Master's Theses

Department

Chemistry

Degree Name

Master of Science (MS)

Abstract

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.

Keywords

Nucleophilic reactions, Nitropropane, Chemical kinetics, Ionization, Illustrations, Analysis

Advisor

Dr. Robert L. Dressler

Date of Award

Spring 1969

Document Type

Thesis - campus only access

Rights

© The Author(s)

Comments

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