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The pKa of ascorbic acid (vitamin C, page 2) is 4.17,

Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr ISBN: 9780321768414 33

Solution for problem 55SP Chapter 1

Organic Chemistry | 8th Edition

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Organic Chemistry | 8th Edition | ISBN: 9780321768414 | Authors: L.G. Wade Jr

Organic Chemistry | 8th Edition

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Problem 55SP

The pKa of ascorbic acid (vitamin C, page 2) is 4.17, showing that it is slightly more acidic than acetic acid (CH3COOH,pKa 4.74).

(a) Show the four 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.

Step-by-Step Solution:
Step 1 of 3

The pKa of ascorbic acid is 4.17 and  pKa of acetic acid is (CH3COOH) 4.7

Ascorbic acid is more acidic than acetic acid.

Step-1

The structure of ascorbic acid is,

Four different conjugate base of ascorbic acid  that formed by deprotonation of the four different OH groups :-

Step-2

Here...

Step 2 of 3

Chapter 1, Problem 55SP is Solved
Step 3 of 3

Textbook: Organic Chemistry
Edition: 8
Author: L.G. Wade Jr
ISBN: 9780321768414

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The pKa of ascorbic acid (vitamin C, page 2) is 4.17,