Alkoxide ions are better proton acceptors than hydroxide ions, indicating stronger bases. Alcohols act as Bronsted bases due to the presence of unshared electron pairs on oxygen, making them capable of accepting protons.
Why are alkoxides considered stronger bases than hydroxide ions, and how do alcohols act as Bronsted bases?
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Alkoxides (RO⁻) are considered stronger bases than hydroxide ions (OH⁻) because the negative charge is distributed over a larger oxygen-carbon bond, making the electron pair more available. Alcohols act as Bronsted bases by donating a proton (H⁺) from the hydroxyl group. In the presence of a strong acid, the alcohol’s oxygen lone pair abstracts a proton, forming water and the conjugate acid. The higher the stability of the resulting conjugate acid, the stronger the base. The ability of alcohols to donate protons makes them Bronsted bases in acidic reactions.