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An NMR Study of Isotope Effect on Keto-Enol Tautomerization. A Physical Organic Chemistry Experiment

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D. Atkinson and V. Chechik

Department of Chemistry, University of York, Heslington, York YO10 5DD, United Kingdom

J. Chem. Educ., 2004, 81 (7), p 1030

DOI: 10.1021/ed081p1030

Publication Date (Web): July 1, 2004

Section:

History, Education, and Documentation

Abstract

A series of physical organic chemistry experiments suitable for second- or third-year undergraduate students is presented. ¹H NMR spectroscopy is used to monitor the enolization of butanone and calculate rate constants, activation parameters, and primary and secondary isotope effects for this reaction. The experiments teach students to handle and interpret NMR spectra and offer a broad range of topics for discussion, including isotope effects, kinetics, activation parameters, regiochemistry, and reaction mechanisms.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

NMR Spectroscopy

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Citing Articles

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

Acid-Catalyzed Enolization of β-Tetralone
Brahmadeo Dewprashad , Anthony Nesturi and Joel Urena
Journal of Chemical Education2008 85 (6), 829
- Acid-Catalyzed Enolization of β-Tetralone
  Brahmadeo Dewprashad , Anthony Nesturi and Joel Urena
  Journal of Chemical Education2008 85 (6), 829
  This experiment allows students to use 1H NMR to directly compare the relative initial rates of substitution of the benzylic and non-benzylic α hydrogens of β-tetralone and correlate their findings with the predictions made by resonance theory. The ...
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Toward the Integration of Liquid- and Solid-State NMR across the Undergraduate Curriculum
N. M. Washton, K. C. Earnheart, D. G. Sykes, M. Ucak-Astarlioglu, and K. T. Mueller
2007 969 (), 20-35
- Toward the Integration of Liquid- and Solid-State NMR across the Undergraduate Curriculum
  N. M. Washton, K. C. Earnheart, D. G. Sykes, M. Ucak-Astarlioglu, and K. T. Mueller
  2007 969 (), 20-35
  This work addresses issues of fundamental reform in the undergraduate chemistry curriculum via advanced integration of liquid- and solid-state nuclear magnetic resonance (NMR) experiments and theory. Our integrated curricula comprises a suite of NMR ...
  Abstract | Hi-Res PDF | PDF w/ Links