Chemistry 331 Concepts of Organic Chemistry I Fall 2012 Section 01

Chemistry 331 Concepts of Organic Chemistry I Fall 2012 Section 01 Instructor: Danielle Solano, Ph.D. Assistant Professor of Chemistry Office: Science II 271 Phone: (661) 654-2785 Email: dsolano@csub.edu Course Website: https://bb.csub.edu/webapps/login/ Lecture: Mon/Wed/Fri 1:00-2:10pm in TBA (CRN 80836) Laboratory: Section 02 ~ Tue 12:45-3:15pm in Science II 278 (CRN 80837) Section 03 ~ Tue 3:30-6:00pm in Science II 261 (CRN 80838) Office Hours: Mon/Wed/Fri 2:15-3:45pm Online Office Hours: Tue 8:00-9:00pm Description Chemistry 331 is the first quarter in a yearlong series on the study of the structure and reactivity of organic compounds. One year of general chemistry (CHEM 211/212/213 or equivalent) is a prerequisite for taking this course. Course Objectives By the end of the CHEM 331/332/333 series, you should be able to demonstrate knowledge of the foundations and contexts of organic chemistry and how it is incorporated and builds on all other areas of chemistry by achieving the following objectives: 1. Name organic compounds using IUPAC nomenclature. 2. Identify organic compounds based on an IUPAC name. 3. Use appropriate terminology to describe and identify different types of organic compounds. 4. Draw organic structures both in two and three dimensions. 5. Analyze organic structures in three dimensions and evaluate the consequences on chemical reactivity and stability. 6. Predict the outcome of organic reactions as well as the reactants necessary to prepare a given organic compound. 7. Represent reactions and reaction mechanisms using the appropriate formalisms. 1

8. Use bonding theories as well as kinetic & thermodynamic considerations to understand reaction patterns. 9. Develop the synthesis of an organic molecule. 10. Work safely in the laboratory and work effectively as a member of a laboratory team. 11. Understand the use of instrumental analysis (IR, UV-Vis, MS, NMR) in organic chemistry. 12. Evaluate experimental results and effectively communicate results orally and in writing. You will be assessed on your achievement of these objectives via the ACS Organic Chemistry exam. Course Materials You can often find these items cheaper online than at the bookstore. I recommend using http://thecollegetextbooks.net/ which compares several websites to find you the best deal possible. 1. Organic Chemistry, 8th ed., by John McMurry, Publisher: CENGAGE Learning, 2011, (ISBN-10: 0840054440, ISBN-13: 9780840054449). If you buy the text from the bookstore, it is available in loose leaf form and comes with the ebook (ISBN: 9781285144658). You can also opt for the version of the textbook that comes bundled with the study guide and solutions manual (ISBN: 9781285128900). If you only want the ebook (cheapest option) it is available at: http://www.coursesmart.com/. 2. A Sapling Learning Account. We will be using Sapling Learning for our homework this quarter Sapling. To get started, go to http://www.saplinglearning.com/. If you already have a Sapling account, login to your account, click "View Available Courses". (If you don t already have a Sapling account, click "create account" located under the username box instead. Supply the requested information and click "Create my new account". Check your email for a message from Sapling Learning and click on the link provided in that email.) Find your course in the list (CSUB - Chem 331 - Fall12 - SOLANO) and click the link. Select your payment options and follow the remaining instructions. Once you have registered and enrolled, you can log in at any time to complete or review your homework assignments. If you have any technical problems or grading issues, send an email to support@saplinglearning.com explaining the issue. 3. i>clicker, by Macmillan (MPS), Publisher: W. H. Freeman, 2006 (ISBN-10: 0716779390, ISBN-13: 978-0716779391). A classroom response system that allows students to instantly provide feedback and answer questions posed in class. 4. A molecular model kit. While not required, a molecular model kit is helpful for understanding stereochemical implications of reactions. If you don t have one, you can purchase one from the chemistry club or online (I recommend HGS 1013A Organic Chemistry Set for Student ). 2

Assignment of Grades Your grade will be determined based on the percentage of points you receive in the course. Greater than 90.0% of the total possible points = A/A-, 80.0 89.9% = B+/B/B-, 70.0 79.9% = C+/C/C-, 60.0 69.9% = D+/D/D-, 59.9% and below = F. I reserve the right to lower these lines, but promise not to raise them. For example, if you earn 80.5% of the total possible points, you are guaranteed at least a B-, but you might receive a B or better. (Note: Last year in CHEM 331 the cutoff for a C- was 68%.) Point Distribution The lecture portion of the course is worth 80% of your overall grade. For more details regarding the lab portion of the course, see the syllabus supplemental for your lab section. Percentage of Grade Lecture 80% Sapling Learning 15% In-Class Quizzes 10% Midterm Exams 33% Final Exam 22% Each assignment is designated a certain number of points based on its percentage of your grade. While I may occasionally make a small error assigning the correct number of points, you can get a very good estimate of your current grade in the class by adding up all of the points you have received, dividing that number by the points possible, and multiplying by 100%. Sapling Learning Ten homework assignments will be conducted and graded online using Sapling Learning. Assignments are due Mondays at noon. You will have unlimited attempts to answer each question, however each incorrect attempt will result in a 5% deduction in the points assigned for that problem. You are allowed 4 one-day extensions that may be used all at once or one at a time (email me to request an extension). I recommend you initially attempt the quizzes on your own, but feel free to ask for help from classmates or at office hours if you do not understand what the question is asking, or if you answer a question incorrectly after one or more attempts. In-class Quizzes Six in-class quizzes will be conducted at the beginning of the lecture period on the dates indicated in the course schedule. They will cover all material through the previous lecture (yes, they are cumulative) and consist of i>clicker questions, group work, or a mixture of both. (Note: If you ever have a disagreement with your group on the answers to the group portion of a quiz, you will always have the option to submit your answers individually.) Your lowest in-class quiz grade will be automatically dropped. No makeups are allowed, so use your dropped quiz wisely! 3

Exams Examinations will be administered on the days specified in the course schedule. Only in extreme cases (e.g., illness, hospitalization, death in family), and with prior notification, will other arrangements be allowed. These exams are cumulative. Re-grading of Assignments In rare circumstances, grading mistakes will occur. In the event of a grading error, return the graded assignment within 72 hours of receiving it. In order to be eligible for a regrade, you must not have changed or written on the assignment, and you must include a brief note stating why you would like to receive a re-grade. Keep in mind that a regrade means just that. There is no guarantee that your score will go up (and occasionally your score may go down)! Students Repeating CHEM 331 If you are repeating CHEM 331, the current department policy is that you do not have to repeat the lab if you: (1) previously took CHEM 331 at CSUB, and (2) received a lab grade of 80% or higher. You are only allowed to use your previous lab score a single time. As we are currently making changes to our lab curriculum, this policy is subject to change. Laboratory Chemistry is an experimental science and, therefore, the laboratory is an indispensable portion of this course. The principal objectives of the lab are to learn organic laboratory techniques and professional methods of record-keeping/reporting. For more details regarding the lab portion of the course, see the syllabus supplemental for your lab section. Attendance Policy While regular lecture attendance is not required, it is strongly encouraged. Students who regularly attend lecture tend to do better in this course. If that isn t enough encouragement, occasionally you will have the opportunity to receive extra credit points via i>clicker questions. (You must have a registered and functioning i>clicker in order to receive these points.) Extra Credit I will occasionally provide opportunities to receive extra credit points for answering designated i>clicker questions correctly, attending chemistry seminars, or completing other organic chemistry-related activities and assignments. While these extra points often make the difference for a student that is close to the next grade level (e.g., boost a grade of A- to an A), it should be noted that they are not significant enough to make up for consistently poor performance in the course. All extra credit opportunities will be made available to all students (under no circumstances will exceptions be made). 4

Academic Integrity Academic dishonesty (cheating) will not be tolerated. CSUB s policy on academic integrity defines academic dishonesty as a broad category of actions that involve fraud and deception to improve a grade or obtain course credit. Some examples include (but are not limited to): looking at another student s answers during an exam, plagiarism, using a cell phone during an exam, falsifying lab data, and using an i>clicker that is not your own. If you are unclear as to what is considered academic dishonesty in this course, ask me. In the event of a violation of the university's policy of academic integrity, I will notify the CSUB Dean of Student Life, the CSUB Student Conduct Coordinator, and the student(s) involved, and then assign a grade penalty that I deem to be appropriate. For more information on the university s academic integrity policy, go to: http://www.csub.edu/studentconduct/documents/academicintegritypolicy.pdf Classroom Behavior Students who disrupt class, fail to respect others confidentiality and privacy, or create an unsafe learning and working environment for others will be asked to leave. This means you must silence or turn off your cell phones before class begins, and do not talk to other classmates during lecture unless instructed to do so. Students with Disabilities Students with disabilities requiring modification of seating, testing, or other class procedures should contact the Office of Services for Students with Disabilities (SSD) as soon as possible. Once you have an accommodation letter from the SSD Office documenting that you have a disability, contact me so that we can discuss the specific accommodations you might need in this class. Learning Organic Chemistry To aid you in learning organic chemistry, recommended readings, problems, and chapter objectives are listed on the course website. However, if you are to be a successful student in this course, you must discover how you learn organic chemistry best. Different people learn in different ways; try lots of ways to study until you find the ones that work for you. Your Personal Learning Style Understanding your personal learning style may help you develop more effective ways to study organic chemistry. You can try to identify your learning style by taking the VARK questionnaire at: http://www.vark-learn.com/english/page.asp?p=questionnaire. VARK also suggests study tips for different learning styles. Practice, practice, practice! You can t learn organic chemistry by cramming the night before the exam. It requires practice and hard work. Organic chemistry has often been described as a language: you 5

have to memorize the vocabulary, study the grammar, and then practice before you can communicate effectively. Given that, here are some things that have worked for me, and students I have taught. Test them out to discover which are most effective for you: 1. Summarizing the lecture notes 2. Reaction flash cards 3. Reaction drill sheets 4. Working practice problems 5. Talking about the material with others (i.e., studying with a group) 6. Doing practice exams Advice from previous CHEM 331 students From day one, stay on top of all assignments, studying for quizzes and exams. Study and review every day. If you fall behind, it's at least 4 times harder to catch up. DON'T allow yourself to fall behind! Ask for help during office hours. Attend all lectures and help sessions - they really do help to reinforce the material and clarify any questions you may have. Treat this like learning a new language - the more you practice, the better you become. Dr. Solano is very willing to help you - take advantage of that by asking any questions you have! Don't fool yourself into thinking that you'll be fine if you just do the minimum and cram before exams - you will definitely be in for a rude awakening when you fail. Instead, set yourself up for success from the beginning by starting with good study habits. Study, study, study! That's what your always told in classes and sometimes you find yourself passing those classes with a good grade and without even trying much, but when it comes to this one, you need to get serious with the studying. Make sure to make good use of the online office hours!!! They really are helpful when trying to learn and understand Ochem 331, and also if Dr.Solano offers to do an on campus study session, GO!!! It really helps to study for midterms or Finals. One last thing, PLEASE STUDY! study study study! It will make such a huge difference, Ochem 331 can be your best friend or your enemy, it depends what you make it. Good luck. Getting a good grade in O-Chem is like a stool, you need to make sure all three legs are there to support you: you need to 1) attend lectures, 2) read the chapters, and 3) do the practice problems or else you'll end up on your rear end looking foolish. Read the appropriate chapter in the book before going to lecture so that lecture will strengthen your understanding of the concepts. I would also recommend going through the lecture notes and translating the major concepts onto a blank sheet of paper to use when studying for the exams. Keep these notes throughout the quarter and use them to study for the final. Study every lecture after it is reviewed in class. Don't fall behind. Stay on top of the material. 6

Learning organic chemistry is like learning a new language: you get better the more you use it. Reread notes, do practice-problems, communicate with classmates, and go to office hours. If you make a mistake, make an effort understand why you were wrong. The class may be tricky, but digestible. Be on your guard for what's about to come. Chem 331 is such a challenging course in which a lot of time devoted to studying and practicing practice problems daily is much required to successfully understand the presented material better. Chemistry 331 is the class will require treating your brain like a muscle. Practice daily to get desirable results. This is a very difficult course, memorizing is not as important in this course as being able to apply those concepts to problems. Expose yourself to as many problems as possible. DONT SLACK DONT SLACK DONT SLACK. THIS STUFF SNOWBALLS INTO A GIANT HEAP OF ORGANIC CHEMISTRY BOULDER ROLLING DOWN THE GRAPEVINE AT 80 MPH, CRUSHING SLACKERS, LAZIES, AND THE UNPREPARED IN ITS PATH. OH YEA AND THE BALL IS ON FIRE. Email Tips To increase the chances of my picking out your email from the spam, please include a descriptive subject (e.g., question about tomorrow s CHEM 331 quiz is better than question, and both are infinitely better then no subject at all). Also, please remember to include your full name in the body of the email. While I do my best to respond to your emails in a timely fashion, please be patient if I cannot. However, if you do not receive a response from me within 48 hours, I recommend sending another email just to make sure I received your message. 7

Course Schedule*** Date Day Material Covered Items due 9/10 Mon Review / Structure & Bonding 9/12 Wed Structure & Bonding / Acids & Bases 9/14 Fri Acids & Bases /Alkanes & Cycloalkanes 9/17 Mon Alkanes & Cycloalkanes Sapling #1 9/19 Wed Quiz #1 9/21 Fri Alkanes & Cycloalkanes 9/24 Mon Alkanes & Cycloalkanes/ Stereochemistry Sapling #2 9/26 Wed Midterm Exam #1 9/28 Fri Stereochemistry 10/1 Mon Stereochemistry Sapling #3 10/3 Wed Quiz #2 10/5 Fri Stereochemistry/ Alkenes 10/8 Mon Alkenes Sapling #4 10/10 Wed Quiz #3 10/12 Fri Alkenes 10/15 Mon Alkenes Sapling #5 10/17 Wed Midterm Exam #2 10/19 Fri Alkenes / Alkynes 10/22 Mon Alkynes Sapling #6 10/24 Wed Quiz #4 10/26 Fri Alkynes / Delocalized Electrons 10/29 Mon Delocalized Electrons Sapling #7 10/31 Wed Quiz #5 11/2 Fri Delocalized Electrons 11/5 Mon Delocalized Electrons / Substitution Reactions Sapling #8 11/7 Wed Midterm Exam #3 11/9 Fri Substitution Reactions / Radicals 11/12 Mon HOLIDAY NO CLASS Sapling #9 11/14 Wed Quiz #6 11/16 Fri Radicals 11/19 Mon Review Sapling #10 TBA TBA Final Exam ***Please note that this schedule is only a close approximation. Pay close attention for possible changes. 8

Chemistry 331 Concepts of Organic Chemistry I Fall 2012 Syllabus Supplemental (Sections 02 & 03) Instructor: Danielle Solano, Ph.D. Assistant Professor of Chemistry Office: Science II 271 Phone: (661) 654-2785 Email: dsolano@csub.edu Course Website: https://bb.csub.edu/webapps/login/ Lecture: Mon/Wed/Fri 1:00-2:10pm in TBA (CRN 80836) Laboratory: Section 02 ~ Tue 12:45-3:15pm in Science II 278 (CRN 80837) Section 03 ~ Tue 3:30-6:00pm in Science II 261 (CRN 80838) Office Hours: Mon/Wed/Fri 2:15-3:45pm Online Office Hours: Tue 8:00-9:00pm Additional Course Materials You can often find these items cheaper online than at the bookstore. I recommend using http://thecollegetextbooks.net/ which compares several websites to find you the best deal possible. 1. Student Lab Companion: Laboratory Techniques for Organic Chemistry (2nd Edition), by John Lehman, Publisher: Prentice Hall, 2008 (ISBN-10: 0131593811, ISBN-13: 978-0131593817). While handouts of labs will be provided, this lab companion is recommended to provide you with a detailed description of the laboratory techniques that will be used. 2. Chemistry Drawing Software. The department has purchased a site license to use ChemDraw Standard (http://www.cambridgesoft.com/software/chemdraw/). This software is available for use on department computers (Science II 176). If you would like to download the software for use on your personal computer, contact Dr. Solano. 3. A bound laboratory notebook with duplicate pages. I recommend the Organic Chemistry Spiral Bound Notebook from Hayden-McNeil (ISBN: 978-1-930882-46-1), although you are welcome to use any lab notebook of this type. Point Distribution The laboratory portion of the course is worth 20% of your overall grade. For more details regarding the lecture portion of the course, see the lecture syllabus. 1

Percentage of Grade Lab 20% Prelabs 6% Lab Reports 7% Lab Notebook 6% Lab Citizenship 1% Prelabs Prelabs will be conducted and graded online using Blackboard. They are due at the beginning of the lab period. For safety reasons, you will not be allowed to begin the experiment until your prelab assignment is complete. Keep in mind that if you spend lab time completing your prelab assignment, you may not have time to complete the lab and will subsequently lose lab citizenship points and/or points on your lab report. Lab Notebook You must have a bound lab notebook and bring it to every lab period. You must include a complete and detailed description of every experiment so that a peer could reproduce your results if necessary (see Appendix II in Lehman for more information). Some organization and neatness is required, but your goal is to record all procedures and observations accurately, not to have a "pretty" notebook. Lab notebooks will be graded at various unannounced times during the quarter. If you are absent or do not have your lab notebook at these times, you are not eligible to receive any points. Important lab notebook pointers: 1. All entries must be made in permanent ink. 2. Mistakes should be corrected by drawing a single line threw through them. 3. Never write information on loose paper! 4. Include a table of contents and number each page. 5. Certain information may be prepared prior to lab (e.g., title, date, reaction scheme, physical data for reagents, hazards, calculations, references), but experimental details must be recorded DURING the lab period. Lab Report Lab reports are due as indicated on the schedule. They must be submitted online before the beginning of lab using Blackboard (SafeAssign). For labs 2 and 3, a physical copy of your lab report must also be submitted (turn in to the instructor at the beginning of the lab period). Five points will be deducted for each day either the electronic or physical copy is late. Unless otherwise indicated, write your report as if you are submitting a paper to the Journal of Organic Chemistry (view J. Org. Chem. 2011, 76, 7569 7572 or any other recent Journal of Organic Chemistry article for a good example). While the specific content will vary a bit from lab to lab, the following is a list of sections that must be included in all reports: 2

1. Abstract (1 paragraph): Two to five sentences summarizing the purpose of the study and your results. 2. Introduction (1-2 paragraphs): Include applicable background information and a description of the purpose of the study. If applicable, state your initial hypothesis (support your hypothesis with references wherever possible). Also outline your experimental strategy (don t include experimental details; just explain your general plan of attack in a sentence or two). 3. Results and Discussion (2 or more paragraphs): Summarize and explain your experiment and your results. While you should talk about your experiment here, remember to save the details (like amounts of reagents used, etc.) for the experimental section. Explain how your experiment worked, and the purpose of each step and/or component. Then describe each result and what information it gave you (i.e., discuss your hypothesis, then how and why your results support or contradict your hypothesis). When discussing a product, be sure to address issues such as product identification, purity, and percent yield. If your results are inconclusive or inconsistent, mention that here and suggest possible sources of error. Don't forget to include any applicable figures, schemes, and/or tables. 4. Conclusion (1 paragraph): Summarize your main findings and explain why they are significant. Suggest studies you might conduct to confirm your results if you had more time and/or resources. 5. Experimental Section (1 paragraph): Include enough detail so that a peer could reproduce your results. (If you keep a good lab notebook, you will just have to type up what you wrote in it.) Don t forget to include any important observations such as the color of your solution, appearance of crystals, yield (grams and percent yield), melting point (apparatus, recorded, equation, and corrected), and/or spectroscopic data (any IR and HNMR values must be reported in ACS standard format). Be sure to use past tense to describe what you did, and use a passive voice (e.g., instead of saying I put HCl in the flask or Add HCl to the flask, say HCl was added to the flask ). 6. References: Helpful in case someone wants to reproduce your study and/or confirm your findings. You should be sure to cite your references in text and list them in the style of the American Chemical Society (ACS). See the section on Proper Method for Citing and Listing References for more information. Don t forget to include obvious references like Catalyst and/or Lehman. Lab Citizenship Good lab citizens have respect their peers, follow good scientific practices, and maintain a safe environment. If you follow these guidelines, you will receive all lab citizenship points. Some ways you may lose points include (but are not limited to): leaving a mess at the balance, removing your goggles during the lab period, showing up to lab wearing flip-flops, not recording results in your lab notebook, and continuing lab work past the end of the lab period. 3

Labs The following is the list of labs that will be completed this quarter. The portion in italics indicates how your lab report should be submitted. (Note: If you ever have a group member that is unable and/or unwilling to contribute to a team report, you will always have the option to leave that person s name off of your report or submit your report individually.) Lab 1 Lab 2 Lab 3 Lab 4 Lab 5 Lab 6 Maintaining a Laboratory Notebook (No Report Required) Melting Point (Team) Extraction (No Report Required) Recrystallization (Partners) Separating and Identifying the Components of a Mixture (Individually) Service Learning (Team) Safety Safety should be everyone's primary concern. In most cases of safety violation, you will receive a warning and lab citizenship points will be deducted. Extreme or continual safety violations will result in dismissal from lab. You must be present for the safety lecture in the first lab class, read the Safety in the Organic Chemistry Laboratory handout, turn in your safety contract, and complete the safety quiz online using Blackboard. Before coming to lab It is in your best interest to come prepared to lab. This includes reading any relevant information in Lehman and/or the lab manual. Additionally, you must complete the prelab online using Blackboard and come to lab with any necessary items noted from the prelab in your notebook. If you do not come adequately prepared to lab, you may run out of time to complete the experiment! At the end of lab All lab work must stop 10 minutes before the end of the lab period to allow time for cleanup. Before leaving make sure that your area is clean, and check with me to see if any of the common areas need cleaning. If the lab is left messy, everyone will lose lab citizenship points! Don t forget to collect all the data you need for your lab report before you leave. Lab Make-ups If you must miss a lab, you risk not being able to complete all of the experiments! Contact me as soon as possible after missing the lab to make arrangements. The easiest thing to do is to makeup the lab in another lab section, but for safety reasons, this will only be allowed if space is available. 4

Helpful links I will maintain a list of useful links on the course website. The most important one is: http://www.sigmaaldrich.com/. (This is where you get all of the information about the hazards of the chemicals you will be using in lab.) Course Schedule*** Date Day Material Covered Items due 9/11 Tues Check-in & Safety 9/14 Fri 9/18 Tues Lab 1 Safety Quiz / Lab 1 Prelab 9/21 Fri 9/25 Tues Lab 2 / Lab 3 Lab 2 Prelab /Lab 3 Prelab 9/28 Fri 10/2 Tues Lab 2 / Lab 3 Journal Article Quiz 10/5 Fri 10/9 Tues Lab 4 Lab 4 Prelab 10/12 Fri Lab 2 Report 10/16 Tues Lab 5 Lab 5 Prelab 10/19 Fri Lab 4 Report 10/23 Tues Lab 5 10/26 Fri 10/30 Tues Lab 5 11/2 Fri 11/6 Tues Lab 6 11/9 Fri Lab 5 Report 11/13 Tues Cleanup & Check-out 11/16 Fri Lab 6 Report ***Please note that this schedule is only a close approximation. Pay close attention for possible changes. 5