Organic Chemistry
Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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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?
Answer ALL parts of this question. (a) Provide the structure and name of the aldehyde with the formula, C2H4O. (b) Draw the two steps of the Strecker synthesis used for the conversion of the aldehyde in part (a) into racemic alanine. (c) Draw the (R) and (S) enantiomers of alanine. Which is the naturally occurring enantiomer? (d) Draw the structure of the dipeptide, Ala-Gly.
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