CHEM 2220 Introductory Organic Chemistry II: Reactivity and Synthesis Course Outline 2017R Session (Winter 2017)

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1 University of Manitoba Department of Chemistry CHEM 2220 Introductory Organic Chemistry II: Reactivity and Synthesis Course Outline 2017R Session (Winter 2017) Dr. Philip G. Hultin 554 Parker Dr. Horace Luong 264B Parker Required Materials: The CHEM 2220 UMLearn site provides complete course content, policy and expectations. Additional supporting information is available at the following website: home.cc.umanitoba.ca/~hultin/chem2220 David R. Klein Organic Chemistry, 2 nd Ed. (same book as for CHEM 2210) David R. Klein Organic Chemistry as a Second Language First Semester Topics 3 rd ed. David R. Klein Organic Chemistry as a Second Language Second Semester Topics 3 rd ed. CHEM 2220 Laboratory Manual (2017 edition) Suggested Supplement: William C. Groutas Organic Reaction Mechanisms: Selected Problems and Solutions. Course Philosophy CHEM 2220 will emphasize the underlying principles of organic reactivity. Examples are given to illustrate these principles, not necessarily because the example itself is intrinsically important. Successful studying will combine learning the principles with practice applying them to solve problems. The course s goal is twofold: First, to provide a sound basis of both fact and principle in organic chemistry; and Second, to teach logical analysis and problem solving. For most of you, the second goal may be most important. All career paths require logical thinking, and you can learn it in any subject if you approach the subject rigorously. This alone is worth the effort that we demand of students, and you will be repaid handsomely for your efforts in years to come. Lectures will not cover everything in the curriculum, but will focus on the central ideas of each topic. Students should expect questions on anything in the assigned textbook readings in tests and exams. Getting Help Dr. Hultin s Office Hours: I am available most days 8:30 am to about 4:30 pm when not actually teaching, attending a meeting, eating lunch or getting coffee. I welcome short questions whenever I am in my office and if I am busy when you come by I will make an appointment with you for later. If you want to see me at a particular time or if you have a lot to talk about, make an appointment (by please). I am happy to see you either singly or in groups. Don t be shy. Dr. Luong s Office Hours: check UMLearn and the bulletin boards outside the laboratories. Supplementary Instruction: Weekly group tutorials run by students who have previously done well in CHEM Details are available on UMLearn and at: There are discussion forums on the UMLearn sites for both the lecture and the laboratory portions of CHEM Marking Scheme: Midterm Test (15%) TAKE-HOME: Wed March 1 Fri March Final Exam (50%) Scheduled in the April 2017 Exam Period. Laboratory (21%) A minimum of 12.6/21 on the laboratory is required to pass the course. All students (INCLUDING THOSE WITH LAB Lab Exam (14%) EXEMPTIONS) must also write the Lab Exam. A total of less than 40% will result in a grade of F. Marks between 40% and 100% will be graded from D to A+. See UMLearn for details of how numerical scores will be converted to letter grades. Midterm: The midterm will be based on lecture and textbook material plus a general understanding of organic chemistry including material originally presented in CHEM The midterm is take-home this year but it will follow a format similar to previous midterms, and similar to the final examination. You are STRONGLY advised to treat this midterm as a closed-book two-hour test even though it is take-home. It is essential that you develop your problem-solving skills in the same environment that you will face on the final exam. The midterm papers will be managed through UMLearn. The test will be available between 5 pm Wednesday March 1 and 5 pm Friday March 3. All students must have uploaded their completed tests by the end of that time window. Full procedural details for the test will be published closer to March 1. Final Examination: The final examination is cumulative. Problems may be drawn from any portion of the CHEM 2220 curriculum, and may also include material initially presented in CHEM 2210.

2 The final must be written by all students. Failure to write the regularly scheduled examination without a valid medical certificate or compassionate reason (e.g., death of an immediate family member) will result in a mark of zero on the examination and a grade of F NP on the course. Deferral can only be granted by the student s home faculty. The deferred final examination will be written in May 2017 (the next deferred exam writing will be in Summer Session 2017). Notes: The midterm, laboratory exam and final will be free response. There will be no multiple-choice questions in this course. The midterm and the final deal directly with course topics and concepts but specific molecules and reactions may differ. You must understand the material well enough to recognize its applicability in new situations. A spectroscopic information sheet will be provided with the midterm and the final. You can preview this summary on the website. For the final exam only, you may bring one 8.5 x 11 sheet of hand-written notes (both sides may be used) into the exam room. You may put anything you wish on this sheet, provided that it is hand-written. There is no minimum mark on the final exam required to pass the course. Laboratory: Laboratory attendance is compulsory. The laboratory sessions begin in the week of Monday January 30 th. All students registered in the laboratory must buy a CHEM 2220 laboratory manual (2017 Edition). The laboratories are in Rooms of the Parker Building. Your room and locker number will be assigned by your name on the bulletin board just across from the laboratories. A lab coat, eye protection and appropriate footwear (consult the laboratory manual for what is deemed "inappropriate") must be worn in the laboratory at all times. The laboratory program in CHEM 2220 consists of an experimental part (with written reports) and an exam. The experimental portion of the lab program accounts for 21% and the laboratory exam counts for 14% of your total mark in CHEM All students (INCLUDING THOSE WITH EXEMPTIONS) must write the lab exam. In order to obtain a passing grade in CHEM 2220, you must earn a minimum of 12.6/21 on the experimental part and you must have written the lab exam, regardless of your grade on the balance of the course work. Laboratory Exemptions: Laboratory exemptions may be granted to students who are re-taking CHEM 2220 after previously completing the course with an unsatisfactory final grade. To qualify for a laboratory exemption the student must have completed the laboratory portion of the course not more than two years preceding. Students re-taking CHEM 2220 may apply for a laboratory exemption using an online form accessed from the Department of Chemistry website ( Students with a laboratory exemption must register in the A11 or A12 sections. Please note that the previously obtained lab marks will be used in the computation of your mark in this course. Practice Problems You will only succeed in this course if you do practice problems diligently. This is the best studying you can do! Work through all the SkillBuilder and Conceptual Checkpoint exercises in the assigned sections of Klein s Organic Chemistry. UMLearn lists suggested end-of-chapter problems from Klein, as well as mechanism problems from Groutas. Practice problems involving spectroscopy are also available through UMLearn. Academic Honesty: We take academic honesty very seriously and we expect the same of you. Any potential infractions of the University s policies on academic honesty will be referred immediately to the Faculty of Science for action. If you are not sure what is expected in terms of academic honesty, contact us or consult the University Calendar. Copying another student s work or copying material from any published source without correct citation of the source is plagiarism. Communicating with any person other than an invigilator during a test or exam, bringing unauthorized materials into a test or exam, or accessing such materials electronically are all considered cheating. Plagiarism and other forms of cheating are prohibited. The full definitions of plagiarism and other forms of cheating and the possible penalties associated with them are outlined on the following website:

3 CHEM 2220 SYLLABUS INTRODUCTION The required textbook package consists of David Klein s Organic Chemistry plus his Organic Chemistry as a Second Language (parts 1 and 2). These will be referred to as OC, SL1 and SL2 respectively. There is also the recommended supplementary book by William Groutas, Organic Reaction Mechanisms, Selected Problems and Solutions which some of you may choose to purchase. For largely historical reasons, most organic chemistry textbooks including Klein s OC are organized around the chemistry of the functional groups. This way of presenting organic chemistry unfortunately tends to obscure the common features of reactions, making it seem that (for example) the reaction of an alcohol with an alkyl halide is different from the reaction of an amine with an alkyl halide, when in fact they are almost exactly identical. CHEM 2220 is built around the idea of reaction mechanisms. Whereas chemists have discovered many thousands of reactions, only twelve common mechanistic motifs and eight less-common pathways can explain the vast majority of these reactions. We will identify these simple building blocks and show you how they make it much easier to learn and understand organic chemistry. OC, SL1 and SL2 present the reaction mechanisms in a very clear way, which is why we have chosen to use these books, but because OC follows the traditional chapter organization, in order to keep the reaction mechanisms unified we will be jumping around a bit in the textbook. Students are responsible for learning and understanding all material in the chapter sections listed and questions based on anything in these sections, presented in lecture, or in the end-of-chapter practice problems may appear on tests or the final exam. Note that test and exam questions probably will not be exactly the same as those you have seen for practice, but all questions will be about chemistry you have learned. Part of your task is to learn to recognize what is going on in a new situation, so do not be fooled by new molecules.

4 TOPIC OC THIRD EDITION CHAPTER SECTIONS SL CHAPTERS Part 1: Addition Reactions of Alkenes (mostly) Ionic addition mechanism Ionic addition to alkynes Hydration of nitriles (page 936, mechanism 20.14) 6.11 Cationic rearrangements (also see pp ) 8.6 Oxymercuration-demercuration 13.5 Ethers by mercuration (page 566) 8.7 Hydroboration/oxidation 8.9 Dihalogenation and halohydrin formation 9.8 Halogenation of alkynes 16.1, 16.2, 16.4, 16.5 Electrophilic addition reactions of dienes Epoxidation of alkenes 8.8 Catalyzed addition of dihydrogen 8.11 syn Dihydroxylation 8.12 Oxidative cleavage SL1 CH 11 (all) Part 2: Aromatic Substitution Reactions and Related Chemistry Reactions and applications of nitrobenzenes 17.6 Reactions at the benzylic position Nucleophilic substitution of aromatic rings SL2 CH 3 (all) SL2 CH SL2 CH 4 Part 3: Pericyclic and Electrocyclic Reactions 16.3 Molecular orbital theory 16.6 Pericyclic reactions (general features) Diels-Alder reactions and cycloadditions 16.9 Electrocyclic reactions Sigmatropic rearrangements These reactions are not included in SL. Part 4: Nucleophilic Additions to Polarized Multiple Bonds All of Chapters 19 and 20. Lectures will cover all of this but in a SL2 CH 5 and CH 6 (all) different order of topics than the book does Reductive amination of carbonyls SL2 CH Reduction of carbonyls to alcohols Part 5: Enols and Enolates All of Chapter 21 SL2 CH 7 (all) Updated January 2018.

5 PRACTICE PROBLEMS Reading your textbook and notes is only the beginning of studying. The real studying consists of doing practice problems. Then, do some more practice problems. Finally, try some additional practice problems. Just for a change, you could also do some practice questions, mix ed with some review problems and sample problems. Did we mention how important it is to do practice problems? You should work through ALL the Conceptual Checkpoint problems in the assigned portions of the OC text. Likewise, do the Skill Builder problems. The Skill Builders work you through the problem-solving strategy appropriate for a particular type of question, and then follow it up with several questions of that type that you can do. This kind of practice is very important for success on tests and exams! Pay attention to the Review of Concepts and Terminology and the Skill Builder Review at the end of each chapter. In addition, there are problems at the ends of the chapters in OC, and the book by William Groutas that is a suggested supplement has many mechanism problems relevant to portions of this course. The table below lists some suggested problems from OC and Groutas that will be helpful. You don t have to do all of these, but as we mentioned, doing problems is the best studying you can do in organic chemistry so we are giving you lots of opportunity! One final note about practice problems. If you do them purely as mechanical exercises, they probably won t teach you very much. It is vital that you look at each one as a learning opportunity. After completing a problem incorrectly, you all know that you need to go back to the text or notes to figure out where you went wrong, what fact you forgot or what feature you overlooked. But it is equally important to take a moment over the problems you got right, to ask why is this correct and what led me to arrive at this correct answer. These questions will focus your attention on the meaning of the problem, and re-inforce your memory of the successful problem-solving strategy you used. Topic Suggested Klein OC 3 rd Edition end-of-chapter problems Suggested Groutas Problems Part 1: Addition Reactions of Alkenes (mostly) , 8.46, 8.47, , , , , 1-8, 11, 13, 17-19, 28-30, 32, , 9.57, 9.65, 13.42, 13.58, Part 2: Aromatic Substitution Reactions and Related , , 18.82, 18.83, 17.42, 17.53, 22.50, 20, 22, 23, 24, 25, 26, 27, 31, 33, 59, 100 Chemistry 22.62, Part 3: Pericyclic and Electrocyclic Reactions , , , , , 16.73, Groutas has no relevant problems for this unit , Part 4: Reactions of Nucleophiles with Polarized Multiple Bonds , , 19.67, 19.69, 19.73, , 19.79, 19.80, 19.83, , 12.42, 12.46, , 22.49, 48, 51, 52, 55, 65, 68, 69, 71, 73-76, 80, 83, 86, 89, 91, 93, , 22.58, , , , 20.59, 20.61, , Part 5: Reactions of Enols and Enolates , , 42, 43, 45, 53, 54, 57, 58, 61, 62, 63, 64, 72, 78, 79, 82, 85, 87, 88, 95, 97, 98 Updated January 2018