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AAT Bioquest

Why are acid-base reactions faster than substitution or addition reactions?

Posted May 23, 2024


Answer

When acids and bases react with atoms like oxygen, sulfur, and nitrogen, minimal rearrangement of atomic nuclei is needed after proton transfer. This makes these reactions quick compared to those where significant nuclear movement or rearrangement is required such as substitution or addition reactions. For instance, when a proton is removed from an O-H group, the oxygen atom gains a new lone pair without significant change in its hybridization. It remains sp3 throughout the process. Consequently, there's minimal movement of atomic nuclei other than the hydrogen atom. In contrast, reactions such as those involving additions to carbonyl carbons require the rearrangement of atomic positions. They involve changing the hybridization of carbon from sp2 to sp3, which necessitates a transition from trigonal planar to tetrahedral geometry. This shift requires significant atomic motion, resulting in a slower reaction compared to acid-base reactions.

Additional resources

Acid Base Reactions Are Fast

Weak Base pH Calculator

Weak Acid pH Calculator