Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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Question

The existence of the NIH shift was established by determining the major product obtained from rearrangement of the following arene oxide, in which a hydrogen has been replaced by a deuterium.


a. What would be the major product if the NIH shift occurs? (Hint: A C¬H bond is easier to break than a C¬D bond.)
b. What would be the major product if the carbocation forms phenol by losing H+ or D+, rather than by going through the NIH shift?

D H- HB+ CH3
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Transcribed Image Text:D H- HB+ CH3
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