Course: CHM303
Instructor: Professor Semmelhack
SU 2016

Description of Course Goals and Curriculum

CHM 303 is a course that a large number of students take every year as a requirement for various departments (CHM, MOL, CBE) or as a pre-med requirement or (hopefully!) because of their interest in Organic Chemistry. Organic chemistry may appear to be daunting and challenging but this course actually provides you a lot of opportunities and help to do well in the course. CHM 303 provides a strong introduction to the broader concepts that govern the various phenomena in organic chemistry as well as a critical foundation to the next semester of organic chemistry (CHM 304/304B).   The course is broken down into 3 major sections: the first section focuses on general concepts (like acids/bases, electronic effects, etc) and how they apply to organic compounds; the second section deviates significantly and focuses more on the chemistry behind experimental spectroscopic methods with which to study organic compounds; the 3rd half focuses on reactions and the mechanisms underlying them.   Lectures introduce the concepts, and Professor Semmelhack likes to introduce the concepts through specific examples in various compounds, often with biological significance. Precepts pick up from the content of lectures that week, providing a quick review, and then provide an opportunity to work through problems based on the concepts in groups under the guidance of the Graduate and Undergraduate TAs. Labs apply the concepts learned in lecture to experimental methods to study reactions, compounds or tools.

Learning From Classroom Instruction

The course presents a lot of avenues to learn informationfrom. For lecture, Professor Semmelhack posts half- completed notes the night before lecture that you are expected to print and bring to lecture. During lecture, Prof. Semmelhack fills out the lecture, the idea being that you follow along and complete the notes. Completed notes are posted later the day of the lecture. The lecture format is usually Professor Semmelhack introducing a concept by providing biological examples of the concept and then talking about trends and functions. This method does a great job of showing the relevance of the concepts that you are learning about and big picture ideas.     The precept picks up from the concepts introduced and provides a better and more focused and targeted explanation of the concepts. Precepts are also extremely important to actually practice problem solving in organic chemistry, which is often quite different from other problem solving methods that students have been exposed to, so do try to ask about how to approach similar problems and understand the thinking behind orgo problem solving rather than asking them about how to solve a particular problem. Precepts usually begin with a quick review of the concepts by the Graduate TA and then the students are divided into smaller groups to work on problem sets together. Working together in these groups is a great way to understand the material, specifically in relation to how it applies to the sort of problems that you are expected to solve for exams. 2 Undergrad TAs and 1 Grad TA are available throughout precept to help you with your problems and answer your questions. From precepts, your main goal should be to orient yourself to broad problem solving techniques and methods.     Labs tend to apply the concepts from lecture, though the material may be covered slightly later in lecture. While working in lab, it might be difficult to see how the concepts apply as the lab work may appear very procedural and sort of like following a recipe. However, in writing the lab reports, the concepts from lecture will guide how you answer the discussion questions.

Learning For and From Assignments

There is a preliminary problem set due at the start of the precept. The idea behind the preliminary problem set is to make students go over the lecture concepts of that week so that they are prepared coming into precept. The problems on the precept problem sets are grouped into sections by concepts, and so they provide a way to check if you understand the different specific concepts. If you find yourself struggling with a particular section, review the lecture notes/readings relevant to that section and seek out help from TAs/McGraw/Professor Semmelhack's office hours. There are many ways to approach problems, and different methods work well for different people. Spend some time to figure out what way to understand problems works best for you. While problem sets don't need to be turned in, complete as much as you can so and compare your answers to the answer keys that are posted. The answer keys also often go into great depth about the problem and present specific ideas as well, so reading through them might be insightful.     There are 3 lab reports and 1 in-lab lab report over the course of the semester. The lab reports are graded on an accepted/rejected basis and have a draft that is due before the final version with corrections marked by your Lab TA. To maximize your learning from the lab reports, make sure that you understand the big ideas that are meant to be the takeaways from the lab, and also make note of how concepts from lecture tie into them, as a large idea of the lab reports is to show applications of concepts.     There are 3 midterms for the class focused on the 3 broad sections of the class, and a cumulative final exam. You are allowed to bring any non-electronic material into the exam, including past exams, problem sets, lecture notes, notes that you take, etc. In preparing for the exam, give yourself enough time to go over all the material that the course provides you to revise. The past exams are a great tool to prepare for the exams, as they provide insights into the sort of concepts that are going to be tested. However, what is also important is reviewing the answer keys because for the exams, the graders are often looking for certain ideas and ways that they are presented. A strategy that worked well for me in preparing for the exam was to first go over the precept problem sets and broadly look at the problems from different concepts. If I struggled with some general concepts, I would review the lecture notes/readings relevant to that particular concept. This allowed me to orient myself actively towards the material being tested in the problem like format that it would be tested in rather than simply reviewing the lecture notes more passively, and I found that the format that I revised the concepts in better equipped me to face the exams. Once I was comfortable with the concepts in general, I would attempt the past exams. Prof. Semmelhack usually provides around 4-5 past exams, and I would do the exams in a couple of different ways. the first exam or two, I would solve one question and look at the answer key for that question before going on to the next question. This method worked for me in starting out in solving exams because I could review the solution to the problem while my thought process in approaching that solution was still fresh in my mind. Say I reason through x to get to y, and wrote down y as my answer. The answer also wrote y but reasoned it through z, but in reviewing my thought process while it was still fresh, I could critically analyze my reasoning of x. Since there are a lot of ways to approach a question in orgo and some are more right than others, evaluating your thought process is equally important in your answers. Also, since a lot of the questions built up on similar concepts, I found that this allowed me to correct my concepts before I used them in further problems as well. I could also read through the key and figure out ways of phrasing my answers in the manner that graders are looking for. For the rest of the exams, I would solve them as a whole like I was taking a practice test and read through the answer key after that. If you do not have enough time to do all the exams, do as many as you can but do read through the answer keys of all of them and try to understand the solutions, because the patterns of the exams remain quite similar from year to year so being familiar with the exams is the best way to orient yourself to them. If you do not understand some reasonings on the exam/key, reach out to TAs to help you understand them.     Of the 3 midterms, the lowest grade is dropped in calculating your grade. If you do better on your final, which is cumulative, than your midterms and final combined, your final grade counts for the entire lecture portion of your grade. So the class gives you a lot of options to improve and learn from your mistakes. Always take time to critically evaluate your learning strategies after an exam and see what worked and what changes you need to make in moving forward to your next exam. Finding a strategy that works for you is important in learning for this course, so take some time to do that.

External Resources

There are a lot of resources available for Orgo. The Orgo Resource center is staffed Monday through friday 1:30 till 4:30 by either Precept TAs or Lab TAs. The specific schedule about who is staffing which time and whether they teach Precept or Lab is posted on the door to the room. Check it out and go to the TAs for help, they are the people that are the most familiar with the specific topics covered by the class. Undergraduate TAs are also available to answer all your questions. Reach out to them via email or in person for questions. Most of them are also available to set up individual one-on-ones based on your schedule. A lot of Undergraduate TAs also have review sessions close to the exam dates. Professor Semmelhack's office hours are also a valuable resource. The McGraw center is staffed with both individual and group tutoring for Orgo every week. The tutors have all taken orgo and understand the workings of the course well so even if you don’t have specific questions, they can help you with broad concepts and review or even tips and tricks to master the material. A lot of people have found resources like Khan Academy useful for understanding some key concepts such as mechanisms or Organic Chemistry as a Second Language for general concepts. But do be careful in using these resources because the way Orgo is taught at Princeton is somewhat different, and so these resources might not cover some parts that are essential to this course and spend significant time talking about concepts that we do not cover in CHM 303. Master Organic Chemistry is another website where you have different articles about various concepts so it might be helpful to review certain problem concepts for you or even have the material presented to you in a different manner.

What Students Should Know About This Course For Purposes Of Course Selection

This course does not have the same level of weekly time commitment as other science courses because it does not require lengthy weekly graded problem sets or assignments. However, to do well in this course, you should try to set aside some time every week to make sure that you stay on top of the concepts since they build off of one another so falling behind might impact understanding of future concepts.The 3 midterms and finals make it so that you are always looking forward to another exam, so this is definitely an exam heavy class. Although CHM 201/202 is a prerequisite, the material does not have significant overlap with General Chemistry. The material of CHM 303 is essential to understanding CHM 304/304B and MOL 345 well, so if you plan on taking these courses, keep the materials that you learnt in this class fresh in your mind.
Organic Chemistry I: Biological Emphasis

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