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Organic Chemistry | 7th Edition | ISBN: 9781269406772 | Authors: Paula Yurkanis Bruice
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Solved: When deuterated phenanthrene oxide undergoes a

Chapter 11, Problem 57P

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QUESTION:

When deuterated phenanthrene oxide undergoes a rearrangement in water to form a phenol, \(81\%\) of the deuterium is retained in the product.

a. What percentage of the deuterium will be retained if an \(\mathrm{NIH}\) shift occurs?

b. What percentage of the deuterium will be retained if an \(\mathrm{NIH}\) shift does not occur?

Equation Transcription:

81%

NIH

Text Transcription:

81%

NIH

Questions & Answers

QUESTION:

When deuterated phenanthrene oxide undergoes a rearrangement in water to form a phenol, \(81\%\) of the deuterium is retained in the product.

a. What percentage of the deuterium will be retained if an \(\mathrm{NIH}\) shift occurs?

b. What percentage of the deuterium will be retained if an \(\mathrm{NIH}\) shift does not occur?

Equation Transcription:

81%

NIH

Text Transcription:

81%

NIH

ANSWER:

Solution 57P

(a)

First, observe the mechanism of the reaction:

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