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 32P
Interpretation Introduction

Interpretation:

The structure of lactose sugar based on the given experimental evidences is to be shown.

Concept introduction:

舧 Chair conformations: It is the most stable conformation, which accurately shows the spatial arrangement of atoms.

舧 Equatorial bonds are parallel to the average plane of the ring, while axial bonds are perpendicular to the average plane of the ring.

舧 The conformation having bonds at the equatorial positions are more stable than those with bonds at the axial position.

舧 On flipping the cyclohexane ring, axial bonds become equatorial bonds and equatorial bonds becomes axial bond.

舧 Bulkier group acquires equatorial positions to form stable conformer due to steric factors.

舧 The most stable configuration of aldopyranoses is when the CH2OH group exists in equatorial conformation.

舧 Stereochemistry: The equatorial orientation refers to the spatial arrangement of CH2OH group at C-2 in the same plane, and the axial orientation refers to the spatial arrangement of CH2OH group at C-2 along the axis.

舧 The anomeric effect is lowest for sugars with equatorial orientation, which results in lower energetic state, and consequently this type of orientation confers higher stability.

舧 The anomeric effect is highest for sugars with axial orientation, which results in higher energetic state, and consequently this type of orientation confers lower stability.

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 32P , additional homework tip  1

舧 Monosaccharides containing six carbon atoms and an aldehyde group are called aldohexoses.

舧 Alditols are compounds produced from aldoses or ketoses on reduction with certain reagents such as sodium borohydride (NaBH4) and hydrogen along with a catalyst.

Organic Chemistry, Chapter 22, Problem 32P , additional homework tip  2

舧 Compounds formed by the reaction of reducing sugars with excess of phenyl hydrazine are called osazones. Osazones are products of oxidation and are produced by all reducing sugars.

Organic Chemistry, Chapter 22, Problem 32P , additional homework tip  3

舧 Fischer projection is a way of representing the structural formulae of compounds through cross formulation of their open chain structures.

舧 Bromine water is an effective reagent that selectively oxidizes the CHO group to COOH moiety, and thereby, converts an aldose into aldonic acid.

Organic Chemistry, Chapter 22, Problem 32P , additional homework tip  4

舧 Lactose is a disaccharide carbohydrate present in milk (mammary glands) of the mammals. It has a reducing nature and undergoes hydrolysis to yield Dgalactose and Dglucose .

Organic Chemistry, Chapter 22, Problem 32P , additional homework tip  5

舧 The aldehyde group of an aldose reacts with three moles of phenylhydrazine to produce phenylosazone at C2 position. Osazones are products of oxidation.

舧 The monosaccharides with five or more carbons atoms form cyclic structures in aqueous solution, and they can form two cyclic stereoisomers from each straight-chain monosaccharide, known as anomers. In aqueous solution, the two anomers and the straight-chain structure of a monosaccharide form an equilibrium mixture through the process of mutarotation.

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