19.48 Phthalic acid and isophthalic acid have protons on two carboxy groupsthat can be removed with base. (a) Explain why the pKa for loss of thefirst proton (pKa1) is lower for phthalic acid than isophthalic acid. (b)Explain why the pKa for loss of the second proton (pKa2) is higher forphthalic acid than isophthalic acid.OHOHphthalic acidpKa1 = 2.9pKa2 = 5.4HOisophthalic acidpkat = 3.7PK a2 = 4.6pKa2Draw out the singleanions (onedeprotonation) and bearin mind that there is freerotationabout C-C single bonds.OH Look for stabilizationbased on theconformations possiblefromSuch rotation.

(a) Explain why the pKa for loss of the first proton (pKa₁) is lower for phthalic acid than…

Answered: 19.48 Phthalic acid and isophthalic…

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter23: Amines

Section: Chapter Questions

Problem 23.31P

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(a) Rank the following compounds in order of increasing acidity. (b) Which compound forms the strongest conjugate base?
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