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Nitrolic acids are
organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon- hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...
s with the
functional group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the res ...
RC(NO2)=NOH. They are prepared by the reaction of
nitroalkane In organic chemistry, nitro compounds are organic compounds that contain one or more nitro functional groups (). The nitro group is one of the most common explosophores (functional group that makes a compound explosive) used globally. The nitr ...
s with base and nitrite sources: :RCH2NO2 + HNO2 → RC(NO2)=NOH + H2O The conversion was first demonstrated by
Victor Meyer Viktor Meyer (8 September 18488 August 1897) was a German chemist and significant contributor to both organic and inorganic chemistry. He is best known for inventing an apparatus for determining vapour densities, the Viktor Meyer apparatus, and ...
using
nitroethane Nitroethane is an organic compound having the chemical formula C2H5NO2. Similar in many regards to nitromethane, nitroethane is an oily liquid at standard temperature and pressure. Pure nitroethane is colorless and has a fruity odor. Preparat ...
.Meyer, V.; Locher, J. "Untersuchungen über die Constitution der Nitrolsäuren (Researches on the constitution of the nitrolic acids)" Deut. Chem. Ges. Ber., 1874, volume 7, pp. 670-5. The reaction proceeds via the intermediacy of the nitronate anion.


Occurrence

Most nitrolic acids are laboratory curiosities. One exception is the compound HO2C(CH2)4C(NO2)=NOH, which is produced by the oxidation of
cyclohexanone Cyclohexanone is the organic compound with the formula (CH2)5CO. The molecule consists of six-carbon cyclic molecule with a ketone functional group. This colorless oily liquid has an odor reminiscent of acetone. Over time, samples of cyclohex ...
with
nitric acid Nitric acid is the inorganic compound with the formula . It is a highly corrosive mineral acid. The compound is colorless, but older samples tend to