Organic Chemistry (8th Edition)

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

Chapter 1 - Introduction and Review - Problems - Page 28: Problem 1-17 b

Answer

ethoxide ion > methylamine > ethanol

Work Step by Step

Methylamine has $pK_b$ of 3.36. Ethoxide's base strength is similar to hydroxide. Since ethoxide is the conjugate base of ethanol, it must be stronger base than ethanol. The basicity of methylamine is between the basicity of ethanol and ethoxide ion. Thus, the decreasing order of basicity is ethoxide ion > methylamine > ethanol
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