@jauhar123 | Posted 02 May. 2019
Sodium Hydride is a base of broad scope and use in organic chemistry. As a superbase, it is competent of deprotonating a range of even weak Bronsted acids to produce the corresponding sodium derivatives. Typical "easy" substrates include O-H, N-H, S-H bonds, including phenols, alcohols, pyrazoles, and thiols.
NaH most reputable is employed to deprotonate carbon acids such as 1,3-dicarbonyls and analogs such as malonic esters. The resulting sodium derivatives posterior be alkylated. NaH is generally used to promote condensation reactions of carbonyl compounds via the Dieckmann condensation, Darzens condensation, ***** condensation, and Claisen condensation.
Pure NaH can easily ignite in air. When it comes into communication with water present in the air, it releases highly inflammable hydrogen gas. When open to air and moisture, NaH also gets quickly hydrolyzed into the strong corrosive base, sodium hydroxide (NaOH). Thus, to stop fires and explosions, sodium hydride is sold as a dispersion in mineral oil, allowing it to be securely handled in air.
Sodium hydride is a strong base generally used in organic chemistry, where it is kept in an inert atmosphere (with 'dry' gases such as argon, nitrogen, etc.). It is insoluble in organic solvents.