The Hofmann Rearrangement Using Household Bleach: Synthesis of 3-Nitroaniline | Zendy

Keith A. Monk | Zendy; Ram S. Mohan | Zendy

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The Hofmann Rearrangement Using Household Bleach: Synthesis of 3-Nitroaniline

Author(s) -

Keith A. Monk,

Ram S. Mohan

Publication year - 1999

Publication title -

journal of chemical education

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.499

H-Index - 84

eISSN - 1938-1328

pISSN - 0021-9584

DOI - 10.1021/ed076p1717

Subject(s) - bleach , nitration , chemistry , rearrangement reaction , simple (philosophy) , combinatorial chemistry , medicinal chemistry , organic chemistry , philosophy , catalysis , epistemology

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.

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