Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 25.4, Problem 8P
Interpretation Introduction

a)

Interpretation:

Fischer projection of D-sugars are to be drawn.

Concept introduction:

Fischer Projections are typically used for depicting monosaccharides and amino acids. They are helpful with depicting monosaccharides, because they have so many stereocenters, and the different monosaccharides are all pretty similar, they are just different about the orientation of the stereocenters. The Fischer Projection allows us to quickly see the orientation of each monosaccharide.

Interpretation Introduction

b)

Interpretation:

Fischer projection of D-sugars are to be drawn.

Concept introduction:

Fischer Projections are typically used for depicting monosaccharides and amino acids. They are helpful with depicting monosaccharides, because they have so many stereocenters, and the different monosaccharides are all pretty similar, they are just different about the orientation of the stereocenters. The Fischer Projection allows us to quickly see the orientation of each monosaccharide.

Interpretation Introduction

c)

Interpretation:

Fischer projection of D-sugars are to be drawn.

Concept introduction:

Fischer Projections are typically used for depicting monosaccharides and amino acids. They are helpful with depicting monosaccharides, because they have so many stereocenters, and the different monosaccharides are all pretty similar, they are just different about the orientation of the stereocenters. The Fischer Projection allows us to quickly see the orientation of each monosaccharide.

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m) Which pyranose ring (A, B, C, or D) in the tetrasaccharide below is derived from D-altrose? The Fischer projections for the four aldohexoses that make up this tetrasaccharide are shown below. B C D HOH CHO CHO CHO CHO HO+H HTOH Fонно н HOH HOH H-OH H-OH H-+-OH H-TOHHOH HOH H+OH HOHнтон нон CHOH CHOH CHOH CHOH De D-glue Dalose Datrone i NH Į HOH STEP 1 OH, HO- answer 1. Just add arrows and charges for steps 1, 2, and 3 in formation of this enamine з no arrows needed here OH н Н ЮН -OH STEP 3 :ÖH н H STEP 2 на это про за поч
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.
6 CH2OH 4 OH 2 ОН 3 OH (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 ОН O. ОН CH2OH ОН ОН

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