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  Home > JCE Print > Journal of Chemical Education > Issues > 1999  > December  >
In the Laboratory
The Hofmann Rearrangement Using Household Bleach: Synthesis of 3-Nitroaniline
Keith A. Monk and Ram S. Mohan
Department of Chemistry, Illinois Wesleyan University, Bloomington, IL 61702
Cover
December 1999
Vol. 76 No. 12
p. 1717
Abstract
The Hofmann rearrangement is an important example of a rearrangement reaction that is discussed in most sophomore organic chemistry texts. Yet very few examples of this reaction can be found in lab texts. We have developed a simple experiment that involves the Hofmann rearrangement of 3-nitrobenzamide to give 3-nitroaniline using household bleach. The synthesis of 3-nitrobenzamide by nitration of benzamide and the subsequent Hofmann rearrangement can be carried out in two-and-a-half hours, making this a new and simple two-step reaction sequence for the organic laboratory.
More Information
*  Citation
 Monk, Keith A.; Mohan, Ram S. J. Chem. Educ. 1999 76 1717.
*  Keywords
 Organic Chemistry; Laboratory Instruction; Organic Synthesis; NMR Spectrometry
*  History
 Created:
Last Updated:		 November 10, 1999
June 23, 2005
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