Lesson 16: SN2, SN1, E2 Practice Problems

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Lesson 16

I. Introduction to Substitution and Elimination Reactions A. Overview of SN2, SN1, and E2 Reactions - SN2: Bimolecular nucleophilic substitution mechanism. - SN1: Unimolecular nucleophilic substitution mechanism. - E2: Bimolecular elimination mechanism.

II. SN2 Practice Problems A. Problem 1: SN2 Reaction - Given substrate and nucleophile. - Step-by-step mechanism: Backside attack, inversion of stereochemistry. - Product analysis: Determining major product based on leaving group and nucleophile.

B. Problem 2: SN2 vs. SN1 Comparison - Comparative analysis: Factors influencing reaction pathway (substrate structure, nucleophile strength). - Reaction kinetics: Rate-determining steps and transition state theory.

III. SN1 Practice Problems A. Problem 3: SN1 Reaction - Substrate with varying leaving groups. - Carbocation stability: Impact on reaction rate and product distribution. - Solvent effects: Polar vs. non-polar solvents on carbocation stability and reaction rate.

B. Problem 4: SN1 vs. SN2 Considerations - Stereochemical outcomes: Inversion vs. retention.

IV. E2 Practice Problems A. Problem 5: E2 Elimination - Substrate with β-hydrogens. - Step-by-step mechanism: Proton abstraction, π-bond formation. - Zaitsev's rule: Predicting major and minor alkene products.

B. Problem 6: SN2 vs. E2 Competition - Competing pathways: Factors influencing SN2 vs. E2 preference (steric hindrance, base strength). - Practical applications: Industrial examples of E2 reactions in chemical synthesis.

V. Practical Applications and Examples A. Integration of Substitution and Elimination Reactions - Designing synthetic routes: Choosing between SN2, SN1, and E2 based on substrate and reaction conditions. - Optimization strategies: Maximizing yield and selectivity in organic synthesis.

VI. Conclusion and Recap A. Summary of Key Concepts - Recapitulation of SN2, SN1, and E2 mechanisms and factors influencing reaction pathways. - Importance in organic chemistry: Linking theory to practical applications in chemical synthesis.