Deprotonation [alkoxide formation]

Deprotonation [alkoxide formation] Definition:


Treatment with alcohols with bases gives their conjugate bases, called alkoxy ions (alkoxides).



Deprotonation [alkoxide formation] Explained:


Alcohols are amphoteric substances because they can act both as acids and as bases. Thus, alcohols are acidic by virtue of the electronegativity of the oxygen and they can give the alkoxide ions with strong bases, also weakly basic, and can be protonated by strong acids to furnish alkyloxonium ions.



To remove a proton from the hydroxide group of an alcohol we must use a base stronger than the alkoxide. This can be achieved by using a strong base (such as alkali metal hydrides) or alkali metals. Alkali metals react with alcohols similarly as with water (alkali metal hydroxides and hydrogen gas are obtained) but the reaction is less vigorous. An alkoxide ion as the conjugate bases of an alcohol exhibits a negative charge on an oxygen atom.