Organic Chemistry (8th Edition)

Published by Pearson
ISBN 10: 0321768418
ISBN 13: 978-0-32176-841-4

Chapter 1 - Introduction and Review - Study Problems - Page 39: 1-43

Answer

Least basic --> Most basic $HSO_4^-$ < $H_2O$ < $CH_3COO^-$ < $NH_3$ < $CH_3O^-$ ~ $NaOH$ < $^-NH_2$

Work Step by Step

The conjugate bases of the weakest acids will be the strongest bases. The $pK_a$ values of the conjugate acids are listed in the brackets. Least basic --> Most basic $HSO_4^-$ (from -5) < $H_2O$ (from -1.7) < $CH_3COO^-$ (from 4.74) < $NH_3$ (from 9.4) < $CH_3O^-$ (from 15.5) ~ $NaOH$ (from 15.7) < $^-NH_2$ (from 33 (or 36))
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