FA20 CHEM UN2443 Syllabus Phillips PDF

Preview

Summary

organic chemistry syllabus...

Description

CHEMUN 2443, Fall 2020 Organic Chemistry I Lecture Monday & Wednesday 11:40 p.m. to 12:55 p.m. on Zoom (Links will be posted on Canvas) Registration in one of the CHEM UN2445 Recitation sections is also required Instructor: Dr. Karen E. S. Phillips; email – [email protected] Zoom Office Hours: Mondays, 2:30 to 3:30 p.m.; Wednesdays, 1:30 to 2:30 p.m.; Fridays 12:00 to 1:00 p.m. Graduate Teaching Assistants: Adam Wang - [email protected] Caroline Dudley - [email protected] Jesse Gray - [email protected] CHAPTER NOTES AND OTHER LECTURE RESOURCES PDF files summarizing each of the chapters covered this semester will be provided on the Canvas site for this class. These chapter summaries will be grouped into four Units, with each Unit corresponding to the material relevant to each of the four exams for this semester, and can be accessed through Modules or Files. Several versions of past exams and answer keys for each of the first three Unit exams are also posted on Canvas. It is recommended that students read each of the chapter summaries before that material is covered in class. This will make it easier to follow along with the lectures during the class period. PowerPoint files with the images and tables used to illustrate concepts in class will also be posted on Canvas. It is recommended that you have these PowerPoint files available to you during the class period, either as printed or electronic documents that you can write on or highlight. As we go through the semester, supplemental lectures will also be posted to help reinforce ideas that might benefit from being illustrated and described more slowly. These supplemental lectures will usually be in the form of written notes accompanied by audio narration. All students are expected to be familiar with all course materials provided, even if they are not explicitly discussed during the class period. TEXTBOOK: A textbook is not required for this class. However, the course will follow the sequence of Organic Chemistry, by John McMurry, 9th Edition, 2016; Brooks/Cole Cengage Learning. Custom bundled versions of this textbook along with online access to the accompanying study guide and solutions manual by Susan McMurry, as well as OWLv2 practice problems are available in the Columbia University Bookstore or from the Cengage Microsite: - http://services.cengagebrain.com/course/site.html?id=4526056. The textbook is only for use as a reference if a student needs one. Students are not required to do any of the problems from the textbook and they will not be discussed in class. In some parts of the semester, the chapters may be covered in a different order from that presented in the text. Some topics from different chapters might also be combined in different ways in order to present the material in a more logical or coherent order. The specific sections covered are shown in the table at the end of this document, which summarizes the lecture content as well as the schedule of exams for the semester. Other books that students have found useful are Organic Chemistry as a Second Language by David Klein, Pushing Electrons by Daniel Weeks, and Organic Chemistry by Solomons and Fryhle (Wiley). QUESTIONS ABOUT MATERIAL COVERER IN THE COURSE Discussion Boards have been organized by Unit within Modules on Canvas for questions about the course content. Students can also get valuable practice by attempting to answer questions posed by your classmates. TAs, Workshop Leaders and by Dr. Phillips will also provide answers, and Dr. Phillips will also check the answers given by others. Please use the Discussion Boards as resources for this purpose rather than sending individual emails. Many students might be confused by similar concepts and this allows everyone to learn most efficiently from the questions and the answers provided without repetition. There is no such thing as a silly question when everyone is learning what is essentially a new language, so please do not hesitate to ask about anything at all.

RECITATION WORKSHOPS: The Recitations associated with this section of the Organic Chemistry Lectures will function as one component of our weekly problem-solving Workshops. Attendance at these Recitation Workshop sessions is mandatory. During each Recitation session, you will discuss and solve a set of relevant Workshop questions, designed by me, Dr. Phillips, to prepare you for my exams. You will work in small groups to solve the problems, guided by TAs and Workshop Leaders. At the beginning of the next Lecture period, representatives from the different discussion groups will present their solution to one of the problems. Group representatives will show their solution to others by sharing your computer, tablet screen or written solution on Zoom, while describing your problem-solving strategy. Other students in attendance are then encouraged to evaluate the solutions and the explanations for them. Representatives from other groups can provide alternative solutions as necessary until there is consensus that the solution and explanation are correct. These conversations are guided by me, Dr. Phillips. In that way, all students will be able to come away from the Workshops knowing how to solve each problem and benefitting from my perspectives on what was important about each of the questions and the thought process behind them. Since answer keys for the Workshop questions will not be posted, this wholeclass presentation and discussion is a critical component of the Workshop process and preparation for exams. MOLECULAR MODEL KITS: Success in Organic Chemistry depends, in part, on an ability to visualize molecules in three dimension and interpret or convert spatial relationships into a format that can be illustrated on paper. Some students are naturally more adept at this than others, and some students actually find this quite challenging. Working with a molecular model kit can help with this, making it possible for you to train yourself to see and represent structures in three-dimensional form. There are a variety of model kits available and some are better for visualizing some things than others. I have posted links to a few different types of model kits on Canvas. From time to time, I will use digital models to illustrate structural features of molecules during lectures. The software used is called Spartan Student, and it is developed and sold by a company called Wavefunction. Student download of the software runs about $50, but does not include the structures that I show in class. ChemSpider, which is one of the sites include under Useful External Links, will also show 3-dimensional models of structures. Having access to molecular models seems to be most helpful for the first half of the semester, when the first five chapters are covered. It is best, therefore, to consider quite early whether you will need to get a model kit of your own. EXAMS, QUIZZES AND GRADES: Your grade for the semester will be computed out of a possible total of 450 points that you can earn from your scores on in-class exams, a comprehensive final exam, and Recitation homework assignments. There will be three exams held during regular class sessions that are each worth 100 points (one Unit). There will also be a three-hour comprehensive final exam worth 200 points (2 units) Your lowest unit grade will be dropped, so that your total examination score will be out of 400 points. If a 100-point exam happens to be your lowest percentage score, that score will be dropped and your grade will be based on the remaining two exams and the final. If the final exam is your lowest percentage score, then all three of your 100-point exams will count toward your grade along with one Unit of your final exam score or half the total points earned on the final. In this way, a low score on the final will not have a greater negative impact on your overall grade than a regular exam would. In addition, there will be eight short homework assignments administered by your Recitation TAs. You also get to drop your three lowest homework scores so your five best homework assignments will count toward your grade. The maximum possible score from homework assignments is, therefore, 50 points, which brings the total score for the semester up to 450 points. There will be absolutely no makeup exams or homework assignments. If you miss an exam or homework assignment for whatever reason, that will be the grade that you drop. If you miss more than one exam, the sum of your remaining scores will still count toward a possible total out of 450 points. Therefore, it could have a significant impact on your grade for the course if you miss more than one exam or if you do not take the final exam, since your score for additional exams missed would be 0.

The actual cutoff ranges for different letter grades can vary from one semester to the next. However, based on typical grade distributions for this class, it is recommended that you aim for at least 85% of the total possible points in order to earn an A– or better, and greater than 35% in order to avoid failing the course with an F. EXAM DATES: Exam 1 - Monday, October 12 (Unit 1 - Chapters 1, 2, 3 and 4) Exam 2 - Monday, November 9 (Unit 2 - Chapter 5 and parts of Chapters 6, 7, 10 and 11 as listed) Exam 3 - Wednesday, December 2 (Unit 3 - parts of Chapters 7 and 8 as listed, Chapters 9 and 12) Final Exam - Projected date and time - Monday, December 21, 9:00 a.m. to 12:00 p.m. Date and time to be confirmed by the Registrar; (Cumulative, with emphasis on Unit 4 – Chapters 10, 13 and 14) HOMEWORK ASSIGNMENT DATES: Homework Assignments will be administered by your Recitation TAs during the weeks of 9/21, 9/28, 10/19, 10/26, 11/19, 11/16, 11/30, 12/07. The TAs will provide more information about when the assignments will be made available and when they will be due for submission. ACADEMIC INTEGRITY: All students in this class are expected to adhere strictly to Columbia University’s student Honor Code, In turn, any instances that appear to violate that Honor Code will not be tolerated and will be subject to the full extent of your school’s Disciplinary Process. As a Columbia College student, you are required to make the following pledge: We, the undergraduate students of Columbia University, hereby pledge to value the integrity of our ideas and the ideas of others by honestly presenting our work, respecting authorship, and striving not simply for answers but for understanding in the pursuit of our common scholastic goals. In this way, we seek to build an academic community governed by our collective efforts, diligence, and Code of Honor. In addition, all Columbia College students are committed to the following honor code: I affirm that I will not plagiarize, use unauthorized materials, or give or receive illegitimate help on assignments, papers, or examinations. I will also uphold equity and honesty in the evaluation of my work and the work of others. I do so to sustain a community built around this Code of Honor. The Disciplinary Process If an instructor believes you to have acted dishonestly, you will be referred to the formal process of Dean's Discipline. Overseen by Student Conduct and Community Standards, the Dean’s Discipline process is an educational one that determines your responsibility using the principle of "preponderance of evidence." If found responsible, and depending on the nature of the dishonesty and whether or not you have a disciplinary record, you could face one of several sanctions. Students will also be referred to meet with your specific school to reflect on the process and reconnect to campus support resources. Parents and guardians may be informed, faculty committees awarding honors will be notified, and the case may remain on your permanent record meaning that employers and graduate schools may also be informed. These sanctions are in addition to whatever determination the instructor makes on how your final grade in the class will be affected. Strategies for Maintaining Academic Integrity To prevent any issues with academic integrity, you should: • Be prepared for class

• Manage your time • Seek clarifications when unsure about course expectations • Communicate with your instructor if you have concerns

Would you like to learn strategies to maintain your academic integrity? Do you have questions about the Academic Integrity policy? Visit the Academic Integrity website that corresponds to your school below: • Columbia College & Columbia Engineering - https://www.cc-seas.columbia.edu/integrity • Barnard College - https://barnard.edu/dos/honorcode • School of General Studies http://bulletin.columbia.edu/general-studies/academic-

policies/academic-integrity-community-standards/ DISABILITY SERVICES: In order to receive disability-related academic accommodations for this course, students must first be registered with their school Disability Services (DS) office. Detailed information is available online for both the Columbia and Barnard registration processes. Refer to the appropriate website for information regarding deadlines, disability documentation requirements, and drop-in hours (Columbia)/intake session (Barnard). Students do not need to provide an accommodation letter to the professor or the Chemistry Department for this course. Students do not need to have the professor or the Chemistry Department sign DS Testing forms for this course SCHEDULE OF LECTURE TOPICS: A tentative schedule of the dates on which particular chapters or subsections of chapters will be covered is shown in the table on the following page. This schedule is only approximate, and may be adjusted as we see how quickly (or slowly) we get through each section during the semester. Some notes on the schedule and the factors that contribute to how it is organized are as follows: ●

Certain chapters and parts of chapters have been broken up in an order that is different from the text. This will help us to most effectively and efficiently get through all of the material. I think that the order indicated here will actually have a more cohesive flow than the order that is presented in the text. Chapter 6 includes general information about the kinetics and thermodynamics of reactions and is woven into discussions about other chapters, not handled as a separate chapter in lectures.

●

Workshop Numbers correspond loosely to the chapters covered on those Workshops.

●

Homework assignments will include material up to and including the Workshop from the previous week. They will not involve topics or skills covered during the same week in which they are administered.

●

Exams are usually scheduled at least a week after topics from that unit are covered. This gives us some room to catch up in the event that we fall behind. More importantly, this also gives you time to assimilate the material and reinforce what you have learned through problem solving in Workshops.

●

Exams will only cover material up to the end of each Unit. However, we will continue with lectures on new material between the end of each Unit and the date for each exam.

●

The Registrar schedules all final exams and information about the final will be confirmed later on, usually at the beginning of November.

Tentative Lecture and Exam Schedule The following is only an approximate schedule of exam dates and topics covered for each class session. This schedule is subject to change and will be updated if necessary during the semester.

Monday

Wednesday

11:40-12:55 pm; On Zoom

11:40-12:55 pm; On Zoom

Labor Day Academic Holiday - No Class

9-09 Class Introduction; Chapter 1: Structure & Bonding

9-09 to 9-11 Workshop 1

9-14 Workshop 1 Discussion Ch 2: Polar Covalent Bonds; Acids & Bases; Ch 6-6.7&6.9

9-16 Ch 2: Polar Covalent Bonds; Acids & Bases; Ch 6 - 6.7 and 6.9

9-16 to 9-18 Workshop 2A

9-21 Workshop 2A Discussion; Continue Ch 2- Polar Covalent Bonds; Acids & Bases; sections 6.7 and 6.9 9-28 Workshop 2B Discussion; Ch 3 Organic Compounds: Alkanes & Their Stereochemistry 10-05 Workshop 3 and 4 Discussion; Ch. 5 Stereochemistry at Tetrahedral Centers

9-23 Finish Ch 2; Ch 3 - Organic Compounds: Alkanes & Their Stereochemistry

9-23 to 9-25 Workshops 2B HW1 9-30 to 10-02; Workshop 3 & 4 HW2 10-07 to10-09 Workshop 5

9-07

Recitation/ Workshop

10-26 Workshop 7 Discussion; Reactions of Alkenes. Ch 6: 6-5; Ch 7: 7-7, 7-8, 7-11, Ch 8: 8-2, 8-3, 8-4, 8-5, 8-7,8-8, 8-9, 8-12, 8-13 11-02 Academic Holiday - No Class

9-30 Ch 4 - Organic Compounds; Cycloalkanes & Their Stereochemistry (End of Unit 1 Lectures) 10-07 Ch. 5 Stereochemistry at Tetrahedral Centers Ch 6: 6.2, 6-3, 6.7, 6-8, 6-9, 6-10; Ch 7: 7-10 10-14 Ch 11: Reactions of Alkyl Halides: Nucleophilic Substitution and Elimination; Ch 6: 6.4, 6.6; Ch 7: 7-9 10-21 Synthesis and Properties of Alkenes. Ch. 8: 8-1, 8-6; Ch. 7: 7-1, 7-2, 7-3, 7-4, 7-5, 7-6 (End of Unit 2 Lectures) 10-28 Reactions of Alkenes. Ch 6: 6-5; Ch 7: 7-7, 7-8, 7-11, Ch 8: 8-2, 8-3, 8-4, 8-5, 8-7,88, 8-9, 8-12, 8-13 11-04 Workshop 8 Discussion; Begin Ch 9: Alkynes: An Introduction to Organic Synthesis

11-09 EXAM 2 - Unit 2 (Chapters 5, 7, 11 & parts of other chapters listed for Unit 2)

11-11 Ch 9: Alkynes: An Introduction to Organic Synthesis

11-11 to11-13 Workshop 9 HW5

11-16 Workshop 9 Discussion; Begin Ch 12 - Structure Determination: Infrared Spectroscopy 11-23 Workshop 12 Discussion; Begin Ch 13: Structure Determination: NMR Spectroscopy 11-30 Ch 13: Structure Determination: Nuclear Magnetic Resonance Spectroscopy

11-18 Ch 12 – Structure Determination: Infrared Spectroscopy (End of Unit 3 Lectures) 11-25 Thanksgiving Eve Academic Holiday - No Classes

11-18 to11-20 Workshop 12 HW6 11-25 to 11-27 No Workshop

12-02 EXAM 3 - Unit 3 – Chapters 8, 9, 12 & parts of other chapters listed for Unit 3)

12-07 Workshop 13 Discussion; Begin Ch 10: 10-3, 10-4; Ch 14: Conjugated Compounds and Ultraviolet Spectroscopy 12-14 Last Official Class Workshop 14 Discussion; Semester wrap up (End of Unit 4 Lectures)

12-09 Ch 10: 10-3, 10-4; Ch 14: Conjugated Compounds and Ultraviolet Spectroscopy

12-02 to 12-04 Workshop 13 HW7 12-09 to 12-11 Workshop 14 HW8 12-16 to 12-18

10-12 EXAM 1 - Unit 1 (Chapters 1, 2, 3 & 4)

10-19 Workshop 5 and 11Discussion; Finish Ch 11 or Begin Ch. 7

12-16

10-14 to 10-16 Workshop 11 10-21 to 10-23 Workshop 7 HW3 10-28 to 10-30 Workshop 8 HW4 11-04 to 11-06 Mid-term review & Election Decompression

STUDY DAY

Comprehensive Final Exam - Emphasis on Parts of Chapter 10, Chapters 13 and 14 Projected Date - Monday, December 21, from 9:00 a.m. to 12:00 p.m. To be confirmed in early November....