Ch4&8 - 1 Chapters 4 & 8 S N 2 Reactions...

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Unformatted text preview: 1 Chapters 4 & 8 S N 2 Reactions 8.2- Mechanism 8.3 Mechanism 8.4, 8.5 & 8.10 Factors substrate, nucleophile & solvent S N 1 Reactions 8.6- Mechanism 8.7 & 8.10- Factors substrate & solvent 8.9 Carbocation Rearrangements 8.8 Ion-pair effect Halogenation of Alkanes ( 4.14-4.18 ) Chapter 9 of Klien can be helpful and harmful. At this point simply know the conditions that favor either S N 2 or S N 1 reactions. Lastly, please know that we are limiting our discussion of substitution chemistry to alkyl halides. 2 4.14-4.18 Halogenation of Alkanes: Free-Radical Halogenation Halogenation : Cl 2 or Br 2 ( Br 2 is most selective) What does this reaction look like on the Hill? Free-Radical Mechanism Initiation, Propagation & Termination (not shown) High temp. or light Very reactive, decreasing in reactivity from a 1 to 3 Alkyl radical Try problem 4.14 4.17, 4.19 C H C H 3 H CH 3 + Br Br C H C H 3 Br CH 3 + H Br 3 Overview (The Big Picture) H O- Cl H H H H H + Chapter 8 Substitution (Example: S N 2) O H H H H H H + Cl- H O- Cl H H H H H + + H H H H O H 2 Chapter 5 Elimination (Example:E2) Factors to Consider Substrate Nucleophile Leaving Group Solvent N.S. E.S. N.S. + Cl- 4 8.2 Factors to Consider : Leaving Group Effect Solvent X H H H H H + Nu No matter the reaction from chapter 8 or 5, you need a good leaving group....
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Ch4&8 - 1 Chapters 4 & 8 S N 2 Reactions...

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