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Synthesis and Kinetics of Hydrolysis of 3,5-Dimethyl-N-acetyl-p-benzoquinone Imine: An Undergraduate Laboratory

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Jeanne M. Buccigross , Christa Metz , Lori Elliot , Pamela Becker , Angela S. Earley and Jerry W. Hayes

College of Mount St. Joseph, Cincinnati, OH 45233-1670

Michael Novak and Gayl A. Underwood

Miami University, Oxford, OH 45056

J. Chem. Educ., 1996, 73 (4), p 364

DOI: 10.1021/ed073p364

Publication Date (Web): April 1, 1996

Section:

History, Education, and Documentation

Abstract

The synthesis of the title compound by a three-step procedure is described. The hydrolysis kinetics, which involve two consecutive psuedo-first-order processes, are also described. The synthesis and kinetics experiments described here are proposed for incorporation into undergraduate laboratory courses under a variety of formats. The compound described here is related to a toxic metabolite of the common analgesics acetaminophen and phenacetin.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Synthesis

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This article has been cited by 2 ACS Journal articles (2 most recent appear below).

Modern Developments in the Physical Chemistry Laboratory
Samuel A. Abrash
2007 973 (), 115-151
- Modern Developments in the Physical Chemistry Laboratory
  Samuel A. Abrash
  2007 973 (), 115-151
  Developments in the physical chemistry laboratory since the publication of the germinal text by Schwenz and Moore (1) are categorized and reviewed. The categories examined include modern instrumentation, current topics in chemistry, integrated ...
  Abstract | Hi-Res PDF | PDF w/ Links
Assessing the Fate of Organic Contaminants in Aquatic Environments: Mechanism and Kinetics of Hydrolysis of a Carboxylic Ester
Jorg Klausen , Markus A. Meier and Rene P. Schwarzenbach
Journal of Chemical Education1997 74 (12), 1440
- Assessing the Fate of Organic Contaminants in Aquatic Environments: Mechanism and Kinetics of Hydrolysis of a Carboxylic Ester
  Jorg Klausen , Markus A. Meier and Rene P. Schwarzenbach
  Journal of Chemical Education1997 74 (12), 1440
  An integrated experiment is proposed for an upper level under-graduate environmental chemistry laboratory. Using 2,4-dinitrophenylacetate (DNPA) as an example, the mechanisms of the abiotic hydrolysis of carboxylic esters are presented and the kinetic ...
  Abstract | Hi-Res PDF | PDF w/ Links