Course: CHM303
Instructor: Semmelhack
F 2016

Description of Course Goals and Curriculum

Welcome to orgo I! This is most likely your first encounter with organic chemistry, and there are some unique twists and tricks to this course at Princeton. There are lots of course evaluations on the Registrar’s site that with great emotion beseech you to do what they say, some of them directly conflicting. I will clear up all the wailing voices and provide specific strategies for succeeding in orgo, and even getting exempted from the final exam. As OneRepublic sings, “[I’m] sick of all the insincere / so I'm gonna give all my secrets away” (“Secrets,” 2010).

The goal of the course (the first of the CHM 303-CHM 304-MOL 345 sequence) is to introduce you to the chemistry that makes up and drives the processes of life. There are three midterms, which all orgo students are required to complain vocally about, but they will be very good for you, forcing you to practice throughout the semester. The three units are a) nomenclature, intramolecular forces, and acid-base reactions; b) spectroscopy four ways (mass, UV, IR, and NMR); and c) 3D molecules and how they react.

Being able to visualize in 3D is a big part of the course and if that isn't as instinctive for you, use the molecular modeling kit
In Orgo, all that matters is practice! The more you practice at solving problems, the more you will learn and the more you will succeed.
Do all the problems sets again before the exam as a review of the material. They have questions from all the main topics covered that week so doing them on your own helps you see the areas that you need to focus on for review and the concepts that you need to work on

Learning From Classroom Instruction

Lecture happens at a brilliant 8:30 am in a huge classroom; you’ll have about 250 classmates. I have on very good confidence that Prof. Semmelhack sympathizes deeply with you, i.e., along with all the students he too wishes he were still in bed at 8:30 am. However, you should attend. Lecture is the core of the course, and the examples presented will reappear on exams.

You will print a partially completed packet of notes before class so that you don’t need to draw every complicated molecule by hand while you process what is going on in your brain. A little-known detail of the course is that if you arrive early enough, you can pick up a packet from the course staff that is printed in color, and that is helpful in some lectures when you need to distinguish among hydrogen atoms or reaction mechanisms. Also, color printing is just pretty and luxurious. Skim the notes packet that Prof. Semmelhack posts the night before so you know approximately what will happen in class and whether you’d like to have the notes in color.

During class Prof. Semmelhack will write a couple words, draw some arrows, and turn the page, talking the whole time. Even as he whips through the notes under a faraway projector, take in what he says and connect it to what you know. He weaves a story about all the topics he covers, and the connections you draw will help you understand and ask good questions.

Weekly precepts offer an opportunity for you to synthesize and utilize what was presented in lecture. Preceptors briefly summarize the most important points of lecture in an accessible, memorable format, then dump a huge packet of problems in front of you. You will almost certainly not finish this packet. Your preceptor might provide a suggested prioritization of problems, and you can work with your peers to discuss and solve problems. Ask any and all questions during precept. Do not worry that your question is too simple because you will be giving a voice to someone shyer with the same question. Someone might approach you to tell you they were wondering the same exact thing and thank you for clarifying it.

Labs move quite fast, especially for those uninitiated in the operating of a chemistry laboratory. Be sure to do your prelab and arrive on time. You will need to work continuously, but don’t rush. You can always return to the lab to finish if you run out of time, but be sure to pause your procedure at a stable stopping point. Lab TAs are wonderfully understanding and helpful as long as you put in sincere effort. Pay attention to what you are accomplishing in lab—the purpose of your procedure and ways it can go wrong will be questioned on exams. You may see labs as separate from lectures and precepts, but in fact they provide hands-on experience in applying the theory you have learned on paper. Lectures, precepts, and labs give you an all-around education in organic chemistry.

Learning For and From Assignments

The required workload for orgo is really very small. You will do a one-page problem set every week, and all your work will fit on the single piece of paper. However, you need to put in work outside of what is required. Those giant packets from precept? You should finish them on your own time. At least 40% of the top five students in my year noted that they completed each week’s precept problem set.

For lab, you will need to read and rewrite your procedure so you know what to do. The four take-home lab reports are very straightforward; do exactly what you are told. There are no tricks and nothing is expected of you beyond what is asked. Your lab TA will evaluate your draft, and if it is not accepted immediately, simply make the corrections that are required. You can always ask for help.

Before each exam, Prof. Semmelhack will post several practice versions that were administered in previous years. These provide the best indication for what is expected from you on the exam. An extremely useful strategy for scoring points is memorizing the key words that answer a question type. For example, “resonance delocalization” and “double-bond character” are phrases commonly repeated in explanations, so you should learn the logic behind their causation. “Intramolecular hydrogen bonding” is a neat phenomenon that appears on exams, but is not emphasized in lecture or precept. Take note of these concepts and keep them in your head as tricks that you might apply in approaching a problem./

As you practice, I hope that you will see the beauty of organic chemistry. You will learn a problem-solving method that helps you reason through complex puzzles. You will use what you know to explain data and predict the future. In some instances, you will work with conflicting trends. If that happens, you will either be given data that clarifies which rule overrides the other, or you can explain your thinking and earn at least partial credit. Be sure to work out practice problems—practice makes perfect.

Start early on doing the practice exams because it is important that you understand them all and spend time solving them and then reading through the solutions
The past exams are super helpful going into the exam because the format of the exams remains quite similar year to year. Try to solve as many exams as possible and read through and understand the logic behind the solutions of all the exams

External Resources

There are so many sources of information about orgo. You have Prof. Semmelhack, Prof. Gingrich, preceptors, lab TAs, and McGraw tutors. Prof. Semmelhack’s office hours should be mandatory attendance, but then they would be even more crowded. They are a seminar-style review of what may have been unclear or skimmed over in lecture, and Prof. Semmelhack openly shares answers to the weekly problem sets that will be collected. You can ask far more questions than in lecture, and students shape the direction of the session to what they need. It is not an obvious or well-advertised fact, but you can go to any course TA’s office hours in the chemistry resource center, Frick A84, which is open 1:30 to 4:30 every weekday afternoon. Many of my classmates were shocked to find out this information. There is a subtle distinction between lab TAs and preceptors, and if you want the most focused and up-to-date information you should ask someone teaching the relevant component of the course.

The reading list includes a very large textbook, a slightly less large solutions manual, and a box of molecular models. None of these is necessary for your success in the course. The model kit helps you see things in the real world if you have difficulty imagining molecules in three dimensions. I see the textbook assignments simply as loose suggestions, although another student exempted from the final exam did read the textbook. A balanced approach might be to use the book as reference material if you need clarification on any concepts that were only briefly touched on in class. Once, a student asked about a concept that was presented only on the reading assignment but never mentioned in lecture or precept. I was lost and worried for a second—and then Prof. Semmelhack clarified that the concept was not covered in the course.

Google is your friend. Because much of organic chemistry is common knowledge and is taught at every school from different perspectives, you can quickly search and learn from other orgo students and teachers. Don’t blindly believe everything the internet tells you, but know that McGraw tutors and preceptors also consult web resources. You have so much support for your orgo journey. Just don’t be afraid to reach out and ask for help.

The 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 if the timings at McGraw or the Resource Center don't work for you
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 all excellent!
McGraw has 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, review or even tips and tricks to master the material

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

Before you enroll in this class: Make sure that your course schedule allows you to dedicate enough time to learning orgo well. You are likely enrolling because it is required for your major or future career, but you should also enjoy the process. The prerequisite is gen chem, but you do not need to recall much detail except what atoms and electrons are. There is no math beyond simple addition and no English beyond writing clearly to communicate your results. So there you have it, a comprehensive guide to acing CHM 303. As promised, I have given all my secrets away.

Organic Chemistry I: Biological Emphasis

8 thoughts on “Organic Chemistry I: Biological Emphasis

  • October 8, 2017 at 11:45 pm
    Permalink

    Do all the problems sets again before the exam as a review of the material. They have questions from all the main topics covered that week so doing them on your own helps you see the areas that you need to focus on for review and the concepts that you need to work on

  • October 8, 2017 at 11:48 pm
    Permalink

    The past exams are super helpful going into the exam because the format of the exams remains quite similar year to year. Try to solve as many exams as possible and read through and understand the logic behind the solutions of all the exams

  • October 8, 2017 at 11:49 pm
    Permalink

    Start early on doing the practice exams because it is important that you understand them all and spend time solving them and then reading through the solutions

  • October 8, 2017 at 11:51 pm
    Permalink

    McGraw has 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, review or even tips and tricks to master the material

  • October 8, 2017 at 11:53 pm
    Permalink

    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 all excellent!

  • October 8, 2017 at 11:54 pm
    Permalink

    The 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 if the timings at McGraw or the Resource Center don’t work for you

  • October 8, 2017 at 11:55 pm
    Permalink

    In Orgo, all that matters is practice! The more you practice at solving problems, the more you will learn and the more you will succeed.

  • October 8, 2017 at 11:56 pm
    Permalink

    Being able to visualize in 3D is a big part of the course and if that isn’t as instinctive for you, use the molecular modeling kit

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