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
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
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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 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.
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.
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 .
Chapter 16 Solutions
Essential Organic Chemistry, Global Edition
Ch. 16.1 - Prob. 1PCh. 16.2 - Prob. 2PCh. 16.3 - Prob. 3PCh. 16.3 - Prob. 4PCh. 16.4 - Prob. 5PCh. 16.4 - Prob. 6PCh. 16.5 - Prob. 7PCh. 16.5 - Prob. 8PCh. 16.6 - Prob. 10PCh. 16.8 - Prob. 12P
Ch. 16.8 - Prob. 14PCh. 16.9 - Prob. 15PCh. 16.10 - Prob. 16PCh. 16.11 - Refer to Figure 16.4 to answer the following...Ch. 16 - Prob. 18PCh. 16 - Prob. 19PCh. 16 - Prob. 20PCh. 16 - Prob. 21PCh. 16 - Prob. 22PCh. 16 - Prob. 23PCh. 16 - Prob. 24PCh. 16 - Prob. 25PCh. 16 - Name the following compounds:Ch. 16 - Prob. 28PCh. 16 - Prob. 29PCh. 16 - Prob. 31PCh. 16 - Prob. 32PCh. 16 - Prob. 33PCh. 16 - Prob. 34PCh. 16 - Prob. 35PCh. 16 - Prob. 36PCh. 16 - Prob. 37PCh. 16 - Draw the mechanism for the acid-catalyzed...Ch. 16 - Prob. 39PCh. 16 - Prob. 40PCh. 16 - Prob. 41P
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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 α or β anomer of D-idose. Explain why the more stable conformation has the CH2OH group in the axial position.arrow_forwardTrehalose 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.arrow_forwardC. Trehalose and isomaltose are both dimers of glucose. However, they have considerably different reactivities. Concisely explain why these differences are observed. HO HO HO HO он HO- OH HO но Но trehalose isomaltose 1. Isomaltose is a reducing sugar while trehalose is not. Isomaltose is a reducing sugar because it contains two glucose units with one glucose unit containing a hemiacetal group that is free, this allows 2. Trehalose is very resistant to acid hydrolysis while isomaltose can be acid-hydrolyzed with ease.arrow_forward
- Trehalose and maltose are both dimers of glucose. However, they have considereably different reactivities. Concisely explain why these differences are observed. OH но но но OH LOH он O'HO- он OH. OHOH HO 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.arrow_forward1) Below you are given the structures of the disaccharides lactose and trehalose. он он но он но но OH но но OH но он но но OH Lactose Trehalose a. Identify clearly the hemiacetal and acetal groups in these disaccharides and determine for each of these identified groups if they have a- or B-configuration.arrow_forwardC. Trehalose and isomaltose are both dimers of glucose. However, they have considerably different reactivities. Concisely explain why these differences are observed. OH HO но но. HO HO OH Но- он но OH HO НО trehalose isomaltose 1. Isomaltose is a reducing sugar while trehalose is not. 2. Trehalose is very resistant to acid hydrolysis while isomaltose can be acid-hydrolyzed with ease.arrow_forward
- 4. An iterative approach to oligosaccharide synthesis involves the use of protected glycals (sugars with C1-C2 double bond) as shown below. The product from the reaction of the first glycal with DMDO under anhydrous conditions is treated with another suitably-protected glycal to form a disaccharide glycal, and the process can be repeated to form a trisaccharide glycal, and so on... Crucial to the success of this approach is the stereoselective formation of the intermediate A in the scheme below. Draw the structure of A. DMDO CH₂Cl2 A OH ZnCl₂, THF OHarrow_forwardTwo sugars differing in configuration at a single asymmetric carbon atom are known as epimers. D-mannose is a C-2 epimer of glucose (Structure I), while D-galactose is a C-4 epimer of glucose. Structure II and III are II: galactose, III: mannose II: mannose; III: galactose II and III are mannose II and III are galactosearrow_forwardC. Trehalose and maltose are both dimers of glucose. However, they have considereably different reactivities. Concisely explain why these differences are observed. HO НО НО HO Но HO OH Он 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.arrow_forward
- Convert the following chair conformation of the sugar a-D-galactose into a structure that shows all the cis & trans relationships as hashed (down) and wedge (up) bonds. . HO + НО- CH₂OH . Use the wedge/hash bond tools to indicate stereochemistry where it exists. In cases where there is more than one answer, just draw one. Use "flat" representations of rings, not chairs, in your drawing. HO OH *** 8) H3C-0 0. HO OH OH OH Sn [F ? Ⓡ ChemDoodlearrow_forwardThe Fischer Projection of Talose is shown below. Draw its methyl glycoside in its lowest energy chair conformation CHO но но H. но HO. ČH,OHarrow_forwardDraw 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.arrow_forward
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