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Thermodynamic and Kinetic Controlled Enolates: A Project for a Problem-Oriented Laboratory Course

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Augustine Silveira Jr., Michael A. Knopp and Jhong Kim

State University of New York at Oswego, Department of Chemistry, 219 Snygg Hall, Oswego, NY 13126

J. Chem. Educ., 1998, 75 (1), p 78

DOI: 10.1021/ed075p78

Publication Date (Web): January 1, 1998

Section:

History, Education, and Documentation

Abstract

This work involves regioselective alkylations of 2-methylcyclohexanone via thermodynamically and kinetically controlled enolates. Despite numerous developments in the area of chemistry of enolates, it still remains difficult, in many cases, to control regiochemistry, stereochemistry, and the number of carbon-carbon bonds formed in the reaction of enolates with carbon electrophiles. In this project, potassium enoxy trialkylborates, readily obtainable by treating potassium enolates with trialkylboranes, undergo remarkably selective reactions with methyl iodide.

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Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Equilibrium

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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 ...
  Abstract | Hi-Res PDF | PDF w/ Links
Quantitative Determination of Methylcyclohexanone Mixtures Using 13C NMR Spectroscopy: A Project for an Advanced Chemistry Laboratory
Joseph W. LeFevre and Augustine Silveira Jr.
Journal of Chemical Education2000 77 (1), 83
- Quantitative Determination of Methylcyclohexanone Mixtures Using 13C NMR Spectroscopy: A Project for an Advanced Chemistry Laboratory
  Joseph W. LeFevre and Augustine Silveira Jr.
  Journal of Chemical Education2000 77 (1), 83
  The percentage composition of mixtures of four methylcyclohexanones was determined using 13C NMR spectroscopy as a quantitative analytical method. The data were acquired using standard broadband proton decoupling and inverse-gated decoupling, the latter ...
  Abstract | Hi-Res PDF | PDF w/ Links