Deprotonation of alcohols to give alkoxides
Description: Treatment of alcohols with bases give their conjugate bases, called alkoxy ions (alkoxides)
Notes: In order to be effective the base must be as strong as (or stronger) than HO(–) or RO(–). The alkoxy ions formed are excellent nucleophiles and can be used in substitution reactions such as the Williamson ether synthesis (and many others).
Notes: In cases where the pKa of the acid formed is similar to that of the alcohol, the reaction will be an equilibrium (example 1, ROH and H2O).
Mechanism: The base removes a proton from the alcohol (Step 1, arrows A and B) forming the alkoxide.