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Why Does Tautomerization Occur?

Maya Lin-Takahashi • • 6 min read
Why Does Tautomerization Occur?

Acid-Catalyzed Tautomerization Mechanism Overview
Tautomerization begins when the partially negative electrons on the alcohol oxygen reaches down to attack the sp2 carbon atom (the one holding the pi bond). In forming a second bond between carbon and oxygen, carbon would have a total of 5 bonds.

Why does tautomerism occur?

Either acid or base can catalyze proton transfer. Hence, tautomerization occurs by two different mechanisms. In the first step of acid-catalyzed tautomerization of the keto form, hydronium ion protonates the carbonyl oxygen atom. Then, water removes the α-hydrogen atom to give the enol.

What are the conditions for Tautomerization to occur?

Tautomerism basically happens in the presence of a catalyst. Acid-catalyst: Here firstly the protonation occurs, cation will be delocalized. Then, deprotonation will occur in the adjacent position of the cation. For base catalysts, deprotonation is the first step.

Maya Lin-Takahashi
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Maya Lin-Takahashi

Maya is a hardware enthusiast who tests and reviews smart home devices, smartphones, wearables, and audio gear. She focuses on practical consumer value and build quality.