Pentavalent Carbon and Competing Reaction Mechanisms - E2, SN1, E1

Explore advanced organic chemistry concepts in this 48-minute lecture from Yale University's Freshman Organic Chemistry II course. Delve into the investigation of pentavalent carbon intermediates using X-ray analysis, and discover why boron can achieve pentavalency in certain environments. Examine competing reaction mechanisms including E2, SN1, and E1, and their impact on SN2 reactions. Gain insights into factors controlling E2 eliminations through kinetic isotope effects, stereochemistry, and regiochemistry. Learn how the competition between E2 and SN2 mechanisms influences synthetic design strategies, particularly those involving carbon nucleophiles. Investigate SN1 and E1 reactions, focusing on carbocation intermediates and potential carbon skeleton rearrangements. The lecture covers six key chapters, providing a comprehensive exploration of these advanced organic chemistry topics.

- Chapter 1. Using X-Ray to Investigate the Possibility of a Pentavalent Carbon Intermediate
.
- Chapter 2. The E2 Reaction and Kinetic Isotope Effects
.
- Chapter 3. Stereochemistry & Regiochemistry of E2 Elimination
.
- Chapter 4. Strategies for Substitution in Organic Synthesis
.
- Chapter 5. SN1 and E1 Reactions - Kinetic Evidence for SN1 Substitution
.
- Chapter 6. Carbocation Intermediates: Competition and Rearrangement
.