Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 3, Problem 3.52AP
Interpretation Introduction

(a)

Interpretation:

The structure of ascorbic acid as it exists at the physiological pH (pH =7.4) is to be stated.

Concept introduction:

The pKa of the acid describes the pH at which the acid will be found in the protonated form or dissociated form. The acid is found in dissociated form in the pH range equal to pKa1 to pKa+1.

Interpretation Introduction

(b)

Interpretation:

The resonance structures of the structure of ascorbic acid as it exists at the physiological pH (pH =7.4) using curved-arrow notation are to be stated.

Concept introduction:

Resonance is the phenomena of the delocalization of pi electrons to give extra stability to the molecule. This extra stability comes from the distribution of the energy of the molecule in the resonance structures formed.

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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.
(a) Rank the following compounds in order of increasing acidity. (b) Which compound forms the strongest conjugate base?
(a) Given that Ka for acetic acid is 1.8 x 10-5 and that forhypochlorous acid is 3.0 x 10-8, which is the stronger acid?(b) Which is the stronger base, the acetate ion or the hypochloriteion? (c) Calculate Kb values for CH3COO- and ClO-.
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