Substitution vs. Elimination Reactions

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Four fundamental types of reactions are addressed in this unit:  SN1, SN2, E1 and E2.  competition among these reactions is stressed throughout, and the manner in which a reaction may be influenced to proceed by one mechanism as opposed to another of the mechanisms is introduced.

A series of important terms are introduced such as leaving group, nucleophile, protic and aprotic solvents, substrates, Walden inversion, and stereospecificity to name just a few.  In each of the four types of reactions, the topics of how the reaction occurs, examples, the nucleophile, solvent effects, steric effects, the substrate, and stereochemistry are addressed.  From the study of the individual mechanisms and influencing factors, comparisons are made SN1 vs SN2, E1 vs E2, and finally competition among the four mechanisms.

The goal of this unit is to help the student make reasoned choices among reaction possibilities and learn to predict within reason the outcome of a given reaction based on the characteristics of the participants.  Organic chemistry can become an ordeal of memorization unless a thorough study of these competing reactions is undertaken.



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