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  Home > JCE Print > Journal of Chemical Education > Issues > 2008  > June  >
In the Laboratory
Acid-Catalyzed Enolization of β-Tetralone
Brahmadeo Dewprashad, Anthony Nesturi, and Joel Urena
Department of Science, BMCC, City University of New York, New York, NY 10007
Cover
June 2008
Vol. 85 No. 6
p. 829
Abstract
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 experiment demonstrates that the benzylic hydrogens undergo α substitution much faster than the non-benzylic hydrogens. The described experiment can be used in the introductory two-semester organic chemistry course sequence to make the concepts of enolization and resonance concrete.
Supplement
Student handout containing the pre-lab and post-lab exercises and additional experimental details; Instructor notes including spectra obtained in the experiment and a table with the compiled integration values
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Contents
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JCE2008p0829W.zip
JCE2008p0829W.doc (Microsoft Word)
More Information
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Citation
Dewprashad, Brahmadeo; Nesturi, Anthony; Urena, Joel. J. Chem. Educ. 2008, 85, 829.
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Keywords
Aldehydes / Ketones; Hands-On Learning / Manipulatives; Isotopes; Laboratory Instruction; Mechanisms of Reactions; NMR Spectroscopy; Organic Chemistry; Reactive Intermediates; Resonance Theory; Second-Year Undergraduate; Synthesis
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History
Created:
Last Updated:
5/5/2008
5/7/2008
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