CHEM*2700 ORGANIC CHEMISTRY I (Spring/Summer Semester 2010) Information Sheet and Course Outline 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 4:30 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: May 14 August 9, 2010, Mondays, Wednesdays & Fridays. 12:30 pm 1:20 pm, MACK 117 (MacKinnon Building). Tutorials/Help Sessions (optional): Every Friday, 1:30 pm 2:20 pm. Location: MACK 117. 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, 9 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, 9 th by T.W.G. Solomons, C. B. Fryhle and R. Johnson, John Wiley & Sons, Inc. This guide provides answers to all problems in the text and also offers addition self test problems. ** A combine package of the textbook and the study guide, as well as two molecular model kits, and the Wiley Plus Access Code, 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). (c) If you already have an older edition of the Solomons textbook (7 th or 8 th edition), I do not recommend you to purchase the new 9 th edition as there is only very little difference between these three editions. However, you will need to purchase the Wiley Plus Access Code separately from the Bookstore in order to do the online quizzes. 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. Robert Reed, SC3114 (Phone: ext.53805, E-mail: rwreed@uoguelph.ca). ** 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 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. Communications: The primary communication between the students and the lecturer concerning issues with the course is through discussions during the lectures (e.g. exams and quizzes coverage, due dates for quizzes, and other announcements related to the course). Although most of the time, announcements and information related to the course will also be made through the course website and/or e-mails to the students, students are expected to attend EVERY lecture. If you miss a lecture, make sure you talk to your classmate to see if there is any important announcement during the lecture that you missed. Electronic Recording of classes: The electronic recording of classes is expressly forbidden without the prior consent of the instructor. This prohibition extends to all components of the course, including, but not limited to, lectures, seminars, and lab instruction whether conducted by the instructor or a seminar leader or demonstrator, or other designated person. When recordings are permitted they are solely for the use of the authorized student and may not be reproduced, or transmitted to others, without the express written consent of the instructor. Mark Distribution: The final grade will be obtained as follows: On-line Quizzes ( open book ): 10% (five quizzes in total) Lab Grade: 25% 1 st Midterm Examination: 15% (date: Saturday, June 19, 2010, Parts 1-3) 2 nd Midterm Examination: 20% (date: Saturday, July 17, 2010, Parts 1-6) Final Examination: 30% (date: Tuesday, August 17, 2010, Parts 1-10) Online Quizzes Coverage: Online registration the latest by May 21, 2010 (Friday) *(Online quizzes must be Online Quiz 1 (Parts I-II) Due dates: TBA submitted online electronically Online Quiz 2 (Parts I-III) Due dates: TBA by 5 pm on the Due Dates) Online Quiz 3 (Parts IV-V) Due dates: TBA Online Quiz 4 (Parts IV-VI) Due dates: TBA Online Quiz 5 (Parts VII-VIII) Due dates: TBA iii
**Examination dates, time and location: 1 st Midterm Exam.: Saturday, June 19, 2010, 10:00 am 11:30 am, MACN 105 and 113. 2 nd Midterm Exam.: Saturday, July 17, 2010, 10:00 am 11:30 am, MACN 105 and 113. Final Exam: Tuesday, August 17, 2010, 11:30 am 1:30 pm, 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. iv
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 2.2-2.15) 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, 4.12-4.14) Chapter 5 (Sections 5.1-5.15) 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 v
Part III: Nucleophilic Substitutions & Elimination Reactions (5 lectures) Reading Assignments: Solomons Chapter 6 (Sections 6.3-6.19) Chapter 7 (Sections 7.3, 7.5-7.8) 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 8.1-8.16, 8.18-8.19, 8.21) Chapter 11 (Section 11.13) 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 vi
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 (3 lectures) Reading Assignments: Solomons Chapter 12 (Sections 12.3, 12.6-12.8) 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 vii
Part VIII: Nucleophilic Acyl Substitution Reactions (2 lectures) Reading Assignments: Solomons Chapter 18 (Sections 18.1-18.2I, 18.4-18.9) 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 viii
CHEM*2700 Lectures and Exams Schedules Week Date Lecture Week Date Lecture May 14 (F) Part I (1) June 28 (M) Part IV (4) 1 17 (M) Part I (2) 7 30 (W) Part V 19 (W) Part I (3) July 2 (F) Part VI (1) 21 (F) Part II (1) 5 (M) Part VI (2) 2 26 (W) Part II (2) 8 7 (W) Part VI (3) 28 (F) Part II (3) 9 (F) Part VII (1) 31 (M) Part II (4) 12 (M) Revision (1) 3 June 2 (W) Part III (1) 14 (W) Revision (2) 9 4 (F) Part III (2) 16 (F) Revision (3) 7 (M) Part III (3) 17 (Sat) 2 nd Midterm Exam 4 9 (W) Part III (4) 19 (M) Part VII (2) 11 (F) Part III (5) 10 21 (W) Part VII (3) 14 (M) Revision (1) 23 (F) Part VIII (1) 5 16 (W) Revision (2) 26 (M) Part VIII (2) 18 (F) Revision (3) 11 28 (W) Part IX (1) 19 (Sat) 1 st Midterm Exam 30 (F) Part IX (2) 21 (M) Part IV (1) Aug 4 (W) Revision (1) 6 23 (W) Part IV (2) 12 6 (F) Revision (2) 25 (F) Part IV (3) 9 (M) Revision (3) Final Exam: Tuesday, August 17, 2010, 11:30 am 1:30 pm, location TBA. July 9 (Friday): 40 th class day, last day to drop the course. 1 st Midterm Exam.: Saturday, June 19, 2010, 10:00 am 11:30 am, MACN 105 and 113. 2 nd Midterm Exam.: Saturday, July 17, 2010, 10:00 am 11:30 am, MACN 105 and 113. Last Lecture. ix