EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Chapter 20, Problem 39P

a)

Interpretation Introduction

Interpretation:

The configuration of each of the asymmetric centers in the Fisher projection of D-glucose is to be stated.

Concept Introduction:

An asymmetric carbon atom is represented as a cross in Fisher projection.  The carbon chain is kept along the vertical line.  The groups attached asymmetric carbon atoms are arranged according to their configuration in Fisher projection.  The enantiomers of a chiral compound can be named the help of right hand and left hand configuration.

In fisher projection, chiral carbon atom is represented by a cross.  When two groups on a fisher projection are interchanged, the configuration of chiral carbon also changes from (R) to (S) or (S) to (R).

b)

Interpretation Introduction

Interpretation:

The configuration of each of the asymmetric centers in the Fisher projection of D-galactose is to be stated.

Concept Introduction:

An asymmetric carbon atom is represented as a cross in Fisher projection.  The carbon chain is kept along the vertical line.  The groups attached asymmetric carbon atoms are arranged according to their configuration in Fisher projection.  The enantiomers of a chiral compound can be named the help of right hand and left hand configuration.

In fisher projection, chiral carbon atom is represented by a cross.  When two groups on a fisher projection are interchanged, the configuration of chiral carbon also changes from (R) to (S) or (S) to (R).

c)

Interpretation Introduction

Interpretation:

The configuration of each of the asymmetric centers in the Fisher projection of D-ribose is to be stated.

Concept Introduction:

An asymmetric carbon atom is represented as a cross in Fisher projection.  The carbon chain is kept along the vertical line.  The groups attached asymmetric carbon atoms are arranged according to their configuration in Fisher projection.  The enantiomers of a chiral compound can be named the help of right hand and left hand configuration.

In fisher projection, chiral carbon atom is represented by a cross. When two groups on a fisher projection are interchanged, the configuration of chiral carbon also changes from (R) to (S) or (S) to (R).

d)

Interpretation Introduction

Interpretation:

The configuration of each of the asymmetric centers in the Fisher projection of D-xylose is to be stated.

Concept Introduction:

An asymmetric carbon atom is represented as a cross in Fisher projection.  The carbon chain is kept along the vertical line.  The groups attached asymmetric carbon atoms are arranged according to their configuration in Fisher projection.  The enantiomers of a chiral compound can be named the help of right hand and left hand configuration.

In fisher projection, chiral carbon atom is represented by a cross.  When two groups on a fisher projection are interchanged, the configuration of chiral carbon also changes from (R) to (S) or (S) to (R).

e)

Interpretation Introduction

Interpretation:

The configuration of each of the asymmetric centers in the Fisher projection of D-sorbose is to be stated.

Concept Introduction:

An asymmetric carbon atom is represented as a cross in Fisher projection.  The carbon chain is kept along the vertical line.  The groups attached asymmetric carbon atoms are arranged according to their configuration in Fisher projection.  The enantiomers of a chiral compound can be named the help of right hand and left hand configuration.

In fisher projection, chiral carbon atom is represented by a cross.  When two groups on a fisher projection are interchanged, the configuration of chiral carbon also changes from (R) to (S) or (S) to (R).

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a. How many stereogenic centers are present in α-D-galactose? b. Label the hemiacetal carbon in α-D-galactose. c. Draw the structure of β-D-galactose. d. Draw the structure of the polyhydroxy aldehyde that cyclizes to α- and β-D-galactose.
Draw the linear form, Haworth formulas and chair conformations (if applicable) for the two anomeric forms of the following monosaccharides: aldohexoses(use pyranose form); aldopentoses/ketohexoses(use furanose form) 1. D-xylose 2. D- psicose 3. D- idose

Chapter 20 Solutions

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