Organic Chemistry Study Guide and Solutions
Organic Chemistry Study Guide and Solutions
6th Edition
ISBN: 9781936221868
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 24, Problem 24.43AP
Interpretation Introduction

(a)

Interpretation:

Whether the given structure of fucose is D- or L- enantiomer is to be predicted.

Concept Introduction:

Enantiomers are the non-super imposable mirror images of each other. Enantiomers rotate the plane of polarization in opposite direction but by the same amount. The compound becomes optically inactive.

Interpretation Introduction

(b)

Interpretation:

The given structure of fucose is α or β - form is to be stated

Concept Introduction:

The carbohydrate can have either α or β form depending upon the position of substituent at anomeric position. α and β forms are anomers of each other. If the -OH group of anomeric carbon is present below the plane then it is α and if it is above the plane then it is β anomer.

Interpretation Introduction

(c)

Interpretation:

Whether fucose is an aldose, ketose or neither of them is to be stated.

Concept Introduction:

Carbohydrates can either be aldose or ketose. Carbohydrates which contain aldehyde group are aldoses and which contain keto group are ketoses. First the pyranose structure of the compound must be converted to the Fischer projection and then ring opening takes place to form the carbohydrate structure. Then see whether it is aldose or ketose.

Interpretation Introduction

(d)

Interpretation:

Fischer projection of the carbonyl group of the given carbohydrate is to be shown.

Concept Introduction:

Fischer projection is used to represent a three dimensional structure of compound in two dimensional plane. The Fischer projection is drawn by taking chiral carbons into consideration. The chiral carbons of the molecule are represented by the intersection of two lines in Fischer projection. The groups attached to the chiral carbon are attached to that intersection point. The D or L form is decided on the basis of the attachment of the hydroxyl group on the chiral carbon which is farthest from the carbonyl carbon.

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