Problem+7

=__PROBLEM 7:__=

DIFFICULTY: med, 4/10 LEVEL: third semester undergraduate organic chemistry course, 1-2 year graduate

Before attempting to solve this reaction mechanism, mind that the cyclopropane carbinol does not participate in the process, even though the medium is strongly acidic and polar. Another point of interest is that the required functionalizaton of C1 (where the sec-OH is), must result in a C-C bond forming reaction. Where does this carbon come from?

Ever since I published problem 5, I find much more convenient for you to have a PDF file of the discussion of possible solutions. instead of cutting and pasting file sections here. So please download the following PDF file for your perusal. Be sure to have Adobe Acrobat Reader in your computer. You may download it free from the Adobe webpage For a discussion open the PDF file by clicking on the button below.



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