ORGANIC CHEMISTRY BOOK& SG/SM
ORGANIC CHEMISTRY BOOK& SG/SM
6th Edition
ISBN: 9781264094493
Author: SMITH
Publisher: MCG
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Chapter 26, Problem 63P
Interpretation Introduction

Interpretation: The stepwise mechanism for the isomerization of D-glucose to form the given compounds is to be drawn.

Concept introduction: Carbohydrates are naturally occurring organic compounds. The monosaccharide glucose is called an Aldohexose as it contains six carbon atoms as well as an aldehyde functional group and fructose is known as ketohexose as it contains six carbons with a ketone functional group.

Glucose and mannose are C2 epimers that is they differ in position of hydroxyl group at second carbon atom.

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The following isomerization reaction, drawn using D-glucose as starting material, occurs with all aldohexoses in the presence of base. Draw a stepwise mechanism that illustrates how each compound is formed. сно сно сно CH2OH C=0 H- OH H- -OH но- H- но H- "OH но H- Но H- но H- H- -H- H20 H- HO- O- H- -O- H- -OH -O- OH ČHOH CH,OH ČH2OH ČH2OH (recovered starting material) D-glucose
Draw the organic products formed in each reaction.
Aldosterone is in equilibrium with its cyclic hemiacetal. Draw the hemiacetal form of aldosterone.

Chapter 26 Solutions

ORGANIC CHEMISTRY BOOK& SG/SM

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