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Sodium amide, commonly called sodamide (systematic name sodium azanide), is the inorganic compound with the formula NaNH 2. It is a salt composed of the sodium cation and the azanide anion. This solid, which is dangerously reactive toward water, is white, but commercial samples are typically gray due to the presence of small quantities of ...
The alkali metal derivatives are best known, although usually referred to as alkali metal amides. Examples include lithium amide, sodium amide, and potassium amide.These salt-like solids are produced by treating liquid ammonia with strong bases or directly with the alkali metals (blue liquid ammonia solutions due to the solvated electron): [1] [2] [4]
Compared to amines, amides are very weak bases. While the conjugate acid of an amine has a pK a of about 9.5, the conjugate acid of an amide has a pK a around −0.5. Therefore, compared to amines, amides do not have acid–base properties that are as noticeable in water. This relative lack of basicity is explained by the withdrawing of ...
In water, OH − is the strongest base. Thus, even though sodium amide (NaNH 2) is an exceptional base (pK a of NH 3 ~ 33), in water it is only as good as sodium hydroxide. On the other hand, NaNH 2 is a far more basic reagent in ammonia than is NaOH. The pH range allowed by a particular solvent is called the acid-base discrimination window. [1]
Sodium hydride: a strong base used in organic synthesis Sodium hydroxide: strong base with many industrial uses; in the laboratory, used with acids to produce the corresponding salt, also used as an electrolyte: Sodium hypochlorite: frequently used as a disinfectant or a bleaching agent Sodium nitrite: used to convert amines into diazo ...
A strong base is a basic chemical compound that can remove a proton (H +) from (or deprotonate) a molecule of even a very weak acid (such as water) in an acid–base reaction. Common examples of strong bases include hydroxides of alkali metals and alkaline earth metals, like NaOH and Ca(OH) 2, respectively. Due to their low solubility, some ...
Other strong non-nucleophilic bases are sodium hydride and potassium hydride. These compounds are dense, salt-like materials that are insoluble and operate by surface reactions. These compounds are dense, salt-like materials that are insoluble and operate by surface reactions.
Sodium amide (also known as sodamide) is synthesized from sodium metal and ammonia with ferric nitrate catalyst. [3] [4] The sodium compound is white, but the presence of metallic iron turns the commercial material gray. 2 Na + 2 NH 3 → 2 NaNH 2 + H 2. Lithium diisopropylamide is a popular non-nucleophilic base used in organic synthesis.