Reactivity in Chemistry

Aliphatic Nucleophilic Substitution

with problems contributed by Kate Graham

NS1. Introduction to Aliphatic Nucleophilic Substitution

NS2.  Possible Mechanisms of Nucleophilic Substitution

NS3.  Rate Laws in Nucleophilic Substitution

NS4.  Stereochemistry in Nucleophilic Substitution

NS5.  Regiochemistry in Nucleophilic Substitution

NS6.  Structural Effects in Nucleophilic Subsitution

NS7.   Solvent Effects in Nucleophilic Substitution

NS8.  Nucleophilicity in Nucleophilic Substitution

NS9.  Enolate Nucleophiles

NS10.  Leaving Group Formation

NS11.  Nucleophilic Addition to Strained Rings

NS12.  Complications: Elimination Reactions

NS13.  Regiochemistry in Elimination

NS14.  Stereochemistry in Elimination

NS15.  Factors Affecting Elimination Mechanism

NS16.  Nucleophilic Substitution in Synthesis: Alcohols and Ethers

NS17.  Nucleophilic Substitutions in Synthesis: Amines

NS18.  Nucelophilic Substitution at Silicon

NS19.  Extra Problems

NS20.  Solutions for Selected Problems


This site is written and maintained by Chris P. Schaller, Ph.D., College of Saint Benedict / Saint John's University (with contributions from other authors as noted).  It is freely available for educational use.

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Structure & Reactivity in Organic, Biological and Inorganic Chemistry by Chris Schaller is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported License

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This material is based upon work supported by the National Science Foundation under Grant No. 1043566.

Any opinions, findings, and conclusions or recommendations expressed in this material are those of the author(s) and do not necessarily reflect the views of the National Science Foundation.



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