Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 22, Problem 40P
Interpretation Introduction

Interpretation:

Based on the given information, the structures of compounds A-F are to be proposed.

Concept introduction:

A carbohydrate is a biomolecule consisting of carbon (C), hydrogen (H) and oxygen (O) atoms, usually with a hydrogen–oxygen atom ratio of 2:1.

The Ruff degradation reaction is used for decreasing the number of carbon atoms of the respective aldoses, thereby shortening the carbon chain of the compound. It works in two steps:

Using bromine water to oxidize an aldose to the respective aldonic acid.

Using H2O2 and Fe2(SO4)3 to carry out oxidative decarboxylation of the aldonic acid to a lower aldose.

Organic Chemistry, Chapter 22, Problem 40P , additional homework tip  1

The Kiliani-Fischer reaction is used for producing epimers of higher aldoses from a lower aldose.

Organic Chemistry, Chapter 22, Problem 40P , additional homework tip  2

Alditols are sugar alcohols formed by the addition of hydrogen to the monosaccharide. Reduction of monosaccharides (carbohydrates containing single units of sugar molecules) results in the formation of alditols.

Organic Chemistry, Chapter 22, Problem 40P , additional homework tip  3

13CNMR, or the carbon-13 nuclear magnetic resonance, is an analytical technique in chemistry to identify the carbon atoms in the structure of a compound. It is an important tool in structure elucidation of organic compounds. However, it can only detect the C13 isotope, and not C12, as the latter has zero net spin.

The molecules that are non-superimposable or not identical with their mirror images are known as chiral molecules.

A pair of two mirror images that are non-identical are known as enantiomers, which are optically active.

The stereoisomers that are non-superimposable on each other and not mirror images of each other are known as diastereomers.

The achiral compounds in which plane of symmetry is present internally and consists of chiral centres are known as meso compounds, but they are optically inactive.

Compounds that have a plane of symmetry tend to exist in meso forms. A meso form arises when the two stereoisomers produce superimposable images, and hence, compounds having meso forms are optically inactive.

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When an optically active D-aldopentose was subjected to Kiliani-Fischer synthesis, followed by NaBH4/H2O, it produced a mixture of an optically active and an optically inactive alditol. When the same D-aldopentose was subjected to Wohl degradation followed by HNO3 it produced an optically inactive aldaric acid. Provide the structure of this D-aldopentose. Н- НО- н- H -ОН НО -H Н- -Н CH₂OH 1 A) 1 B) II C) III осн H D) IV НО осн -H Н- -OH H- H HỌ CH₂OH П -OH H -OH H Н -H CH₂OH Ш _H -OH HO -OH H- -OH H- осн -H -OH CH₂OH IV -OH CH₂OH V
A D-aldopentose A is oxidized to an optically inactive aldaric acid with HNO3. A is formed by the Kiliani–Fischer synthesis of a D-aldotetrose B, which is also oxidized to an optically inactive aldaric acid with HNO3. What are the structures of A and B?
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