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EC number: 201-188-9
CAS number: 79-24-3
Nitroalkanes are not hydrolysed to any measurable extent by the action of water alone and even in the presence of strong acids, high concentrations and temperatures are required.
The strong acid-catalysed hydrolysis of nitroethane in aqueous solution to yield hydroxylamine and the corresponding carboxylic acid has been studied. The slow rate-determining reaction, with an activation energy of about 25 kcal. mole-l, appears to be the loss of a proton from the cation RCH2NO2H+which competes wlth the raprd reversible reformatron of the normal nltroalkane. The production of hydroxylamine from the aci-nitroalkane is most readily explained in terms of a mechanism which involves a nitrile oxide. It is apparent that the related Nef reaction occurs by a ready reaction between the aci-anion and the hydroxonium ion whlch does not produce the aa-nitroalkane as usually assumed. In the presence of nitric acid oxidation of the hydrolysis products occurs.
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