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30aw9 - the nucleophile solvent properties branching...

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Chem 30A, W’06 Prof. Garrell CHEM 30A Week 9 Synopsis: Substitution & Elimination Reactions: The Rest! Goals and Assignments for March 6 – March 10 TOPICS: (Continued) Nucleophilicity, basicity and solvent effects on S N reactions • Neighboring group effects on nucleophilic substitution β -Elimination: E1 and E2 Mechanisms, kinetics, regioselectivity and sterioselectivity • Substitution vs. elimination GOALS: Recognize the roles of neighboring groups in S N reactions, including steric effects and intramolecular S N 2 processes. Know what a phase transfer catalyst is, and why it is useful. Understand the mechanisms and kinetics of E1 and E2 elimination reactions. Understand the regioselectivity and stereoselectivity of E1 and E2 reactions; Be able to predict and explain the outcome (product distribution, relative reaction rates) of reactions involving nucleophiles, weighing such factors as the nucleophilicity and basicity of
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Unformatted text preview: the nucleophile, solvent properties, branching, sterics, carbocation stability, and leaving group stability. ASSIGNMENTS: Background: As needed, review basicities and nucleophilicities from Ch.4, and early in Ch. 9, energy diagrams (discussed early in Chem 30A), and kinetics of first- and second-order reactions (from your General Chemistry course; see any Gen. Chem. text). Readings: BFI §9.5 – 9.11. PROBLEMS BFI Ch. 9: In-chapter problems plus end-of chapter problems 37 through 53. UPCOMING DATES & DEADLINES: Midterm 2 will be returned at the end of class Wednesday, March 8. Quizzes: ***See e-mail sent 3/5 and in-class announcement 3/6!*** • This week on material from week 8 • Next week : comprehensive on S N and Elimination reactions. MoM assignment is due THIS FRIDAY, March 10. No extensions! See your handout....
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