Organic synthesis is the construction of organic molecules via chemical processes.... . Preparation and structure Sodium amide can be prepared by the reaction of sodiumSodium Sodium is a chemical element which has the symbol Na , atomic number 11, atomic mass 22.9898 g/mol, oxidation number +1.... with ammonia gas, but it is usually prepared by the reaction in liquid ammonia using iron(III) nitrateIron(III) nitrate Iron nitrate, or ferric nitrate, is most commonly encountered as the nonahydrate Fe3·9H2O.... as a catalystCatalyst In chemistry, a catalyst is a substance that decreases the activation energy of a chemical reaction without itself being c... . The reaction is fastest at the boiling point of the ammonia, ca. -33 °C. 2 Na + 2 NH₃ ? 2 NaNH₂ + H₂ NaNH₂ is a salt-like material and as such, crystallizes as an infinite polymer. The geometry about sodium is tetrahedral. In ammonia, NaNH₂ forms conductive solutions, consistent with the presence of Na(NH₃)₆⁺ and NH₂^- anions. Uses Sodium amide is used in the industrial production of indigoIndigo dye Indigo dye is an important dyestuff with a distinctive blue color .... , hydrazineHydrazine Hydrazine is the chemical compound with formula N2H4.... , and sodium cyanideSodium cyanide Sodium cyanide is a highly toxic chemical compound, also known as sodium salt of hydrocyanic acid and cyanogran.... . It is the reagent of choice for the drying of ammoniaAmmonia Ammonia is a compound of nitrogen and hydrogen with the formula NH3.... (liquid or gaseous) and is also widely used as a strong baseBase (chemistry) DefinitionA base is a substance which has a free pair of electrons to bind a proton .... in organic chemistry, often in liquid ammonia solution. One of the main advantages to the use of sodamide is that it is an excellent base and rarely serves as a nucleophile. It is however poorly soluble and its use has been superseded by the related reagents such as sodium hydrideSodium hydride Sodium hydride is the chemical compound with the formula NaH.... , sodium bis(trimethylsilyl)amideFacts About Sodium bis(trimethylsilyl)amide Sodium bisamide is the chemical compound with the formula3Si)2NNa.... (NaHMDS), and lithium diisopropylamideLithium diisopropylamide Overview Lithium diisopropylamide with the formula [2CH]2NLi, is a strong base, widely used in organic chemistry for the generation o... (LDA). Preparation of alkynes Sodium amide induces the loss of two molecules of hydrogen bromideHydrogen bromide Hydrogen bromide is the diatomic molecule HBr.... from a vicinalVicinal (chemistry) In chemistry vicinal stands for any two functional groups bonded to two adjacent carbon atoms.... dibromoalkane to give a carbon-carbon triple bond, as in the preparation of phenylacetylenePhenylacetylene Phenylacetylene is an alkyne hydrocarbon containing a phenyl group.... below. Hydrogen chlorideHydrogen chloride Hydrogen chloride, also known under the name HCl, is a highly corrosive and toxic colorless gas that forms white fumes... and/or ethanolEthanol Summary This article is about the chemical compound.... can also be eliminated in this way, Bou, Anna; Pericàs, Miquel A.; Riera, Antoni; Serratosa, Fèlix (1987). "". Org. Synth. 65:68; Coll. Vol. 8:161. Magriotis, Plato A.; Brown, John T. (1995). "". Org. Synth. 72:252; Coll. Vol. 9:656. Ashworth, P. J.; Mansfield, G. H.; Whiting, M. C. (1955). "". Org. Synth. 35:20; Coll. Vol. 4:128. as in the preparation of 1-ethoxy-1-butyne. Cyclization reactions Where there is no ß-hydrogen to be eliminated, cyclic compounds may be formed, as in the preparation of methylenecyclopropane below. CyclopropeneCyclopropene Cyclopropene is the simplest cycloalkene.... s, aziridineAziridine Aziridines are a group of organic compounds sharing the aziridine functional group which is a three membered heterocycle wit... s and cyclobutaneCyclobutane Cyclobutane, C4H8, with a molecular mass of 56.107g/mol, is a four carbon alkane in which all the carbon atoms are arranged ... s may be formed in a similar manner. Deprotonation of carbon and nitrogen acids Carbon acids which can be deprotonatedDeprotonation Deprotonation is a chemistry term that refers to the removal of a proton from a molecule, forming the conjugate base.... by sodium amide in liquid ammonia include terminal alkyneAlkyne Overview Alkynes are hydrocarbons that have at least one triple bond between two carbon atoms.... s, Peterson, P. E.; Dunham, M. (1977). "". Org. Synth. 57:26; Coll. Vol. 6:273. Kauer, J. C.; Brown, M. (1962). "". Org. Synth. 42:97; Coll. Vol. 5:1043. methyl ketoneFacts About Ketone A ketone is either the functional group characterized by a carbonyl group linked to two other carbon atoms or a chemical co... s, Hauser, C. R.; Adams, J. T.; Levine, R. (1948). "". Org. Synth. 28:44; Coll. Vol. 3:291. cyclohexanoneCyclohexanone Overview Cyclohexanone is a six-carbon cyclic molecule with a ketone functional group.... , phenylacetic acidPhenylacetic acid Phenylacetic acid is an organic compound containing a phenyl moiety and an acetic acid moiety.... and its derivatives Kaiser, Edwin M.; Kenyon, William G.; Hauser, Charles R. (1967). "". Org. Synth. 47:72; Coll. Vol. 5:559. Wawzonek, Stanley; Smolin, Edwin M. (1951). "". Org. Synth. 31:52; Coll. Vol. 4:387. and diphenylmethaneDiphenylmethane Diphenylmethane is a compound consisting of two phenyl groups joined to a single carbon.... . AcetylacetoneAcetylacetone Acetylacetone is an organic compound with molecular formula C5H8O2.... loses two protons to form a dianion. Hampton, K. Gerald; Harris, Thomas M.; Hauser, Charles R. (1967). Sodium amide will also deprotonate indoleIndole Indole is an aromatic heterocyclic organic compound.... and piperidinePiperidine Piperidine is an organic compound with the molecular formula C5H11N.... . Other reactions Rearrangement with orthodeprotonation Oxirane synthesis (by carbene reaction?) Indole synthesis Chichibabin reactionChichibabin reaction The Chichibabin reaction is a method for producing 2-aminopyridine derivatives by the reaction of pyridine with sodium amide... Safety Sodium amide reacts violently with water to produce ammoniaAmmonia Ammonia is a compound of nitrogen and hydrogen with the formula NH3.... and sodium hydroxideSodium hydroxide Overview Sodium hydroxide , also known as lye or caustic soda, is a caustic metallic base.... : and will burn in air to give oxides of sodiumSodium Overview Sodium is a chemical element which has the symbol Na , atomic number 11, atomic mass 22.9898 g/mol, oxidation number +1.... and nitrogenNitrogen Nitrogen is a chemical element which has the symbol N and atomic number 7 in the periodic table.... . NaNH₂ + H₂O ? NH₃ + NaOH 2NaNH₂ + 4O₂ ? Na₂O₂Sodium peroxide Overview Sodium peroxide has formula Na2O2.... + 2NO₂Nitrogen dioxide \|-\| align="center" colspan="2" bgcolor="#ffffff" \| \|-... + 2H₂O In the presence of limited quantities of air and moisture, such as in a poorly closed container, explosive mixtures of oxidation products can form. This is accompanied by a yellowing or browning of the solid. As such, sodium amide should always be stored in a tightly closed container, if possible under an atmosphere of nitrogen gas. Sodium amide samples which are yellow or brown in color should be destroyed immediately: one method for destruction is the careful addition of ethanolEthanol This article is about the chemical compound.... to a suspension of sodium amide in a hydrocarbonHydrocarbon In chemistry, a hydrocarbon is any chemical compound that consists only of the elements carbon and hydrogen .... solvent. Sodium amide may be expected to be corrosive to the skin, eyes and mucous membranes. Care should be taken to avoid dispersal of the dust. See also Lithium amideLithium amide Lithium amide is an inorganic compound that is composed of lithium cation and the conjugate base of ammonia.... Sodium bis(trimethylsilyl)amideFacts About Sodium bis(trimethylsilyl)amide Sodium bisamide is the chemical compound with the formula3Si)2NNa.... External links (from Organic SynthesesOrganic Syntheses *Organic Syntheses* is a scientific journal that since 1921 has provided the chemistry community with annual collections o... )