CHEM*2700 ORGANIC CHEMISTRY I (Winter Semester 2007) Information Sheet and Course Outline-Revised

CHEM*2700 ORGANIC CHEMISTRY I (Winter Semester 2007) Information Sheet and Course Outline-Revised Instructor: Professor William Tam Office: MacN 332 Phone: 824-4120 (Ext.52268) E-mail: wtam@uoguelph.ca ** You are welcome to visit me anytime (Monday-Friday, 9:30 am to 5:30 pm) to discuss problems. Calendar Description: An introduction to organic chemistry covering the stereochemistry and mechanisms of the main classes of organic reactions. Prerequisites: CHEM*1040 and CHEM*1050. Objectives: Chemistry CHEM*2700 is an appropriate one-semester course in Organic Chemistry. However, CHEM*2700 and CHEM*3750 have been designed to provide a comprehensive introduction to Organic Chemistry. This will properly serve the students who require a year of Organic Chemistry in addition to their first year General Chemistry. In CHEM*2700, the emphasis is on the understanding of the factors that control reactions and the reaction products. This course is a prerequisite for CHEM*3750. Course Web Page: http://www.chembio.uoguelph.ca/tam/chem2700.htm This web page will be updated regularly. Lecture slides, answers for assignments, tutorial and revision materials, as well as exam grades and statistics will be posted. Please visit this website regularly, especially before exams. Lectures: January 8 April 5, 2006, Mondays, Wednesdays & Fridays. 11:30 am 12:20 pm, THRN 1200 (Thornbrough Building). Tutorials/Help Classes (optional): Every (Monday or Tuesday, TBA), 5:45 pm 6:45 pm. Location: MACN 113. Lectures Notes: The lectures notes for CHEM*2700, Organic Chemistry I, will be available for sale from the department at the beginning of the semester. It is assumed that you are familiar with the organic chemistry materials covered in CHEM*1040 (prerequisite for the course) and you may wish to have the notes available to review topic as needed. i

Textbooks: (a) Organic Chemistry, 7 th Edition or 7 th Edition Upgrade or 8 th Edition, by T. W. G. Solomons and C. B. Fryhle, John Wiley & Sons, Inc. I strongly recommend that you purchase the textbook as it will effectively supplement the lecture material. Reading assignments and some problems will be chosen from it. (b) Study Guide and Solutions Manual to Organic Chemistry, 7 th or 8 th Ed., by T.W.G. Solomons, C. B. Fryhle and R. Johnson, John Wiley & Sons, Inc., 2000. This guide provides answers to all problems in the text and also offers addition self test problems. Several copies of this guide are available in the Library on 2-hour reserve but purchasing a copy is recommended. ** A combine package of the textbook (a) and the study guide (b) is available at the Bookstore for a substantially reduced price. You are encouraged to consider this package. Solomons is also the textbook for CHEM*3750 (Organic Chemistry II) and CHEM*3760 (Organic Chemistry III). Molecular Model Kit: A molecular model kit can be purchased from the Bookstore and will be used in one of the experiment in the Lab. It is very useful to those who have difficulty with stereochemistry. Laboratory: The lab manual CHEM*2700, Organic Chemistry I, Laboratory Manual, will be available for sale in the Department. Students are also required to have a Blue Lab Note book and must provide their own safety goggles (both of these may be purchased in the Department together with the lab manual). Students are also required to provide their own lab coats. A student without eye protection will not be permitted to work in the laboratory. Contact lenses are extremely hazardous in a laboratory environment and their use is prohibited in the lab. SAFETY GOGGLES MUST BE WORN AT ALL TIMES IN THE CHEM*2700 LABORATORY. ** For any problems associated with the lab please contact the lab coordinator Dr. Albert Woon-Fat, SC3114 (Phone: ext.53094), or Ms. Bonnie Lasby, SC2517 (Phone: ext.53805) if Dr. Woon-Fat is not available. ** Organic Chemistry I lab location: SC2111/2112. ** Students must complete at least 60% of the laboratory work to receive a grade for the course. ** The Organic Chem Lab Survival Manual by J. W. Zubrick, contains helpful hints on a variety of techniques and apparatus employed in the organic chemistry laboratory. It is available in the Library on 2-hour reserve. **IMPORTANT NOTE: Students can only get lab exemptions if the course was taken within the past 12 months. Any student who would like to get lab exemption must get approval from me and the lab coordinator within the first week of the semester. ii

Course Outline and Reading Assignments: On the following pages (iv-vii) is a detailed outline of the course. The reading assignments in the Solomons textbook will provide a different and more detailed perspective of the course material. The number of lectures allocated for each topic is approximate. Problem assignments are attached at the end of each Part of the lecture notes and answers for the assignments will be posted on the course web page. Mark Distribution: The final grade will be obtained as follows: On-line Quizzes ( open book ): 10% (see below for due dates) Lab Grade: 25% 1 st Midterm Examination: 15% (date: February 10, 2007, Chapters 1-3) 2 nd Midterm Examination: 20% (date: March 21, 2007, Chapters 1-6) Final Examination: 30% (date: April 19, 2007, Chapters 1-10) Online Quizzes Due Dates: **Online registration January 15, 2007 (Monday) *(Online quizzes must be Online Quiz 1 January 24, 2007 (Wednesday) submitted online electronically Online Quiz 2 February 2, 2007 (Friday) by 5 pm on the Due Dates) Online Quiz 3 February 28, 2007 (Wednesday) Online Quiz 4 March 14, 2007 (Wednesday) Online Quiz 5 April 4, 2007 (Wednesday) **Examination dates, time and location: 1 st Midterm Exam.: Saturday, February 10, 2007, 4:00 pm 5:30 pm, MACN 105 & 113. 2 nd Midterm Exam.: Saturday, March 24, 2007, 4:00 pm 5:30 pm, MACN 105 & 113. Final Exam: Thurs., April 19, 2007, 8:30 am 10:30 am, Location: TBA. **Only valid excuses on medical or compassionate grounds will prevent a grade of zero for a missed examination. Midterm papers may be submitted to the instructor for correction of grading errors within 5 days of the return of the graded papers. Only papers written in ink may be submitted for re-grading. iii

CHEM*2700 ORGANIC CHEMISTRY I Course Outline Part I: Introduction (3 lectures) Reading Assignments: Solomons Chapter 1 (Sections 1.4-1.8, 1.12-1.14) Chapter 2 (Sections 2.2-2.14) Chapter 3 (Sections 3.2-3.7, 3.10, 3.12) Topics: Bonding & Hybridization Octet Rule, Hybridization, Bond Length & Bond Strength, Polar Bonds & Polar Molecules Functional Groups Alkanes, Alkenes, Alkynes, Benzene & Aromatics, Alkyl Halides, Alcohols, Ethers, Aldehydes & Ketones, Carboxylic Acids & Derivatives, Amines Resonance Acidity & Basicity Part II: Nomenclature, Isomerism & Stereochemistry (4 lectures) Reading Assignments: Solomons Chapter 4 (Sections 4.1-4.6, 4.8-4.9) Chapter 5 (Sections 5.1-5.2, 5.5-5.8, 5.11-5.14) Chapter 7 (Sections 7.1-7.2) Chapter 11 (Section 11.1), Chapter 14 (Section 14.2) Chapter 16 (Section 16.2), Chapter 18 (Section 18.2) Topics: Nomenclature of Organic Compounds Alkanes, Alkenes & Alkynes, Alkyl Halides, Ethers, Benzene & Aromatics, Alcohols, Aldehydes & Ketones, Carboxylic Acids & Derivatives, Priorities of Functional Groups in IUPAC System Isomerism Chain Isomerism, Position Isomerism, Functional Group Isomerism, Tautomerism, Stereoisomerism Stereochemistry Newman Projection, conformers, Conformation Analysis of Butane, Conformations of Cyclohexanes, Stereochemistry of Double Bonds, Chiral Molecules iv

Part III: Nucleophilic Substitutions & Elimination Reactions (5 lectures) Reading Assignments: Solomons Chapter 6 (Sections 6.3-6.20) Topics: S N 2 Reactions Kinetics, Mechanism, Free Energy Diagram, Stereochemistry, Steric Effect of the Substrate, Reactivity of the Nucleophile, Reactivity of the Leaving Group, Effect of Solvent S N 1 Reactions Mechanism, Kinetics, Free Energy Diagram, Order of Reactivity of the Substrates, Stereochemistry, Reactivity of the Nucleophile, Reactivity of the Leaving Group, Effect of Solvent, Rearrangement of Carbocations Acidity & Basicity S N 1 vs S N 2 E 2 Eliminations Mechanism, Regiochemistry E 1 Eliminations Nucleophilic Substitution vs Elimination Part IV: Electrophilic Addition Reactions of Alkenes & Alkynes (4 lectures) Reading Assignments: Solomons Chapter 8 (Sections 8.1-8.10, 8.12-8.13) Chapter 11 (Sections 11.5-11.7, 11.17) Topics: Electrophilic Addition of Alkenes Markovnikov s Rule, Addition of Hydrogen Halides, Acid-Catalyzed Hydration, Halogenation, Halohydrin Formation, Electrophilic Epoxidation, Cyclopropanation, Dihydroxylation, Oxymercuration, Hydroboration Electrophilic Addition of Alkynes Addition of Hydrogen Halides, Halogenation, Mercury (II)-Catalyzed Hydration, Hydroboration-Oxidation v

Part V: Radical Reactions (1 lecture) Reading Assignments: Solomons Chapter 10 (Sections 10.1-10.10) Topics: Radicals Heterolytic & Homolytic Bond Cleavage, Geometry of Alkyl Radicals, Relative Stability Halogenation of Alkanes Mechanism, Halogenation of Higher Alkanes Anti-Markovnikov Addition of HBr to Alkenes Radical Polymerization of Alkenes Part VI: Electrophilic Aromatic Substitutions (3 lectures) Reading Assignments: Solomons Chapter 14 (Sections 14.1-14.6) Chapter 15 (Sections 15.1-15.8, 15.10-15.11) Topics: Benzene & Aromaticity Substituted Benzene Electrophilic Aromatic Substitutions of Benzene Mechanism, Halogenation, Nitration, Sulfonation, Friedel-Crafts Alkylation, Friedel-Crafts Acylation Electrophilic Aromatic Substitutions of Mono-Substituted Benzene Classification of Different Substituents, Reactivity, Regiochemistry Electrophilic Aromatic Substitutions of Di-Substituted Benzene Part VII: Nucleophilic Addition Reactions of Carbonyl Compounds (2 lectures) Reading Assignments: Solomons Chapter 12 (Sections 12.3, 12.6B, 12.7A, 12.8) Chapter 16 (Sections 16.6-16.11) Topics: Addition of Hydride Addition of Grignard Reagents Addition of Water and Alcohols Hydration, Acetal & Ketal Addition of Primary Amines and Hydrazines Addition of HCN vi

Part VIII: Nucleophilic Acyl Substitution Reactions (2 lectures) Reading Assignments: Solomons Chapter 18 (Sections 18.1-18.2H, 18.4-18.8F) Topics: Relative Reactivity of Carboxylic Acid Derivatives Nucleophilic Acyl Substitution Reactions of Carboxylic Acids, Acid Chlorides, Acid Anhydrides, Esters, Amdies, Saponification, Transesterification, Aminolysis Polyesters & Polyamides Part IX: Functional Groups Interconversions (2 lectures) Topics: New Reactions and New Techniques in Functional Groups Interconversions Hydrogenation, Clemmensen Ketone Reduction, Lindlar Catalyst, Dissolving Metal Reduction, Dehalogenation, Oxidation Cleavage of Alkenes, Ozonolysis, Dehydrohalogenation, Epoxide Ring Opening, Jones Oxidation, PCC Oxidation, Hypochlorite Oxidation, Oxidation Cleavage of 1,2-Diols, Williamson Ether Synthesis, Hydrolysis of Nitriles, Dehydration of Amides. Part X: Summary of Organic Reactions Topics: Review and Summary of All the Reactions Covered From Parts I-IX Preparation of Each Functional Groups by Different Methods vii

CHEM*2700 Lectures and Exams Schedules Week Date Lecture Wee Date Lecture k Jan. 8 (M) Part I (1) Feb. 26 (M) Part IV (4) 1 10 (W) Part I (2) 7 28 (W) Part V 12 (F) Part I (3) Mar. 2 (F) Part VI (1) 15 (M) Part II (1) 5 (M) Part VI (2) 2 17 (W) Part II (2) 8 7 (W) Part VI (3) 19 (F) Part II (3) 9 (F) Part VII (1) 22 (M) Part II (4) 12 (M) Part VII (2) 3 24 (W) Part III (1) 9 14 (W) Part VIII (1) 26 (F) Part III (2) 16 (F) Part VIII (2) 29 (M) Part III (3) 19 (M) Revision (1) 4 31 (W) Part III (4) 21 (W) Revision (2) 10 Feb. 2 (F) Part III (5) 23 (F) Revision (3) 5 (M) Revision (1) 24 (Sat.) 2 nd Midterm Exam 5 7 (W) Revision (2) 26 (M) Part IX (1) 9 (F) Revision (3) 11 28 (W) Part IX (2) 10 (Sat.) 1 st Midterm Exam 30 (F) Revision (1) 12 (M) Part IV (1) Apr. 2 (M) Revision (2) 6 14 (W) Part IV (2) 12 4 (W) Revision (3) 16 (F) Part IV (3) Winter Break: February 19-23 Final Exam: April 19, 2007 (Thursday), 8:30-10:30 am (Location: TBA) January 9 (Friday): 40 th class day, last day to drop the course. 1 st Midterm Exam.: Saturday, February 10, 2007, 4:00 pm 5:30 pm, MACN 105 & 113. 2 nd Midterm Exam.: Saturday, March 24, 2007, 4:00 pm 5:30 pm, MACN 105 & 113. Last Lecture. viii

CHEM*2700 Laboratory Schedule Week Dates Experiment 1 January 8 12 Check In Expt. 1 Thin Layer Chromatography (TLC) 2 January 15 19 Expt. 2 Isolation of Eugenol 3 January 22 26 Expt. 3 Molecular Modeling &Computational Chemistry 4 January 29 Feb. 2 Expt. 4 Nucleophilic Substitution of 2-Butanol (part 1) 5 February 5 9 Expt. 4 Nucleophilic Substitution of 2-Butanol (part 2) 6 February 12 16 Expt. 5 Kinetics Study of the Hydrolysis of t-butyl Chloride (and Lab Quiz.) 7 February 19 23 Winter Break (no lab scheduled) 8 February 26 March 2 Expt. 6 Electrophilic Addition: Bromination of Stilbene 9 March 5 9 Expt. 7 Nitration of Methyl Benzoate 10 March 13 16 Expt. 8 Preparation of Triphenylmethanol 11 March 19 23 Expt. 9 Oxidation of 2-Octanol 12 March 26 30 Check Out and Lab Final ix