Course: CHM301
Instructor: Martin Semmelhack
F 2019

Description of Course Goals and Curriculum

The first semester of Organic Chemistry (Orgo) is intended to provide the foundation for the two-semester sequence, including the core principles of bonding and reactivity of organic compounds. These concepts of organic chemistry properties and mechanisms in the classroom are underscored by work in the lab each week. The syllabus of the class divides the course into twelve tentative topics, one per week, which can be generalized as the following broad categories: Bonding and Molecular Associations; Acidity and Basicity; Spectroscopy; Molecular Conformations and Chirality; Reaction Mechanisms.

Learning From Classroom Instruction

Course instruction is divided by twice-weekly lectures (80 minutes each) and a weekly precept (75 minutes). While the course material is dense and complicated, Professor Semmelhack’s lectures are easily accessible. Most notably, he pre-writes and prints out note templates for the class before each lecture, which eliminates the need for trying to replicate the complicated molecules on the screen while also digesting the content.

If concepts in lecture are not understood, there are several opportunities for clarification. In weekly precepts, many, if not all, of the preceptors begin with a mini-lecture summarizing some of the more complex concepts discussed in the week’s lectures, with time for further questions. These concepts are then further solidified with a packet of problems that the precept works to solve, either in groups or individuals, with undergraduate TA’s available to assist. There are also many opportunities to meet with the professor or preceptors during office hours, and students are very much encouraged to take advantage of these times.

In addition to the lecture content, there are also weekly labs. Many of the experiments span several lab sessions over two or more weeks, so while pre-labs and lab reports are required for each lab, these are more bi- or tri-weekly assignments. Additionally, for each lab report, there is an initial due date for a first draft, which is critiqued by the lab TA and then returned for the student to make any changes or improvements necessary. These changes are required by the second and final due date when, if completed, a student receives full credit.

Learning For and From Assignments

There are three midterm exams in each orgo semester, followed by a final exam. Your grade in the class is 40% midterms, 40% final exam, and 20% lab. While there are three midterms, Prof. Semmelhack drops the lowest grade of the three, so each is worth 20% of your grade. However, if your grade on the final exam, curve considered, is higher than the average of your two best midterms, the midterm grade is dropped and the final is considered as 80% of the grade. All this is to say that midterms are important, but there is room for improvement if one, or even all, of the midterms don’t go too well. Furthermore, after each exam is returned, there is an opportunity to submit a regrade request. Unlike other courses, regrades are not only meant to resolve clerical errors in grade calculation, and grades will never be lowered following a regrade request. Instead, the request is an opportunity to explain your thinking on a problem, and perhaps demonstrate why your answer is deserving of more points than it was awarded. While the preceptors are bound by a strict rubric in grading your exam, Professor Semmelhack handles all the regrade requests personally, and is able to award more points for creative answers.

While the knowledge gained in lecture is important for basic understanding of the conceptual side of orgo, most of what is tested on the exams is problem-solving ability: considering how numerous properties and factors affect a molecule’s behavior or mechanism, and applying that knowledge to a previously unencountered context. Thus, the best way to prepare for examinations in organic chemistry is to take advantage of the expansive reserve of problems, taking each practice exam and working through as many of the problem set questions as possible. Reviewing lecture notes and reading the textbook should be used only when a particular concept is challenging or obscure, and not as an initial study strategy. However, it is important to note that all exams are completely open notes, meaning you can even bring your textbook to a midterm if you want. The midterms are 2 hours each and the final is 3 hours, which means that time is a big factor in using the notes that you may have. For this reason, it is very helpful to compile condensed versions of your notes before exams—mechanism cheat sheets or nomenclature—so that the information you need will be more quickly and readily available to you during the tests.

The bank of organic chemistry problems that a student encounters is comprised of several source materials: weekly preliminary problem sets, which a student completes individually each weeks and turns in during precept; weekly problem sets, which are longer, more robust versions of the preliminary problem sets, to be completed in precept; and past exams, five of which are provided in advance of each exam during the semester. Problem sets questions are often pulled from past exams, so there is a strong overlap between the type of problem-solving that is performed each week and that which is required of a student on the exam. It is worth noting that the preliminary problem sets are graded for completion, not correctness. So while the problem sets are a great way to check your own grasp of the material if it’s a difficult week and you don’t have time for office hours, you can turn in something that shows that you made some effort to solve the problem, apologize to your undergraduate TA, and remember to come back to it later on.

External Resources

Seeking help in orgo is very common and very helpful. Professor Semmelhack has weekly office hours on Sunday mornings for those very motivated. Additionally, there are office hours throughout the week hosted by preceptors and lab TA’s, who have much more time to explain concepts and go over problems with individual students. Many have specific times they have allotted to office hours, but all are usually available to schedule office hours by appointment as well.

In addition to the regular weekly office hours offered, there are also additional review sessions before exams and lab reports. Before each examination, the preceptors will typically host three review sessions during the weekend leading up to that Monday’s exam, where students can ask questions about previous exam questions or any other content-based questions. This can be helpful if you have your own questions prepared, or by listening to other students’ questions and the preceptor’s explanations. Additionally, before lab reports are due, Professor Gingrich hosts lab review sessions, to explain certain techniques in advance, or to review any special skills that might be needed to answer the questions in the lab report. These help sessions can be very helpful, but are not always needed, so it’s best to check out the lab report discussion questions in advance to anticipate whether or not there will be new information provided.

In addition to the course-provided resource, there are also tons of sites online that have incredible resources for students struggling through organic chemistry. This includes step-by-step problem solving, reviews of complicated mechanisms, and much more. There is nothing that you won’t be able to find in your lecture notes/textbook, but it can help to have the information conveyed using in a different medium.

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

Organic Chemistry is a notoriously difficult class, and has not unfairly gained this reputation. The material is complex, and the assessments require very high-level problem solving skills and ability to make connections between different concepts. However, CHM301 is an incredibly well-run course, which makes the material much more accessible for students and provides tons of resources for those who need them. The course does not rely very heavily on the material learned in General Chemistry, so you need not worry if you didn’t do so well in that class; orgo is a totally different subject, and requires a unique skillset. The class demands a lot of time and attention, but in return the professors offer much of their own time, and as much leniency as they can in terms of grading. Overall, CHM301 is a challenging course, but a worthwhile one, and the way of thinking that it teaches you will be helpful in any further academic endeavors.
Organic Chemistry I: Biological Emphasis

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