Organic Chemistry
Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 21.5, Problem 10P
Interpretation Introduction

Interpretation:

The mechanism for the base-catalyzed conversion of D-fructose to D-glucose and D-mannose has to be written.

Concept Introduction:

In the conversion of D-fructose to D-glucose the base is required as a catalyst.  Therefore, such reactions are called base catalyzed reactions.  The base first removes a proton from carbon position 1 and forms an enolate ion.  The enolate ion is further protonated by the other proton.  That proton comes from the top or from the bottom of the planar sp2-hybridized carbon.

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