CHM 25500 Lecture Notes - Lecture 28: Nucleophilic Substitution, Leaving Group, Alpha And Beta Carbon

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CHM 255 - Lecture 28 - Properties of Sn2 Reactions
Stereochemical Properties of Sn2 Reactions
In nucleophilic substitution reactions, the nucleophile always attacks from the
side opposite the leaving group
This results in inversion of configuration
Structure of Alkyl Halides and Rate of Sn2 Reactions
The more substituted the alpha carbon (the carbon bonded to the halogen) the
slower the rate of reaction
This is because the substituents block the nucleophile from attacking the
nucleophilic carbon
Branching on a beta carbon (a carbon next to the alpha carbon) can also
slow down the reaction
Leaving Groups and Rate of Sn2 Reactions
The leaving group that can best accept the electron pair is the best leaving group
The most stable leaving group when separated from the substrate is the best
leaving group
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