Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 25.3, Problem 25.4P
Interpretation Introduction

Interpretation:

To methyl α-D-mannopyranoside (methyl α-D-mannoside), Haworth projection and chair conformations has to be given and the anomeric carbon and the glycosidic bond has to be labelled.

Concept Introduction:

The aldehydes or ketones reacts with alcohol to form cyclic hemiacetal.  If hemiacetal reacts with another alcohol molecule it forms acetal.  Acetal is also known as glycoside.

The bond formed between the anomeric carbon and the alcohol molecule is said to be glycosidic bond.

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Draw the structure of:  a polysaccharide formed by joining D-mannose units in 1→4-β- glycosidic linkages;
Draw a chair conformation for the b-anomer of a disaccharide in which two units of d-glucopyranose are joined by an a-1,6-glycosidic bond.
1. Draw Haworth projections of B-D-arabinofuranose and a-L-mannopyranose. 2. Consider the structure of the disaccharide drawn at right: НО `CH2 В ОН (a) Give the names and D/L designation for the two monosaccharides linked together. H,C-O OHO „OH OH А: НО НО A В: ОН (b) In the structure, circle the anomeric carbon of each saccharide. (c) Is each saccharide present in its a or ß anomer? Specify both A and B (d) Would this disaccharide undergo mutarotation? Why or why not? (e) Would this disaccharide react with Tollens and/or Benedicts reagent? Why or why not? (f) There are two reasons this is very unlikely to be a naturally occurring disaccharide. What about its structure suggests this is true? Give both reasons.
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