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Molecular Modeling of Non-Trivial Cyclohexane Derivatives: A Discovery Approach

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Gail Horowitz

Department of Chemistry, Yeshiva University, New York, NY 10033

J. Chem. Educ., 2004, 81 (7), p 1006

DOI: 10.1021/ed081p1006

Publication Date (Web): July 1, 2004

Section:

History, Education, and Documentation

Abstract

An experiment is described that utilizes molecular modeling to study the effects of sp² hybridization, bond elongation, and heteroatom substitution upon the stabilities of the axial and equatorial conformers of cyclohexane. Students are faced with unfamiliar structural features: sp² hybridized ring carbons or ring carbons that have been replaced with silicon or oxygen. This experiment features a discovery approach intended both to expand student thinking regarding conformational analysis, as well as to reinforce fundamental topics such as torsional strain, gauche interactions, and Newman projections. It is appropriate for first semester organic chemistry students who have already been exposed to the topic of the conformational analysis of alkanes and cycloalkanes.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Feature):

Molecular Modeling Exercises and Experiments

Keywords (Pedagogy):

Hands-On Learning / Manipulatives

Keywords (Subject):

Molecular Modeling

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

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