но HO но он The pK, of ascorbic acid (vitamin C) is 4.17, showing that it is slightly more acidic than acetic acid (CH3CO0H, pKa 4.74). (a) Show the fou r different conjugate bases that would be formed by deprotonation of the four different OH groups in ascorbic acid. (b) Compare the stabilities of these four conjugate bases, and predict which OH group of ascorbic acid is the most acidic. (c) Compare the most stable conjugate base of ascorbic acid with the conjugate base of acetic acid, and suggest why these two compounds have similar acidities, even though ascorbic acid lacks the carboxylic acid (COOH) group.
но HO но он The pK, of ascorbic acid (vitamin C) is 4.17, showing that it is slightly more acidic than acetic acid (CH3CO0H, pKa 4.74). (a) Show the fou r different conjugate bases that would be formed by deprotonation of the four different OH groups in ascorbic acid. (b) Compare the stabilities of these four conjugate bases, and predict which OH group of ascorbic acid is the most acidic. (c) Compare the most stable conjugate base of ascorbic acid with the conjugate base of acetic acid, and suggest why these two compounds have similar acidities, even though ascorbic acid lacks the carboxylic acid (COOH) group.
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
Chapter4: Acids And Bases
Section: Chapter Questions
Problem 4.18P: If the G for a reaction is 4.5 kcal/mol at 298 K, what is the Keq for this reaction? What is the...
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![но
HO
но
он
The pK, of ascorbic acid (vitamin C) is 4.17, showing that it is slightly more acidic
than acetic acid (CH3CO0H, pKa 4.74).
(a) Show the fou
r different conjugate bases that would be formed by deprotonation
of the four different OH groups in ascorbic acid.
(b)
Compare the stabilities of these four conjugate bases, and predict which OH
group of ascorbic acid is the most acidic.
(c) Compare the most stable conjugate base of ascorbic acid with the conjugate base
of acetic acid, and suggest why these two compounds have similar acidities, even
though ascorbic acid lacks the carboxylic acid (COOH) group.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F4813644a-a8fd-49c0-9dcc-db87f9ac9428%2F34813ed5-e21f-4cc5-9ed9-ee185edbe6fe%2F10ba2km.jpeg&w=3840&q=75)
Transcribed Image Text:но
HO
но
он
The pK, of ascorbic acid (vitamin C) is 4.17, showing that it is slightly more acidic
than acetic acid (CH3CO0H, pKa 4.74).
(a) Show the fou
r different conjugate bases that would be formed by deprotonation
of the four different OH groups in ascorbic acid.
(b)
Compare the stabilities of these four conjugate bases, and predict which OH
group of ascorbic acid is the most acidic.
(c) Compare the most stable conjugate base of ascorbic acid with the conjugate base
of acetic acid, and suggest why these two compounds have similar acidities, even
though ascorbic acid lacks the carboxylic acid (COOH) group.
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