Chapter 10

CHAPTER 10

No formal answers will be provided for the questions in this chapter. Your answers should be submitted to and
discussed with your instructor. Struggling with a synthesis and then discussing its strong and weak points with
someone knowledgeable about synthesis is the best way to learn about a synthesis proposal.
In all previous chapters, and in succeeding chapters, the synthetic problems were designed to provide practice
with reactions and concepts rather than stimulate creativity. Indeed, many of the questions stifled creativity by
setting arbitrary conditions on the synthesis. If answers were provided here, there might be a tendency to view
them as the "correct" answer. In fact, for problems of this type and for molecules of this complexity, there is no
correct answer. There are many correct answers, some elegant, some not. Your creativity and knowledge of
organic chemistry will be tested in doing these problems. By devising your own approach, you will become
personally involved in each synthesis and with each aspect of it. By discussing this synthesis and having it
critiqued (much as is done in Chapter 14 of the text), you can think about your approach, fix what is wrong, come
up with an alternative approach, or argue about why you think your view is correct. You will learn much more
from this process than by studying an answer that I could provide, which would have my own interests and
prejudices and may not be as good as the approach you come up with.
There is no doubt that your instructor will have strong views about which problems to do and how to approach
the problems in this chapter, and will probably have others for you to work on. For question 2, you can use the
tables in Chapter 1, the approach in Chapter 10, or any method you like to determine "strategic bonds."
Good luck.
In some of the homework problems, literature references are available so you can compare your answer to the
original work. These were omitted from the problem to give you a chance to work independently, and to encourage
you to go to the literature. For those problems, the literature citation is provided here.,
3a. See J. Am. Chem. Soc., 1997, 119, 10935
3b. See J. Am. Chem. Soc., 1999, 121, 10012
3c. See J. Org. Chem., 1999, 64, 1383
4a. See J. Am. Chem. Soc., 2003, 125, 9554.
4b. See Org. Lett., 2002, 4, 2491.
4c. See J. Org. Chem., 2004, 69, 3488.
4d. See J. Am. Chem. Soc., 2004, 126, 1038.
4g. See Org. Lett., 2002, 4, 687.
4i. See Org. Lett., 2003, 5, 3771.

Organic Synthesis Solutions Manual

6a. See Org. Lett., 2003, 5, 4911.

6b. See J. Org. Chem., 1999, 64, 4914
6c. See Tetrahedron, 2002, 58, 9765
6d. See J. Org. Chem., 1999, 64, 8263
6e. See Tetrahedron Lett., 2000, 41, 2111
6f. See Chem. Commun., 1999, 2365
6g. See Org. Lett., 2004, 6, 811.
6h. See Org. Lett., 2003, 5, 2335.
7. See Org. Lett., 2004, 6, 2055

8. See Org. Lett., 2004, 6, 2587-2590.

10a. See J. Org. Chem., 2003, 68, 2398
10b. See Org. Lett., 2003, 5, 1358.
10c. See J. Org. Chem., 1999, 64, 9727
10d. See Organic Letters, 2002, 4, 1655.

16a. See J. Am. Chem. Soc., 2003, 125, 15000.

16b. See Org. Lett., 2002, 4, 941.
16c. See Eur. J. Org. Chem., 2003, 848.
16d. See J. Am. Chem. Soc., 2003, 125, 14722.