Sodium amide, also called sodamide, is NaNH₂. This solid is highly reactive, dangerously so in the presence of moisture or air. It hydrolyzes readily to ammonia. The pure solid is white, but commercial samples are often grey in colour due to the presence of small quantities of metallic iron from the manufacturing process: this does not usually affect the use of the product. Sodium amide samples which are yellow or brown in colour should be destroyed immediately (see Safety below). A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... Density (symbol: ρ - Greek: rho) is a measure of mass per volume. ... In the physical sciences, a phase is a set of states of a macroscopic physical system that have relatively uniform chemical composition and physical properties (i. ... It has been suggested that this article or section be merged with Solution. ... This article describes water from a scientific and technical perspective. ... The melting point of a solid is the temperature at which it changes state from solid to liquid. ... The boiling point of a substance is the temperature at which it can change its state from a liquid to a gas throughout the bulk of the liquid at a given pressure. ... In chemistry and biochemistry, the acid dissociation constant, the acidity constant, or the acid-ionization constant (Ka) is a specific type of equilibrium constant that indicates the extent of dissociation of hydrogen ions from an acid. ... The coordination geometry of an atom is the geometrical pattern formed by its neighbors in a molecule or a crystal. ... Rose des Sables (Sand Rose), formed of gypsum crystals In mineralogy and crystallography, a crystal structure is a unique arrangement of atoms in a crystal. ... A material safety data sheet or MSDS is a form containing data regarding the properties of a particular substance. ... Council Directive 67/548/EEC of 27 June 1967 on the approximation of laws, regulations and administrative provisions relating to the classification, packaging and labelling of dangerous substances (as amended) is the main source of European Union law concerning chemical safety. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... The flash point of a flammable liquid is the lowest temperature at which it can form an ignitable mixture with air. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... The refractive index (or index of refraction) of a material is the factor by which the phase velocity of electromagnetic radiation is slowed in that material, relative to its velocity in a vacuum. ... The dielectric constant εr (represented as or K in some cases) is defined as the ratio: where εs is the static permittivity of the material in question, and ε0 is the vacuum permittivity. ... Ultraviolet-Visible Spectroscopy or Ultraviolet-Visible Spectrophotometry (UV/ VIS) involves the spectroscopy of photons (spectrophotometry). ... IR spectrum of a thin film of liquid ethanol. ... Nuclear Magnetic Resonance Spectroscopy most commonly known as NMR Spectroscopy is the name given to the technique which exploits the magnetic properties of nuclei. ... Basic schematic of a mass spectrometer Mass spectrometry (also know as mass spectroscopy (incorrect)[1] or in common speech mass-spec) is an analytical technique used to measure the mass-to-charge ratio of ions. ... An ion is an atom or group of atoms that normally are electrically neutral and achieve their status as an ion by loss (or addition) of an electron. ... Sodium hydroxide (NaOH), also known as lye or caustic soda, is a caustic metallic base. ... An ion is an atom or group of atoms that normally are electrically neutral and achieve their status as an ion by loss (or addition) of an electron. ... Ammonia is a compound of nitrogen and hydrogen with the formula NH3. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... Ammonia is a compound of nitrogen and hydrogen with the formula NH3. ...

Preparation

Sodium amide can be prepared by the reaction of sodium with ammonia gas,^[1] but it is usually prepared by the reaction in liquid ammonia using iron(III) nitrate as a catalyst.^[2] General Name, Symbol, Number sodium, Na, 11 Chemical series alkali metals Group, Period, Block 1, 3, s Appearance silvery white Atomic mass 22. ... This article lacks information on the importance of the subject matter. ... In chemistry, a catalyst (Greek: καταλύτης, catalytēs) is a substance that decreases the activation energy of a chemical reaction (see also catalysis) without itself being changed at the end of the chemical reaction. ...

2Na + 2NH₃ → 2NaNH₂ + H₂

Uses

Sodium amide is used in the industrial production of indigo, hydrazine, and sodium cyanide.^[3] It is the reagent of choice for the drying of ammonia (liquid or gaseous) and is also widely used as a strong base in organic chemistry, often in liquid ammonia solution. Its use has been superseded by the popularization of related reagents such as NaH, NaN[Si(CH₃)₃]₂, and LiN[CH(CH₃)₂]₂. Indigo dye indigo molecule Indigo dye is an important dyestuff with a distinctive blue color (see indigo). ... Hydrazine is the chemical compound with formula N2H4. ... Sodium cyanide is a highly toxic chemical compound, also known as sodium salt of hydrocyanic acid and cyanogran. ... Ammonia is a compound of nitrogen and hydrogen with the formula NH3. ... A bases in chemistry is a chemical substance which has a free pair of electrons to bind a Hydrogen ion commonly referred to as a proton (IUPAC definition). ...

Preparation of alkynes

Sodium amide induces the loss of two molecules of hydrogen bromide from a vicinal dibromoalkane to give a carbon-carbon triple bond, as in the preparation of phenylacetylene below.^[4] Flash point Non flammable Supplementary data page Structure and properties n, εr, etc. ... In chemistry vicinal stands for any two functional groups bonded to two adjacent carbon atoms. ... Phenylacetylene is an alkyne hydrocarbon containing a phenyl group. ...

Image File history File links Download high-resolution version (7162x1350, 27 KB) Summary Description: Preparation of phenylacetylene. ...

Hydrogen chloride and/or ethanol can also be eliminated in this way,^[5][6][7][8] as in the preparation of 1-ethoxy-1-butyne.^[9] R-phrases , S-phrases , , , , Flash point non-flammable Supplementary data page Structure and properties n, εr, etc. ... Ethanol, also known as ethyl alcohol or grain alcohol, is a flammable, colorless, mildly toxic chemical compound with a distinctive perfume-like odor, and is the alcohol found in alcoholic beverages. ...

Image File history File links Download high-resolution version (12601x1714, 47 KB) Summary Description: Preparation of 1-ethoxy-1-butyne. ...

Cyclization reactions

Where there is no β-hydrogen to be eliminated, cyclic compounds may be formed, as in the preparation of methylenecyclopropane below.^[10]

Image File history File links Download high-resolution version (6759x1393, 36 KB) Summary Description: Preparation of methylenecyclopropane. ...

Cyclopropenes,^[11] aziridines^[12] and cyclobutanes^[13] may be formed in a similar manner. Cyclopropene is the simplest cycloalkene. ... Aziridine parent compound Aziridines are a group of organic compounds sharing the aziridine functional group which is a three membered heterocycle with one amine group and two methylene groups 1,2. ... Cyclobutane, C4H8, with a molecular mass of 56. ...

Deprotonation of carbon and nitrogen acids

Carbon acids which can be deprotonated by sodium amide in liquid ammonia include terminal alkynes,^[14][15][16] methyl ketones,^[17][18] cyclohexanone,^[19] phenylacetic acid and its derivatives^[20][21][22] and diphenylmethane.^[23] Acetylacetone loses two protons to form a dianion.^[24] Deprotonation is a chemistry term that refers to the removal of a proton (hydrogen ion H+) from a molecule, forming the conjugate base. ... Alkynes are hydrocarbons that have at least one triple bond between two carbon atoms. ... Ketone group A ketone is either the functional group characterized by a carbonyl group linked to two other carbon atoms or a chemical compound that contains this functional group. ... Cyclohexanone is six-carbon cyclic molecule with a ketone functional group. ... Phenylacetic acid (synonyms: α-Toluic acid, benzeneacetic acid, alpha tolylic acid, 2-phenylacetic acid) is an organic compound containing a phenyl moiety and an acetic acid moiety. ... Diphenylmethane is a compound consisting of two phenyl groups joined to a single carbon. ... R-phrases , S-phrases , , , Flash point 34 °C Autoignition temperature 340 °C Explosive limits 2. ... An anion is an ion with negative charge. ...

Image File history File links Download high-resolution version (9615x2084, 58 KB) Summary Description: Double deprotonation of acetylacetone with sodium amide. ...

Sodium amide will also deprotonate indole^[25] and piperidine.^[26] Indole is an aromatic heterocyclic organic compound. ... R-phrases , , S-phrases , , , , Flash point 16 °C RTECS number TM3500000 Related compounds Related compounds pyridine pyrrolidine piperazine Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references Piperidine is an organic compound with the molecular formula C5H11N...

Other reactions

• Rearrangement with orthodeprotonation^[27]
• Oxirane synthesis (by carbene reaction?)^[28]
• Indole synthesis^[29]

Safety

Sodium amide reacts violently with water to produce ammonia and sodium hydroxide: and will burn in air to give oxides of sodium and nitrogen. Ammonia is a compound of nitrogen and hydrogen with the formula NH3. ... Sodium hydroxide (NaOH), also known as lye or caustic soda, is a caustic metallic base. ... General Name, Symbol, Number sodium, Na, 11 Chemical series alkali metals Group, Period, Block 1, 3, s Appearance silvery white Atomic mass 22. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless Atomic mass 14. ...

NaNH₂ + H₂O → NH₃ + NaOH

2NaNH₂ + 4O₂ → Na₂O₂ + 2NO₂ + 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 colour should be destroyed immediately: one method for destruction is the careful addition of ethanol to a suspension of sodium amide in a hydrocarbon solvent. Sodium peroxide has formula Na2O2. ... [1] R-phrases , S-phrases , , , , , Supplementary data page Structure and properties n, εr, etc. ... Ethanol, also known as ethyl alcohol or grain alcohol, is a flammable, colorless, mildly toxic chemical compound with a distinctive perfume-like odor, and is the alcohol found in alcoholic beverages. ... Hydrocarbons are refined at oil refineries and processed at chemical plants In chemistry, a hydrocarbon is any chemical compound that consists only of the elements carbon (C) and hydrogen (H). ...

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.

References

1. ↑  Bergstrom, F. W. (1955). "Sodium amide". Org. Synth. Coll. Vol. 3:778.
2. ↑  Greenlee, K. W.; Henne, A. L. (1946). "Sodium Amide". Inorg. Synth. 2:128–35.
3. ↑  Merck Index (12th Edn.)
4. ↑  Campbell, Kenneth N.; Campbell, Barbara K. (1950). "Phenylacetylene". Org. Synth. 30:72; Coll. Vol. 4:763.
5. ↑  Jones, E. R. H.; Eglinton, Geoffrey; Whiting, M. C.; Shaw, B. L. (1954). "Ethoxyacetylene". Org. Synth. 34:46; Coll. Vol. 4:404.
6. ↑  Bou, Anna; Pericàs, Miquel A.; Riera, Antoni; Serratosa, Fèlix (1987). "Dialkoxyacetylenes: di-tert-butoxyethyne, a valuable synthetic intermediate". Org. Synth. 65:68; Coll. Vol. 8:161.
7. ↑  Magriotis, Plato A.; Brown, John T. (1995). "Phenylthioacetylene". Org. Synth. 72:252; Coll. Vol. 9:656.
8. ↑  Ashworth, P. J.; Mansfield, G. H.; Whiting, M. C. (1955). "2-Butyn-1-ol". Org. Synth. 35:20; Coll. Vol. 4:128.
9. ↑  Newman, Melvin S.; Stalick, W. M. (1977). "1-Ethoxy-1-butyne". Org. Synth. 57:65; 6:564.
10. ↑  Salaun, J. R.; Champion, J.; Conia, J. M. (1977). "Cyclobutanone from methylenecyclopropane via oxaspiropentane". Org. Synth. 57:36; Coll. Vol. 6:320.
11. ↑  Nakamura, Masuharu; Wang, Xio Qun; Isaka, Masahiko; Yamago, Shigeru; Nakamura, Eiichi (2003). "Synthesis and (3+2)-cycloaddition of a 2,2-dialkoxy-1-methylenecyclopropane: 6,6-dimethyl-1-methylene-4,8-dioxaspiro(2.5)octane and cis-5-(5,5-dimethyl-1,3-dioxan-2-ylidene)hexahydro-1(2H)-pentalen-2-one". Org. Synth. 80:144.
12. ↑  Bottini, Albert T.; Olsen, Robert E. (1964). "N-Ethylallenimine". Org. Synth. 44:53; Coll. Vol. 5:541.
13. ↑  Skorcz, J. A.; Kaminski, F. E. (1968). "1-Cyanobenzocyclobutene". Org. Synth. 48:55; Coll. Vol. 5:263.
14. ↑  Saunders, J. H. (1949). "1-Ethynylcyclohexanol". Org. Synth. 29:47; Coll. Vol. 3:416.
15. ↑  Peterson, P. E.; Dunham, M. (1977). "(Z)-4-Chloro-4-hexenyl trifluoroacetate". Org. Synth. 57:26; Coll. Vol. 6:273.
16. ↑  Kauer, J. C.; Brown, M. (1962). "Tetrolic acid". Org. Synth. 42:97; Coll. Vol. 5:1043.
17. ↑  Coffman, Donald D. (1940). "Dimethylethynylcarbinol". Org. Synth. 20:40; Coll. Vol. 3:320.
18. ↑  Hauser, C. R.; Adams, J. T.; Levine, R. (1948). "Diisovalerylmethane". Org. Synth. 28:44; Coll. Vol. 3:291.
19. ↑  Vanderwerf, Calvin A.; Lemmerman, Leo V. (1948). "2-Allylcyclohexanone". Org. Synth. 28:8; Coll. Vol. 3:44.
20. ↑  Hauser, Charles R.; Dunnavant, W. R. (1960). "α,β-Diphenylpropionic acid". Org. Synth. 40:38; Coll. Vol. 5:526.
21. ↑  Kaiser, Edwin M.; Kenyon, William G.; Hauser, Charles R. (1967). "Ethyl 2,4-diphenylbutanoate". Org. Synth. 47:72; Coll. Vol. 5:559.
22. ↑  Wawzonek, Stanley; Smolin, Edwin M. (1951). "α,β-Diphenylcinnamonitrile". Org. Synth. 31:52; Coll. Vol. 4:387.
23. ↑  Murphy, William S.; Hamrick, Phillip J.; Hauser, Charles R. (1968). "1,1-Diphenylpentane". Org. Synth. 48:80; Coll. Vol. 5:523.
24. ↑  Hampton, K. Gerald; Harris, Thomas M.; Hauser, Charles R. (1971). "Phenylation of diphenyliodonium chloride: 1-phenyl-2,4-pentanedione". Org. Synth. 51:128; Coll. Vol. 6:928. Hampton, K. Gerald; Harris, Thomas M.; Hauser, Charles R. (1967). "2,4-Nonanedione". Org. Synth. 47:92; Coll. Vol. 5:848.
25. ↑  Potts, K. T.; Saxton, J. E. (1960). "1-Methylindole". Org. Synth. 40:68; Coll. Vol. 5:769.
26. ↑  Bunnett, J. F.; Brotherton, T. K.; Williamson, S. M. (1960). "N-β-Naphthylpiperidine". Org. Synth. 40:74; Coll. Vol. 5:816.
27. ↑  Brazen, W. R.; Hauser, C. R. (1954). "2-Methylbenzyldimethylamine". Org. Synth. 34:61; Coll. Vol. 4:585.
28. ↑  Allen, C. F. H.; VanAllen, J. (1944). "Phenylmethylglycidic ester". Org. Synth. 24:82; Coll. Vol. 3:727.
29. ↑  Allen, C. F. H.; VanAllen, James (1942). "2-Methylindole". Org. Synth. 22:94; Coll. Vol. 3:597.

Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ... Organic Syntheses is a scientific journal that since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ...

External links

• Sodium amide reactions (from Organic Syntheses)

• Link page to external chemical sources.

www.google.com.au Organic Syntheses is a scientific journal that Since 1921 has provided the chemistry community with annual collections of detailed and checked procedures for the organic synthesis of organic compounds. ...