Chap08 - Substitution Reactions of Alkyl Halides Chapter 8...

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Chapter 8 1 Substitution Reactions of Alkyl Substitution Reactions of Alkyl Halides: Halides: Chapter 8 Chapter 8
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Chapter 8 2 Contents of Chapter 8 Reactivity Considerations The S N 2 Reaction Reversibility of the S N 2 Reaction The S N 1 Reaction Stereochemistry of S N 2 and S N 1 Reactions Competition between S N 2 and S N 1 Reactions Role of the Solvent No Biological Methylating Reagents
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Chapter 8 3 Substitution and Elimination A compound with an sp 3 hybridized carbon bonded to a halogen can undergo two types of reactions Two different mechanisms for substitution are S N 1 and S N 2 mechanisms These result in diff prods under diff conditions
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Chapter 8 4 S N 2 Mechanism S N 2 mechanism: C–X bond weakens as nucleophile approaches all in one step
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Chapter 8 5 S N 1 Mechanism S N 1 mechanism: C–X bond breaks first without any help from nucleophile This is a two-step process slow step fast step
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Chapter 8 6 Substitution Reactions Both mechanisms are called nucleophilic substitutions Which one takes place depends on the structure of the alkyl halide the reactivity and structure of the nucleophile the concentration of the nucleophile, and the solvent in which reaction is carried out
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Chapter 8 7 The S N 2 Reaction Bimolecular nucleophilic substitution rate = k [alkyl halide][nucleophile]
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Chapter 8 8 The S N 2 Reaction The inversion of configuration resembles the way an umbrella turns inside out in the wind If a single chiral enantiomer reacts a single chiral product (inverted) results.
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Chapter 8 9 Steric Accessibility in the S N 2 Reaction
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Chapter 8 10 The S N 2 Reaction: Leaving Group Stability
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Chapter 8 11 The S N 2 Reaction: Nucleophile Basicity stronger base weaker base better nucleophile poorer nucleophile HO > H 2 O CH 3 O > CH 3 OH NH 2 > NH 3 CH 3 CH 2 NH > CH 3 CH 2 NH 2
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Chapter 8 12 The S N 2 Reaction: Nucleophile Basicity Comparing nucleophiles with attacking atoms of approximately the same size, the stronger base is also the stronger nucleophile
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Chapter 8 13 The S N 2 Reaction: Nucleophile Size In nonpolar solvents nucleophilicity order same as basicity order- size doesn’t matter
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Chapter 8 14 The S N 2 Reaction: Nucleophile Size Size is related to polarizability
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Chapter 8 15 The S N 2 Reaction: Nucleophile Size and Type Nucleophilicity ~ both size and basicity
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Chap08 - Substitution Reactions of Alkyl Halides Chapter 8...

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