CHE321 Syllabus Fall2020 PDF

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CHE 321 Syllabus...

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Chemistry Department Online Syllabus Important Note: Every effort will be made to avoid changing the course schedule, but the possibility exists that unforeseen events will make syllabus changes necessary. It is your responsibility to check Blackboard for corrections or updates to the syllabus. Any changes will be clearly noted in course announcements or through Stony Brook email.

Part 1: Course Information Course title: Organic Chemistry I Course catalog # and section: CHE 321 (2 sections) Credit hours: 4 General education designation(s) (SBC): STEM+ Instructor name: Robert B. Grubbs, Dale Drueckhammer, Zachary Katsamanis Course e-mail address: [email protected]; Coordinator Office hours: Dr. Katsamanis – Tuesday 10:00-11:30am, Thursday 12:00-1:30pm (974-208-3323) Teaching Assistants: contact information and office hours for each TA (and instructor) will be provided on our course website (OSCER) before the semester begins. If you cannot reach Dr. Grubbs, Dr. Drueckhammer, Dr. Katsamanis, or any TA, please email [email protected] Course Description: An introduction to the structure, reactivity, and properties of organic compounds is presented using modern views of chemical bonding. These fundamental ideas are applied to topics ranging from synthetic chemistry to complex functional structures such as lipid bilayers.

Required Course Textbook and Materials: Organic Chemistry, 6th edition, by Loudon and Parise. (Paperback ISBN:9781936221349; E-book ISBN:9781319110536)

This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License

CHE 321: Organic Chemistry I

Fall 2020

Recommended Materials: Molecular Model Kit (available through the bookstore; any model kit focused on organic molecules should be similarly useful). While it is not required to purchase models, they are very useful tools for visualizing molecular structure. Plus, you are allowed to use them on any exam. How We Will Communicate: The course website (https://organic.cc.stonybrook.edu/che321-20/) and the Blackboard supported web site (https://blackboard.stonybrook.edu) should be checked on a regular basis. Online quizzes (workshop quizzes and lecture quizzes), exams, course announcements, lecture notes, lecture videos and various other course materials can be found there. Course information, grades, old examinations (posted selectively), and workshop copies can be found on the course websites. The most recent class notice and/or announcement will be emailed through Blackboard. In order to receive the most recent email notice and/or announcement through Blackboard, you must check the email account associated with Blackboard. There are several features on Oscerfolio but we will only use some of them. You can post a note or question using the Howler, which is our version of Twitter. You can post short messages to the class and attach a photo taken with your cell phone. You can use the Howler to post solutions to problems or to ask a question. More will be explained during lecture and by your TAs. Course-related questions should be posted in the Howler section of Oscerfolio. For personal/private issues, send an email message to [email protected]. If you use Blackboard’s email tool from the course site, it will automatically include your full name, course name and section when you send an email. Please allow between 24-48 hours for an email reply. Your Stony Brook University email must be used for all University-related communications. You must have an active Stony Brook University email account and access to the Internet. All instructor correspondence will be sent to your SBU email account. Plan on checking your SBU email account regularly for course-related messages. To log in to Stony Brook Google Mail, go to http://www.stonybrook.edu/mycloud and sign in with your NetID and password. Regular announcements will be sent from Blackboard. These will be posted in the course site and may or may not be sent by email. Regular communication is essential in online classes. Logging in once a day, and participating with your colleagues ensures that you are able to remain an active member of the class and earn full points for participation. Course Delivery Mode and Structure: This is an online course, that will be taught both synchronously and asynchronously using the Zoom platform and the OSCER system. We will use Zoom as the primary platform for

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synchronous teaching. Sign into Zoom at stonybrook.zoom.us using your Stony Brook NetID and NetID password. Each scheduled Zoom meeting will be accessed within the Blackboard site. Students must be mindful of all course expectations, deliverables and due dates, especially because the online portion of the course requires significant time management. All assignments and course interactions will utilize internet technologies. All documents, exams, quizzes, grades and announcements will be delivered in Blackboard (https://blackboard.stonybrook.edu) and OSCER (https://organic.cc.stonybrook.edu/che321-20/). Both require your NetID and NetID password. See “Technical Requirements” section for more information. General weekly schedule (see below for more details of each activity) Mondays – Lecture quiz due 9:00 am, Optional/informal lecture sessions run by TAs Wednesdays – Workshop quiz due 9:00 am, Optional/informal lecture sessions run by Profs. Grubbs or Drueckhammer. Workshop at your scheduled time on Wednesday or Thursday. (There will be no lecture quizzes due on Wednesdays.) Fridays – On alternating Fridays beginning the second week (Sept. 4) there will be an online mini-exam during your assigned lecture time. On Fridays when there is no exam, there will be a lecture quiz due at 9:00 am. Lectures Pre-recorded lecture videos will be posted regularly in either Blackboard or Oscer (pay attention to e-mail announcements) that will be associated with lecture quizzes (which will become available when the videos are posted). Instead of one long lecture video corresponding to the textbook sections listed on the schedule section, the content will be divided into multiple videos. Optional Lecture sessions will be conducted on Zoom on Mondays (Section 1: 10:30-11:25 am; Section 2: 3:30-4:25 pm; all times Eastern Time). These sessions will be run by TAs. They will focus on select problems/topics from the lecture quizzes due on Mondays. The sessions will be somewhat informal, encouraging students to discuss and ask questions openly. Similar sessions will be held during class on Wednesdays run by Prof. Grubbs or Drueckhammer. These sessions may include discussion of some questions from the workshop quiz due that morning. The lecture quizzes will remain open for a certain number of days. Pay attention to due dates. Each quiz will always close at 9:00 am on its due date. Each lecture quiz will be worth 4 lecture points. Lecture quizzes will be graded but you earn 1 lecture point simply for completing the quiz. For the first lecture quiz, the due date is extended to Wednesday, August 26, 2020. When you take a graded lecture quiz you will see two buttons. The Save button saves your work, the Submit button submits your work. You can save as often as you like, but the number of submissions is limited. When you submit, the Oscerfolio program will tell you which answers are correct and which are incorrect. Many of the quizzes use OscerSketch , a chemical drawing 3

CHE 321: Organic Chemistry I

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program. You press a button to open the OscerSketch window, draw your answer in the drawing window, and then hit the save button above the drawing window. When you close the window, you should see your drawn structure saved on the quiz page. When you submit your quiz for grading, Oscerfolio will assess your structure. NOTE: when taking any quiz or exam on Oscer, make sure that you do not have multiple Oscer windows open simultaneously and take your quiz as a single page (as opposed to the one question per page format). We found that these are the reasons behind most technical issues with quizzes. Workshops Each workshop (recitation session) will have a workshop quiz associated with it due by 9:00 am every Wednesday. A workshop quiz will go live every Thursday evening at 9:00pm. The workshop quizzes will be graded (full credit for correctly answering 70%, and 2 points for correctly answering at least 30%). Full credit for each workshop quiz is worth 5 workshop points. For the first workshop quiz, the due date is extended to Thursday, August 27, 2020. Zoom attendance and participation at your recitation section is required and will be worth 5 workshop points. During workshop, you will log into Oscerfolio and complete ‘Exercise’ problems and upload them into the system. TAs will guide you during these Zoom meetings and lead discussions. Students will also have the ability to interact and share answers. Exams There will be 7 mini-exams and one final exam. Each mini-exam will be worth 40 points. The final exam will be worth 120 points. Each mini-exam will be an hour long and administered during your scheduled lecture time (Section 1: 10:30-11:30am, Section 2: 3:30-4:30pm) on the following dates (Fridays): September 4, September 18, October 2, October 16, October 30, November 13, December 4). The final exam will take place on Friday, December 11 (8:00 – 10:30am). You will take each exam on Oscerfolio, but you may be required to log into Zoom and turn on your webcam for proctoring purposes. Please read the exam taking protocol file that will be posted on our site early on in the semester. You will be responsible for reading it. Exams will be based on the content of lectures, the textbook chapters, workshops, workshop quizzes, and lecture quizzes. The questions will be a mix of multiple choice and short answers. For these exams, use of your textbook and other course materials will be allowed, including molecular models. You are not allowed to consult with anyone else during any mini-exam or quiz unless it is explicitly announced that it will be allowed. Any student who violates this privilege will be charged with academic dishonesty. There are no make-up exams for the mini-exams missed due to illness or other personal matters. An exam grade will be generated for the missed mini-exam, based on the other six mini-exams and the final exam (scaled to account for differences in class averages). Situations of students who miss more than one mini-exam due to illness will be handled on a case-by-case

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basis. If an exam date falls on a religious holiday that you observe, the instructor should be

informed as early in the semester as possible. All students must take a final exam. Any student missing the final exam must notify the instructors ([email protected]) within 24 hours in order to be eligible for the make-up exam. The make-up exam is primarily used to determine whether or not the student deserves the grade indicated by the student’s average. The make-up final cannot be used to raise a student’s grade above that indicated by the midterm exams. The date for the make-up exam will be determined upon notification of a missed final exam. Exam Regrade Request Procedure Although extraordinary care is taken to assure an error free process, errors may occur. If you believe there is an error in the grading, then you can request a regrade. You must send an email to [email protected] (with “Exam Regrade” in the title of the email) asking which problem(s) to be reviewed and why. Make sure you review the answer key before requesting a regrade. Only request a regrade if you feel there was an error in grading, not because you disagree with the key. The deadline for each exam regrade is the next exam (i.e. once miniexam 2 has been given, you can no longer request a regrade for mini-exam 1). Regrade requests will not be considered past the deadline. Technical Requirements: This course uses Blackboard for the facilitation of communications between faculty and students, submission of assignments, and posting of grades and feedback. The Blackboard course site can be accessed at https://blackboard.stonybrook.edu If you are unsure of your NetID, visit https://it.stonybrook.edu/help/kb/finding-your-netid-andpassword for more information. You are responsible for having a reliable computer and Internet connection throughout the term. Problems submitting answers to online quizzes are most often due to an insufficient internet connection. Caution! You will be at a disadvantage if you attempt to complete all coursework on a smart phone or tablet. It may not be possible to submit the files required for your homework assignments. Students should be able to use email, a word processor, spreadsheet program, and presentation software to complete this course successfully. The following list details a minimum recommended computer set-up and the software packages you will need to have access to, and be able to use: • • • • •

PC with Windows 10 or higher (we recommend a 3-year Warranty) Macintosh with OS 10.11 or higher (we recommend a 3-year Warranty) Intel Core i5 or higher 250 GB Hard Drive 8 GB RAM 5

CHE 321: Organic Chemistry I

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Latest version of Chrome or Firefox; Mac users may use Chrome or Firefox. (A complete list of supported browsers and operating systems can be found on the My Institution page when you log in to Blackboard.) High speed internet connection Word processing software (Microsoft Word, Google Docs, etc.) Headphones/earbuds and a microphone

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Webcam (it is advantageous if we can see you during lecture and workshop discussions)

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Printer (optional) Ability to download and install free software applications and plug-ins (note: you must have administrator access to install applications and plug-ins).

Technical Assistance: If you need technical assistance at any time during the course or to report a problem with Blackboard you can: • • •

Phone: 631-632-9800 (client support, Wi-Fi, software and hardware) Submit a help request ticket: https://it.stonybrook.edu/services/itsm If you are on campus, visit the Walk-Up Tech Support Station in the Educational Communications Center (ECC) building. Part 2: Course Learning Objectives and Assessments

Upon completion of the course, students will be able to: 1. Identify how molecular structure affects reactivity and physical properties of organic molecules and apply this knowledge to predict reactivity and physical properties of other organic molecules. 2. Design strategies for the synthesis of organic molecules by choosing from a set of organic reactions that we will discuss. In two other learning objectives that will not explicitly be evaluated on exams, students will : 3. Be able to cite specific examples of the role organic chemistry has played in the development of our modern society. 4. Develop team skills to solve complex problems. Exam questions for evaluating learning objectives 1 and 2. Learning Objective 1. The knowledge of organic chemistry is often evaluated using multiple choice questions such as the following:

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(a) Choose the order that has the following structures (compounds) correctly arranged with respect to some physical of chemical property such as boiling point, solubility, acidity, reactivity, etc. (b) Choose the major product of the following reaction. (c) Choose the reactant and reagents that would give the following compound. (d) Choose the compound most consistent with the following data. The knowledge of organic chemistry is also evaluated using short answer questions. An advantage of short answer questions is that they require a written answer rather than a selection from a list. Some examples are the following: (a) Give the major product of the following reaction. (b) Give reactants and reagents for performing the following transformation. (c) Give the correct name (structure) of the following structure (name). Learning Objective 2. The application of the knowledge of organic chemistry to the solution of complex problems must be accomplished using written rather than multiple choice questions. Common questions are the following: (a) Give the structures of compounds A-E consistent with the following observations. (b) Using the curved arrow formalism show how the bond making and bond breaking occurs in the following transformation. (c) Show how the following compound could be prepared from reactants and reagents containing four carbon atoms or less. This problem develops skills of working a problem backwards. How to Succeed in this Course: • • • •

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Complete all assigned readings in the course in a timely fashion Complete all lecture and workshop quizzes Participate during lecture sessions and workshops Attendance and participation in this online course is crucial. You cannot make up work in this class, so failing to stay on top of your course responsibilities can quickly spiral into a failing grade for the course. The material learned early on in this course is essential to build upon and develop a deeper understanding of subsequent chapters. Therefore, it is vital to keep up with the coursework and not fall behind. It is always recommended to complete assignments in advance of deadlines in case of technical difficulties or in case they require more time than expected. 7

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How much time should students devote to an online course? Time on task information, see NY State Education Department: http://www.nysed.gov/college-universityevaluation/distance-education-program-policies Part 3: Course Schedule

***subject to changes*** Aug. 24

Chapter 1

Chemical bonding and resonance

Aug. 28

Chapter 2

Alkanes

Aug. 31

Chapter 3

Acids and bases. Curved arrows

Sept. 4

Mini-exam 1

Sept. 7

Labor Day – No class

Sept. 11

4.1-4.7

Sept. 14

4.8, 4.9, 5.1, 5.2

Sept. 18

Mini-exam 2

Sept. 21

5.3-5.7 Addition reactions of alkenes

Sept. 25

Introduction to chemical synthesis, 6.1, 6.2 chirality

Sept. 28

6.3-6.8

Oct. 2

Mini-exam 3

Oct. 5

7.1-7.4

Cyclohexane

Oct. 9

7.5-7.8

Other rings, stereochemistry of reactions

Oct. 12

Chapter 8

Noncovalent intermolecular interactions

Oct. 16

Mini-exam 4

Oct. 19

9.1-9.4

Alkyl halides, SN2 reactions

Oct. 23

9.5-9.8

Other reactions of alkyl halides

Oct. 26

Chapter 10

Alcohols and thiols

Oct. 30

Mini-exam 5

Nov. 2

11.1-11.5

Nov. 6

11.6, 11.8, 12.1, 12.2 Glycols, intramolecular reactions, IR theory

Nov. 9

12.3-12.6

Nov. 13

Mini-exam 6

Nov. 16

13.1-13.4, 13.7

Alkenes Reactions of alkenes

Stereochemistry

Ethers and epoxides

IR spectroscopy and mass spectrometry

NMR spectroscopy 8

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Nov. 20

13.9, 13.10, 14.1-14.3

NMR interpretation, alkynes

Nov. 23 - 27

Thanksgiving Break – No class

Nov. 30

14.4-14.8

Dec. 4

Mini-exam 7

Dec. 7

Final review

Fri., Dec. 11

Final Exam ...