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This course covers intermediate topics on the structure and reactivity of organic compounds with an emphasis on electronic structure, pericyclic reactions and the chemistry of heteroaromatic compounds. Mechanistic concepts and models of reactivity are developed to build intuition about how organic compounds undergo their chemical transformations. An emphasis will be placed on developing problem-solving skills using frontier molecular orbitals to prepare students to think critically about the organic chemistry of living systems (e.g., nucleic acids, aromatic and heteroaromatic amino acids, etc.). This course and Part 2 are equivalent to a second-semester organic chemistry course, and these courses are especially suited for students in agricultural, nutritional and biological sciences, as well as premedical, predental, and preveterinary programs.
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Week 1: Structural Fundamentals; The Curved-arrow Formalism; Introduction to Orbital Theory
Week 2: Constructing & Interpreting Molecular Orbitals; Frontier Molecular Orbital Theory; Non-traditional Resonance
Week 3: π Delocalization & Color; Aromaticity & Cyclic, π-type Molecular Orbitals; Aromatic Heterocycles
Week 4: Cycloaddition Reactions; Cycloaddition Theory; Other Pericyclic Reactions
Week 5: Organic Reaction Mechanisms & Proton Transfer; Strategies for Drawing Mechanisms; Patterns in Electron Flow & Reactivity
Week 6: Reaction Intermediates, Transition States & Stability Trends; Radical Chemistry
Week 7: Photochemical Reactions; Kinetics & Thermodynamics; Catalysis
Week 8: Stereotopic Relationships; Stereochemistry & Symmetry; Facial Stereotopic Relationships
