Following are structural formulas for propanoic acid and the conjugate acids of isopropylamine and alanine, along with pK, values for each functional group. pк, 10.78 O pK, 4.78 O pK, 2.35 CH,CH,ČOH- CH,CHCOH pK, 9.87 CH;CHCH, NH,* NH,* Conjugate acid of isopropylamine Conjugate acid of alanine Propanoic acid

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
Section23.6: Reactions With Acids
Problem 23.8P
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How do you account for the fact that the -NH3+ group of the conjugate acid of alanine is a stronger acid than the -NH3+ group of the conjugate acid of isopropylamine?

Following are structural formulas for propanoic acid and the conjugate acids of
isopropylamine and alanine, along with pK, values for each functional group.
pк, 10.78
O pK, 4.78
O pK, 2.35
CH,CH,ČOH-
CH,CHCOH pK, 9.87
CH;CHCH,
NH,*
NH,*
Conjugate acid of
isopropylamine
Conjugate acid of
alanine
Propanoic acid
Transcribed Image Text:Following are structural formulas for propanoic acid and the conjugate acids of isopropylamine and alanine, along with pK, values for each functional group. pк, 10.78 O pK, 4.78 O pK, 2.35 CH,CH,ČOH- CH,CHCOH pK, 9.87 CH;CHCH, NH,* NH,* Conjugate acid of isopropylamine Conjugate acid of alanine Propanoic acid
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