2: The correct stereochemistry of only one stereocenter is indicated on the above structure. The actual stereochemistry of methyl glucoside is such that, when it is in a chair form, aill of the substituents fall in the equatorial positions, except for the -OMe, which is found in the axial position. Given this information, draw a clear, correct representation of methyl glucoside in a chair conformation, with all substituents properly indicated. HO HO, 12 HQ 3. When glucose is in its open-chain form, its stereochemistry can best be represented using a Fischer projection. On the skeleton Fischer projection shown at right, fill in the H and OH groups of the glucose "backbone" with the correct stereochemistry as determined from your structure shown above. H. H- HO HO H

2: The correct stereochemistry of only one stereocenter is indicated on the above structure. The actual stereochemistry of methyl glucoside is such that, when it is in a chair form, aill of the substituents fall in the equatorial positions, except for the -OMe, which is found in the axial position. Given this information, draw a clear, correct representation of methyl glucoside in a chair conformation, with all substituents properly indicated. HO HO, 12 HQ 3. When glucose is in its open-chain form, its stereochemistry can best be represented using a Fischer projection. On the skeleton Fischer projection shown at right, fill in the H and OH groups of the glucose "backbone" with the correct stereochemistry as determined from your structure shown above. H. H- HO HO H

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter25: Biomolecules: Carbohydrates

Section25.SE: Something Extra

Problem 44AP

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Without referring to the chapter, draw the chair conformations of(a) b-d-mannopyranose (the C2 epimer of glucose).(b) a-d-allopyranose (the C3 epimer of glucose).(c) b-d-galactopyranose (the C4 epimer of glucose)
The most stable conformation of the pyranose ring of most Daldohexosesplaces the largest group, CH2OH, in the equatorial position.An exception to this is the aldohexose D-idose. Draw the two possiblechair conformations of either the α or β anomer of D-idose. Explain whythe more stable conformation has the CH2OH group in the axial position .
Without referring to the chapter, draw the chair conformations of(a) b-d-mannopyranose (the C2 epimer of glucose).
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are these meso compounds, or identical, or both?
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Compound A is a D-aldopentose that can be oxidized to an optically inactive aldaric acid B. On Kiliani-Fischer chain extension, A is converted into C and D; C can be oxidized to an optically active aldaric acid E, but D is oxidized to an optically inactive aldaric acid F. What is the structure of compound F? • Use the wedge/hash bond tools to indicate stereochemistry where it exists. You do not have to explicitly draw H atoms. If a group is achiral, do not use wedged or hashed bonds on it. • Show stereochemistry in a meso compound. • Do not include lone pairs in your answer. They will not be considered in the grading.
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