Date of Award
Master of Science (MS)
Harold S. Choguill
The present research confirmed that the probable reaction between sodium iodide and 1-bromo-1-nitropropane in acetone is a second order reaction with the rate constant 0.0686 mole min-1 liter-1. The rate determining step is indicated to be formation of the activated complex. [Chemical formula here] Sodium iodide in acetone was added to 1-bromo-1-nitropropane and samples were removed at timed intervals. The reaction was stopped by the addition of water. The halogens present were titrated with a standard silver nitrate solution containing barium nitrate and nitric acid using a Fisher titrimeter. From these data, tile rate of replacement was determined and reaction constants determined. The kinetic measurement could not be extended to the completion of the reaction because the formation of free iodine became significant, indicating a possible side reaction or, more correctly, the decomposition of the end product. Consequently constants are based on the initial reaction rates. This worker was not able to identify any product other than the expected 1-iodo-1-nitropropane. However, the infrared spectrum did not show a very weak alkene absorption. Also no evidence of inversion of structure during reaction was found because of difficulty of resolving the d and 1 isomers of 1-iodo-1-nitropropane.
Copyright 1965 Harlie Parish
Parish, Harlie, "Nucleophilic Substitution of Halogenated Nitroparaffins" (1965). Master's Theses. 936.