EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
9th Edition
ISBN: 9780100591318
Author: McMurry
Publisher: YUZU
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Chapter 25.SE, Problem 46AP
Interpretation Introduction

a)

EBK ORGANIC CHEMISTRY, Chapter 25.SE, Problem 46AP , additional homework tip  1

Interpretation:

The open-chain form of the sugar given is to be drawn.

Concept introduction:

The pyranose form is a cyclic hemiacetal form with a six membered ring formed by the nucleophilic addition of the –OH group on C5 to the C1 carbonyl group. The furanose form is a cyclic hemiacetal form with a five membered ring formed by the nucleophilic addition of the –OH group on C5 to the C2 carbonyl group.

The orientation of –OH group differs in α- and β- anomers. In α- anomer the OH on C1 is cis to the –OH at the lowest chirality center in Fischer projection while in β- anomer the –OH on C1 is trans to the –OH at the lowest chirality center in Fischer projection.

D sugars have the –O- at C5 on the right in the uncoiled form while L sugars have -O- at C5 on the left.

To draw:

The open-chain form of the sugar given.

Interpretation Introduction

b)

EBK ORGANIC CHEMISTRY, Chapter 25.SE, Problem 46AP , additional homework tip  2

Interpretation:

The open-chain form of the sugar given is to be drawn.

Concept introduction:

The pyranose form is a cyclic hemiacetal form with a six membered ring formed by the nucleophilic addition of the –OH group on C5 to the C1 carbonyl group. The furanose form is a cyclic hemiacetal form with a five membered ring formed by the nucleophilic addition of the –OH group on C5 to the C2 carbonyl group.

The orientation of –OH group differs in α- and β- anomers. In the α- anomer the OH on C1 is cis to the –OH at the lowest chirality center in Fischer projection, while in β- anomer the –OH on C1 is trans to the –OH at the lowest chirality center in Fischer projection.

D sugars have the –O- at C5 on the right in the uncoiled form while L sugars have -O- at C5 on the left.

To draw:

The open-chain form of the sugar given.

Interpretation Introduction

c)

EBK ORGANIC CHEMISTRY, Chapter 25.SE, Problem 46AP , additional homework tip  3

Interpretation:

The open-chain form of the sugar given is to be drawn.

Concept introduction:

The pyranose form is a cyclic hemiacetal form with a six membered ring formed by the nucleophilic addition of the –OH group on C5 to the C1 carbonyl group. The furanose form is a cyclic hemiacetal form with a five membered ring formed by the nucleophilic addition of the –OH group on C5 to the C2 carbonyl group.

The orientation of –OH group differs in α- and β- anomers. In the α- anomer the OH on C1 is cis to the –OH at the lowest chirality center in Fischer projection, while in β- anomer the –OH on C1 is trans to the –OH at the lowest chirality center in Fischer projection.

D sugars have the –O- at C5 on the right in the uncoiled form while L sugars have -O- at C5 on the left.

To draw:

The open-chain form of the sugar given.

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Chapter 25 Solutions

EBK ORGANIC CHEMISTRY

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