Chemistry 2410 (section 400): Organic Chemistry I Fall 2013 Instructor: Dr. Laura Serbulea Office: Chemistry Bldg. 229 Phone: (434) 924-0924 Email: lls3s@virginia.edu Office Hours: Tu 2:00-4:00 pm We 12:00-2:00 pm Teaching Assistant: Thomas Dawson tkd5gx@virginia.edu Course Meetings: Lecture (#10487) Tu & Th 12:30-1:45 pm, Clark Hall 108 Discussion (#10489) We 6:30-8:30 pm, Chemistry 402 Course Description and Objectives: Why are carrots and flamingos orange? How can insect populations be controlled? Why is fish served with lemon? How do compounds in biological systems recognize each other? Learning organic chemistry concepts and principles will pave the way to answer such questions and others relevant to our world. Organic chemistry is about designing, synthesizing, characterizing and developing applications for carbon-containing molecules. Where are organic compounds? They are all around us: in pharmaceuticals, food, plastics, fuels, cosmetics, detergents, fertilizers etc. During this course you will: a) develop an understanding of the structure, properties, and reactions of organic compounds; b) apply the concepts learned to solve problems by reasoning your way to the solution; c) make connections between concepts in organic chemistry and other science courses (biology, biochemistry, materials science etc.); d) develop effective communication skills and the ability to work efficiently with others. Specifically, at the conclusion of the course you will be able to: Draw structures of organic molecules, as well as conformational structures using the wedge dash formalism and Newman projections Name organic molecules using IUPAC nomenclature Represent reactions and reaction mechanisms using the appropriate arrow formalisms Analyze the stability of organic molecules based on bond strengths as well as electronic and steric interactions Evaluate molecular reactivity using molecular orbital theory, resonance theory and reaction coordinate diagrams Compose the synthesis of an organic compound by evaluating multiple pathways and using learned reactions 1
Required Materials: Organic Chemistry, 7 th Edition, by Paula Y. Bruice (ISBN 0321803221) Organic Chemistry: A Guided Inquiry, 2 nd Edition, by Andrei Straumanis (ISBN 0618974121) iclicker 2 remote (ISBN 1429280476) Sapling Learning access for online homework assignments: www.saplinglearning.com Optional Materials: Molecular model set (highly recommended!): http://www.maruzen.info/hgs/catalog/product_info.php?products_id=616 Get Ready for Organic Chemistry, 2 nd Edition, by Joel Karty (ISBN 0321774124) Student Solutions Manual to accompany Organic Chemistry, 7 th Edition, Paula Y. Bruice (ISBN 0321826590) Course Deadlines: In case that you decide to drop the course, it is your responsibility to take the necessary steps to drop/withdraw from the class by the university deadlines. The last day to drop without a penalty is September 11, 2013. The last day to withdraw from the course ( W recorded) is October 22, 2013. How to Succeed in Organic Chemistry: Learning organic chemistry requires a great deal of responsibility and perseverance, but it can be fun if you give it a chance. Here are some recommendations: 1) Attend ALL class meetings (lectures and discussions) and feel free to ask for help whenever needed. Please arrive on time and turn off any ringing tones of your cell phone while in class. 2) Study daily: In order to master the concepts presented in this course you should plan to spend 12-15 hours per week for study. It is however crucial that you study 1-2 hours every day rather than spending several hours of studying over the weekend. Reading the textbook, class notes AND solving in-chapter & end-of-chapter and online homework problems, as well as attending all class activities will give you the greatest chance for success in this class. 3) Learn the concepts through reasoning and understanding, not by memorization! There are relatively few fundamental concepts that organic chemistry is built on- understanding and applying these concepts in various ways is key to learning organic chemistry that will result in long lasting knowledge. 4) Utilize the resources available to you! Attend office hours whenever you need clarification on any of the concepts learned. Additional help will be available for organic chemistry students through the Chem Resource Center (4 th floor of the Chemistry building; Fall 2013 schedule to be posted soon). 2
Activities and Assessments iclicker quizzes will be used in every lecture, and discussion sessions. To receive credit for your responses, iclicker remotes must be registered online through the link provided on the course site in Collab. Lecture iclicker quizzes: typically 3-4 questions will be administered; the time to answer each question will be 30-45 seconds. Points are received for both participation and correct answers using the iclicker remote. Regardless of the number of questions administered in a lecture, the maximum points possible for iclicker responses per lecture will be the same (typically 10 points). No make-up iclicker quizzes are available. The four lowest lecture iclicker quizzes will be dropped when calculating your semester iclicker lecture %score. Discussion (recitation) sessions Attendance of the discussion sessions is required (not optional!); during these sessions both individual and group activities (ChemActivity) will be carried out, except for those dates when exams are administered. iclicker quizzes on the announced topic (see schedule on the last page of the syllabus) will be administered during these sessions. The lowest iclicker quiz will be dropped when calculating your semester discussion quizzes %score. For every discussion session, make sure that you bring with you the ChemActivities (CA) from the Organic Chemistry: A Guided Inquiry textbook, according to the schedule on the last page of the syllabus. Check the Announcements section on the course site in Collab for any changes/updates of this schedule. Homework The homework assignments are created and administered through Sapling Learning. There will be 13 graded homework assignments. Each homework set will consist of 20 questions on a specified topic. You will have multiple attempts available to answer each question; however, there will be a 5% penalty for each incorrect answer. All answers must be submitted online (through Sapling), and will not be accepted in any other way. Each assignment becomes available on Monday at 12 am and will be due the following Sunday at 11:55 pm. Homework problems must be completed by the due dates listed online (and on the schedule for each assignment). No extension of the due dates will be granted, so please plan accordingly. To register, do the following: 1. Go to http://saplinglearning.com and click "US Higher Ed" at the top right. 2. To avoid being dropped from the course in Sapling, make sure that you sign up using your first and last name as provided on the class roster AND use your UVa email account. a. If you already have a Sapling Learning account, log in and skip to step 3. b. If you have Facebook account, you can use it to quickly create a SaplingLearning account. Click the blue button with the Facebook symbol on it (just to the left of the username field). The form will auto-fill with information from your Facebook account (you may need to log into Facebook in the popup window first). Choose a password and timezone, accept the site 3
policy agreement, and click "Create my new account". You can then skip to step 3. c. Otherwise, click "create account. Supply the requested information and click "Create my new account". Check your email (and spam filter) for a message from Sapling Learning and click on the link provided in that email. 3. Find your course in the list (listed by subject, term, and instructor) and click the link. 4. Enter your section number as the key code: 400 5. Select a payment option and follow the remaining instructions. The cost for using Sapling Learning is $29.99/semester. Once you have registered and enrolled, you can log in at any time to complete or review your homework assignments. During sign up and throughout the term if you have any technical problems or grading issues, send an email to support@saplinglearning.com explaining the issue. Exams Three midterm exams are planned for September 18th, October 16th, and November 13th. All midterm exams will be administered during discussion session time. The final examination is cumulative and is scheduled for Tuesday, December 10, 2013, 2:00-5:00 pm in Clark Hall 108. There are no make-up exams, except for documented medical emergencies. All examinations will be based on the material covered in lectures, discussions, and homework assignments. During any type of assignment you will be allowed to use only a nonprogrammable, non-graphing calculator. You must bring your own calculator - no sharing allowed, or be prepared to take the exam without it. You may use your own molecular modeling kit during exams; however, no sharing will be allowed. Only scratch paper provided by the instructor will be allowed during exams. Grading Policy: The following items and their corresponding weights will be used in the calculation of the grade for the course: Items % Weight Exam I 13% Exam II 13% Exam III 13% Final exam (cumulative) 33% Homework (Sapling Learning assignments) 13% Lecture iclicker quizzes 5% Discussion session iclicker quizzes 10% Total 100% All items will receive a % score (0-100%). The final % grade for the course is calculated using the following formula: 4
% Grade = (% score % Weight ) 100 The letter grade will be determined based on your overall score (% grade), according to the following scale (+/- assigned): A = 90-100%; B =80-89%; C = 70-79%; D =60-69%; F =0-59%. Please be advised that this course uses an absolute grading scale, not a curved one. The Honor System On my honor, I pledge that I have neither given nor received help on this assignment. The principles of truth and honesty are recognized as fundamental to a community of teachers and scholars. The University expects that students will honor these principles and in so doing will protect the integrity of all academic work and grades. Students are expected to do all graded work assigned to them without unauthorized assistance and not to give unauthorized assistance. While collaboration among students in preparation for an examination is encouraged, discussion of the specific homework questions among students is not acceptable. Communication among students during iclicker quizzes, both in lectures and discussion sessions, are not permitted. Topics Organization I. Electronic structure, bonding, acid-base chemistry (chapters 1-2) II. Alkanes and cycloalkanes: Nomenclature, physical properties, conformational analysis (chapter 3) Reactions of alkanes (chapter 13; sections 13.1-13.5) III. Stereoisomers (chapter 4) IV. Alkenes Structure, nomenclature, reactivity (chapters 5) Stereochemistry of addition reactions (chapters 6) Radical Additions and Substitutions (chapter 13, sections 13.6-13.11) V. Alkynes (chapter 7) VI. Electron delocalization and aromaticity (chapter 8) VII. Reactions of alkyl halides: Substitution reactions (chapter 9) Elimination reactions (chapter 10) VIII. Reactions of benzene and substituted benzenes (chapter 19) 5
Tentative Lecture and Exam Schedule Week Lecture Date and Topic Discussion*/Exam Date Sapling Homework Due Dates 1 08/27 Course Intro & Chapter 1 08/29 Chapter 2 08/29 No discussion session (IntroActivity)** 2 09/03 Chapter 2 09/04 ChemActivity/ Ch.1-2 09/08 HW1/ Ch.1 09/05 Chapter 3 CA 4, CA 5 3 09/10 Chapter 3 09/11 ChemActivity/ Ch.3 09/15 HW2/ Ch.2 09/12 Chapter 13 (13.1-13.5) CA 6A, CA 7 (NW1)** 4 09/17 Chapter 4 09/18 Exam I 09/22 HW3/ Ch.3 09/19 Chapter 4 6:30-8:30 pm, Chem. 402 5 09/24 Chapter 5 09/25 ChemActivity/ Ch.4 09/29 HW4/ Ch. 4 09/26 Chapter 5 CA 12, CA 6BC 6 10/01 Chapter 6 10/02 ChemActivity/Ch.13 10/06 HW5/ Ch. 5 10/03 Chapter 6 CA 15A 7 10/08 Chapter 13 (13.6-13.11) 10/09 ChemActivity/ Ch.5-6 10/13 HW6/ Ch. 6 10/10 Chapter 7 CA 8, CA 9A 8 10/15 Reading day 10/16 Exam II 10/20 HW 7/ Ch.13 10/17 Chapter 7 6:30-8:30 pm, Chem. 402 9 10/22 Chapter 8 10/23 ChemActivity/ Ch.7 10/27 HW 8/ Ch.7 10/24 Chapter 8 CA 11, CA 16 10 10/29 Chapter 8 10/30 ChemActivity/ Ch.8 11/03 HW 9/ Ch.8-p1 10/31 Chapter 8 (CA 17), CA 18 11 11/05 Chapter 9 11/06 ChemActivity/ Ch.9 11/10 HW10/Ch.8-p2 11/07 Chapter 9 CA 13 12 11/12 Chapter 9 11/13 Exam III 11/17 HW 11/ Ch. 9 11/14 Chapter 10 6:30-8:30 pm, Chem. 402 13 11/19 Chapter 10 11/20 ChemActivity/ Ch.10 11/24 HW 12/ Ch. 10 11/21 Chapter 19 CA 14 14 11/26 Chapter 19 11/28 Thanksgiving Holiday 11/27 No discussion session 12/01 No homework due 15 12/03 Chapter 19 12/04 ChemActivity/ Ch.19 12/08 HW 13/ Ch. 19 12/05 Review CA 19 (CA 21) 12/10 Final Exam 2:00 pm 5:00 pm, Clark Hall 108 Note: Any changes to this schedule remains at the discretion of the instructor and will be announced in class and/or posted on the course site on UVaCollab. *ChemActivity (CA) assignments are from Organic Chemistry: A Guided Inquiry (2 nd ed) workbook. **Activities to be done at home 6