Module 6, 'Nucleophilic substitution reactions', discusses nucleophilic substitution reactions from the basics to details of reaction mechanisms. The material presented should allow prediction of reaction mechanism from reactants. Module 6 references chapter 8 of Soderberg.
Big ideas:
1. SN mechanisms depend on the strength of Nu:, stability of E+ and quality of LGs. 2. Carbocations are intermediates whose 'stability' depends on their structures. Module 6 slide sets: Nucleophilic substitution reactions
(Click on the links below to download each slide set for the lecture.) Introduction: Why aren't identical twins identical? Just ask SAM. 6.1: Two mechanistic models for nucleophilic substitution 6.1A: The SN2 mechanism 6.1B: The SN1 mechanism 6.2: Nucleophiles > What is a nucleophile? > Protonation state > Periodic trends in nucleophilicity > Resonance effects on nucleophilicity > Steric effects on nucleophilicity 6.3: Electrophiles > Steric hindrance at the electrophile > Carbocation stability 6.4: Leaving groups 6.5: SN1 reactions with allylic electrophile 6.6: SN1 or SN2? Predicting the mechanism 6.7: Biological nucleophilic substitution reactions 6.7A: A biochemical SN2 reaction 6.7B: A biochemical SN1 reaction 6.7C: A biochemical SN1/SN2 hybrid reaction 6.8: Nucleophilic substitution in the lab 6.8A: The Williamson ether synthesis 6.8B: Turning a poor leaving group into a good one: tosylates Resources for students:
> Module 6 lecture outline (PDF) > Module 6 lecture with instructor's notes (PDF) > Module 6 key concepts > Module 6 practice problems > Practice problems KEY > Guide to strength of Nu:, E+ and LG > Guide (summary) comparing SN1 and SN2 reactions and mechanisms > Diagnostic chart for substitution, addition and elimination reactions > Substitution reaction mechanism animations |
*Assignments:
> Homework set 6 |
Video tutorials for Module 6:
> SN2 reactions (University of Surrey)
> SN1 reactions (University of Surrey)
> Nucleophilicity (Khan Academy)
> Identifying nucleophilic and electrophilic centers (Khan Academy)
> SN2 reactions (University of Surrey)
> SN1 reactions (University of Surrey)
> Nucleophilicity (Khan Academy)
> Identifying nucleophilic and electrophilic centers (Khan Academy)