Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 22, Problem 8PP
Interpretation Introduction

Interpretation:

The structures of the two different γlactones produced by lactonization of D-glucaric acid are to be determined.

Concept introduction:

舧 A carbohydrate is a biomolecule consisting of carbon (C), hydrogen (H) and oxygen (O) atoms, usually with a hydrogen-oxygen atom ratio of 2:1

HNO3 is an oxidizing agent.

舧 Carbohydrates are oxidized by HNO3 to give aldaric acid as a product.

舧 Aldaric acids are carbohydrates having two carboxylic acids. They are formed due to oxidation reaction of aldoses with dilute HNO3 and their general reaction can be represented as:

Organic Chemistry, Chapter 22, Problem 8PP , additional homework tip  1

Biomolecules containing an ester group (OCO) as part of their ring structures are called lactones. They are derived from their respective hydroxycarboxylic acids. Formation of lactones is called lactonization. They mainly exist as λ and δ forms.

舧 Aldaric acids (obtained from oxidation of aldohexoses) produces lactones of the same order that is as:

Organic Chemistry, Chapter 22, Problem 8PP , additional homework tip  2

舧 The reaction in which there is removal of water molecule is called dehydration reaction.

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