The problem, and a Suggested solution
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Organic Chemistry has a negative reputation with many students. Part is earned, part is myth, and part is the result of former students complaining about not passing the course, or not getting the grade(s) that they have been accustomed to. Organic can be difficult if approached the wrong way, yet it can be immensely rewarding if the student brings to the table a mix of talent, dedication, and work ethic, along with a desire to develop their problem-solving skills.
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General Chemistry is a very different beast to Organic Chemistry. The first year course is more mathematical with many calculations and not so much deep thinking. Organic has very few calculations and all kinds of thinking. The step up to the Organic sequence needs to be seen for what it is - a big leap in difficulty and expectation that requires a change of approach. Many students get stuck in first gear trying to memorize and not understanding the concepts.
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The transition from the General Chemistry sequence to Organic and then, for many students, to Biochemistry should be as seamless as possible. These subjects need to be seen as a study in scale in which the basics of how chemicals behave are presented in General Chemistry, the bigger ideas of molecular structure, construction, and detailed analysis developed in Organic, and then the application of macromolecules to biosynthesis in Biochemistry.
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After two semesters of General Chemistry, students must bring with them a solid idea of how the Periodic Table works and they must be willing to change their approach in the Organic classes. While any new subject requires a basic collection of material that needs to be memorized, it is the connecting of that material with concepts in Organic that will push even the best students. They need to be willing to adapt and work harder than they have before.
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Whichever textbook is used, sophomore Organic classes aim to cover the material shown in the table shown here. We have used Klein for years, which is known to be quite student-friendly in its approach. The first chapters provide a shift from General Chemistry into the world of carbon frameworks with Acids and Bases being the first reactions covered. After a look at conformation and configuration, the study of mechanism begins, which is where things start to go wrong for many. Topics in red are the danger areas that need special attention in order to be ready for the second semester.
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Organic Chemistry has been likened to a spiral staircase in which we need to look in all directions in order to make safe progress. The same topics appear over and over and we keep coming back to the same ideas from Organic 1. Delocalization possibilities explain many acid strengths found within the Acid-Base chapter, which is central to many reaction pathways that follow. The basic Organic ideas of Substitution, Elimination, and Addition reactions sets up most of the second semester.
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Except for sections on Spectroscopy (IR, MS, and NMR), most chapters from the middle of Organic 1 require an understanding of reaction mechanism. Those paths are split into concerted or stepwise, and feature acid-base chemistry, resonance patterns, and outcomes based on steric or electronic factors or both. All of these ideas are introduced in Organic 1 and are used in Organic 2. Weakness in student performance is easily traced to not being solid in those core chapters.