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 30P
Interpretation Introduction

Interpretation:

The stereochemistry of αDidopyranose with respect to equatorial and axial chair conformations is to be explained.

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, whereas 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 stability of the atom can be estimated at the values of the anomeric effect of the O:OH bonds.

Organic Chemistry, Chapter 22, Problem 30P

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.

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