CHM 313: Organic Chemistry Laboratory II (3)
Prerequisites: CHM 213, CHM 311
Learning Objectives:
This is an advanced organic chemistry practical course. In this laboratory course, students would be able to use their knowledge of selectivity in synthesis (chemo-, regio- and stereoselectivity) to plan and execute the preparation of complex organic compounds using modern C-C and C-hetero bond-forming reactions. This course would involve multi-step synthesis and chromatographic analysis of complex mixtures and advanced characterization techniques. Upon completion of this laboratory course, a student would be confident on working in a synthesis laboratory and also be able to characterize simple compounds using various modern spectroscopic techniques.
Suggested Experiments:
- Preparation of Corey-Bakshi-Shibata (CBS) reagent and enantioselective reduction of a carbonyl compound.
- Preparation of pentacyclic dione via Diels-Alder and photochemical cyclizations.
- Preparation of a Wittig salt and olefination of a carbonyl compound
- Preparation of Evans chiral auxiliary and its use in asymmetric aldol reaction
- Preparation of a Grignard reagent and its addition to a carbonyl compound
- Generation and trapping of benzyne
- Generation of a carbene: The Reimer-Tiemann reaction
- The Fischer indole synthesis
- Sonogashira/Suzuki/Heck coupling reaction
- Olefin metathesis (using Grubbs 1st generation catalyst)
- Baylis-Hillman reaction
- Synthesis of L-Prolinamide ligands
- Synthesis of BINOL
- Synthesis of β-nitro styrene (Henry reaction)
- Ugi multicomponent coupling.
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