Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 25.1, Problem 25.1P
Interpretation Introduction

Interpretation:

The Fischer Projections of all 2-ketopentoses has to be drawn and among that D-2-ketopentoses, L-2-ketopentoses and enantiomers has to be identified.

Concept Introduction:

  • The two dimensional representations of Carbohydrates is known as Fischer Projections.
  • The Ketopentoses contain the formula C5H10O5.
  • The 2-ketopentose contain ketone group at the second carbon.

D-ketopentose: The penultimate carbon contains OH on right side of the structure.  The D stands for Dextrorotatory.

L-ketopentose: The penultimate carbon contains OH on left side of the structure.  The L stands for Levorotatory.

Enantiomers: The stereoisomers which are mirror images and are non-superimposable are known as enantiomers.

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Classify the structures as being either an enantiomer, diastereomer or diastereomer/epimer of D-glucose. Structure A: CH H- -OH Structure B: но- H- H- OH Structure C: H- он H- -H D-Glucose: OH || CH CH CH он H- он но -H H- он но он но но- H- но H- OH OH но -- H- -H H -Ç-H Structure A: OH Structure B: OH Structure C: OH
The structure of 4 isomers of ketopentose are shown.  1) select every structure that is a diastereomer of structure D A, B, or C? 2) select every structure that is a enantiomer of structure C A, B, or D 3) select every structure that is a stereoisomer of structure C A, B, or D
Draw Fischer projections for all 2-ketopentoses. Which are d-2-ketopentoses, which are l-2-ketopentoses, and which are enantiomers?
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