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

Confirmations are the arrangements obtained by rotating the molecule along a C-C single bond.…

Answered: The most stable conformation of the…

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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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 ß anomer of D-idose. Explain why the more stable conformation has the CH2OH group in the axial position.
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 .
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 α or β anomer of D-idose. Explain why the more stable conformation has the CH2OH group in the axial position.
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 Fischer Projection of Talose is shown below. Draw its methyl glycoside in its lowest energy chair conformation CHO но но H. но HO. ČH,OH
5. Provide suitable responses for questions (a) – (). 6 CH2OH 4 OH OH 3 OH (a) What is the relative configuration of the above monosaccharide? (b) Which labeled carbon is the anomeric carbon? (c) Trace and identify the acetal in the above monosaccharide. (d) Draw the hemiacetal that results from above acetal. (e) Draw the open chain equivalent of the sugar in part (d). (f) Classify the monosaccharide below as a D-sugar or an L-sugar. H. OH O. OH CH,OH OH OH
(g) Using appropriate prefixes/infixes/suffixes (ketoheptose, aldoheptose, etc.), classify each of the monosaccharides shown below. CHO CH2OH Но IH но- HO- HO- HO H. CH2OH CH2OH I II (h) Identify B-D-altrose and a-D-altrose from the monosaccharides shown below. CH2OH CH2OH CH2OH CH2OH OH OH OH ОН OH ОН ОН OH OH OH OH OH OH OH OH OH I II II IV (i) Identify B-D-altrose and a-D-altrose from the monosaccharides shown below. VI I CH2OH O CH2OH II H V ОН, III IV OH OH H
Draw the 4C1 chair conformation and 1C4 chair conformation of beta-D-mannose .
Provide suitable responses for questions (a) –(j).| 6 CH2OH 4 ОН OH OH 2.
Trehalose and maltose are both dimers of glucose. However, they have considereably different reactivities. Concisely explain why these differences are observed. но но HO HO но "HO он но он OH O HO OHOH но trehalose maltose 1. Malthose is a reducing sugar while trehalose is not. 2. Trehalose is very resistant to acid hydrolysis while maltose can be acid-hydrolyzed with ease.
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 the structure of alpha-d-glucopyranose in straight chain cyclic, Haworth and cyclohexane-chair format. Draw the structures of two aldohexoses which are diastereomers but not epimers

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