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

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Keith A. Monk and Ram S. Mohan

Department of Chemistry, Illinois Wesleyan University, Bloomington, IL 61702

J. Chem. Educ., 1999, 76 (12), p 1717

DOI: 10.1021/ed076p1717

Publication Date (Web): December 1, 1999

Section:

History, Education, and Documentation

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.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

NMR Spectroscopy

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Received: August 03, 2009

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

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A Mild and Efficient Modified Hofmann Rearrangement

Synthesis of N-Methyl-2-trichloroacetylpyrrole-A Key Building Block in Peptides That Bind DNA: Micro-, Semimicro-, and Macro-Scale Organic Lab Experiments

A Convenient Synthesis of the Tetrasubstituted Pyrrole: An Undergraduate Heterocyclic Laboratory Experiment

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