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 18PP
Interpretation Introduction

Interpretation:

The other product yield when compounds γlactones of Dglucaric acid subjected to procedure is 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 18PP , additional homework tip  1

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.

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 γ and δ forms.

舧 Aldaric acids (obtained from oxidation of aldohexoses) produce lactones of the order.

Organic Chemistry, Chapter 22, Problem 18PP , additional homework tip  2

舧 Fischer formulated new aldohexose products from glucose by interchanging the end-groups of the (+)glucose chain. These aldohexoses were the Lsugars that were the mirror images of DGulose

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