CHE 262 (03): Organic Chemistry II Spring 2018 Syllabus MWF 12:50-1:50 in Phillips Lecture Hall Professor: Dr. Mark V. Wilson Office: Hoyt 360 Email: wilsonmv@westminster.edu (Best way to contact me.) Phone: 724-946-7296 Office hours: M 2-3, T 10-12, or by appointment COURSE OVERVIEW Course description: A study of organic reactivity. This course details organic molecules by reactivity and emphasizes the differences between organic reactions. Specifically, organic reactions will be surveyed by type of reaction keying on the movement of electrons, molecular orbitals, and energetics. Spectroscopy is employed to monitor structural changes. Laboratory activities also probe the reactivity of molecules and explore the relationship between structure and reactivity. Mandatory texts: 1. Organic Chemistry by L.G. Wade, any edition. ISBN: 0-321-76741-8 Useful Materials: 1. Darling Models, Inc. Organic Model Kit. ISBN: 978-09648837-2-7 or 978-09648837-3-4 Course outcomes: At the end of this course, students should be able to Explain a variety of condensation reactions and their ability to rapidly construct complex molecules Explain radical reactions and their application to produce polymers Explain cross-coupling reactions used in a broad range of scientific fields Understand the stability and reactivity of aromatic compounds Understand the emerging field of enzymes as organic catalysts Design multi-step syntheses to construct molecules from simpler building blocks Develop psychomotor skills by applying material learned in the class to hands-on laboratory work Make connections between material to answer complex and multi-step problems 1
COURSE GRADING Grade distribution: Exams (4@12.5 % each): 50% Final Exam 20% Homework and quizzes: 10% Laboratory: 20% Grade range: A 93 100% B+ 87 89.9% C+ 77 79.9% D+ 67 69.9% F 0 59.9% A- 90 92.9% B 83 86.9% C 73 76.9% D 63 66.9% B 80 82.9% C 70 72.9% D 60 62.9% * These grade ranges are guaranteed minimums. Final grade ranges may, at the instructor s discretion, be moved downward. However, this should not be expected. Under extreme circumstances, improvement in the course may be used to bump up a grade, but again this should not be expected. COURSE MATERIALS AND ASSIGNMENTS Exams: Each of the four exams during the semester will cover specific unit material. The general format of the exam may include multiple choice, short answer, reactions/structures and essay. The compounding nature of chemistry requires a knowledge base; therefore, some concepts from the first semester and earlier in the course may be seen on later examinations. Final Exam: The course will conclude with a comprehensive standardized final exam. Final exam scores will be rationalized based off of national norms. That means that the score received on the final will NOT be a simple percentage of correct answers (as a normal exam), but rather will be scaled. If the final exam score received outperforms any of the four hour exams, the final exam score will replace the lowest exam score (a maximum of one exam replacement). Homework: The purpose of the homework assignments is to cultivate learning by applying concepts learned in class to new problems. Problems will be assigned on a semi-regular basis and will require you to actively apply the course material to new questions. To get the most out of your homework assignments, work on them alone first, and then work in a group. If you are struggling with ANY concepts, come by the professor s office to work the problem together with the instructor. Your homework must reflect your own work. Studying in groups is encouraged, but copying someone s homework is a violation of the College s academic integrity policy and will be penalized. Laboratory: The laboratory component of this course is designed to reinforce concepts learned in the classroom. Before the laboratory period, you will be given the laboratory experiment and you should review it prior to lab. See the laboratory syllabus for further explanations and requirements for the laboratory section of this course. 2
COURSE POLICIES Attendance: 1. Classroom attendance is expected. Under no circumstances should students expect private lectures for missed material, either excused or unexcused. In-class homework problems are not able to be turned in late. 2. The decision to excuse absences is made solely by the instructor. 3. If you foresee an absence (e.g. athletic competition, field trip) for either lab or an exam, you must notify the instructor one week prior to the absence to make alternate arrangements. No provision for makeup of labs or exams will be provided for foreseeable causes after the lab or exam had taken place. 4. Absences from lab or exams for unexpected emergencies can be accommodated. Contact the instructor within 72 hours of the end of the emergency to make arrangements. 5. Homework must be turned in on time. Late homework will be penalized at 10% per day late, in full-day increments. One minute late is the same as one day late. As it is always possible to turn in homework early or send it to class with a friend, an absence, even excused, is not a reason for late homework. See the instructor for consideration in the case of unexpected emergencies within 72 hours of the end of the emergency. Academic Integrity Policy: The Westminster undergraduate catalog states, Academic dishonesty...can take several forms, including, but not limited to, plagiarism, cheating, misrepresentation of facts or experimental results, unauthorized use of or intentional intrusion into another s computer files and/or programs, intentional damage to a computer system, and unauthorized use of library materials and privileges. Academic dishonesty will not be tolerated. The first citation of academic dishonesty will result in a grade of zero for the assignment. The second citation will result in a failing grade for the course. All citations of academic dishonesty will be reported to the Dean of the College, in accordance with policy. Available Support Services: Westminster College makes every effort to accommodate and serve students with a variety of support services. The Learning Center is a great place to get additional free tutoring, contact the director, Sally Huey at x 6700. Students with disabilities can utilize Disability Resources by contacting the director, Faith Craig at extension 7192 or 724-946-7192 from off campus. Tips on how to succeed in this class: 1. Come to the professor if you are having difficulty understanding the material. 2. Prepare for class by reading your text. 3. Review material between each class period. 4. Use multiple resources (professor, peers, text, videos, tutorials) to help you understand the material. 5. Work problems more than once and do extra problems in the textbook. 6. Work hard and work smart. Learn to learn on your own. It is OK if you don t understand everything the first time it is covered in class. 7. Don t be afraid to ask questions in class. Most likely, other students have the same question. 8. Come to the professor after your first exam if you did not earn at least a C. 3
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CHEM 262 Lecture Schedule (Suggested readings/problems for the 8 th edition of the book) Jan. 17: Review: Reactions of Carbonyls- Grignards, Oxidation, and Reductions. Jan. 19: Review: Reactions of Carbonyls- Esterification, Hydrolysis, Amidation Suggested Problems: Review Worksheet Jan. 22: Enols and Enolates: Formation and Behavior Suggested Reading: Sections 22-1 to 22-4 (pages 1045-1054) Suggested Problems: 60, 61 Jan. 24: Enols and Enolates: Alkylation and Halogenation Suggested Reading: Sections 22-5 to 22-6 (pages 1054-1060) Suggested Problems: 68a-c, 68e-h, 69a-b Jan. 26: Enols and Enolates: Aldol Condensation Suggested Reading: Sections 22-7 to 22-8 (pages 1060-1065) Suggested Problems: 62a, 68a Jan. 29: Enols and Enolates: Cross Aldols Suggested Reading: Sections 22-9 to 22-11 (pages 1065-1070) Suggested Problems: 62, Enolate Worksheet (Part 1) Jan. 31: Enols and Enolates: Claisen and Cross-Claisen Condensations Suggested Reading: Sections 22-12 to 22-14 (pages 1070-1077) Suggested Problems: 63, 64 Feb 2: Enols and Enolates: Claisen and Cross-Claisen Condensations Suggested Reading: Sections 22-15 to 22-17 (pages 1077 to 1085) Suggested Problems: 70-73, Enolate Worksheet (Part 2) Feb 5: Enols and Enolates: Michael Additions Suggested Reading: Sections 22-18 to 22-19 (pages 1085-1091) Suggested Problems: 66-67 Feb 7: Enols and Enolates: Wittig Reaction and Its Variations Suggested Reading: Sections 18-12 (pages 843-847) Suggested Problems: Enolate Worksheet (Part 3) Feb 9: Catch-up and Review Day Feb 12: Exam One 1
Feb 14: Radicals: Halogenation Suggested Reading: Sections 4-2 to 4-3 (pages 132-137); Sections 4-13 (pages 151-157) Suggested Problems: 41-46 Feb 16: Radicals: Halogenation continued Suggested Reading: Section 6-6 (pages 226-230), Section 8-3B (pages 334-337); Section 17-15B (pages 799-800) Feb 19: Radicals: Polymerization of Alkenes Suggested Reading: Section 18-16 (pages 369 to 373); Section 26-2a (pages 1223-1226) Suggested Problems: Radical Worksheet Feb 21: Cross-Coupling: General Idea and Transmetallation Suggested Reading: Cross-Coupling Handout Feb 23: Cross-Coupling: Gillman and Stille Suggested Reading: Cross-Coupling Handout, Section 17-13 (pages 790-792) Suggested Problems: In Text Problems 26-27 Feb 26: Cross-Coupling: Suzuki and Heck Mechanistic Variations Suggested Reading: Section 17-13 (pages 792-796) Suggested Problems: Cross-Coupling Worksheet, 49 Feb 28: Catch-up and Review Day Mar 2: Exam Two Mar 3-11: Spring Break Mar 12: Mar 14: Review: Electrophilic Addition Review: Electrophilic Addition Mar 16: Reactions of Benzene: Aromaticity Suggested Reading: Sections 16-1 to 16-9 (pages 713-735) Suggested Problems: 30, 32, 34, 35, 36 Mar 19: Reactions of Benzene: Regioselective Groups and Electrophilic Aromatic Substitution Mechanism Suggested Reading: Sections 16-13 (pages 740-742), 17-1 (pages 756-757) Mar 21: Reactions of Benzene: Halogenation, Nitration, and Sulfonation Suggested Reading: Section 17-2 to 17-9 (page 758-777) 2
Mar. 23: Reactions of Benzene: Friedel-Crafts Alkylation and Acylation Suggested Reading: Section 17-10 to 17-11(pages 777-785) Mar. 26: Reactions of Benzene: Modification of Substitution Products Suggested Reading: Section 17-11 (pages 784-787) Suggested Problems: Aromatic Substitution Worksheet (Part 1) Mar 28: Reactions of Benzene: SNAr- General Mechanisms and Regioselectivity Suggested Reading: Section 17-12 (pages 786-790) Apr 3: Reactions of Benzene: The Benzyne Mechanism Suggested Reading: Section 17-12 (pages 786-790) Apr 4: Reactions of Benzene: Putting It Together to Make Substituted Benzenes Suggested Problems: Aromatic Substitution Worksheet (Part 2), 46-48, 51, 54 Apr. 6: Review Day and Catch-Up Apr. 9: Exam Three Apr. 11: Pericyclic Reactions: Introduction to Conjugated Pi Systems Suggested Reading: Section 15-3 (pages 669-673), Section 15-11 (pages 684-692) Apr 13: Pericyclic Reactions: Diels Alder and Inverse Demand Diels Alder Suggested Reading: 15-12A (pages 692-694) Apr. 16: Pericyclic Reactions: The Forbidden [2+2] and Huisgen s [1,3] Cycloaddition Suggested Reading: 15-12B (pages 694-695) Apr. 20: Pericyclic Reactions: Alkene Metathesis with a [2+2] intermediate- Schrock and Grubbs Catalysts Suggested Reading: Section 8-17 (pages 373-376) Suggested Problems: Pericyclic Reaction Worksheet Apr. 23: Enzymes as Organic Catalysts: Protein Structure and the Lock and Key Model Suggested Reading: Sections 24-1 to 24-4 (pages 1155-1164), 24-8 (1173-1177), 24-12 to 24-14 (pages 1190-1195) Apr. 25: Enzymes as Organic Catalysts: Useful Organic Transformations Apr. 27: Enzymes as Organic Catalysts: Kinetic Resolution Apr. 30: Review and Catch-up Day May 2: Exam Four 3
May 4: May 7: Final Exam Review FINAL 4