Convert 2-Phenylethyl bromide to 2-Bromo-1-phenylethanol using any necessary organic and inorganic reagents. It will require multiple steps.

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Convert 2-Phenylethyl bromide to 2-Bromo-1-phenylethanol using any necessary organic and
inorganic reagents. It will require multiple steps.
Transcribed Image Text:Convert 2-Phenylethyl bromide to 2-Bromo-1-phenylethanol using any necessary organic and inorganic reagents. It will require multiple steps.
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I don't see how the first part of this reaction is correct. My textbook says that primary alkyl halides react with most alkoxide bases by an SN2 mechanism over E2. 

It also says that if the base itself is crowded such as potassium tert-butoxide,  primary alkyl halides undergo elimination. 

I am confused, because I used potassium tert-butoxide in tert-butyl alcohol for this problem, but I was marked incorrect. Can you explain? 

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