The validation of the fact that cis-cycloctene is a meso compound under the original definition, but not under working definition. Interpretation: The validation of the fact that cis-cycloctene is a meso compound under the original definition, but not under working definition is to be stated. Concept introduction: The class of diastereoisomers includes stereoisomers that are not enantiomers. They are not mirror images of each other. There are two or more chiral centers generally present in diastereoisomers. Structures of diastereoisomers are not the same, but they are stereoisomers because they differ in the spatial arrangement of atoms.

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Chapter 5, Problem 5.41SP

(a)

Interpretation Introduction

To determine: The validation of the fact that cis-cycloctene is a meso compound under the original definition, but not under working definition.

Interpretation: The validation of the fact that cis-cycloctene is a meso compound under the original definition, but not under working definition is to be stated.

Concept introduction: The class of diastereoisomers includes stereoisomers that are not enantiomers. They are not mirror images of each other. There are two or more chiral centers generally present in diastereoisomers. Structures of diastereoisomers are not the same, but they are stereoisomers because they differ in the spatial arrangement of atoms.

(b)

Interpretation Introduction

To determine: The validation of the fact that a double allene is a meso compound under the original definition, but not under working definition.

Interpretation: The validation of the fact that a double allene is a meso compound under the original definition, but not under working definition is to be stated.

Concept introduction: The class of diastereoisomers includes stereoisomers that are not enantiomers. They are not the mirror images of each other. There are two or more chiral centers generally present in diastereoisomers. Structures of diastereoisomers are not the same, but they are stereoisomers because they differ in the spatial arrangement of atoms.

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a) How many chiral centers exist in the following molecule structure A? b) How many possible stereoisomers would exist for structure A (including structure A) based on the correct number of chiral centers

The original definition of meso is “an achiral compound that has chiral diastereomers.” Our working definition of meso is “an achiral compound that has chiral centers (usually asymmetric carbon atoms).” The working definition is much easier to apply because we don’t have to envision all possible chiral diastereomers of the compound. Still, the working definition is not quite as complete as the original definition. Show how cis-cyclooctene is defined as a meso compound under the original definition, but not under our working definition.

The original definition of meso is “an achiral compound that has chiral diastereomers.” Our working definition of meso is “an achiral compound that has chiral centers (usually asymmetric carbon atoms).” The working definition is much easier to apply because we don’t have to envision all possible chiral diastereomers of the compound. Still, the working definition is not quite as complete as the original definition. See if you can construct a double allene that is achiral, although it has chiral diastereomers, and is, therefore, a meso compound under the original definition. The allene structure is not a chiral center, but it can be a chiral axis.