Organic Chemistry 9th Edition

Published by Brooks Cole
ISBN 10: 1305080483
ISBN 13: 978-1-30508-048-5

Chapter 17 - Alcohols and Phenols - Problem - Page 533: 5

Answer

See the explanation below for this scenario.

Work Step by Step

Notice that the NO2 is Electron withdrawing group causing the stabilization to the alkoxide ion, however, OCH3 is Electron donating group it destabilizes the alkoxide ion. Also remember that p-nitrobenzyl alcohol is more acidic than benzyl.
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