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1-nitropropane is produced industrially by the reaction of propane and nitric acid. This reaction forms four nitroalkanes: nitromethane, nitroethane, 1-nitropropane, and 2-nitropropane. 1-nitropropane is also a byproduct of the process for making 2-nitropropane, which is done by vapour phase nitration of propane.
In the so-called Ter Meer reaction (1876) named after Edmund ter Meer, [14] the reactant is a 1,1-halonitroalkane: The reaction mechanism is proposed in which in the first slow step a proton is abstracted from nitroalkane 1 to a carbanion 2 followed by protonation to an aci-nitro 3 and finally nucleophilic displacement of chlorine based on an ...
The reaction process begins with the deprotonation of 2-nitropropane at the α carbon to form a nitronate. This compound then initiates an S N 2 reaction to displace the benzyl halide. Unlike in the nitroaldol reaction , where the deprotonated carbon of the nitroalkyl group is the nucleophilic atom, it is instead an oxygen of the nitro itself ...
This exothermic reaction produces four industrially significant nitroalkanes: nitromethane, nitroethane, 1-nitropropane, and 2-nitropropane. The reaction involves free radicals, such as CH 3 CH 2 CH 2 O., which arise via homolysis of the corresponding nitrite ester. These alkoxy radicals are susceptible to C—C fragmentation reactions, which ...
The mechanism of epoxidation with dioxiranes likely involves concerted oxygen transfer through a spiro transition state. As oxygen transfer occurs, the plane of the oxirane is perpendicular to and bisects the plane of the alkene pi system. The configuration of the alkene is maintained in the product, ruling out long-lived radical intermediates.
In this type of substitution reaction, one group of the substrate participates initially in the reaction and thereby affects the reaction. A classic example of NGP is the reaction of a sulfur or nitrogen mustard with a nucleophile, the rate of reaction is much higher for the sulfur mustard and a nucleophile than it would be for a primary or secondary alkyl chloride without a heteroatom.
The figure below illustrates one of the commonly accepted models for stereoselection without any modification to the Henry reaction. In this model, stereoselectivity is governed by the size of the R groups in the model (such as a carbon chain), as well as by a transition state that minimizes dipole by orienting the nitro group and carbonyl oxygen anti each other (on opposite sides of the ...
The reaction has been the subject of several literature reviews. [1] [2] [3] The Nef reaction: 1. Salt of a nitroalkane 3. Ketone 4. Nitrous oxide. The reaction was reported in 1894 by the chemist John Ulric Nef, [4] who treated the sodium salt of nitroethane with sulfuric acid resulting in an 85–89% yield of nitrous oxide and at least 70% ...