Organic Chemistry (9th Edition)
Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 24.7C, Problem 24.17P
Interpretation Introduction

Interpretation: The delocalization of the negative charge in the Ruhemann’s purple anion with the help of their resonance forms is to be determined.

Concept introduction: Resonance structures are defined as a set of more than two Lewis Structures that collectively show the delocalization of the electrons in the molecule.

To determine: The delocalization of the negative charge in the Ruhemann’s purple anion with the help of their resonance forms.

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The structure of Vitamin C (ascorbic acid) is shown below. As the name indicates, the molecule is somewhat acidic. Actually, one of the hydrogens on the four OH groups is much more acidic than the other three ones. Which one is the acidic hydrogen? Hints: To find the answer, you will again have to draw some resonance structures of the product formed after loss of H+. Consider the product after the loss of H+ for each of the OH groups. Only two of the OH groups have resonance structures after deprotonation; one of these two groups has a much better resonance structure than the other one (again after deprotonation). Note that the oxygen atom that is part of the five-membered ring has nothing to do with the problem.

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Organic Chemistry (9th Edition)

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