Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 21, Problem 42P
Interpretation Introduction

Interpretation:

The hexose obtained after three successive Killiani-Fisher synthesis of (+)-glyceraldehyde is to be predicted on the basis of given information.

Concept Introduction:

In Killiani-Fisher synthesis, hydrogen cyanide attacks the carbonyl group.  The carbonyl carbon is converted to an asymmetric center.  The CN bond is reduced to an imine which is partially deactivated by palladium catalyst to prevent the reduction of imine to an amine.  The two imines are hydrolyzed to two aldoses.

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