ORGANIC CHEMISTRY BOOK& SG/SM
ORGANIC CHEMISTRY BOOK& SG/SM
6th Edition
ISBN: 9781264094493
Author: SMITH
Publisher: MCG
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Chapter 26.2, Problem 6P
Interpretation Introduction

(a)

Interpretation: The given compounds A, B and C are to be labeled as D or L-sugar.

Concept introduction: A sugar molecule in which hydroxyl group of second last carbon atom is on the left and right side of the horizontal line is known as L-sugar and D-sugar, respectively.

Interpretation Introduction

(b)

Interpretation: The relation between A and B, A and C, B and C is to be determined from enantiomers, diastereomers and constitutional isomers.

Concept introduction: Two compounds which are non-superimposable mirror images of each other are known as enantiomers. Whereas two compounds which are neither superimposable nor mirror images to each other are known as diastereomer. On the other hand, two compounds that have same molecular formula but different structural arrangement of atoms are known as constitutional isomers.

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(a) Label compounds A, B, and C as D- or L-sugars. (b) How are compounds A and B related? A and C? B and C? Choose from enantiomers, diastereomers, or constitutional isomers.
(a) Convert each cyclic monosaccharide into a Fischer projection of its acyclic form. (b) Name each monosaccharide. (c) Label the anomer as α or β.
(d) Draw the structure of the expected product when monosaccharide B undergo mutarotation upon dissolving in water in the presence of Tollens reagent (AGNO3, NHẠOH). он OH O. OH OH OH monosaccharide B

Chapter 26 Solutions

ORGANIC CHEMISTRY BOOK& SG/SM

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