Alkoxide

An alkoxide is the conjugate base of an alcohol and therefore consists of an organic group bonded to a negatively charged oxygen atom. They can be written as RO−, where R is the organic substituent. Alkoxides are strong bases and, when R is not bulky, good nucleophiles and good ligands. Alkoxides, although generally not stable in protic solvents such as water, occur widely as intermediates in various reactions, including the Williamson ether synthesis. Transition metal alkoxides are widely used for coatings and as catalysts.

Enolates are unsaturated alkoxide derived by deprotonation of a C-H bond adjacent to a ketone or aldehyde. The nucleophilic center for simple alkoxides is located on the oxygen, whereas the nucleophilic site on enolates is delocalized onto both carbon and oxygen sites.

Phenoxides are closely related to alkoxides, except the organic substitutent is a derivative of benzene. Phenol is more acidic than a typical alcohol, thus phenoxides are correspondingly less basic and less nucleophilic. They are however often easier to handle and yield derivatives that are more crystalline than the alkoxides.

Read more about AlkoxideIllustrative Alkoxides

Other articles related to "alkoxide, alkoxides":

Aldol Reaction - Mechanisms - Enolate Mechanism
... a moderate base such as hydroxide ion or an alkoxide, the aldol reaction occurs via nucleophilic attack by the resonance-stabilized enolate on the carbonyl group of another ... The product is the alkoxide salt of the aldol product ... formation is irreversible, and the aldol product is not formed until the metal alkoxide of the aldol product is protonated in a separate workup step ...
Alcool - Reactions - Deprotonation
... The deprotonation reaction to produce an alkoxide salt is performed either with a strong base such as sodium hydride or n-butyllithium or with sodium or potassium metal ... The bases used and the alkoxides created are both highly moisture-sensitive chemical reagents ... affected by the overall stability of the alkoxide ion ...
Aldol Reaction - Modern Variations and Methods - "Direct" Aldol Additions
... The enolate is added to an aldehyde or ketone, which forms an alkoxide, which is then protonated on workup ... The general problem is that the addition generates an alkoxide, which is much more basic than the starting materials ... A silicon reagent such as TMSCl is added in the reaction, which replaces the metal on the alkoxide, allowing turnover of the metal catalyst ...
Oppenauer Oxidation - Mechanism
... aluminum to form a complex (3), which then, in the second step, gets deprotonated by an alkoxide ion (4) to generate an alkoxide intermediate (5) ... aluminum which activates it for the hydride transfer from the alkoxide ...
Cannizzaro Reaction - Mechanism
... In the final step of the reaction, the acid and alkoxide ions formed exchange a proton ... a hydride ion is transferred to the second molecule of aldehyde to form carboxylate and alkoxide ions ... Subsequently, the alkoxide ion acquires a proton from the solvent ...