This course focuses on the mechanisms, stereochemistry, and synthetic applications of reactions involving carbanions or potential carbanions with various carbonyl compounds. Key topics include:

Mechanisms:

  • Formation of Carbanions: Understanding the conditions and reagents that favor carbanion formation.
  • Reaction Pathways: Detailed study of the mechanisms through which carbanions react with carbonyl compounds, including nucleophilic addition and substitution reactions.

Stereochemistry:

  • Stereochemical Outcomes: Analysis of the stereochemical outcomes of reactions involving carbanions.
  • Chirality and Configuration: Understanding how carbanion reactions can create or influence chiral centers and the implications for the stereochemical configuration of products.

Synthetic Applications:

  • Aldol Reactions: Utilizing carbanions in aldol reactions for the formation of β-hydroxy carbonyl compounds.
  • Michael Additions: Applications of carbanions in Michael additions for the formation of 1,4-addition products.
  • Enolate Chemistry: Use of enolates (a type of carbanion) in various synthetic transformations, including the formation of C-C bonds.
  • Organometallic Reagents: Employing organometallic reagents (e.g., Grignard and organolithium reagents) in synthetic strategies involving carbanions.
  • Carbonyl Compound Reactions: Comprehensive study of carbanion reactions with aldehydes, ketones, esters, amides, and other carbonyl-containing compounds.
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CHEM 344