Alkanoxide

Alkanoxide refers to the conjugate base of an alcohol. It is formed when an alcohol molecule loses a proton (H+). The general formula for an alkanoxide ion is RO-, where R represents an alkyl group and O- is the negatively charged oxygen atom. Alkanoxides are strong bases and nucleophiles. Their reactivity is influenced by the nature of the alkyl group. Larger or more branched alkyl groups can increase steric hindrance, potentially affecting their nucleophilicity.

The formation of alkanoxides typically involves the reaction of an alcohol with a strong base, such as an alkali metal hydride (e.g., sodium hydride, NaH) or an alkali metal (e.g., sodium, Na). For example, the reaction of ethanol with sodium metal produces sodium ethoxide and hydrogen gas: 2 C2H5OH + 2 Na -> 2 C2H5O- Na+ + H2.

Alkanoxides are important reagents in organic chemistry, widely used in various reactions, including Williamson ether synthesis, dehydrohalogenation reactions, and aldol condensations. They are also employed as catalysts in certain polymerization processes. Due to their strong basicity, alkanoxides are often prepared and used in situ to avoid decomposition or reaction with atmospheric moisture and carbon dioxide. Their solubility depends on the counterion and the solvent.