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Substitution and Elimination. Reactions of Alkyl Halides. Substitution, Nucleophilic, Bimolecular – S N 2. Reaction Profile for S N 2 Reaction (Wade). Stereochemistry of S N 2 Reaction Inversion of Configuration. Proof of Inversion of Configuration at a Chiral Center.

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substitution and elimination

Substitution and Elimination

Reactions of Alkyl Halides

substrate reactivity
Substrate Reactivity

Since the energy of the transition state is significant in determining the rate of the reaction, a primary substrate will react more rapidly than secondary (which is much more rapid than tertiary).

hammond s postulate
Hammond’s Postulate
  • Related species that are close in energy are close in structure.
  • In an endothermic reaction, the transition state is similar to the product in structure and stability.
  • In an exothermic reaction, the transition state is similar to the reactant in structure and stability.
  • i.e. the structure of the transition state resembles the structure of the most stable species.
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