The existence of the NIH shift was established by determining the major product obtained

Chapter 11, Problem 32

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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by determining the major product obtained from rearrangement of the following arene oxide, in which a hydrogen has been replaced by a deuterium.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 CiH bond is easier to break than a CiD bond.) b. What would be the major product if the carbocation forms phenol by losing a proton, rather than by going through the NIH shift?

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