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Class Projects in Physical Organic Chemistry: The Hammett Equation

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Peter S. Marrs

Department of Chemistry, University of Victoria, Victoria, BC V8W 3P6, Canada

J. Chem. Educ., 2001, 78 (4), p 527

DOI: 10.1021/ed078p527

Publication Date (Web): April 1, 2001

Section:

History, Education, and Documentation

Abstract

This paper provides a brief introduction to the Hammett equation. A laboratory experiment is described that requires students to determine the pK_a of three para-substituted phenols through the use of UV-spectroscopy. A student's individual data are combined with other students' data to provide a class set. The students analyze the class set of data to determine whether σ_p or σ_p^- is more appropriate for the reaction studied, and they also determine ρ for the reaction.

Keywords (Audience):

Upper-Division Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Collaborative / Cooperative Learning

Keywords (Subject):

Acids / Bases

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This article has been cited by 3 ACS Journal articles (3 most recent appear below).

Determination of Hammett Equation Rho Constant for the Hydrolysis of p-Nitrophenyl Benzoate Esters
Sheue L. Keenan , Karl P. Peterson , Kelly Peterson and Kyle Jacobson
Journal of Chemical Education2008 85 (4), 558
- Determination of Hammett Equation Rho Constant for the Hydrolysis of p-Nitrophenyl Benzoate Esters
  Sheue L. Keenan , Karl P. Peterson , Kelly Peterson and Kyle Jacobson
  Journal of Chemical Education2008 85 (4), 558
  Seven p-nitrophenyl benzoate esters (p-nitrophenyl benzoate, p-nitrophenyl m-anisate, p-nitrophenyl p-anisate, p-nitrophenyl m-chlorobenzoate, p-nitrophenyl p-chlorobenzoate, p-nitrophenyl m-toluate, p-nitrophenyl p-toluate) were synthesized and ...
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The Hammett Equation: Probing the Mechanism of Aromatic Semicarbazone Formation
Glenn K. Ikeda , Karen Jang , Scott O. C. Mundle and Andrew P. Dicks
Journal of Chemical Education2006 83 (9), 1341
- The Hammett Equation: Probing the Mechanism of Aromatic Semicarbazone Formation
  Glenn K. Ikeda , Karen Jang , Scott O. C. Mundle and Andrew P. Dicks
  Journal of Chemical Education2006 83 (9), 1341
  An organic class project is described where upper-level undergraduates measure kinetic rate constants for semicarbazone formation, by reacting semicarbazide with a meta- or para-substituted benzaldehyde. UV-vis spectroscopy is used to follow product ...
  Abstract | Hi-Res PDF | PDF w/ Links
Competition Experiments as a Means of Evaluating Linear Free Energy Relationships. An Experiment for the Advanced Undergraduate Organic Chemistry Lab
Richard J. Mullins , Andrei Vedernikov and Rajesh Viswanathan
Journal of Chemical Education2004 81 (9), 1357
- Competition Experiments as a Means of Evaluating Linear Free Energy Relationships. An Experiment for the Advanced Undergraduate Organic Chemistry Lab
  Richard J. Mullins , Andrei Vedernikov and Rajesh Viswanathan
  Journal of Chemical Education2004 81 (9), 1357
  A novel approach to exploring Hammett relationships in the undergraduate teaching lab is described. The use of competition experiments proved to be a reliable method for the construction of Hammett plots with good correlation. Reactions that were studied ...
  Abstract | Hi-Res PDF | PDF w/ Links