Organic Chemistry II CHEM-2425 Ch 21 Substitution Reactions at the Alpha Carbon Part 2

Chapter 21 Lecture Video Part 2 Section 21.7 Halogenation at the α Carbon: Draw the mechanism for both acid-catalyzed halogenation and base-catalyzed halogenation at the α carbon. Explain what is meant by a positive result with the iodoform test. Identify and use in a synthetic scheme the two useful reactions that can be done with an α-halo carbonyl compound. Section 21.8 Direct Enolate Alkylation: Predict the product when a ketone is deprotonated and then reacted with an alkyl halide. Predict kinetic vs. thermodynamic alkylation products. Section 21.9 Malonic Ester Synthesis: Predict whether a keto acid or a diacid will undergo decarboxylation based on the position of the two carbonyl groups. Propose a synthetic pathway to generate a substituted carboxylic acid from an alkyl halide and diethyl malonate. Use retrosynthetic analysis to determine your pathway. Section 21.10 Acetoacetic Ester Synthesis: Propose a synthetic pathway to generate a particular ketone from an alkyl halide and ethyl acetoacetate. These are the lectures that I use in my Organic Chemistry II course. The textbook I use is Smith, Janice "Organic Chemistry", McGraw Hill, 6th Ed., 2020, ISBN13: 9781260119107. Some images used in this video come from that textbook.