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Click here to download a printer friendly pdf version of this page Roadmaps Click here for a copy of TA Chris' completed roadmap from Fall 2017 Click here for a copy or TA Chris' SN2 roadmap from Fall 2017 As stated in the syllabus, the point of organic chemistry is synthesis, the construction of more complex molecules from simpler ones. By the end of the semester, you will have to solve synthesis problems in which you put together a sequence of several reactions to convert a starting molecule into a product molecule or product molecules. How do you study to prepare yourself for these problems? I believe the best way to review/learn organic chemistry reactions is through the creation of a so-called roadmap.
Click here to see
the suggested arrangement of functional groups for a first semester
roadmap (320M/328M), with some representative examples filled in. This
arrangement was chosen to minimize the number of arrows that must
cross each other, although some will. Write the functional groups
in this arrangement on your large piece of paper, leaving plenty of
space between functional groups. I recommend you view the map as being roughly analogous to the state of Texas, with the I-35 corridor represented by alkanes (like San Antonio in the south), followed by alkyl halides (San Marcos), alkenes (Austin), vicinal or geminal dihalides (Waco) and alkynes (Dallas). You will find that as you convert different functional groups in synthesis problems, you will often travel along this path. Even more, you will notice that the alkenes, aka Austin, is the most versatile functional group covered in 320M/328M and it is the center of the "action", as is Austin in real life, of course. Most syntheses involve alkenes in one step or another (just like Texans generally find some reason to go through Austin whenever traveling within the state).
To assist in this process, I have created a brief chart summarizing the important reactions from 320M/328M. Click here to see the chart. Note that I have not included the important mechanistic points of each reaction on the chart such as regiochemistry, stereochemistry and the key transition state or intermediate. You must recall those on your own and add them to your roadmap. For this semester, use the 320N roadmap template. Fill in reactions as we go so you continually see the "big picture" of how each individual reaction relates to the others we have learned. Keep your 320M/328M roadmap handy as you will always be responsible for those reactions as we go through this semester. Notice that this semester the carbonyl chemistry is the center of the map, and we make many, many more carbon-carbon bonds! A final comment. Many students find it helpful to keep the large roadmaps posted on their wall. This will not only reinforce the material several times a day as you glance at it, it will also greatly impress your friends, parents, and roommates who do not know organic chemistry. As you go through the semester in 320N, add new reactions to the roadmap after each lecture. It will help provide a big picture understanding of the chemistry you are learning! Here are some finished roadmaps from the textbook for your reference. Roadmaps for Chapters 15-18 and 19
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