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: 1-42

Answer

Least acidic --> Most acidic $NH_3$ < $H_2O$ ~$CH_3OH$ < $CH_3COOH$ < $HF$ < $H_3O^+$ < $H_2SO_4$

Work Step by Step

Using the $pK_a$ values from table 1-5 and appendix 4, the answer can be determined. The lower the $pK_a$, the stronger the acid. The water and $CH_3OH$ are very close. The $pK_a$ are given in the brackets. Least acidic --> Most acidic High $pK_a$ --> low $pK_a$ $NH_3$ (33) < $H_2O$ (15.7) ~$CH_3OH$ (15.5) < $CH_3COOH$ (4.74) < $HF$ (3.2) < $H_3O^+$ (-1.7) < $H_2SO_4$ (-5)
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