The following reaction, called the benzylic acid rearrangement, takes place by typical carbonyl group reactions. HO Ph+ Ph Ph 1. NaOH, H₂O 2. H₂O* Ph Ph (Ph = phenyl) benzil benzylic acid Propose structures for the first two intermediates in this reaction. You do not have to consider stereochemistry. • Do not include counter-ions, e.g., Na*, I, in your answer. *** • In cases where there is more than one answer, just give one. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures using the sign from the drop-down menu. OH ChemDoodle OO° [] 21

The following reaction, called the benzylic acid rearrangement, takes place by typical carbonyl group reactions. HO Ph+ Ph Ph 1. NaOH, H₂O 2. H₂O* Ph Ph (Ph = phenyl) benzil benzylic acid Propose structures for the first two intermediates in this reaction. You do not have to consider stereochemistry. • Do not include counter-ions, e.g., Na*, I, in your answer. *** • In cases where there is more than one answer, just give one. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures using the sign from the drop-down menu. OH ChemDoodle OO° [] 21

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter10: Alcohols

Section: Chapter Questions

Problem 10.50P

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In the reaction series below, write down the appropriate reagents that can be used where there are question marks.
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