Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 25.SE, Problem 54AP
Interpretation Introduction

Interpretation:

Gentiobiose is a disaccharide composed of two units of D-glucose joined with a β(1→6) linkage.

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Treatment with NaBH 4 converts aldose U into an optically inactive (meso) alditol V. Ruff degradation ofU gives W, whose alditol is optically inactive. Ruff degradation of W forms D-glyceraldehyde, thesimplest aldose. Upon Kiliani-Fischer synthesis, U is converted to two aldoses, X and Y. X is oxidized toan optically active aldaric acid Z. Y is oxidized to an optically inactive aldaric acid. Draw the structuresof D-glyceraldehyde, V, W, X, Y, and Z. Structure of compound U is shown below.
An aldose A, is reduced by sodium borohydride to an optically inactive alditol B. The Ruff degredation of A forms C. Oxidation of C by nitric acid generates the optically inactive diacid D. The ruff degreation of C forms D-glyceraldehyde. draw the structures for compounds A through D and discuss a mechanism for the reduction step using sodium borohydride
Treatment of either anomer of fructose with excess ethanol in the presence of a trace ofHCl gives a mixture of the a and b anomers of ethyl-d-fructofuranoside. Draw the startingmaterials, reagents, and products for this reaction. Circle the aglycone in each product

Chapter 25 Solutions

Organic Chemistry

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