Organic Chemistry (8th Edition)

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

Chapter 20 - Carboxylic Acids - Problems - Page 948: Problem 20-3 c

Answer

The order of acidity is : $CH_3CH_2COOH \lt CH_3CHClCOOH \lt CH_3CHCNCOOH \lt CH_3CHNO_2COOH$

Work Step by Step

We know, the stronger acid has a more stable conjugate base. In these compounds, the stronger is the electron withdrawing effect of the substituent , the more stable is the carboxylate ion, and the acid is stronger. The electron withdrawing effect of $NO_2$ is stronger than that of $CN$, $Cl$ and $H$. So, The order of acidity is : $CH_3CH_2COOH \lt CH_3CHClCOOH \lt CH_3CHCNCOOH \lt CH_3CHNO_2COOH$
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