Chapter 15, Problem 15.19P

We now continue the introduction of organic chemistry reaction roadmaps. Because of the many new functional groups that will be introduced in coming chapters, we recommend that you make a new roadmap to accommodate the reactions in Chapters 15–18.

To make your own reaction roadmap for Chapters 15–18, take a blank sheet of paper and write the following functional groups in the orientations shown. Fill the entire sheet of paper and leave plenty of room between functional groups. Most students find it helpful to use a poster-sized piece of paper filled out in landscape orientation.

Refer to the “Study Guide” section 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. Then record any regiochemistry or stereochemistry considerations relevant to the reaction. You should also record any key aspects of the mechanism, such as formation of a carbocation intermediate, as a helpful reminder. It is important to keep track of all reactions that make carbon-carbon bonds, because these will help you build large molecules from smaller fragments.

On the above organic chemistry reaction roadmap template, the information for the Simmons-Smith reaction, the seventh reaction in the “Study Guide” section has been added to help you get started. For this reaction roadmap, do not write an arrow for reactions 1, 2, and 4 explicitly, because these are considered reagents, which are prepared immediately prior to use. A reaction roadmap is used to indicate interconversion of molecules with more stable functional groups. Appendix 10 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.