Organic Chemistry II - Nucleophiles, Leaving Groups, and SN2 Reactions - Lecture 8

Explore the intricacies of SN2 reactions in this 48-minute lecture from Yale University's Freshman Organic Chemistry II course. Delve into the impact of nucleophiles and leaving groups on reaction rates, and discover how hydrogen-bonding solvents can alter nucleophile reactivity. Learn about converting poor leaving groups like amino and hydroxyl into more reactive species, even in bridgehead positions. Examine the application of SN2 mechanism understanding in PET scanning for medical imaging through the preparation of a radioactive fluorine-containing sugar analogue. Investigate the quantum mechanical perspective on the pentavalent carbon species in the SN2 reaction pathway. The lecture covers nucleophilicity and solvent influence, leaving groups and bridgehead substitution, making OH a leaving group, accelerating SN2 reactions for PET scanning, and theoretical investigations of pentavalent carbon intermediates.

- Chapter 1. Chapter 1. Nucleophilicity and the Influence of Solvent
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- Chapter 2. Leaving Groups & Bridgehead Substitution
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- Chapter 3. Making OH a Leaving Group
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- Chapter 4. Accelerating SN2 to Support PET Scanning
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- Chapter 5. Using Theory to Investigate the Possibility of a Pentavalent Carbon Intermediate
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