The Substitution–Elimination Mechanistic Disc Method

Paul T. Buonora and Yu Jin Lim
Department of Chemistry and Biochemistry, California State University–Long Beach, Long Beach, CA 90840-3903
J. Chem. Educ., 2004, 81 (3), p 368
DOI: 10.1021/ed081p368
Publication Date (Web): March 1, 2004
History, Education, and Documentation

Abstract

Many students of organic chemistry find it difficult to determine the extent to which substitution and elimination reactions compete to produce distributions of products. Similarly the competition between monomolecular and bimolecular mechanisms can be confusing. By viewing these phenomena as part of a circular E2, E1, SN1, and SN2 mechanistic continuum the student is capable of determining the relative product distribution without memorizing oversimplified tables. In this manuscript a mnemonic device designed to facilitate presentation of the competing SN1, SN2, E1, and E2 mechanisms is presented.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Mnemonics / Rote Learning

Keywords (Subject):

Mechanisms of Reactions
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History

  • Received: August 03, 2009

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