Sodium ethoxide

Sodium ethoxide is the ionic compound NaOC₂H₅, consisting of sodium ions and ethoxide ions. It serves as a strong base and nucleophile in organic synthesis.

Claisen condensation: A carbon–carbon bond-forming reaction in which ester enolates combine with esters to produce β-keto esters. Sodium ethoxide commonly generates the ester enolate used in this reaction.
Ethoxide: The negatively charged conjugate base of ethanol, with formula C₂H₅O⁻. This is the reactive ion supplied by sodium ethoxide.
Ionic compound: A substance composed of positively and negatively charged ions held together by electrostatic attraction. Sodium ethoxide consists of sodium cations and ethoxide anions.
Sodium methoxide: An ionic compound, NaOCH₃, used as a base and nucleophile in organic synthesis. Its smaller methoxide ion can favor different substitution and elimination outcomes.
Dieckmann condensation: An intramolecular Claisen condensation that converts a diester into a cyclic β-keto ester. Sodium ethoxide promotes ring-forming enolate chemistry in this named reaction.
Brønsted–Lowry base: A species that accepts a proton from another species. Ethoxide’s proton-accepting behavior accounts for its use in enolate formation and elimination.
Sodium: A metallic chemical element with symbol Na and atomic number 11. Sodium forms the counterion paired with ethoxide in the compound.
Potassium tert-butoxide: A bulky potassium alkoxide commonly used as a strong, sterically hindered base. Its bulk favors proton abstraction over nucleophilic substitution more than ethoxide does.
E2 reaction: A concerted elimination in which a base removes a proton as a leaving group departs, forming an alkene. Ethoxide can act as the base that drives this one-step elimination.
Nucleophile: A species that donates an electron pair to form a bond with an electrophile. Ethoxide can attack electrophilic carbon centers as well as remove protons.

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Barbituric acidRelated: It promotes the classical condensation of diethyl malonate and urea.