Essential Organic Chemistry, Global Edition
Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 16, Problem 41P
Interpretation Introduction

Interpretation:

The explanation corresponding to the given statement that 80% of Didose exists in the anhydrous form in an aqueous solution at 100°C, but only 0.1% of Didose exists in the anhydro form under the same condition has to be given.

Concept Introduction:

The chair conformers are stable forms of cyclic compounds.  In chair conformation, substituent’s prefers to place at equatorial positions.  This is due to unwanted interactions between those substituent’s that are placed at axial positions.  These interactions cause repulsion and that leads to the un-stability in molecule.  The general interactions that occur between axial substituents are 1,3 diaxial interactions.

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When a pyranose is in the chair conformation in which the CH2OH group and the C-1 OH group are both in axial positions, the two groups can react toform an acetal. This is called the anhydro form of the sugar (it has “lost water”). The anhydro form of d-idose is shown here. Explain why about 80% of d-idose exists in the anhydro form in an aqueous solution at 100 °C, but only about 0.1% of d-glucose exists in the anhydro form under the same conditions.
Draw Fischer projections for five aldoses below: glucose, mannose, galactose, arabinose and xylose. Now draw Fischer projections for the reduced and acetylated derivatives of these aldoses. From the Fischer drawings, select the meso molecules and redraw them, this time adding a plane of symmetry. Then select the molecules having an axis of symmetry, this time adding a line that skewers the middle of the drawing to indicate this symmetry.
The most stable conformation of most aldopyranoses is one in which the largest group, the CH2OH group, is equatorial. However, alpha-D-idopyranose exists primarily in a conformation with an axial CH2OH group. Write formulas for the two chair conformations of a-D-idopyranose (one with the CH2OH group axial and one with the CH2OH group equatorial) and provide an explanation
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