Document Type

Syllabus

Publication Date

Spring 2024

Course Description

Organic chemistry is the basis of a multibillion dollar business. In 2017 the top selling drug in the U.S. was Humira. It sold $18.6 billion worldwide. Many drugs are what the industry commonly refers to as small molecule (small relative to biomolecules like proteins or DNA). These are mostly organic compounds and they are mostly made via organic synthesis. Organic synthesis is when simple organic compounds undergo reactions and are built up to larger and more complex molecules. To do organic synthesis requires an understanding of how organic molecules react. This understanding of how organic molecules react is what we call mechanism. In the same way that structure helps us understand properties of organic molecules (Chem 120), inorganic compounds (Chem 130), and function of biomolecules (Chem 240), mechanism helps us understand reactivity of organic molecules and how to apply this to synthesis of organic molecules such as those made in the pharmaceutical industry. In this course we will also expand our understanding of Nuclear Magnetic Resonance Spectroscopy (NMR). We will find this most useful in the laboratory part of the course. Concurrently we will begin building an understanding of how organic molecules react. We will discover that understanding a few basic principles of mechanism allows us to apply that understanding to a wide range of organic reactions. Along the way we will also learn how to use the reactions we encounter for organic synthesis. Together we will explore organic synthesis by discussing journal articles in which organic synthesis is featured. The quality of the class will depend to a large extent on your preparation and willingness to contribute to these discussions. Consequently, part of your grade will depend on your participation in discussions during class. My role in this will be primarily to serve as an expert consultant when the need arises. Additionally I will provide some review and introduction to the topic early in the term.

Student Outcomes

By the end of the semester you will be able to: 1. Increase your ability to use spectroscopy to determine the structure of organic compounds. 2. Apply your knowledge of acidity/basicity and other basic concepts to understanding organic reaction mechanisms. 3. Write mechanisms for the basic types of organic reactions. 4. Use your knowledge of organic reaction mechanisms to postulate mechanisms for reactions you haven’t seen before. 5. Propose a multistep synthesis for simple organic molecules. 6. Understand a retrosynthetic plan and the corresponding sequence of reactions used to carry out the synthesis. 7. Obtain 1D and 2D NMR spectra of reaction products and use them to verify the structure of the product. 8. Replicate a journal-style experimental procedure.

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