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 19PP
Interpretation Introduction

Interpretation:

The conversion of D-galactose to D-galacturonic acid is to be suggested, by carrying out specific oxidation.

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 19PP

舧 The molecules that are nonsuperimposable or not identical with their mirror images are known as chiral molecules.

舧 A pair of two mirror images that are nonidentical is known as enantiomers, which are optically active.

舧 The stereoisomers that are nonsuperimposable on each other and not mirror images of each other are known as diastereomers.

舧 The achiral compounds in which plane of symmetry is present internally and consists of chiral centres are known as meso compounds, but they are optically inactive.

舧 Compounds that have a plane of symmetry tend to exist in meso forms. A meso form arises when the two stereoisomers produce superimposable images, and hence, compounds having meso forms are optically inactive.

舧 The reaction in which there is removal of water molecule is called dehydration reaction. H2SO4 is a dehydrating agent.

KMnO4 is a oxidizing agent.

舧 Monosaccharide carbohydrates that have their CH2OH placed at the C6 atom specifically oxidize to a carbonyl group are called uronic acids. Uronic acid of glucose is called glucuronic acid and that of galactose is called galacturonic acid.

舧 Based on the given information, direct oxidation of an aldose affects its aldehyde group first, converting it to a carboxylic acid. Most oxidizing agents that attack 1o alcohol groups also attack 2o alcohol groups. Hence, the synthesis of a uronic acid from an aldose needs protection of these groups from getting oxidized.

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Identify A, B, C, and D in the preceding problem if D is oxidized to an optically inactive aldaric acid; if A, B, and C are oxidized to optically active aldaric acids; and if interchanging the aldehyde and alcohol groups of A leads to a different sugar.
A D-aldopentose A is oxidized to an optically inactive aldaric acid with HNO3. A is formed by the Kiliani–Fischer synthesis of a D-aldotetrose B, which is also oxidized to an optically inactive aldaric acid with HNO3. What are the structures of A and B?
Draw the organic products formed in the following reaction.
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