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)

DateTopic(s ) Sept. 6Introduction, Acid-Base, Formal Charge Sept. 8Covalent Bonding and Hybridization Sept. 13Nomenclature, Alkanes and Alkenes Sept. 15Conformations of Alkanes/Cycloalkanes Sept. 20Free Radical Halogenation Sept. 22Stereochemistry Sept. 29, Oct. 4Nucleophilic Substitution, S N 2, S N 1 Oct. 6,11Elimination Reactions Oct. 13Addition Reactions, Alkenes Oct. 20Addition Reactions, Conjugated  -systems Nov. 1Infrared and Mass Spectroscopy Nov. 3,8Nuclear Magnetic Resonance Spectroscopy Nov. 10Aromaticity Nov. 15Electrophilic Aromatic Substitution Nov. 17Reactions of Alcohols, Oxidation Nov. 29Carbonyl Chemistry: Ketones, Aldehydes, Grignards Dec 1Carbonyl Chemistry: Imines, Synthesis, Amines, Acetals Dec 6Carboxylic Acids Dec 8Carboxylic Acid Derivatives Dec 13Enolates, Aldol Condensation Chem 205: Principles of Organic Chemistry ~130 students a year. Offered Spring and Fall

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

DateTopics February 7Radical Reactions February 9Radical Polymerization February 14Additions Reactions to  -systems: Alkynes February 16Carbenes February 21Reduction of of  -systems February 23Oxidation of  -systems March 1Reactions of Ethers and Epoxides March 6Synthesis March 8  -Molecular Orbital Theory March 13Frontier MO theory, UV Spectroscopy March 15,20Pericyclic Reactions April 3 Electrophilic Aromatic Substitution April 5Reaction of Aromatic side chains and Substituents April 10Diazonium salts and Synthesis of Aromatic Compounds April 12Carbanions, Organometallic Reagents April 19, 24Enolates May 1Conjugate Addition and Michael Reactions May 3Multi-Step Synthesis May 8Nucleophilic Aromatic Substitution May 10Benzynes Chem 325: Organic Mechanisms and Synthesis ~20 students a year. Offer in the Spring semester.

Chem 254: Bioorganic Chemistry (Jason Belitsky) ~ 60 students a year. Offered in the Spring semester WeekTopics 1Class Introduction 1Basics of Chemistry and Molecular Biology 2Covalent / Noncovalent /Small /Large 2Carboxyls / Esters / Amides / Amines 3Aromatic & Heterocyclic Chemistry 3Metals in Biology 4Metals in Synthesis 5Carbonyl Chemistry 5Enolate Chemistry 6Lipids 6Lipid / Natural Product Biosynthesis 7Carbohydrates 9Peptide / Protein Synthesis 9Protein Structure 10Enzymatic Catalysis 11Phosphate Esters, Nucleotides 12Nucleic Acids 13Biological Information Flow 13Drug Discovery 14Biological Probes 14Chemical Biology

Textbook for Bioorganic Chemistry ????

Textbook for Bioorganic Chemistry ???? Bill Fuchsman has written a manuscript for his course. at:

"New" Curriculum: Chemistry Major (1994)