We now introduce the concept of an organic chemistry
Chapter 6, Problem 6.54(choose chapter or problem)
We now introduce the concept of an organic chemistry roadmap. An organic chemistry roadmap is a graphical representation of the different reactions that can be used to interconvert functional groups in molecules. Comparing the organic chemistry roadmap to a real roadmap, the functional groups are analogous to cities, and the reactions are the roads between them. The power of the organic chemistry roadmap is that it helps students visualize how to interconvert key functional groups for use in multi-step syntheses problems. It also will be a useful place for you to keep track of the reactions we encounter in future chapters, so that you can see how they complement the reactions from all previous chapters. To make your own roadmap, take a blank full sheet of paper and write the following functional groups in the orientations shown. Make sure to fi ll the entire sheet of paper and leave plenty of room between functional groups. Most students fi nd it helpful to use a poster-sized piece of paper fi lled out in the landscape orientation. alkenes vicinal dihaloalkanes aldehydes/ ketones vicinal diols alkynes alcohols vicinal tetrahaloalkanes geminal dihaloalkanes thiols thioethers alkyl azides amines ethers nitriles allylic halides silyl ethers carboxylic acids vicinal aminoalcohols epoxides halohydrins haloakanes alkanes HX Markovnikov regiochemistry Mixed stereochemistry of addition Carbocation intermediate Refer to the Key Reactions section at the end of this chapter. Draw arrows between functional groups to account for each reaction. Write the reagents required to bring about each reaction next to the arrow. Next, record any regiochemistry or stereochemistry considerations relevant to the reaction such as Markovnikov regiochemistry or anti addition stereochemistry. You should also record any key aspects of the mechanism such as formation of a carbocation intermediate as a helpful reminder. On the above organic chemistry roadmap template, the information for the fi rst reaction, hydrohalogenation of an alkene, has been added to help you get started. For this initial roadmap do not write an arrow for reaction 10, enantioselective reduction, because it is of a highly specifi c nature and a roadmap is intended to organize reactions that are of more general use. Note that the roadmap template applies to chapters 611, so you will not use all of the functional groups listed until you are fi nished with Chapter 11. Appendix 11 contains a series of roadmaps for different sections of the book, but you should use those for reference only after you have completed your own.
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