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Chapter 21, Problem 66P
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.
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 to form 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.
The most stable conformation of the pyranose ring of most D-aldohexoses places the largest group, CH2OH, in the equatorial position. An exception to this is the aldohexose D-idose. Draw the two possible chair conformations of either the a or B anomer of D-idose. Explain why the more stable conformation has the CH2OH group in the axial position.

Chapter 21 Solutions

Organic Chemistry; Modified MasteringChemistry with Pearson eText -- ValuePack Access Card; Study Guide and Student Solutions Manual for Organic Chemistry, Books a la Carte Edition (7th Edition)

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