JEFFERSON COLLEGE COURSE SYLLABUS CHM200 ORGANIC CHEMISTRY I 5 Credit Hours Prepared by: Richard A. Pierce Revised Date: January 2008 by Ryan H. Groeneman Arts & Science Education Dr. Mindy Selsor, Dean CHM200 Organic Chemistry I
I. CATALOGUE DESCRIPTION A. Prerequisite: CHM112 or CHM111 and approval from instructor B. 5 Credit Hours C. Organic Chemistry I is the study of the structure, nomenclature, usage, and properties of aliphatic hydrocarbons, alkyl halides, alkenes, and alkynes. Units on organic chemical reactions with their mechanisms and stereochemistry are also included. Organic Chemistry I involves three hours of lecture and four hours of laboratory a week. (F,D) II. EXPECTED LEARNING OUTCOMES/ASSESSMENT MEASURES Demonstrate a knowledge of atomic properties, properties of ionic and covalent bonds, and intermolecular forces and how they affect the properties of molecules Understand the role of hybrid orbitals and molecular orbital theory in the bonding and properties of organic compounds Understand the relationship of structure to reactivity for organic molecules. Explain the importance of resonance in describing the properties of multiplybonded organic compounds Define and describe reaction intermediates and their role in reaction mechanisms Understand structural isomerism and the different kinds of isomers Demonstrate a knowledge of the general rules of nomenclature of organic compounds Understand the stereochemical aspects of organic molecules and reactions Demonstrate a knowledge of the structure, physical properties, nomenclature, and reactions of alkyl halides Understand the stereochemistry and mechanism of free-radical reactions. Demonstrate a knowledge of the structure, physical properties, nomenclature, methods of preparation, and reactions of alcohols Demonstrate a knowledge of the physical
properties, nomenclature, methods of preparation, and reactions of ethers, epoxides, and sulfides Demonstrate a knowledge of the structure, physical properties, nomenclature, methods of preparation, and reactions of alkenes and alkynes. Design on paper multi-step syntheses of simple organic molecules III. COURSE OUTLINE WITH UNIT OBJECTIVES A. Atoms and Molecules--A Review 1. Introduction to organic chemistry 2. Electronic structure of the atom 3. Atomic properties 4. Introduction to the chemical bond including Lewis Dot Structures 5. Chemical formulas in organic chemistry 6. Electronegativity and bond polarity 7. Resonance 8. Structural and line-angle formulas 7. Arrhenius acids and bases 11. Bronsted and Lowry acids and bases 12. Lewis acids and bases B. Structure and Properties of Organic Molecules 1. Introduction to theories of covalent bonding 2. Properties of waves 3. Molecular orbitals 4. Bonding and antibonding orbitals 5. Hybrid orbitals of carbon 6. Hybrid orbitals of nitrogen and oxygen 7. Drawing three-dimensional molecules 8. Bond rotation 9. Constitutional Isomers 10. Stereoisomers 11. Polar covalent bonds 12. Dipole moment 13. Intermolecular forces 14. Solubility of organic compounds 15. Types of hydrocarbons 16. Functional groups a. oxygen based b. nitrogen based C. Structure and Stereochemistry of Alkanes 1. Definitions of alkanes
2. Molecular formulas of alkanes 3. Nomenclature of alkanes 4. Physical properties of alkanes 5. Uses and sources of alkanes 6. Reactions of alkanes 7. Conformation of ethane, propane, and butane 8. Cycloalkanes 9. Ring strain and conformations of cycloalkanes 10. Conformations of substituted cycloalkanes a. monosubstituted b. disubstituted 11. Bicyclic compounds D. The Study of Chemical Reactions 1. Free-radical chain reactions 2. Equilibrium equations 3. Gibbs free energy 4. Enthalpy a. exothermic b. endothermic 5. Entropy 6. Bond-dissociation enthalpies a. homolytic cleavage b. heterolytic cleavage 7. Kinetics and rate equations 8. Activation energy 9. Reaction-energy diagrams a. transition state b. intermediate c. rate-limiting step 10. Selectivity in halogenation 11. Hammond Postulate 12. Reactive intermediates a. carbocations b. free radicals c. caranions d. carbenes E. Stereochemistry 1. Chirality 2. Assignment of configuration: the (R) and (S) system 3. Optical activity 4. Rotation of plane-polarized light 5. Racemic mixture 6. Enantiomeric excess and optical purity 7. Chirality without asymmetric carbons
8. Fischer projections 9. Diastereomers and enantiomers 10. Meso compounds 11. Stereoisomers of compounds with more than one chiral carbon 12. Physical properties of diastereomers 13. Resolution of a racemic mixture and of enantiomers F. Alkyl Halides: Nucleophilic Substitution and Elimination 1. Nomenclature of alkyl halide compounds 2. Structure and physical properties of alkyl halides 3. Preparation of alkyl halides 4. A preview of substitution and elimination reactions 5. The S N 2 reaction 6. The S N 1 reaction 7. The E1 reaction 8. The E2 reaction 9. Factors governing substitution and elimination reactions G. Structure and Synthesis of Alkenes 1. Elements of unsaturation 2. Nomenclature of alkenes a. cis and trans b. E and Z 3. Commercial reactions and importance of alkenes 4. Stability of alkenes 5. Physical properties of alkenes 6. Alkene synthesis a. Elimination of alkyl halide b. Dehydration of alcohols c. Catalytic cracking H. Reaction of Alkenes 1. Electrophilic additions 2. Hydrogen halide additions a. Markovnikov Products b. Anti- Markovnikov Products 3. Hydration of alkenes 4. Oxymercuration-demercuration 5. Alkoxymercuration-demercuration 7. Hydroboration 8. Halogen additions 9. Halohydrin formation 10. Catalytic hydrogenation 11. Carbene addition 12. Epoxidation 13. Acid-catalyzed opening of epoxides
14. Syn hydroxylation a. Osmium tetraoxide hydroxylation b. Permanganate hydroxylation 15. Oxidative cleavage 16. Polymerization of alkenes a. Cationic b. Free-radical c. Anionic I. Alkynes 1. Nomenclature of alkynes 2. Physical properties of alkynes 3. Commercial reactions and importance of alkynes 4. Acidity of alkynes 5. Alkylation of acetylide ions 6. Addition of acetylide ions to carbonyl groups 7. Elimination reactions to form alkynes 8. Catalytic hydrogenation 9. Addition reactions a. halogens b. hydrogen halides c. hydration d. hydroboration 10. Oxidation of alkynes a. Permanganate b. Ozonolysis IV. METHOD OF INSTRUCTION A. Lectures B. Class Discussion C. Laboratory Work D. Research Paper V. REQUIRED TEXTBOOK (with publication formation) Wade, L.G., Organic Chemistry, 6 th ed. (2006) Prentice Hall Lehman, John W., Multiscale Operational Organic Chemistry, (2002) Prentice Hall VI. REQUIRED MATERIALS
Textbook Notebook paper Pens/pencils Scientific calculator Laboratory Notebook Molecular Model Set VII. SUPPLEMENTAL MATERIALS None VIII. METHOD OF EVALUATION A. Exams 35% B. Quizzes 20% C. Laboratory Notebook 20% D. Research Paper 5% E. Final 20% F. Grading Scale A: 90-100 B: 80-89 C: 70-79 D: 60-69 F: 0-59 IX. ADA STATEMENT Any statement requiring special accommodations should inform the instructor and the Coordinator of Disability Support Services (Library; phone 636-797-3000, ext. 169). X. ACADEMIC HONESTY STATEMENT All students are responsible for complying with campus policies as stated in the Student Handbook (see College Website).