Organic Chemistry (8th Edition)

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

Chapter 1 - Introduction and Review - Problems - Page 30: Problem 1-18 i

Answer

The equation for the acid base reaction and the conjugate acids and bases are shown in the picture. The equilibrium favors the products.

Work Step by Step

$FCH_2CH_2COO^-$ can accept a proton from $CH_3CHFCOOH$. So the following reaction will take place. $CH_3CHFCOO^-$ is the conjugate base because it losses a proton and $FCH_2CH_2COOH$ is conjugate acid because it gains a proton. Stronger acid and base are on the reactant side. The equilibrium will favor the weaker side and thus, products will be favored. The weaker base is resonance stabilized, where the electrons in the double bond between carbon and oxygen are delocalized. Moreover, the stronger base is also resonance stabilized, where the electrons in the double bond between carbon and oxygen are delocalized. The presence of electronegative atom like F make the acids stronger due to the inductive effect.
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