Organic Chemistry-Package(Custom)
Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 5, Problem 5.56P

Draw all possible stereoisomers for each cycloalkane. Label pairs of enantiomers and diastereomers. Label any meso compound.

a. Chapter 5, Problem 5.56P, Draw all possible stereoisomers for each cycloalkane. Label pairs of enantiomers and diastereomers. , example  1 b. Chapter 5, Problem 5.56P, Draw all possible stereoisomers for each cycloalkane. Label pairs of enantiomers and diastereomers. , example  2 c. Chapter 5, Problem 5.56P, Draw all possible stereoisomers for each cycloalkane. Label pairs of enantiomers and diastereomers. , example  3

Expert Solution
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Interpretation Introduction

(a)

Interpretation: The possible stereoisomers for the given cycloalkane are to be drawn. The labeling of any enantiomers, diastereomers or meso compound is to be stated.

Concept introduction: A carbon atom that has four nonequivalent atoms or groups attached to it is known as chiral carbon atom. Chiral carbon centers are also called as asymmetric or stereogenic centers.

The stereocenters are carbon atoms on which the interchanging of two atoms or groups results in the formation of new stereoisomers. The stereocenters are also known as stereogenic centers. R,S configurations can be used to determine the relation between the two compounds. Enantiomer of a compound has opposite configuration. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

Answer to Problem 5.56P

The possible stereoisomers for the given cycloalkane are three. Among the three stereoisomers, the labeling of two enantiomers of the given cycloalkane is (1R,3R)1,3dimethylcyclohexane and (1S,3S)1,3dimethylcyclohexane. The labeling of one remaining meso compound is done as (1R,3S)1,3dimethylcyclohexane.

Explanation of Solution

The given cycloalkane is,

Organic Chemistry-Package(Custom), Chapter 5, Problem 5.56P , additional homework tip  1

Figure 1

Due to the presence of cyclohexane ring attached with two methyl groups, the IUPAC name of this cycloalkane is 1,3dimethylcyclohexane. The total number of chiral centers for 1,3dimethylcyclohexane is two. The total number of stereoisomers of 1,3dimethylcyclohexane is calculated by the formula,

Numberofstereoisomers=2n

Where,

n is the total number of chiral centers.

Substitute the number of chiral centers of 1,3dimethylcyclohexane in the above expression.

Numberofstereoisomers=22=4

Thus, the total number of stereoisomers of 1,3dimethylcyclohexane is 4. This 1,3dimethylcyclohexane has a plane of symmetry as shown below.

Organic Chemistry-Package(Custom), Chapter 5, Problem 5.56P , additional homework tip  2

Figure 2

Thus, this compound forms only three stereoisomers instead of four. Among the three stereoisomers of 1,3dimethylcyclohexane, two stereoisomers are enantiomers as shown below.

Organic Chemistry-Package(Custom), Chapter 5, Problem 5.56P , additional homework tip  3

Figure 3

The remaining one stereoisomer of 1,3dimethylcyclohexane is a meso compound as labeled below.

Organic Chemistry-Package(Custom), Chapter 5, Problem 5.56P , additional homework tip  4

Figure 4

Conclusion

The possible stereoisomers for the given cycloalkane are three. Among the three stereoisomers, the labeling of two enantiomers of the given cycloalkane is (1R,3R)1,3dimethylcyclohexane and (1S,3S)1,3dimethylcyclohexane. The labeling of one remaining meso compound is done as (1R,3S)1,3dimethylcyclohexane.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The possible stereoisomers for the given cycloalkane are to be drawn. The labeling of any enantiomers, diastereomers or meso compound is to be stated.

Concept introduction: A carbon atom that has four nonequivalent atoms or groups attached to it is known as chiral carbon atom. Chiral carbon centers are also called as asymmetric or stereogenic centers.

The stereocenters are carbon atoms on which the interchanging of two atoms or groups results in the formation of new stereoisomers. The stereocenters are also known as stereogenic centers. R,S configurations can be used to determine the relation between the two compounds. Enantiomer of a compound has opposite configuration. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

Answer to Problem 5.56P

The possible stereoisomers for the given cycloalkane are two. Both are meso compounds and these meso compound are labeled as done as Cis1,4dimethylcyclohexane and Trans1,4dimethylcyclohexane.

Explanation of Solution

The given cycloalkane is,

Organic Chemistry-Package(Custom), Chapter 5, Problem 5.56P , additional homework tip  5

Figure 5

Due to the presence of cyclohexane ring attached with two methyl groups at first and fourth carbon atoms, the IUPAC name of this cycloalkane is 1,4dimethylcyclohexane. This compound does not possess any chiral carbon atom.

This 1,4dimethylcyclohexane has a plane of symmetry as shown below.

Organic Chemistry-Package(Custom), Chapter 5, Problem 5.56P , additional homework tip  6

Figure 6

Thus, this compound forms only two stereoisomers one is cis isomer and second is trans isomer. The given compound, 1,4dimethylcyclohexane exist in the chair conformation in both cis and trans forms as shown below.

Organic Chemistry-Package(Custom), Chapter 5, Problem 5.56P , additional homework tip  7

Figure 7

Thus, 1,4dimethylcyclohexane possess only two sreeroisomers which are also the meso compounds.

Conclusion

The possible stereoisomers for the given cycloalkane are two. Both are meso compounds and these meso compound are labeled as done as Cis1,4dimethylcyclohexane and Trans1,4dimethylcyclohexane.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The possible stereoisomers for the given cycloalkane are to be drawn. The labeling of any enantiomers, diastereomers or meso compound is to be stated.

Concept introduction: A carbon atom that has four nonequivalent atoms or groups attached to it is known as chiral carbon atom. Chiral carbon centers are also called as asymmetric or stereogenic centers.

The stereocenters are carbon atoms on which the interchanging of two atoms or groups results in the formation of new stereoisomers. The stereocenters are also known as stereogenic centers. R,S configurations can be used to determine the relation between the two compounds. Enantiomer of a compound has opposite configuration. Diastereomers of a compound have at least one stereogenic centre with same configuration and at least one with opposite configuration.

Answer to Problem 5.56P

The possible stereoisomers for the given cycloalkane are four. It contains two pairs of enantiomers, the labeling of two pairs of enantiomers of the given cycloalkane is (1S,2R)1bromo2chlorocyclopentane, (1R,2S)1bromo2chlorocyclopentane and (1R,2R)1bromo2chlorocyclopentane, (1S,2S)1bromo2chlorocyclopentane.

Explanation of Solution

The given cycloalkane is,

Organic Chemistry-Package(Custom), Chapter 5, Problem 5.56P , additional homework tip  8

Figure 8

Due to the presence of cyclopentane ring attached with one bromine atom and one chlorine atom at first and second carbon atom respectively, the IUPAC name of this cycloalkane is 1bromo2chlorocyclopentane. The total number of chiral centers for 1bromo2chlorocyclopentane is two. The total number of stereoisomers of 1bromo2chlorocyclopentane is calculated by the formula,

Numberofstereoisomers=2n

Where,

n is the total number of chiral centers.

Substitute the number of chiral centers of 1bromo2chlorocyclopentane in the above expression.

Numberofstereoisomers=22=4

Thus, the total number of stereoisomers of 1bromo2chlorocyclopentane is 4. This 1bromo2chlorocyclopentane compound does not possess plane of symmetry as shown below.

The four stereoisomers of 1bromo2chlorocyclopentane are shown as,

Organic Chemistry-Package(Custom), Chapter 5, Problem 5.56P , additional homework tip  9

Figure 9

The compound, 1bromo2chlorocyclopentane possess two pairs of enantiomers which are labeled as,

Organic Chemistry-Package(Custom), Chapter 5, Problem 5.56P , additional homework tip  10

Figure 10

Conclusion

The possible stereoisomers for the given cycloalkane are four. It contains two pairs of enantiomers, the labeling of two pairs of enantiomers of the given cycloalkane is (1S,2R)1bromo2chlorocyclopentane, (1R,2S)1bromo2chlorocyclopentane and (1R,2R)1bromo2chlorocyclopentane, (1S,2S)1bromo2chlorocyclopentane.

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Chapter 5 Solutions

Organic Chemistry-Package(Custom)

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Chapter 4 Alkanes and Cycloalkanes Lesson 2; Author: Linda Hanson;https://www.youtube.com/watch?v=AL_CM_Btef4;License: Standard YouTube License, CC-BY
Chapter 4 Alkanes and Cycloalkanes Lesson 1; Author: Linda Hanson;https://www.youtube.com/watch?v=PPIa6EHJMJw;License: Standard Youtube License