OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card for McMurry's Organic Chemistry, 9th
OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card for McMurry's Organic Chemistry, 9th
9th Edition
ISBN: 9781305671874
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 25.SE, Problem 47AP
Interpretation Introduction

Interpretation:

The five- membered cyclic β- hemiactal form of D-ribulose 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 C adjacent to CH2OH on the right in the uncoiled form while L sugars have the -O- at C adjacent to CH2OH on the left.

To draw:

The five- membered cyclic β- hemiactal form of D-ribulose.

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Chapter 25 Solutions

OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card for McMurry's Organic Chemistry, 9th

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