Why do bulky alcohols react more slowly with active organometallic compounds?

Created from Britannica articles using AI. AI can make mistakes, so verify using Britannica articles.

periodic table with group numbers and the s, p, d, and f blocks — organometallic compound The periodic table of the elements, displaying the group numbers and the s, p, d, and f blocks. Elements in the shaded area are the metals of organometallic chemistry.

Bulky alcohols react more slowly with active organometallic compounds due to the steric hindrance created by their large organic groups.

In these reactions, the organometallic compound acts as a strong base, performing a protolysis (proton-transfer) reaction with the alcohol. When the alcohol possesses bulky substituents—such as in tert-butyl alcohol—the physical size of these groups obstructs the approach of the organometallic reagent to the acidic proton. This spatial interference significantly hinders the reaction rate compared to smaller alcohols or water. Because of this slow reactivity, bulky alcohols like tert-butyl alcohol are frequently used in laboratory settings to safely neutralize and destroy reactive organometallic waste.1