CHEM 125b - Lecture 8 - Solvent, Leaving Group, Bridgehead Substitution, and Pentavalent Carbon

Lecture 8 - Solvent, Leaving Group, Bridgehead Substitution, and Pentavalent Carbon

Overview

The nature of nucleophiles and leaving groups has strong influence on the rate of SN2 reactions. Generally a good nucleophile or strong base is a poor leaving group, but hydrogen-bonding solvents can alter nucleophile reactivity. Although amino and hydroxyl groups are poor leaving groups, they may be converted to groups that leave easily, even from bridgehead positions. Designing the preparation of a sugar analogue containing radioactive fluorine shows how understanding the SN2 mechanism enables PET scanning for medical imaging. Quantum mechanics suggests that the pentavalent carbon species on the SN2 reaction pathway is a transition state, not a stable structure.

Resources

Professor McBride's website resource for CHEM 125b (Spring 2011)

https://webspace.yale.edu/chem125/

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