Organic Chemistry 9th Edition

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

Chapter 17 - Alcohols and Phenols - Problem: 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.
Update this answer!

You can help us out by revising, improving and updating this answer.

Update this answer

After you claim an answer you’ll have 24 hours to send in a draft. An editor will review the submission and either publish your submission or provide feedback.