SYLLABUS THE UNIVERSITY OF MARYLAND ORGANIC CHEMISTRY II LECTURE

CHEMISTRY 241 Lecture Discussion

Mondays Wednesdays

6:30 - 9:30 PM 6:30 - 7:30 PM

SPRING 2012 PLS 1130 PLS 1184

INSTRUCTOR: Dr. Howard M. Fribush; [email protected] (Mon−Fri); (703) 603-8831 (voice mail); [Address: Department of Chemistry & Biochemistry; University of Maryland; College Park, MD 20742] Feel free to call or email the instructor with any questions you may have. You may also schedule a conference if you prefer. REQUIRED BOOKS Loudon, Marc, Organic Chemistry, Fifth Edition. ISBN 978-0-981-5194-3-2 RECOMMENDED BOOKS AND MATERIALS There are several organic chemistry educational aids that can help you immensely with this course and which are highly recommended. Some of these are listed below. 1. Loudon, M. and Stowell, J.G., Organic Chemistry, Study Guide and Solutions Manual. ISBN 978-0981519449 (Answer guide) 2. Molecular Models. If you don‘t already have models, you can purchase a model set with rigid plastic sticks for bonds. These can be purchased for about $15 at http://www.molecularvisions.com/Molecular-Model-Kits/Kit-3AV-Molecular-Model-Set-ISBN978-09648837-6-5/prod_8.html (Kit #3AV is recommended). Organic chemistry is a threedimensional science; a molecular model kit is an indispensable tool for understanding the spatial arrangements of the molecules we will be studying and for working problems. 3. Chemistry 241 Evenings Website. Check the site regularly for announcements and handouts. Go to the course website at www.elms.umd.edu for information on the course and to assist you in learning organic chemistry. In the module entitled ‗Course Information,‘ read ‗What You Can Expect,‘ ‗Frequently Asked Questions,‘ and look at what other schools say about the course - this is recommended even if you have done something similar for Organic I. Read the syllabus and navigate the site. To access documents, make sure your browser is compatible with Blackboard and that you have the latest version of Adobe. If you cannot open a document, save it to your desktop and open it there. Website help can be accessed at (301) 405-1500. Keep your email address up to date. Go to http://www.testudo.umd.edu/, click on ‗Keep your email address up to date‘, and be sure that your email address is the one you normally use. If your email is not current, you will not receive any email messages from the instructors.

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COURSE DESCRIPTION, DESIGN, AND OBJECTIVES We will continue looking at the nomenclature (naming), molecular structures, properties, synthesis and reactions, and mechanisms of reactions for additional classes of compounds. Organic molecules are the building blocks of all living things, of other naturally-occurring substances, such as petroleum and coal, as well as many synthetic products. Examples include antifreeze and alcohols, antibodies and androgens, biochemicals and benzene, caffeine and cholesterol, detergents and drugs, enzymes and explosives, herbicides and hormones, nicotine and narcotics, nylon and nucleic acids, pesticides and pheromones, polymers and plastics, peptides and proteins, sugars and starch, saccharine and steroids, and testosterone and toxins. Since organic chemistry is associated with nearly every aspect of our existence, we would be wise to understand it as best we can. This course will be of a blended lecture format with opportunity for questions and discussion. Grades are mainly based on exams, but could include homework, attendance, participation, quizzes and/or drills. The overall objectives of the course are to broaden your knowledge of and enhance your appreciation of organic chemistry, to show you, where possible, applications of organic chemistry in everyday life, and to prepare you for more advanced, related curricula. Secondary objectives are associated with the course requirements, and are outlined as follows. The lectures and exams are designed to stimulate curiosity about the relationships among the different classes of organic molecules, and to encourage creative thinking. The purpose of quizzes or drills, if included, is to assist you in learning the basics of each topic, so that you are not overwhelmed by the time you start studying for the exams. The purpose of homework is to reinforce basic ideas of organic chemistry, make interconnections between concepts, and develop skill in the analysis of problems. The laboratory, which is a companion course to this one, has been designed to increase your expertise in handling chemicals, learning basic techniques and safety, and to develop skill in interpreting factual data. Organic chemistry is the basis for biochemistry, medicinal chemistry, and pharmacology. But perhaps most importantly, the creative problem-solving techniques you will learn in this course will help prepare you for a career in fields that also involve creative problem-solving, such as engineering, science, or health care. Learning organic chemistry will help you develop critical academic discipline, effective study habits, and flexible learning skills, learn how to think creatively and the ability to work through new problems and situations, and learn to read technical information with ease. Organic chemistry, perhaps to a greater extent than many other courses, provides an index to the student's ability to learn and retain a lot of material – fundamentals – in a relatively short period of time, assimilate information to analyze, classify, and predict, and to use the information in an active, creative way to carry out the prediction. This approach parallels the study of health care: health related fields require students to learn and retain a lot of fundamental material in a short period of time, and a medical professional uses an understanding of fundamentals to analyze, classify, diagnose, and to use the information to treat, sometimes creatively. Course Outcomes 1. Name common acyclic or cyclic organic compounds consistent with the structural formula and draw the correct structure of the compound corresponding to its name. 2

2. Identify reactive sites in molecules and ions and predict/explain the relative reactivities of substances based on structural (inductive, electronic, resonance, steric) effects. 3. Identify stereochemical relationships and draw structures of stereoisomers using conventional notations to express the correct absolute configurations of molecules containing chirality (or asymmetric) centers. 4. Use the concept of hybridized orbitals and bonds to explain the geometry and reactivity of common organic compounds. 5. Predict and explain predominant reaction pathways of substitution, elimination, addition, and rearrangement reactions based on accepted notations depicting electron flow, or on an analysis of thermodynamics and kinetic theory. 6. Describe the role of nucleophiles, electrophiles, free radicals, acids, and bases in organic reaction mechanisms. 7. Predict reaction products of and suggest appropriate reagents to perform organic reactions on examples similar to those studied in the course. 8. Describe and interpret various spectroscopic methods of analysis. 9. For laboratory, demonstrate the ability to operate basic instrumentation, conduct basic experiments, gather data, analyze data, and generate conclusions in a laboratory or observational setting. 10. The most important things you will learn by taking organic chemistry are (a) how to solve problems, (b) how to mange your time, (c) motivating yourself, and (d) good study habits. The professional graduate schools want to see good grades in organic chemistry, not because they want you to know the details of organic chemistry, but because a good grade indicates that you have learned to solve problems, manage your time, become self-motivated, and developed good study habits, which will give you a very good chance of succeeding as a doctor, a dentist, or a veterinarian COURSE REQUIREMENTS First exam Second exam Third exam Final exam Online Homework Totals

20 % 20 20 20 20 100.0 %

100 points 100 100 100 100% 500 points

In addition to exams, each week you will need to read, take notes, work problems, review, and ask questions to help understand the material.

GRADING The course is normally curved from the standard academic grading scale. In determining the curve, all or parts of the standard scale may be adjusted to account for variations in exam and class averages. The grading scale will normally not be entirely consistent among the individual exams, and the final curve may differ somewhat from the individual exam averages/ grades. Additional information is provided in the document entitled ―Frequently Asked Questions and their Answers,‖ which can be found in the Course Information module on the course website. In addition to the course requirements, grades may reflect lecture and discussion attendance, and participation.

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COURSE POLICIES You are responsible for knowing the course policies, any changes as indicated in announcements posted on the website, and for keeping current on all required and suggested work. 1. Exams ● ● ●

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Focus mostly on lecture including problems, assigned problems, and any handouts

Each exam is designed to take 50 minutes. You will typically be given about 75 minutes to complete each exam. You may not leave the room during the exam. Exams should be taken using black ink for an exam to be eligible for a re-grade. Calculators or other electronic devices (cell phones, hand-held devices, etc) are not necessary or permitted. All exams must be turned in for a grade by the time the exams are collected, or no credit will be given for that exam. Organic chemistry, and thus exams, tend to be cumulative. Exams will focus on the material covered since the last exam; however, you are still responsible for information presented previously. This is because organic chemistry builds upon the previously-covered material. Every year, most students think that their exam is more difficult than the exams given in the previous year. University policy requires students to produce identification before taking an exam when asked, and requests students to write and sign an honor pledge (http://www.jpo.umd.edu). Re-grades. If you have some questions on the grading of your exam, you can submit it for re-grading no later than one week after the exam is returned. Attach the re-grade form (available in the Syllabus tab on the course website) to the exam that explains the problem and submit the exam to the instructor on the day the examination is returned. Do not write or mark on the exam, or it will not be re-graded. Exams taken in pencil will not be regraded. The entire exam will be re-graded. If the answer to a question is not clear, such that the answer indicates you (a) were not able to determine the answer or (b) did not understand the question, no credit will be given for that answer.

Make-Up Exams A make-up exam will be given only for excused absences for illness (self or dependent), religious observances, participation in University activities at the request of University authorities, and compelling circumstances beyond the student's control (i.e., true emergencies). An injury or illness that is too severe or contagious for the student to take a scheduled exam will need to be documented at the time the injury or illness occurs. Students must submit the request in writing and supply appropriate documentation to the instructor‘s satisfaction that describes the student‘s inability to take the exam on the scheduled day or at the scheduled time. The University states that conflicts with work are not considered a compelling circumstance that would necessitate a make-up exam. Therefore, check your schedule as soon as possible and adjust it accordingly, and make any needed arrangements now to be sure you are available to take an exam on the date that it is scheduled, as well as the following week in case the exam is postponed. The university's policy for excused absences is here: http://www.umiacs.umd.edu/users/resnik/ling773_sp2009/excused_absence.html. 4

Once you qualify for taking a make-up exam (i.e., let the instructor know before the exam, and promptly submit official supporting documentation), you may take the make-up exam on the day on which the make-up exam is scheduled. The make-up exam is usually scheduled on the Wednesday evening before or after the final exam. The make-up exam will be cumulative and will give equal weight to each chapter that has been covered (e.g., 3-4 questions from each chapter). If you miss the make-up exam due to an excused absence and you take the final exam, you will receive an incomplete (I) for the course. If you miss two exams due to excused absences, you no longer qualify for an incomplete and will be given the option to retroactively withdraw from the course. 2. Homework. Working problems (and not cramming) are the keys to learning organic chemistry. Problems from the textbook will be suggested. Weekly online homework may be assigned, and may be mandatory (see Course Requirements on page 3). See the accompanying section in this syllabus entitled Homework. 3. Attendance. Attend every lecture - you will always learn something new. You are responsible for material covered and announcements made in class (including discussion class) whether or not you are in attendance. Our experience is that students who skip lectures do not do well in the course. Please see the instructor if you cannot be at class. You are encouraged to ask thoughtful questions during the lecture. Grades may reflect regular attendance in lecture and discussion. Please exercise common courtesy - silence your cell phone, refrain from needless talking, and enter through the rear door if you are late. 4. Recitation. Discussion class is a help session. It gives you an opportunity to ask questions about lecture material and problems with which you don‘t understand. Did we say it is an opportunity? Take advantage of it – you are paying good money for it. 5. Academic Integrity. Academic integrity is a vital component of academic success. The University has strict standards concerning academic integrity. You should be familiar with the university's academic integrity standards as outlined at http://www.jpo.umd.edu and consequences associated with deviations from these standards. All work submitted for grading must be the original work of the student whose name appears on the work. Academic dishonesty by a student in this class will result in that student's course grade being limited to a maximum grade of 'F', with official records being retained in the Central Disciplinary File located in the Undergraduate Dean's office. Webster defines plagiarism as stealing and using the ideas, writings, or work of another as one's own. Academic dishonesty includes but is not limited to the following: ● ● ● ● ● ● ● ●

Copying answers from a classmate‘s exam or quiz. Allowing a classmate to copy answers from your exam or quiz. Using some form of crib sheet during an exam or quiz. Altering an exam before submitting it for regrading. Having someone else take your exam for you. Copying some or all information from a classmate's laboratory report. Handing in a classmate's laboratory report as your own. Making up data for your laboratory report (―dry labbing‖).

Most of these, when they occur, are typically obvious to the instructors. 5

6. Class Cancellations. Classes are rarely canceled because of inclement weather. The Science in the Evening program does not necessarily follow the university‘s official policy, since that policy is geared toward the day program. Look for a communication from the instructor that will announce if class is canceled or will be held, and for any make-up procedures. Official University closings or delays can be found at (301) 405-SNOW (7669) or http://www.umd.edu (click on Weather Emergency). Additional sources of information include radio (e.g., 1500 AM or 103.5 FM), or any local TV station. If classes are held during inclement weather or other events, and you decide to attend class, be sure to arrange your schedule to give yourself plenty of time to arrive to class safely and on time. If the weather clears before this class is scheduled, class may be held. HOMEWORK Organic chemistry focuses on two general areas. (1) The first is solving problems from learned concepts; therefore, working problems is essential. Although careful reading and rereading of the text is important, reading alone is not enough. (2) The second is that you must also be able to work with the information you have just read and be able to use your knowledge in new situations. Working problems gives you the opportunity to do this. The creative problem-solving techniques you will learn in this course will help prepare you for a career in fields that also involve creative problem-solving, such as engineering, science, or health care. Working problems acts as a beginning to provide you with intellectual skills you will ultimately need in your career. You can‘t expect to tackle non-routine problems later on in your career without having experience with solving difficult ―practice‖ problems like the ones you will see in this course. ● ● ● ●

The more problems you work, the better you will understand the material, and the better you are likely to do on the exams. You will likely be provided a minimum list of recommended problems to perform. Working problems means sitting down with pencil and paper, and actively working through each problem. If you only read the question, and then read the answer in the study guide, you will not learn how to solve the problem. Textbook problems will not be checked, but feel free to ask the instructors about any of them. You should expect the exams to contain some textbook problems or similar problems.

Each chapter in your text provides different types of problems. The in-chapter exercises are placed for immediate reinforcement of new ideas just presented. The end-of-chapter problems provide additional practice and are of two types: drill and thought. Of the end-of-chapter problems, the early problems are primarily of the drill type, providing an opportunity for you to practice your command of the fundamentals. Later problems tend to be more thought-provoking, and some are real challenges to your depth of understanding, as these problems often connect current topics with those previously covered. Once you have drilled with the fundamentals, the thought problems increase your depth of knowledge – these later problems are good tests to see how well you really understand the material. Some tips on solving problems: 6

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Recognize the difference: Drills tend to reinforce new ideas just presented; they require little manipulation. Problems require you to understand the new ideas and integrate them in solving something not readily apparent. Understand. Make sure you understand what the problem is asking. Estimate. See if you can estimate the answer, or determine several possible answers. To estimate an answer, ask if this is similar to something you learned previously. Or try working backwards, from the unknown to the known. Identify a connection between the given information and the estimated answer(s), by looking for relationships between the information given in the problem and the answer, and fit the relationships together. [Given info —> Info needed —> Answer sought] Set up the problem solution following the route you have devised. This may be a series of steps that must be taken to reach the answer. Check that the answer you have obtained matches with your estimate. Ask if your answer seem to make sense, and check to see if you have answered the problem completely. Then, present your answer in a manner which befits the effort, the thought, and the imagination that you have put in to reaching an answer. In organic chemistry, the answer often involves a brief written explanation, clarified with a structural representation or diagram. Maintain a homework binder devoted exclusively to homework. See the reference, How to Solve Chemistry Problems’ on the course website in the module ‗How to Do Chemistry Things.‘

Online Homework Assignments The university is encouraging and supporting the use of multi-media and active learning techniques in its courses. Online homework may be assigned from the Sapling Learning website that correlates with the chapter problems from the textbook (see Course Requirements, page 3). The Sapling Learning online homework service is interactive – it leads you to the correct answer and gives tutorial help when needed, and requires you to work problems much the same way that you would on an exam. You must register for and purchase the online homework service at http://saplinglearning.com. The program grades your answers and assigns a score for each assignment. There will typically be two sets of 10 online homework problems per week. It normally takes about an hour to do 10 problems. Important: If you have any questions regarding administrative issues, wording of problems, or scoring, you must contact [email protected]. If you do not contact Sapling Learning, the issues will not be addressed. Background, getting started, and policies are provided in the Homework tab on the course website. HOW TO DO WELL IN ORGANIC CHEMISTRY Most people struggle with organic chemistry because they don‘t know how to study for it. The study techniques people have been using for their other courses (especially cramming and memorization) are not effective for organic chemistry because (1) the topics are heavily integrated, (2) modifications to the common examples provided are considered normal, (3) the pace of the lectures may be faster than what you have seen before, and (4) of the amount of information that is normally covered. The keys are to keep up with the material and not put off studying until the exam 7

is near – prepare for lecture, re-write your lecture notes, and review your notes and work the problems until you know it. Organic chemistry is not hard…it just requires hard work. Here are some guidelines to consider to be successful: 1. 2. 3. 4.

Attend lectures and recitation and take clear notes. Rewrite your notes if necessary. Review your notes before class and ask questions at the beginning of class. Read the appropriate sections of the text before lecture and take notes. Complete the in-chapter questions before lecture, then the assigned problems and other challenging problems at the end of each chapter after lecture. 5. Keep your notes and problems organized, and keep an open mind. 6. Review your notes often, make a list of reactions, and update it regularly. One student who did very well in the course said he did the following. (1) Read the chapter before coming to class; (2) work the in-chapter problems with answers while reading the chapter; (3) take notes on the reading - outline the notes by (a) structure, properties, and reactivity; (b) general reaction, mechanism, examples, HW problems; (c) synthesis; (4) attend lecture and discussion and take good notes; (5) merge the two sets of notes together; (6) review the consolidated notes every day. The student put in about 12 hours a week (the time that most instructors recommend) and did not have to go hard on the studying before the exams. STUDY TIPS – HOW TO DO THE EXERCISES LISTED ABOVE The following study tips have been compiled from several organic chemistry courses offered at different colleges. Do the ones that you feel you can readily accomplish or which make the most sense to you. General Tips 1. Have a positive attitude and an open mind. Forget about the scary rumors that you may have heard about the course; most of these comments originate from people who were not prepared or organized to do the work. Using the methods described here gives you a pronounced advantage. The greatest enhancement of self-esteem possible comes from tackling a difficult job and doing well at it by effort and perseverance. 2. Organic chemistry is cumulative. Organic chemistry is a cumulative subject in which each section builds on the previous sections. Consequently, an understanding of one section is required for the understanding of another. If you forget the information from the up front chapters, you will likely have difficulty with the later chapters. 3. Organic chemistry is highly integrated. It is not a series of separate topics. We typically teach the course one topic at a time to facilitate learning, but omitting one or more topic, or ranking the priority of topics can very easily lead to a situation where you need the omitted or lower-ranked topic to answer questions, which may - and often do - appear on exams.

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4. There are no short cuts. If there were, we‘d tell you what they are. Learning organic chemistry, like learning the piano or basketball, takes time and effort. Make sure you have sufficient time in your schedule to apply to the course (see #5 below). 5. Learning is greatly aided by repetition. Don‘t expect to be ready for an exam when you walk out of lecture. Each week you should read the text, review the notes, and work problems, and then do it all again, and then again. Thus, all of you may expect to spend more time studying for this course than anticipated. This may involve 10-15 hours outside of class, spread over at least 4-5 days, each week (a consensus among many instructors). To be successful, you will need to be organized and committed to stick to a fairly rigorous and time-demanding schedule. Would you begin studying for your piano recital 3 days before the recital? Would you start your very first basketball practice 3 days before your tryout or the big game? If you wanted to get in physical shape, would you go to the gym just once? Like excelling in sports, playing a musical instrument well, or proficiency at speaking a foreign language, practicing organic chemistry requires a daily workout. Beginning the serious studying only a few days before the exam is a recipe for failure. Dr. Michael A. Ansell of LaPositas College states, ―If success in this class is not important enough for you to spend at least 10-15 per week outside of class, then you must be satisfied with the very distinct possibility of lower than your usual grades.‖ 6. You may need to develop new study skills. You may find that the learning skills that you have developed and which have worked well previously (e.g., cramming, memorization) are inadequate for learning organic chemistry. If students find themselves thinking "I did not learn because the instructor did not teach me well enough," or ―I do well in all my other courses except this one,‖ then they are requiring far too much of the instructor and not enough of themselves. Similarly, if students conclude that "This course just did not match the way I learn," then they are missing the point about building new skills on the foundation of old ones. Becoming a more flexible learner can only help you improve your ability to learn. Identifying new study skills is the purpose of this ―Study Tips‖ section. 7. Learn, don’t memorize. The more you understand, the less you have to memorize. Learning consists of evaluating new information in relation to information that has previously been understood. Thus, memorizing everything, or ―rote learning‖ is not learning at all. Instead, study by understanding the material - not by blindly memorizing it. Passive study will not provide the ability to discern relationships between one molecule and another, one reaction and another, one mechanism of reaction and another, or one chemical test and another. Merely memorizing one's notes will not prepare you for the exams, which are designed to require an analysis of data or facts, the synthesis of ideas to reach conclusions, and the evaluation of possible approaches. In fact, answering a problem with something you have memorized, without working through the problem, often gets you the wrong answer. Organic chemistry consists of a few basic principles, with many extensions and applications of those principles. Learn the principles instead of memorizing examples. From time to time, some memorization will be required (e.g., fundamental rules, some common names). Relatively little memorization is required if you grasp the major principles and develop flexibility in applying those principles . Thus, memorization alone is not enough. Most students view organic chemistry as that course where you have to memorize everything because they typically don’t take the time and effort 9

to actually learn the material. Rather than take the time to learn how to solve problems, many students instead just want to know what the answer is, or what will be on the exam. In organic chemistry, there are many common threads that allow you to use what you have learned in one situation to predict what will happen in other situations. In fact, organic chemistry is a wonderfully logical subject that is unified by a few broad themes. And when these themes are understood, learning organic chemistry becomes much easier and rote memorization is minimized. So, as you read the book and study your notes, always try to understand why each thing happens. If the reasons behind chemical behavior (reactivity) are understood, most reactions can actually be predicted - you will be able to figure out what happens. So, read and re-read the material, and actively work lots of problems, until you begin to understand it. 8. Don’t cram. This is the biggie that causes most of the problems for most students, since students say it has always worked before in all their other courses. Cramming doesn‘t work in organic chemistry. Doing very little until a few days or even a week before the exam is a recipe for failure. Cramming will not allow you retain previously-learned material, and the later chapters will be more difficult than they would if you had learned the material. Cramming will not allow you to develop the problem-solving skills that are so crucial to understanding this material. Cramming will cause you to try to remember what the answer should be (instead of being able to work through the problem), and you are likely to remember wrong. Cramming will make normal problems in organic chemistry - and the exams - appear more difficult than they really are. Cramming is not learning. 9. Don’t fall behind. Organic chemistry is a concentrated and fast-moving subject; the single factor that gives students the most trouble is falling behind. Without exception, all organic chemistry courses require students to learn a lot of material in a relatively short period of time and retain it. Falling behind will require you to cram (see # 8 above). Falling behind is death. If you play catch-up, you will be caught. Get behind, and you can kiss your ―A‖ goodbye. 10. Think creatively while studying. Active, creative thought is essential to the study--not just passive, mechanical, rote memorization. Write it, summarize it, say it, work it, think about interconnections, and ask questions. Ask yourself questions as you read − ask yourself how this fits into the overall picture. Itemize key points on paper and compare them for different classes of compounds or reactions. Think about interconnections − what you learn in one place can help you understand something new. Rather than going into shock when faced with a new problem, ask yourself what you have learned previously that can apply to the problem. Start with the certainty of ―This is like (fill in blank with something you previously learned that seems similar).‖ 11. Use the same activities when you study that you will face on an exam. Write things down without looking at the text, the answered problems, or your notes. Avoid only reading or just looking at it. 12. Clear up the unclear. Ask thoughtful questions in both lecture and discussion class and get help if necessary. Make sure your lecture notes clearly tell the story. The best questions involve applying principles you learned in one section or reaction to another (What is the stereochemistry of this reaction?), and differences between what is taught in lecture, problems, and lab vs your own conclusions and ideas (I worked this problem and got a different answer than the book, or I thought that this functional group worked this way but in this case it doesn‘t. Why?). If you can't seem to 10

understand it, seek help. See the syllabus section entitled ‗Outside Help.‘ Harris J. Silverstone III, Johns Hopkins University, states ―There is no shame in not knowing - only shame in not asking.‖ 13. Find a study buddy. Study regularly with other students. Try to make at least one friend with whom to study, share ideas, and talk chemistry. Meet regularly to talk through your lecture notes, which will improve your understanding, and to work the harder problems. If you are out at dinner with your study buddy, talk chemistry, get out a napkin and draw out chemical ideas. 14. Take care of yourself. Exercise to reduce stress. Take a 10-minute break out of every hour of studying − stretch and walk around, get yourself a cold drink (not beer), make a short telephone call. The break is your reward for your effort during the preceding 50 minutes. Get a good night‘s sleep before the exam. Don‘t pull any ―all-nighters.‖ Relax for a few hours before the exam. 15. Begin concentrated studying a full week before the exam. 16. Test anxiety is not an excuse. Do you get severe test anxiety, to the point where it interferes with your ability to answer questions? Does your mind go blank when you look at an exam or a question on an exam? The key to overcoming test anxiety is having the confidence of understanding the material and the ability to work the assigned problems without looking at the answers and when presented out of context. Therefore, you must practice, and you may need to practice more than other students. The more practice you have that allows you to develop confidence, the better off you will be. Specific Study Tips 1. Be familiar with general chemistry. Organic chemistry builds on principles learned in general chemistry, especially the modern theories of atomic and molecular structure, structural and physical properties, acidity and basicity, principles of chemical reactions and solutions, and thermodynamics and kinetics. If you‘re rusty, review these topics in a general chemistry text, and practice a few problems. See the document on the course website entitled ―It‘s Been a Long Time Since I Took Chemistry,‖ and any provided review material and links on the website. 2. Prepare. Read the text chapter before it is covered in lecture, take notes on your reading assignments, and work the in-chapter exercises as you go along. Mark any parts that you find confusing. Write down the key points of each section. Bring your reading notes to lecture, and use your reading notes as the basis for taking notes in lecture, so that you can merge the two together. Use your lecture notes and/or the text to figure out the confusing parts you had marked. Provided chapter summaries and slides, while very popular with students, are not a substitute for preparing for and attending class. 3. Attend every lecture - you will always learn something new. Attend lecture, take notes, and think about what is being covered. If lecture slides are provided, condense the slides, focusing on the purpose of each section. Your reading notes should enable you to devote time to thinking during class. Avoid blindly writing everything the instructor is saying, even though it‘s difficult not to. You will miss a lot if your study buddy attends class in your place. 11

4. Before the discussion class, look over or work the problems. You can‘t ask your Teaching Assistant for help on a problem you haven‘t tried yet. Bring your questions to discussion class. 5. Review your notes as often as you can. Work at it daily! Make sure your lecture notes clearly tell the story. Make note of concepts you don‘t understand and seek help. Learning occurs in small steps - don't expect to digest it all the night or weekend before an exam. 6. Work problems. Really work them. You will not be able to understand organic chemistry until you are able to actively work problems. No one can expect to walk out of a lecture knowing the material well – much of the learning must be done outside of class. So work (and re-work) the problems using pencil and paper; don‘t just read the answers from the study guide. As you work, draw structures for molecules mentioned by name. You should also be able to work the problems out of context. 7. Think about it. Visualize formulas, structures, and key points with your eyes shut, until you can "see" them in space. 8. Learn the vocabulary and the artwork of organic chemistry. Be precise in your chemical (and everyday) descriptions. If you use the wrong words, or draw the wrong picture, or draw a bad picture, you have not conveyed a correct answer. Say ‗the ball that is in the corner,‘ not ‗that thing over there.‘ In organic chemistry, a good structure, diagram, or reaction is worth a thousand words! 9. When learning reactions, make two types of reaction summaries: (a) reactions of the functional groups (good for drills), and (b) reactions that produce a particular functional group (good for synthesis). Include regiochemistry, stereochemistry, and any limitations. Check the end summary section of the chapters in the textbook or provided summaries (e.g., on the course website). Study the reactions in both directions (i.e., given reactants and reagents, predict the product; given the product and reagents, predict the reactant). 10. Study your exams to understand what you did wrong and how to avoid repeating your mistakes, as painful as it may be. If you think an exam question was written poorly, try to rewrite it yourself (and show the instructor). Write out in words the thought process you used to create an answer and look for where you went wrong. 11. Supplement with flashcards. Are you ‗on the go,‘ with little time to study? Bring a stack of flashcards with you and drill with (think through, not look at) them during lunchtime, while you‘re on the bus or subway, waiting in an office, standing in line, etc. Write individual reactions, concepts, and homework problems on index cards. (Don‘t study while driving.) Or check out http://chemistry.umeche.maine.edu/CHY251/flash.html, then http://www.chemistry.ohiostate.edu/organic/flashcards or http://www.chemistrycards.com or http://www.bryanedwards.com/Products/Detailindex.cfm?isbn=187857616X. Flashcards and index cards are supplements; do not rely solely on them. 12. Listen to your gut. If you don‘t feel you know the material, you are probably not ready for an exam. You are probably best prepared for the exam when you can visualize and understand the lecture material (able to explain your ideas out loud and in writing) and when you have worked and 12

understand the homework problems (and can work them when they are out of context). Don‘t focus your studying on just one area, and don‘t cram for exams. If you can do the homework problems without looking back at the text, you have remembered the important things. 13. Tips for the make-up exam. Review your lecture notes. Review your lists of reactions. Read the chapter summaries provided on the course website or any end-of-chapter summaries. Review the assigned text problems. Re-take the exams, and any other provided previous exams. 14. The Bottom Line. Quite simply, if you decide to make this course a high-enough priority in your life, go to classes, keep up with the material as it is being taught, avoid cramming, and seek answers to questions on areas you do not understand, you will have few problems. If you wait until a week before the exam to begin studying, you will struggle and will have problems, and you therefore must be realistic about how much you can expect to achieve. OUTSIDE HELP You are encouraged to seek outside help if you believe it will be necessary. Tutors may be available through the Chemistry Department (C0107; 301-405-1793). TA‘s may hold office hours in C1115; check the schedule in the room. You may also check the bulletin boards on the first floor of the chemistry and physics buildings for information regarding tutoring. The chemistry honor fraternity, Alpha Chi Sigma (301-405-1862), has an office in the Chemistry Department and may also offer assistance. You may also wish to determine the office hours of the daytime TA‘s for organic chemistry (from the Chemistry department), and ask them if they would be willing to assist you. Disability accommodations, if needed, can be obtained through the University‘s Disability Support Service (http://www.counseling.umd.edu/DSS; (301) 314-7682; 0106 Shoemaker Building). IMPROVING YOUR EXAM PERFORMANCE If you want to improve your exam performance, there are several things you can do. First, what is your background in chemistry? Do you know the pre-requisites? How did you do in that course? It is quite possible you did not learn it as well as you were led to believe and thus may not be prepared for this course. Be realistic. See the document on the website entitled ―It‘s Been a Long Time Since I Took Chemistry.‖ Second, review the study tips and the section entitled How to Do Well in Organic Chemistry provided previously, and check your study habits against each item. Third, divide the exam into general topics like reactions, reactivity, synthesis, physical properties, mechanism, and naming, and see where you missed the bulk of your points. This exercise may show you where you are weakest and where you may need to concentrate your studying. Fourth, make sure you understand the answers to questions you missed, and how the correct answers were obtained. Compare your approach to the correct approach. Fifth, re-write questions that you feel were worded poorly, compare them, and discuss them with the instructor if necessary. Sixth, if these approaches do not help sufficiently, consider a tutor. See the Outside Help section of this syllabus. If you want to greatly increase your chances of performing well on exams, (1) prepare for and attend all classes; (2) study frequently, looking for interconnections; (3) actively work and re-work problems; and (4) study by understanding the material. If you want to greatly increase your chances 13

of not performing well on exams, (a) come to class unprepared or skip classes; (b) memorize without understanding; (c) look at (not work) the problems; and (d) begin studying a few days before from the exam. Remember though, that your instructors do care about your progress. Feel free to consult with them when you need help, and don't forget the value which also arises from studying with other students. Organic chemistry is unlike any other course you are likely to have studied so far. While it is based upon the chemistry you have learned in general chemistry, there is much more qualitative reasoning and considerably less quantitative reasoning. Consequently, success in general chemistry does not guarantee success in organic I, and success in organic I does not guarantee success in organic II, nor does it preclude success - organic chemistry is just different. And remember – you will gain a lifelong intuition for solving all kinds of problems while it has the added advantage of being a fascinating subject as well!

Imagination is more important than knowledge. For knowledge is limited to all we now know and understand, while imagination embraces the entire world, and all there ever will be to know and understand. Albert Einstein, 1879 - 1955 Live as if you were to die tomorrow. Learn as if you were to live forever. Mahatma Gandhi, 1869-1948 Learning without thought is labor lost; thought without learning is perilous. Confucius, 551 - 479 BCE You do not really understand something unless you can explain it to your grandmother. Albert Einstein, 1879 - 1955 The hope of the future lies in organic chemistry. Sigmund Freud, January 15, 1930 (1856-1939)

14

Approximate Schedule

12/13/11

NOTE: The following schedule is approximate; it generally corresponds to a chapter per week. Every effort will be made to adhere to the schedule. If we fall too far behind, the schedule will be adjusted. If we finish a chapter early, we may start the next chapter that evening. Lecture may be held after an exam. Therefore, it is very important to make sure you are available to attend each class, especially in the event that an exam date (and corresponding chapters) are also adjusted. Date

Text Reading

Topic

Jan

30

Chapter 15

Dienes, Resonance, and Aromaticity

Feb

6

Chapter 16

Benzene and Derivatives of Benzene

13

Chapter 17

Allylic and Benzylic Chemistry

20

Exam 1

Chapters 15 – 17. Lecture – Chapter 18 (Phenols)

27

Chapter 18

Phenols, Vinyl Halides, and Aryl Halides

Mar 5

Chapter 19

Aldehydes and Ketones

12

Exam 2

Chapters 18 – 19. Lecture – Chapter 20

19

------

26

Chapter 20

Carboxylic Acids and Nitriles

2

Chapter 21

Derivatives of Carboxylic Acids

9

Chapter 22A

Enolate Anions and Enols I

16

Exam 3

Chapters 20 – 21. Lecture – Chapter 22B

23

Chapter 22B

Enolate Anions and Enols II

30

Chapter 23

Amines

May 7

Chapter 24

Carbohydrates

14

Final Exam

Chapters 23 – 24

16 (Wed)

Make-up Exam

Chapters 15 – 23

Apr

Spring Break

15