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CH 6-2: SN2 Reaction-II Stereochemistry in The SN2 Reaction: A Stereospecific Reaction

CH 6-2: SN2 Reaction-II Stereochemistry in The SN2 Reaction: A Stereospecific Reaction. (S). (R). “Inversion of Configuration”……..Why?. Example: SN2 Reaction?. (R). (S). What is the configuration at the chiral center in reactant and product?. Is there an “Inversion of Configuration”?.

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CH 6-2: SN2 Reaction-II Stereochemistry in The SN2 Reaction: A Stereospecific Reaction

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  1. CH 6-2: SN2 Reaction-II Stereochemistry in The SN2 Reaction:A Stereospecific Reaction (S) (R) “Inversion of Configuration”……..Why?

  2. Example: SN2 Reaction? (R) (S) • What is the configuration at the chiral center in reactant and product? • Is there an “Inversion of Configuration”? • Is this an SN2 reaction?

  3. Re-cap: The SN2 Substitution Reaction • A bimolecular, concerted mechanism • Energy Diagram: minimum of one step (one T.S.) • “Pentavalent Carbon” in the T.S.; crowded T.S. • Nuc “grabs” the electrophilic carbon 180o opposite the Lg. • Stereospecific reaction; inversion of configuration

  4. Alkyl Halide Structure in SN2 Reactions • What was the significance of the SN2 Transition State? CROWDED! • How would large “R” groups effect the reaction? • Rank the following substrates in order of SN2 reactivity: Methyl >>> 1o > 2o >>>>> 3o (NR)

  5. Alkyl Halide Structure in SN2 Reactions Methyl >>> 1o > 2o >>>>>>>>>>>>> 3o (NR)

  6. Alkyl Halide Structure in SN2 Reactions • Halogens bonded to sp2 carbon (vinyl and phenyl halides) do not undergo substitution: WHY NOT?

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