FARMINGDALE STATE COLLEGE DEPARTMENT OF CHEMISTRY COURSE OUTLINE: COURSE TITLE: Dr. M. De Castro September 2011 Organic Chemistry I COURSE NUMBER: CHM 270 CREDITS: 5 CONTACT HOURS: Lecture: 3 Laboratory: 4 CATALOG DESCRIPTION: A study of the compounds of carbon involving a thorough integration of fact and theory and emphasizing the relationships between structures, properties, mechanisms, and reactions. This course, intended for science and preprofessional majors, covers topics such as bonding and structure, alkanes, alkenes, alkynes, cycloaliphatic hydrocarbons, stereochemistry, dienes and spectroscopy and structure determination and includes laboratory. PREREQUSITE: CHM 153 IMPORTANT NOTE: ELECTIVE FOR: BOTH THEORY AND LABORATORY PARTS OF THIS COURSE MUST BE TAKEN CONCURRENTLY IN ORDER TO RECEIVE CREDIT. Liberal Arts and Sciences, and Bioscience
2 REQUIRED TEXT: Organic Chemistry, 7th edition by Wade, Pearson Publishing LABORATORY MANUAL: Organic Chemistry Laboratory Manual CHM 270 edited by Dr. Michael DeCastro OPTIONAL TEXTS: 1) Contemporary Organic Chemistry by Ternay. 2) Organic Chemistry, by Streitwiesser. 3) Electron Movements, by Weeks. 4) Naming Organic Compounds, by Banks. 5) Organic Chemistry, 1 st Edition, by Fox & Whitesell. 6) Organic Chemistry, by McMurray. REQUIRED SUPPLIES: Lab coat and safety glasses.
3 FARMINGDALE STATE COLLEGE DEPARTMENT OF CHEMISTRY CHM 270 Organic Chemistry I LECTURE SCHEDULE I. Introduction Review of structural theory, atomic orbitals, ionic bonding, covalent bonding, molecular geometry, electronegativity, molecular orbitals and acid-base theories. Section 1. - 1. Predict the number of valence-shell electrons of an element. 2. Predict the electronegativity of an element. 3. Draw Lewis electron dot structures for simple compounds. 4. Draw line-bond structures for compounds. 5. Predict and describe the hybridization of bonds in organic compounds. 6. Draw organic structures with correct threedimensional geometry. 7. Identify bonds in a molecule as ionic or covalent. 8. Predict the polarity of a bond. 9. Distinguish between a sigma and a Pi molecular orbital. 10. Identify the conjugate acid-base pairs in Bronsted- Lowry acid-base reactions. 10. Identify Lewis acids and bases. 11. Familiar with Kekule and Skeletal Structures.
4 II. Alkanes Structures, nomenclature, physical properties, preparations, chemical eactions, mechanisms and free radical intermediates. Section II. - 1. Draw all isomers of a given alkane molecular formula. 2. Name alkanes by the IUPAC system. 3. Draw structures of alkanes corresponding to a given IUPAC name. 4. Identify carbon atoms as primary, secondary, tertiary or quarternarly. 5. Identify and draw structures of alkyl groups. 6. List methods of preparing alkanes. 7. List reactions of alkanes. 8. Write a mechanism for the halogenation of an alkane. 9. Apply the free radical mechanism to other compounds. Unit Exam I- on Units I and II. III. Alkenes Structure, nomenclature, physical properties, preparations, chemical reactions, mechanisms and carbocation intermediates. Section III. - 1. Name alkenes by the IUPAC system. 2. Draw structures of alkenes corresponding to a given IUPAC name. 3. Draw all the isomers of a given alkene molecule. 4. Draw a molecular orbital picture of an alkene. 5. Differentiate between cis and trans isomers. 6. Write chemical equations for the preparation of alkenes.
5 7. Write chemical equations for the reactions of alkenes. 8. Write a general mechanism for addition reactions of alkenes. 9. Explain Markovnikov s Rule and the peroxide effect. 10. Write a mechanism for Markovnikov s addition reactions. 11. Write a mechanism for anti-markovnikov s addition reaction. 12. Explain how a carbanion forms. IV Alkynes and Dienes Structure, nomenclature, physical properties, preparations, chemical reactions, and mechanisms. Section IV. - Unit Exam II- on Units III and IV. 1. Name alkynes and dienes by the IUPAC system. 2. Draw structures of alkynes and dienes corresponding to a given IUPAC name. 3. Draw all isomers of a given alkyne molecule. 4. Draw the molecular orbital picture of a typical alkyne and diene. 5. Explain resonance and resonance energy concepts. 6. Write chemical equations for the preparation of alkynes and dienes. 7. Write chemical equations for the reactions of alkynes and dienes. 8. Explain the principle behind 1, 4 addition reactions of dienes. 9. Propose a mechanism for 1, 4 addition reactions. 10. Explain keto-enol tautomerization. V Cyclic Aliphatic Hydrocarbons Structure, nomenclature, physical properties, preparations, stereochemistry, chemical reactions, mechanisms and carbene intermediates.
6 Section V. - 1. Explain the reactivity of small rings. 2. Define Baeyer, Transannular and Pitzer strains. 3. Write chemical equations for the formation of cycloalkanes. 4. Explain how carbenes are formed. 5. Explain carbene insertion reaction mechanism. 6. Describe the three dimensional shapes of cycloalkanes of five carbon atoms or less. 7. Describe the three dimensional shapes of cycloalkanes of six carbon atoms or greater. 8. Locate axial and equitorial positions on cyclohexane. 9. Identify cis and trans positions on a cyclohexane ring. 10. Write chemical equations for the formation of cycloalkenes and cycloalkynes. VI Stereochemistry Isomer number, optical activity, specific rotation, enantiomerism, chiral carbon, racemic modification, projections, Cahn- Ingold-Prelog (r,s) nomenclature, stereoisomers, and stereospecific reactions. Section VI. - 1. Explain the meaning of isomer number. 2. Explain the causes of optical activity. 3. Calculate the specific rotation of a solution. 4. Decide whether objects are chiral. 5. Locate stereocenters in molecules. 6. Draw the enantiomer of a given chiral compound. 7. Draw the diastereoisomer of a given chiral compound. 8. Apply Van t Hoff s Rule. 9. Identify racemic modifications. 10. Draw chiral molecules in Newman and Sawhorse projections. 11. Assign priorities to substituents around a carbon
7 stereocenter. 12. Assign r,s configurations to stereocenters. 13. Decide if a stereoisomer is a meso compound. 14. Predict the stereochemistry of reaction products. VII Spectroscopy and Structure Mass spectroscopy, infrared spectroscopy, ultraviolet spectroscopy, nuclear magnetic resonance spectroscopy and structural determination via spectroscopy. Section VII. - 1. Explain how molecular weights are determined via mass spectrometry. 2. Apply splitting rules to simple organic molecules. 3. Identify the functional group giving rise to specific infrared absorptions. 4. Use infrared spectroscopy to identify compounds. 5. Predict if compounds show ultraviolet absorption in the range 100 400 nm. 6. Predict the number of chemical shifts appearing in the HNMR spectra of compounds. 7. Explain the relationships, which exist between delta values, chemical shifts and spectrometer operating frequency. 8. Explain J values. 9. Predict chemical shifts. 10. Use integration values of chemical shifts to calculate the number of protons giving rise to specific absorptions. 11. Predict first order splitting patterns in NMR spectra. 12. Propose structures for compounds given their NMR Spectra 13. Propose structures for complex organic molecules given their mass, infrared, ultraviolet, and nuclear magnetic resonance spectras. Unit Exam III- on Units V, VI, and VII.
8 FARMINGDALE STATECOLLEGE DEPARTMENT OF CHEMISTRY CHM 270 Organic Chemistry I LABORATORY SCHEDULE TEXT: Introduction to Organic Laboratory Techniques by Pavia, Lampman and Kriz Lab Period Experiment 1 Check In, Safety Lecture 2 Acetyl Salicylic Acid 3 Melting Points of Organic Compounds 4 TLC Analysis of Analgesics 5 Isolation of Caffeine from Tea 6 Column Chromatography of Lycopene and Carotene 7 UV Analysis of Carotenes 8 Separation and ID of unknowns by Gas Chromatography 9 Preparation of Isoamyl Acetate 10 Vacuum Distillation of Carvones Polarimetry Index of Refraction 11, 12, 13 Identification of unknowns by IR, NMR, Refractive Index
9 14 Check Out CHM 270 Organic Chemistry I GRADING POLICY Lecture There will be 3 exams throughout the course and a final comprehensive exam. The final comprehensive can be used to replace a missed or poor examination grade. Students will be given at least 1 week notice of when the exam will be given. There are no makeup exams and the lowest grade will be dropped. Laboratory The laboratory portion of the course constitutes 30 % of the final grade. There are 13 laboratory experiments in total. The lowest laboratory grade will be dropped. The final laboratory grade will be an average of all laboratory report grades. FINAL GRADE = 70% LECTURE + 30 % LAB GRADE.