Sodium amide

Sodium amide (NaNH₂) is an ionic inorganic compound consisting of sodium cations and amide anions. It is a strong base and nucleophile used in chemical synthesis.

Amide ion: The nitrogen-centered anion NH₂⁻, the conjugate base of ammonia. This anion is the reactive part of sodium amide.
Alkyne synthesis: The preparation of carbon–carbon triple bonds through chemical reactions. Sodium amide can drive eliminations that produce alkynes from suitable precursors.
Ionic compound: A substance composed of oppositely charged ions held together by electrostatic attraction. Sodium amide is an ionic solid rather than a covalent sodium–nitrogen molecule.
Lithium diisopropylamide: A bulky, strong lithium amide base commonly used to form enolates. Its steric bulk often favors selective deprotonation without sodium amide's nucleophilicity.
Acid–base reaction: A reaction involving transfer of a proton from an acid to a base. Sodium amide commonly reacts by removing protons from weak acids.
Alkylation: A chemical reaction that adds an alkyl group to a molecule. It can generate carbanions that form carbon–carbon bonds with alkylating agents.
Ammonia: The molecular compound NH₃, a weak base and nitrogen hydride. The amide ion is formed by removing a proton from ammonia.
Sodium bis(trimethylsilyl)amide: A sterically hindered sodium amide base with formula NaN(Si(CH₃)₃)₂. This soluble, hindered amide is often chosen when nucleophilic attack by NH₂⁻ is unwanted.
Deprotonation: The removal of a proton from a molecule or ion. This is the central step when sodium amide generates carbon nucleophiles.
Acetylide: An anion containing a carbon–carbon triple bond with a negatively charged terminal carbon. Sodium amide deprotonates terminal alkynes to produce acetylide nucleophiles.

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Sodium ethoxideCompared with: Amide is substantially more basic than ethoxide and can deprotonate less acidic compounds.