Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 25.SE, Problem 48AP
Interpretation Introduction

Interpretation:

The pyranose form of β-anomer of D-talose is to be drawn. The ring substituents are to be identified as axial or equatorial.

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 pyranose form of β-anomer of D-talose and to identify the ring substituents as axial or equatorial.

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Classify the following monosaccharides as an aldose or ketose. I need help on number 5, a-d.
Carbohydrates. Determination of the extent of branching in glycogen. The amount of branching (number of α 1⟶ 6 glycosidic bonds) in glycogen can be determined by the following procedure. A sample of glycogen is exhaustively methylated-treated with a methylating agent (methyl iodide) that replaces the hydrogen of every sugar hydroxyl with a methyl group, converting –OH to –OCH3. All the glycosidic bonds in the treated sample are then hydrolyzed in aqueous acid, and the amounts of α -D-2,3-di-O-methylglucopyranose and α -D-2,3,6-tri-O-methylglucopyranose formed are measured. 1- Draw the cyclic structure of α-D-glucopyranose, α-D-2,3-di-O-methylglucopyranose and α-D-2,3,6-tri-O-methylglucopyranose, including the numbering of carbon atoms. 2- Which of α-D-2,3-di-O-methylglucopyranose or α-D-2,3,6-tri-O-methylglucopyranose represents a glucose unit in glycogen which was originally carrying a α 1⟶ 6 glycosidic bond? Explain.
Fill in the empty blanks and spaces in the table. The structure of d-galactose is in the next picture for reference.

Chapter 25 Solutions

Organic Chemistry

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