Master's Theses

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Date of Award

Spring 1969

Degree Name

Master of Science (MS)




Robert L. Dressler


This research was designed to investigate the behavior of ±-halogenated nitroparaffins toward nucleophilic reagents. 2-Bromo-2-nitropropane was used as the substrate and the effects of four different nucleophiles, hydroxide, ethoxide, cyanide, and iodide were studied. It was found that the coupling product, 2, 3-dimethy 1-2, 3-dinitrobutane, was the main product obtained from the reaction with hydroxide, ethoxide and cyanide. Substitution, leading to the formation of 2-iodo-2-nitropropane, was found in the reaction with iodine. The kinetics of the substitution reaction in formation of 2-iodo-2-nitropropane had been found to be first order with respects to the concentration of 2-bromo-2-nitropropane. An ionization process leading to the anion of 2-nitropropane, followed by condensation with another molecule of starting material to form a new carbon-carbon bond may be proposed as the reaction pathway of the coupling reaction.


Copyright 1969 Gloria Tzyy-Fang Tsai Chen


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