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Second Semester Organic Chemistry Options: Bioorganic or Organic Mechanism and Synthesis Albert Matlin and Jason Belitsky Department of Chemistry and Biochemistry Oberlin College, Oberlin, OH Motivation 1. More flexibility and choice for Chemistry majors. 2. Introduce Biological Chemistry into the Chemistry major. 3. Offer an Organic Chemistry course (Chem 254) that is more relevant to students interested in biological sciences: Biochemistry, Biology, Molecular Biology, Neuroscience and Pre-Medical. 4. Offer a second semester Organic Chemistry course primarily for majors. 5. Biology department reduced the chemistry requirement for their major to one semester of organic chemistry. "New" Curriculum: Chemistry Major (1994) "New" Curriculum: Chemistry Major (1994) "New" Curriculum: Chemistry Major (1994) Chem 205: Principles of Organic Chemistry • ~130 students a year. Offered Spring and Fall Date Topic(s) Sept. 6 Sept. 8 Introduction, Acid-Base, Formal Charge Covalent Bonding and Hybridization Sept. 13 Sept. 15 Sept. 20 Sept. 22 Nomenclature, Alkanes and Alkenes Conformations of Alkanes/Cycloalkanes Free Radical Halogenation Stereochemistry Sept. 29, Oct. 4 Oct. 6,11 Nucleophilic Substitution, SN2, SN1 Elimination Reactions Oct. 13 Oct. 20 Addition Reactions, Alkenes Addition Reactions, Conjugated Nov. 1 Nov. 3,8 Infrared and Mass Spectroscopy Nuclear Magnetic Resonance Spectroscopy Nov. 10 Nov. 15 Nov. 17 Aromaticity Electrophilic Aromatic Substitution Reactions of Alcohols, Oxidation Nov. 29 Dec 1 Dec 6 Dec 8 Dec 13 Carbonyl Chemistry: Ketones, Aldehydes, Grignards Carbonyl Chemistry: Imines, Synthesis, Amines, Acetals Carboxylic Acids Carboxylic Acid Derivatives Enolates, Aldol Condensation -systems Topics Not Covered in Chem 205 (Partial List) Epoxides Ethers (except for EAS) Thiols Diols Phenols (except for EAS) Diels Alder Reaction Alkynes (except acetylide basicity and nucleophilicity) Allylic radical substitution (NBS) Polymerization Chem 325: Organic Mechanisms and Synthesis ~20 students a year. Offer in the Spring semester. Date February 7 February 9 Topics Radical Reactions Radical Polymerization February 14 February 16 February 21 February 23 March 1 March 6 Additions Reactions to p-systems: Alkynes Carbenes Reduction of of p-systems Oxidation of p-systems Reactions of Ethers and Epoxides Synthesis March 8 March 13 March 15,20 p-Molecular Orbital Theory Frontier MO theory, UV Spectroscopy Pericyclic Reactions April 3 April 5 April 10 Electrophilic Aromatic Substitution Reaction of Aromatic side chains and Substituents Diazonium salts and Synthesis of Aromatic Compounds April 12 April 19, 24 May 1 May 3 Carbanions, Organometallic Reagents Enolates Conjugate Addition and Michael Reactions Multi-Step Synthesis May 8 May 10 Nucleophilic Aromatic Substitution Benzynes Chem 254: Bioorganic Chemistry (Jason Belitsky) ~60 students a year. Offered in the Spring semester Week Topics 1 1 Class Introduction Basics of Chemistry and Molecular Biology 2 2 3 3 4 5 5 Covalent / Noncovalent /Small /Large Carboxyls / Esters / Amides / Amines Aromatic & Heterocyclic Chemistry Metals in Biology Metals in Synthesis Carbonyl Chemistry Enolate Chemistry 6 6 7 9 9 10 Lipids Lipid / Natural Product Biosynthesis Carbohydrates Peptide / Protein Synthesis Protein Structure Enzymatic Catalysis 11 12 13 13 14 14 Phosphate Esters, Nucleotides Nucleic Acids Biological Information Flow Drug Discovery Biological Probes Chemical Biology Textbook for Bioorganic Chemistry ???? Textbook for Bioorganic Chemistry ???? Bill Fuchsman has written a manuscript for his course. Email at: [email protected] "New" Curriculum: Chemistry Major (1994)