Cyclopropane Carboxylic Acid
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Cyclopropane carboxylic acid is the
organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
with the formula . It is the carboxylic acid derivative of
cyclopropane Cyclopropane is the cycloalkane with the molecular formula (CH2)3, consisting of three methylene groups (CH2) linked to each other to form a triangular ring. The small size of the ring creates substantial ring strain in the structure. Cyclopropane ...
. It can be prepared by hydrolysis of cyanocyclopropane, which is obtained by base-induced cyclization of 4-chloro
butyronitrile Butyronitrile or butanenitrile or propyl cyanide, is a nitrile with the formula C3H7CN. This colorless liquid is miscible with most polar organic solvents. Uses Butyronitrile is mainly used as a precursor to the poultry drug amprolium.Peter Polla ...
.


Reactions

Cyclopropane carboxylic acid has al
pKa In chemistry, an acid dissociation constant (also known as acidity constant, or acid-ionization constant; denoted ) is a quantitative measure of the strength of an acid in solution. It is the equilibrium constant for a chemical reaction :H ...
of 4.65, fairly typical for similar compounds. Esterification is conveniently done with
Lewis acid A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty orbital which is capable of accepting an electron pair from a Lewis base to form a Lewis adduct. A Lewis base, then, is any ...
catalysts. The compound has been used to probe the biosynthesis of
ethylene Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon–carbon bond, carbon–carbon doub ...
.


References

{{Reflist Carboxylic acids Cyclopropanes