Search results
Results from the WOW.Com Content Network
Sodium amide is mainly used as a strong base in organic chemistry, often suspended (it is insoluble [7]) in liquid ammonia solution.One of the main advantages to the use of sodium amide is its relatively low nucleophilicity.
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.
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 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.
The choice of base used for extraction is critical, as a strong base (e.g. sodium hydroxide) will hydrolyze the ester. Another common example of acid-base extraction occurs following peptide coupling , where the amide product must be separated from leftover carboxylic acid and amine .
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 ...
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]