Vinyl Alcohol, Tautomerism, and Earth’s Atmosphere

vinyl alcohol
Sea spray salt aerosol
The simplest alcohols contain only carbon, oxygen, and hydrogen. Whereas water contains a hydrogen atom attached to a hydroxyl group, a simple alcohol consists of a chain of carbon and hydrogen atoms attached to a hydroxyl group. Vinyl alcohol is one of the simplest. In fact, it differs by just two hydrogen atoms from ordinary ethyl alcohol.

Ethyl alcohol or ethanol is written, CH₃CH₂–OH. Vinyl alcohol or ethenol is CH₂=CH–OH. Ethanol has very ordinary, straightforward behavior, typical of an alcohol. Vinyl alcohol, however, because of its double bond (also referred to as its unsaturation), behaves considerably different.


Vinyl alcohol rearranges slightly under ordinary conditions. It tautomerizes to the more stable species acetaldehyde. This variety of tautomerization is termed keto-enol tautomerism. The keto part refers to the carbonyl group typical of ketones and aldehydes, –C=O. The enol part refers to the two functionalities, -ene and -ol, or a double bond and a hydroxyl.

vinyl alcohol

Vinyl Alcohol and Acetaldehyde

The difference in stability between vinyl alcohol and its tautomer, acetaldehyde is considerable; it amounts to more than 42 kilojoules per mole. Thus one does not approach the reagent shelf to pull down a bottle of vinyl alcohol. However, theoretical chemistry and simulation studies suggest this alcohol and other enol alcohols play a role in upper atmosphere organic acid synthesis.

vinyl alcohol
Tautomerization of vinyl alcohol and acetaldehyde

Organic Acids and Sea Salt

Such organic acids appear to deplete lofted sea salt particles of some of their chloride, liberating hydrogen chloride into the atmosphere and forming the corresponding organic acid salts.

Undoubtedly an increase in these substances is due to human activity. These, in turn, can affect the way our atmosphere radiates energy. Organic acid salts can also modify cloud nucleation. These two effects, however minimal, may contribute to global climate change.

Note: You might also enjoy Polymeric Water Clusters

References: ← Back to Environment
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