Why is it considered nearly impossible to have both an oxonium group and an alcohol group in the same molecule?

Alkyl oxonium cations are notoriously strong electrophiles that react instantly with any species bearing a lone pair of electrons—such as water, alcohols, or halides—making their coexistence with an alcohol group in the same molecule seemingly impossible, as stated by Mark Mascal: 'You can’t use them anywhere near water or alcohols or halides . . . they’ll be gone in an instant.'

What does the phrase 'this molecule lives on the brink of self-destruction' suggest about alkyl oxonium cations?

The phrase reflects the extreme intrinsic reactivity of alkyl oxonium cations, emphasizing their thermodynamic instability and kinetic susceptibility to immediate intramolecular or intermolecular reaction—particularly with nearby nucleophiles like alcohol groups—so that their very existence in proximity to such functional groups appears unsustainable under normal conditions.

This molecule lives on the brink of self-destruction

May 20, 2026

Scientists stabilized alkyl oxonium cations alongside alcohol groups within a single molecule, defying expectations of immediate reaction. Mark Mascal from UC Davis highlights the significance of stabilizing these highly reactive electrophiles.

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2026-05-20

This molecule lives on the brink of self-destruction

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Reaction Rounds Up Atoms into Unusual Cyclic Compounds

This molecule lives on the brink of self-destruction

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