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Following are structural formulas for propanoic acid and

Organic Chemistry | 6th Edition | ISBN: 9780840054982 | Authors: William H. Brown, Christopher S. Foote , Brent L. Iverson, Eric Anslyn ISBN: 9780840054982 88

Solution for problem 23.8 Chapter 23

Organic Chemistry | 6th Edition

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Organic Chemistry | 6th Edition | ISBN: 9780840054982 | Authors: William H. Brown, Christopher S. Foote , Brent L. Iverson, Eric Anslyn

Organic Chemistry | 6th Edition

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Problem 23.8

Following are structural formulas for propanoic acid and the conjugate acids of isopropylamine and alanine, along with pKa values for each functional group. pKa 10.78 pKa 4.78 pKa 2.35 NH3 1 Conjugate acid of isopropylamine CH3CHCH3 pKa 9.87 NH3 1 Conjugate acid of alanine CH3CHCOH O Propanoic acid CH3CH2COH O (a) How do you account for the fact that the !NH3 1 group of the conjugate acid of alanine is a stronger acid than the !NH3 1 group of the conjugate acid of isopropylamine? (b) How do you account for the fact that the !COOH group of the conjugate acid of alanine is a stronger acid than the !COOH group of propanoic acid?

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Chapter 23, Problem 23.8 is Solved
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Textbook: Organic Chemistry
Edition: 6
Author: William H. Brown, Christopher S. Foote , Brent L. Iverson, Eric Anslyn
ISBN: 9780840054982

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Following are structural formulas for propanoic acid and

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