Organic Chemistry (8th Edition)
Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 20, Problem 38P

(a)

Interpretation Introduction

Interpretation:

The aldopentoses which are enantiomers out of the eight aldopentoses are to be stated.

Concept Introduction:

Enantiomers are the pairs which are mirror images of each other.  These mirror images are non-superimposable to each other.  This means the forms of a compound which exists in two non-superimposable forms each of which is a mirror image of other form is known as enantiomers.

(b)

Interpretation Introduction

Interpretation:

The aldopentoses which are C-2 epimers out of the eight aldopentoses are to be stated.

Concept Introduction:

C-2 epimers are the compounds which has different configuration at second carbon atom and have same configuration at all other carbon atoms.

The stereogenic center present in the compound which makes the orientation of molecules different is known as epimers.

(c)

Interpretation Introduction

Interpretation:

The aldopentoses which forms an optically active compound on oxidation with nitric acid is to be stated.

Concept introduction:

Aldopentoses are the compounds containing five carbon atoms and one aldehyde group at one end of carbon chain which gives dicarboxylic acids called aldaric acids on oxidation with nitric acids.  Aldaric acid is the molecule containing six carbon atoms having carboxylic acid group on both the sides.

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Answer the following questions about the eight aldopentoses: a. Which are enantiomers? b. Which are C-2 epimers? c. Which form an optically active compound when oxidized with nitric acid?
Answer the following questions about monosaccharide B.a. Draw the β anomer of B in a Haworth projection.b. Draw the α anomer of B in a three-dimensional representation using a chair conformation.c. What products are formed when B undergoes the Kiliani–Fischer synthesis?d. What product is formed when B is treated with NaBH4 in CH3OH?e. Draw the disaccharide formed when two molecules of B are joined by a 1→4-β-glycosidic linkage.
Answer the following questions about the eight aldopentoses: Which are enantiomers?

Chapter 20 Solutions

Organic Chemistry (8th Edition)

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