Chemistry 255: Foundations of Organic Chemistry I

Seattle University

Syllabus for Chem 255 Winter Quarter 2014

Instructor Information Instructor: Office: Phone: E-mail: Dr. Shamila Gunatilleke ENGR 610 220-8218 gunatils@seattleu.edu

Course Information Course Number: Section: Class Time: Lecture room: Office hours: Website: Study Groups:

CHEM 255 01 (Dr. Gunatilleke) MWF 12:30 pm 1:35 pm LEML 122 M 1:45 pm 3.45 pm (or by appointment made via e-mail at least 24 hours in advance) https://seattleu.instructure.com (Canvas) Tu 11:30 1:00 pm; LEML 369; Amber & John W 5:30 7:00 pm; LEML 369; Danielle & Steven

About this Course This course, CHEM 255, is the companion course to CHEM 265 lab. CHEM 255 will introduce you to the fundamental ideas, concepts, and tools required to understand and predict the structure and reactivity of organic molecules. Text Required: Organic Chemistry: Structure and Function, 6th Edition. Vollhardt, K.P.C.; Schore, N.E. 2010; Freeman. (ISBN-10: 142920494X; ISBN-13: 978-1429204941) NOT the 5th edition. HGS Molecular Structure Model Kit, W.H. Freeman (ISBN: 1429284919) Recommended: Study Guide and Solutions Manual for Organic Chemistry, 6th Edition. Schore, N.E. 2009; Freeman. (ISBN-10: 142923136X | ISBN-13: 978-1429231367) Personal Learning Goals My hope and expectation is that by participating actively and earnestly in class you will: (i) Work comfortably, confidently, and responsibly in an independent manner. (ii) Work effectively and supportively in groups and value each useful skill your colleagues offer. (iii) Learn to give and receive constructive feedback in group settings. (iv) Develop comfort speaking in class and discussing chemistry outside of class. (v) Identify and use the study practices that work best for you. (vi) Enjoy the subject and look forward to coming to class. (vii) Behave in a professional, courteous, well-organized manner. Academic Learning Outcomes Upon successful completion of this course, you will be able to: (i) Draw 3-D representations of organic molecules using bond-line formulas, wedges/dashes, Newman projections, and Fisher projections. (ii) Describe the underlying principles that govern molecular structure and reactivity (the R2ICHES2). (iii) Apply the R2ICHES2 to explain chemical phenomena. (iv) Illustrate reaction mechanisms for radical substitution, SN1, SN2, E1, and E2 reactions using curved arrow notation. (v) Interpret NMR spectra to determine molecular structure.
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Chemistry 255: Foundations of Organic Chemistry I

Seattle University

Lecture Schedule
Class No. Class Date 1 2 3 4 5 6 --7 8 9 10 11 12 13 14 15 16 17 --18 19 20 21 22 23 24 25 26 27 28 29 Mon. Jan. 6 Wed. Jan. 8 Fri. Jan. 10 Mon. Jan. 13 Wed. Jan. 15 Fri. Jan. 17 Mon. Jan. 20 Wed. Jan. 22 Fri. Jan. 24 Mon. Jan. 27 Wed. Jan. 29 Fri. Jan. 31 Mon. Feb. 3 Wed. Feb. 5 Fri. Feb. 7 Mon. Feb. 10 Wed. Feb. 12 Fri. Feb. 14 Mon. Feb. 17 Wed. Feb. 19 Fri. Feb. 21 Mon. Feb. 24 Wed. Feb. 26 Fri. Feb. 28 Mon. Mar. 3 Wed. Mar. 5 Fri. Mar. 7 Mon. Mar. 10 Wed. Mar. 12 Fri. Mar. 14 Mon. Mar. 17 Chapter Ch. 1 Ch. 1 Ch. 1 Ch. 2 Ch. 2 Ch. 2 --------Ch. 3 Ch. 3 Ch. 3 --------Ch. 4 Ch. 4 Ch. 4 Ch. 5 Ch. 5 Ch. 5 Ch. 5 --------Ch. 6 Ch. 6 Ch. 6 --------Ch. 7 Ch. 7 Ch. 7 Ch. 7 Ch. 10 Ch. 10 Ch. 10 Ch. 10 Read Sections 04 59 --------02 02 38 --------03 4 10 ----------------03 4 57 01 0 2 and 5 35 48 --------06 79 ----------------78 0-6 9 --------05 49 49 --------Topics Covered Structure & Bonding Structure & Bonding Structure & Bonding Structure & Reactivity and QUIZ 1 Structure & Reactivity Structure & Reactivity Martin Luther King Jr. Day Holiday Reactions of Alkanes Reactions of Alkanes and QUIZ 2 Reactions of Alkanes EXAM 1 (Chapters 1 - 3) Cycloalkanes Cycloalkanes Cycloalkanes Stereoiosmers and QUIZ 3 Stereoiosmers Stereoiosmers Stereoiosmers Presidents Day Holiday SN1, SN2, E1, & E2 and QUIZ 4 SN1, SN2, E1, & E2 SN1, SN2, E1, & E2 EXAM 2 (Chapters 1 - 6) SN1, SN2, E1, & E2 SN1, SN2, E1, & E2 SN1, SN2, E1, & E2 SN1, SN2, E1, & E2 NMR Spectroscopy and QUIZ 5 NMR Spectroscopy NMR Spectroscopy NMR Spectroscopy

IMPORTANT DATES Last day to register, Add/Drop, or Change grading option: January 12th Last day to withdraw: February 14th FINAL EXAM Section 1 Friday, March 21st 2:00 pm 3:50 pm

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Chemistry 255: Foundations of Organic Chemistry I

Seattle University

Description of Assessment Tools

Grading Policy Your course grade will be based on the following 1. 2. 3. 4. Problem of the Day (POD) Five quizzes (20 points each) Two one-hour exams (100 points each) One final exam TOTAL 25 points 100 points 200 points 150 points 475 points

Final grades will be calculated using the following 10-point grading scale. > 93 = A 83 80 = B70 67 = D+ 93 90 = A80 77 = C+ 67 63 = D 90 87 = B+ 77 73 = C 63 60 = D87 83 = B 73 70 = C< 60 = F Problem of the Day (POD) Once a quarter, each student is responsible for solving a POD and presenting it to the class on their assigned day, according to the schedule on Canvas. You may work together with your co-presenter to solve and present your POD. Your presentation grade will be based on earnestness, rather than correctness. Signs of earnestness are: you were ready to present immediately when class starts; youve worked out a proposed answer in advance rather than at the last minute; you are prepared to answer questions. Ordinarily, make-ups for missed POD presentations will not be given. If you are ill or have a family emergency, it is your responsibility to contact your professor by email or telephone BEFORE your POD class begins, to provide documentation substantiating your absence, and to contact me about make-up arrangements. Quizzes, One-Hour Exams and the Final Exam All quizzes and exams are cumulative in nature and are scheduled (see lecture schedule). You must take exams at the announced times. Ordinarily, make-ups for missed quizzes and exams will not be given. If you are ill or have a family emergency, it is your responsibility to contact your professor by email or telephone BEFORE the exam begins to provide documentation substantiating the reason for your absence, and to set-up suitable make-up arrangements. Reward for Improvement If your final exam percentage score is higher than one of your one-hour exam percentage scores (or quiz average percentage), the percentage score on your final exam will replace the score on your lowest one-hour exam (or quiz average). Re-grade Requests for Exams and Quizzes If, after you have compared your answers to those on the key, you think that we have made any grading errors, you may re-submit your quiz or exam to your instructor WITHIN 7 DAYS, with a WRITTEN (TYPED) STATEMENT of what you want us to re-grade. We have this policy in order to streamline our responses to your questions. ALL petitions must follow this policy we simply do not have time to discuss the quiz and exam with each individual student. Do not make any marks or changes on your exam after it is returned to you. After grading, we photocopy or scan selected quizzes and exams to discourage anyone who is inclined to change their answer and resubmit their work for a re-grade.

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Chemistry 255: Foundations of Organic Chemistry I

Seattle University

Problem Solving Portfolio

The Importance of Problem Solving and Maintaining a Portfolio Success in organic chemistry is highly correlated with doing practice problems; the more you practice, the easier organic chemistry will become. Because of this, I expect you to maintain a problem solving portfolio in the form of a three ring binder organized into four sections: book problems, PODs, quizzes, and exams. Your portfolio will be my primary tool to diagnose the cause of any difficulties you might be having with course material; I will expect you to bring it with you to office hours appointments. While practicing problem solving is important, it is insufficient; the right kind of practice is critical. Rationalizing a study guide answer is not as valuable as struggling with a problem. Thus, avoid the temptation to cheapen the value of problems by looking at the solutions manual before you have struggled with a problem (for at least 30 minutes). If you are having difficulty and you need to make a stab in the dark, then do sothis is what you would do during an exam. When you ultimately check your answers, re-tune your study focus to problems that gave you difficulty. This will help you to determine what you need to study, re-read, or ask about in office hours or study group. Recommended book problems Because it will help you to succeed in this course, I strongly recommend that you do all of the problems in every chapter of our textbook, Organic Chemistry by Vollhardt and Schore. To help you prioritize your work during the busiest times of the quarter, the most important problems in Vollhardt are listed below. For all problems showing a reaction, I recommend drawing the reaction mechanism. Chapter 1: 25, 27, 28, 31, 32, 38, 43, 50, 51, 56 Chapter 2: 27, 29, 31, 35, 36, 39, 41, 42, 44b & c, 53 Chapter 3: 15, 16, 20, 21a & b, 22, 27, 29, 30, 32, 37 Chapter 4: 23, 24, 30, 32, 34, 35, 42, 44, 48, 57 Chapter 5: 33, 39, 41, 45, 55, 56, 58, 61, 69, 70 Chapter 6: 31, 32, 38, 42, 45, 46, 48, 54, 56, 57, 59 (draw mechanisms for all rxns) Chapter 7: 25, 26, 31, 33, 38, 40, 42, 44, 46, 50, 59 (draw mechanisms for all rxns) Chapter 10: 34, 35, 37, 44, 47, 49, 50, 54, 58, 66

Problems of the Day As mentioned on p. 3, to facilitate your learning I will supply you with a handout called Problems of the Day. This handout contains exam-level problems for your practice. While, each problem is assigned to students who are responsible for solving it and presenting it to the class on their assigned day, you should work each POD yourself in advance of the date it will be presented. Working PODs before you have the solution is one of the best ways to study for quizzes and exams.

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Chemistry 255: Foundations of Organic Chemistry I

Seattle University

Course Policies
Attendance You are strongly encouraged to attend all lectures; however, we will not take attendance after the first class day, and attendance does not affect your grade. If you miss a class, it is YOUR responsibility to obtain notes from one of your colleagues. Faculty will NOT provide copies of lecture notes to students. Cell Phones Cell phones should be SWITCHED OFF OR ON SILENT MODE throughout class. If you absolutely need to keep your phone on during class, you must notify me prior to class. Examples would be: You have childcare commitments, you are looking after a frail relative, or a close relative is in the hospital. Please be respectful of other students time and commitment to their studies by not breaching this policy. You should not text or view text messages during class. If your cell phone does accidentally go off, I expect you to turn it off immediately and NOT TO ANSWER THE CALL. Late Work In this class, you are expected to conduct yourselves as professional, courteous, and well-organized individuals this is what any organization will expect of you when you complete your degree. Acting in this way helps give Seattle University graduates a reputation as excellent and reliable colleagues, and in turn it means that your degree is worth more in a competitive marketplace. One of the most important ways that you will demonstrate these behaviors is by ensuring that YOUR WORK IS ALWAYS ON TIME. It is essential that you plan ahead for all eventualities to ensure that none of your work is late and that you take quizzes and exams on time. MAKE-UP QUIZZES AND EXAMS WILL NOT BE GRANTED, EXCEPT FOR UNIVERSITY-APPROVED EXCUSED ABSENCES (A DOCUMENTED ILLNESS OR EMERGENCY).

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Chemistry 255: Foundations of Organic Chemistry I

Seattle University

University Resources and Policies

Academic Resources Library and Learning Commons (http://www.seattleu.edu/learningcommons/) Including: Learning Assistance Programs, Research [Library] Services, Writing Center, Math Lab Academic Integrity Tutorial (found on SU Online) Academic Policies on Registrar website (https://www.seattleu.edu/registrar/academics/performance/) Academic Integrity Policy Academic Grading Grievance Policy Professional Conduct Policy (only for those professional programs to which it applies) Cheating on Exams or Quizzes Definition of cheating on exams or quizzes: Acting dishonestly or deceptively in connection with an examination or quiz. Examples of cheating include, but are not limited to: Copying another persons work during an examination Allowing another person to copy ones work Using, receiving, or transmitting unauthorized materials or other information during an examination Obtaining test materials before they are administered Sharing test materials with someone else before they are administered Having someone take an exam in ones place Taking an exam for someone else It is the responsibility of the student to consult with the faculty member concerning what constitutes permissible collaboration. No credit (i.e., a zero grade) will be given for an exam or quiz on which a student cheated. Other penalties may also be given. For more information, please see the SU Academic Integrity Policy at: https://www.seattleu.edu/registrar/academics/performance/ Notice for Students Concerning Disabilities If you have, or think you may have, a disability (including an invisible disability such as a learning disability, a chronic health problem, or a mental health condition) that interferes with your performance as a student in this class, you are encouraged to arrange support services and/or accommodations through Disabilities Services staff located in Loyola 100, (206) 296-5740. Disability-based adjustments to course expectations can be arranged only through this process.

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Chemistry 255: Foundations of Organic Chemistry I

Seattle University

Expectations and Advice for Success

Welcome to the winter quarter of organic chemistry! In this class you will gain a treasure trove of information and concepts that is central to a host of fields including drug discovery, biochemistry, molecular biology, materials science, nanotechnology, and food science. Not only is organic chemistry an extremely practical field of study, but organic chemists exercise extraordinary measures of creativity when solving problems and making new discoveries. Thus, even one with no practical interest in the natural sciences can appreciate organic chemistry for its historical integrity and intellectual aesthetics. Learning organic chemistry can be very challenging. Contrary to advice you may have received, success in this course is not dependent on your ability to recall copious amounts of information that youve crammed into your mental hard drive. Memorizing may allow you to keep your head above water for a time, but ultimately it will prevent you from performing well in the course. The key to success in organic chemistry is to identify and articulate the fundamental concepts that link together information, and to learn how to apply these concepts to unfamiliar problems. Once you have gained mastery over fundamental concepts in organic chemistry, memorizing reactions and mechanisms becomes unnecessary because you will be equipped to successfully predict the outcome of even unfamiliar reactions. In this course, you will learn the key chemical concepts and you will practice applying them to new situations. My job as the professor is to create a learning environment that will help you gain conceptual fluency and problem solving ability. In my lectures, I will identify common threads that unify information, and emphasize fundamental concepts. We will use chemical models in the classroom when appropriate to provide a hands-on 3-D representation of what we are discussing on the chalkboard. Supplemental inclass group activities, problems-of-the-day, and recommended book problems are designed to provide you with experience applying fundamental concepts to unfamiliar situations before you are asked to do so on an exam. I strongly encourage you to attend office hours to discuss with me any difficulties you might be having with the material or doing problems, and to describe any new insights you want to test. My job is to create an engaging learning environment your job is to do the learning. Mastering organic chemistry requires a very high level of involvement in the course. What do I mean by involvement? Merely taking notes, reading the book , and outlining chapters is insufficient. If you do all the problems quickly, in a disengaged manner, with your solutions manual in hand, you wont be successful either. Read the text assignment before class and do all the textbook problems, but do this with model kits in hand, drawing out reaction mechanisms in grizzly detail, searching for conceptual threads, discussing problems and new understandings with your classmates. Engage organic chemistry with this type of enthusiasm, and you will be well prepared for the exams. Some High Quality Learning Resources at Seattle University Your professor is an excellent resource for you in this course. Both Chem 255 professors have dedicated office hours specifically for you; appointments are also available. The SU Writing Center is not to be considered as a place for remedial writing but as an asset for good writers, or writers who desire to get better, who recognize that good writing is the result of dialogue, idea sharing, exploratory drafting, and all the other useful exercises that ought to take place before the submission of a final draft. See: seattleu.edu/writingcenter/ The SU Learning Center has numerous resources for you including, Tutoring services, individual consultations, study groups, and workshops. For more information, see: seattleu.edu/sas/learningassistance/Default.aspx?id=29100 Excellent handouts on numerous useful topics. For more information, see: seattleu.edu/sas/learningassistance/Inner.aspx?id=29302&linkidentifier=id&itemid=29302 Anxiety & Stress Learning Styles Memory Note taking Class participation Reading Study groups Test preparation Test taking Time management Writing

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Chemistry 255: Foundations of Organic Chemistry I

Seattle University

Tips for Studying Organic Chemistry

Read the text before coming to class. You can only truly participate in class discussions if you have done the readings beforehand. The questions you generate from partial understandings are the best and most effective fuel for classroom discussion. You are responsible for everything in the assigned reading, including material that we do not cover in class, as well as all the problems in the textbook. Participate in class. Class meetings are designed primarily to summarize selected topics in the reading and to discuss our collective understanding of the material, not a time to merely take notes (i.e., avoid being in court transcriptionist mode so that you can try to understand later). It is incumbent upon each of you to contribute to this discussion and to stop me if a point is not understood. Catching up on your sleep in class is the least effective form of class participation. Devote sufficient time to organic chemistry. School is perhaps best thought of as a job. For every classroom hour, we expect that you invest another 3 hours toward reading and homework. If you are taking three five-credit classes, this adds up to 36-40 hours per week, or the commitment for a full-time job. Many of you also have extracurricular activities, athletics, family responsibilities, and/or work-study positions, which require time. Similarly, many non-students have full-time jobs and lead Scouts, volunteer for EMS, serve in the National Guard, sing in a choir, or work at an additional part-time job. Having a well-rounded life is important, but just as the primary occupation for non-students must remain a high priority, so too your coursework must remain a high priority, regardless of your other commitments. Utilize your time efficiently and effectively. Make sure you study at a time when you are alert and focused. Studying to the stereo or television might seem to ease the pain of academic effort, but these ultimately serve as distractions. Organic chemistry deals with abstract concepts, and you must allow yourself the mental space and time to formulate ideas without having your thoughts vaporized by intrusion from distractions. Do not cheapen the value of problems by looking at the solutions manual before you struggle and think. Rationalizing a study guide answer is not the same as solving a problem. If you cant figure out an answer and you have to take a stab in the dark, then do so this is what you would do during an exam. When you ultimately check your answers, re-tune your study focus to problems that challenged you. Eventually, you will see trends in the difficulties that you have; this makes an excellent set of questions to bring to office hours or study groups. Work in small groups. Form your own study groups or go to the Learning Center to join a study group. Practice explaining concepts and problems to one another. Teaching provides for deeper understanding, and remember that you will teach your professor what you have learned when you take the quizzes and exams. Participate meaningfully in office hours. Focused discussion with faculty is another way to deeper your understanding. Come to office hours with questions prepared merely basking in a faculty members presence will not have a significant impact upon your learning. Dont wait until the day or two before an exam to come to office hours . Take care of yourself. Sleep deprivation and substance abuse rob you of your academic potential. These issues can often be addressed by the application of good judgment and prioritization of time. However, if you find yourself in a difficult behavior pattern, then seek help. A good starting point is Counseling and Psychology Services (CAPS; seattleu.edu/CAPS/).

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