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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The electrons flow from the electron-rich atoms of the nucleophile to the electrons poor atoms of the alkyl halide. Identify the electron rich in the nucleophile. Enter the element symbol only, do not include any changes.
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