For the chair-like transition state of a [3,3] - Sigmatropic shift, the analogous pictures for an allowed boat-like reaction geometry have to be shown. Concept Introduction: [ 3 , 3 ] - Sigmatropic shift: It is a special class of pericyclic reaction in which a σ -bond moves on the phase of one or more π-bonds . However, there will be redistribution of six electrons as the characteristic of a pericyclic reaction. The numbering in the nomenclature of the shift indicates the formation of a new sigma bond in between the two numbered positions of any two allylic systems as shown in the following example: Stereochemistry in [ 3 , 3 ] - Sigmatropic shift: Two types of transition states are likely to occur in this shift such as chair-like and boat-like transition states. According to the Frontier-Molecular-Orbital theory, both the transition states are allowed transition states inspite of the stability difference. The product obtained from the chair-like transition state has trans-conformation whereas the product obtained from the boat-like transition state has cis-conformation.

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Answer 1

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Chapter 20, Problem 20.48P

(a)

Interpretation Introduction

Interpretation: For the chair-like transition state of a [3,3]- Sigmatropic shift, the analogous pictures for an allowed boat-like reaction geometry have to be shown.

Concept Introduction:

[3,3]- Sigmatropic shift:

It is a special class of pericyclic reaction in which a σ-bond moves on the phase of one or more π-bonds. However, there will be redistribution of six electrons as the characteristic of a pericyclic reaction. The numbering in the nomenclature of the shift indicates the formation of a new sigma bond in between the two numbered positions of any two allylic systems as shown in the following example:

Stereochemistry in [3,3]- Sigmatropic shift:

Two types of transition states are likely to occur in this shift such as chair-like and boat-like transition states. According to the Frontier-Molecular-Orbital theory, both the transition states are allowed transition states inspite of the stability difference. The product obtained from the chair-like transition state has trans-conformation whereas the product obtained from the boat-like transition state has cis-conformation.

(b)

Interpretation Introduction

Interpretation: The reason for why the products with boat-like conformation are formed to a lower extent than those with chair-like conformation.

Concept Introduction:

[3,3]- Sigmatropic shift:

It is a special class of pericyclic reaction in which a σ-bond moves on the phase of one or more π-bonds. However, there will be redistribution of six electrons as the characteristic of a pericyclic reaction. The numbering in the nomenclature of the shift indicates the formation of a new sigma bond in between the two numbered positions of any two allylic systems as shown in the following example:

Stereochemistry in [3,3]- Sigmatropic shift:

Two types of transition states are likely to occur in this shift such as chair-like and boat-like transition states. According to the Frontier-Molecular-Orbital theory, both the transition states are allowed transition states inspite of the stability difference. The product obtained from the chair-like transition state has trans-conformation whereas the product obtained from the boat-like transition state has cis-conformation.

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CHEM2323 E Tt PS CH03 Draw and name all monobromo derivatives of pentane, C5H11Br. Problem 3-33 Name: Draw structures for the following: (a) 2-Methylheptane (d) 2,4,4-Trimethylheptane Problem 3-35 (b) 4-Ethyl-2,2-dimethylhexane (e) 3,3-Diethyl-2,5-dimethylnonane (c) 4-Ethyl-3,4-dimethyloctane 2 (f) 4-Isopropyl-3-methylheptane KNIE>

Problem 3-42 Consider 2-methylbutane (isopentane). Sighting along the C2-C3 bond: (a) Draw a Newman projection of the most stable conformation. (b) Draw a Newman projection of the least stable conformation. Problem 3-44 Construct a qualitative potential-energy diagram for rotation about the C-C bond of 1,2-dibromoethane. Which conformation would you expect to be most stable? Label the anti and gauche conformations of 1,2- dibromoethane. Problem 3-45 Which conformation of 1,2-dibromoethane (Problem 3-44) would you expect to have the largest dipole moment? The observed dipole moment of 1,2-dibromoethane is µ = 1.0 D. What does this tell you about the actual conformation of the molecule?

Answer 2

Question

Chapter 20, Problem 20.48P

(a)

Interpretation Introduction

Interpretation: For the chair-like transition state of a [3,3]- Sigmatropic shift, the analogous pictures for an allowed boat-like reaction geometry have to be shown.

Concept Introduction:

[3,3]- Sigmatropic shift:

It is a special class of pericyclic reaction in which a σ-bond moves on the phase of one or more π-bonds. However, there will be redistribution of six electrons as the characteristic of a pericyclic reaction. The numbering in the nomenclature of the shift indicates the formation of a new sigma bond in between the two numbered positions of any two allylic systems as shown in the following example:

Stereochemistry in [3,3]- Sigmatropic shift:

Two types of transition states are likely to occur in this shift such as chair-like and boat-like transition states. According to the Frontier-Molecular-Orbital theory, both the transition states are allowed transition states inspite of the stability difference. The product obtained from the chair-like transition state has trans-conformation whereas the product obtained from the boat-like transition state has cis-conformation.

(b)

Interpretation Introduction

Interpretation: The reason for why the products with boat-like conformation are formed to a lower extent than those with chair-like conformation.

Concept Introduction:

[3,3]- Sigmatropic shift:

It is a special class of pericyclic reaction in which a σ-bond moves on the phase of one or more π-bonds. However, there will be redistribution of six electrons as the characteristic of a pericyclic reaction. The numbering in the nomenclature of the shift indicates the formation of a new sigma bond in between the two numbered positions of any two allylic systems as shown in the following example:

Stereochemistry in [3,3]- Sigmatropic shift:

Two types of transition states are likely to occur in this shift such as chair-like and boat-like transition states. According to the Frontier-Molecular-Orbital theory, both the transition states are allowed transition states inspite of the stability difference. The product obtained from the chair-like transition state has trans-conformation whereas the product obtained from the boat-like transition state has cis-conformation.

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Answer 3

Question

Chapter 20, Problem 20.48P

(a)

Interpretation Introduction

Interpretation: For the chair-like transition state of a [3,3]- Sigmatropic shift, the analogous pictures for an allowed boat-like reaction geometry have to be shown.

Concept Introduction:

[3,3]- Sigmatropic shift:

It is a special class of pericyclic reaction in which a σ-bond moves on the phase of one or more π-bonds. However, there will be redistribution of six electrons as the characteristic of a pericyclic reaction. The numbering in the nomenclature of the shift indicates the formation of a new sigma bond in between the two numbered positions of any two allylic systems as shown in the following example:

Stereochemistry in [3,3]- Sigmatropic shift:

Two types of transition states are likely to occur in this shift such as chair-like and boat-like transition states. According to the Frontier-Molecular-Orbital theory, both the transition states are allowed transition states inspite of the stability difference. The product obtained from the chair-like transition state has trans-conformation whereas the product obtained from the boat-like transition state has cis-conformation.

(b)

Interpretation Introduction

Interpretation: The reason for why the products with boat-like conformation are formed to a lower extent than those with chair-like conformation.

Concept Introduction:

[3,3]- Sigmatropic shift:

It is a special class of pericyclic reaction in which a σ-bond moves on the phase of one or more π-bonds. However, there will be redistribution of six electrons as the characteristic of a pericyclic reaction. The numbering in the nomenclature of the shift indicates the formation of a new sigma bond in between the two numbered positions of any two allylic systems as shown in the following example:

Stereochemistry in [3,3]- Sigmatropic shift:

Two types of transition states are likely to occur in this shift such as chair-like and boat-like transition states. According to the Frontier-Molecular-Orbital theory, both the transition states are allowed transition states inspite of the stability difference. The product obtained from the chair-like transition state has trans-conformation whereas the product obtained from the boat-like transition state has cis-conformation.

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Answer 4

Question

Chapter 20, Problem 20.48P

(a)

Interpretation Introduction

Interpretation: For the chair-like transition state of a [3,3]- Sigmatropic shift, the analogous pictures for an allowed boat-like reaction geometry have to be shown.

Concept Introduction:

[3,3]- Sigmatropic shift:

It is a special class of pericyclic reaction in which a σ-bond moves on the phase of one or more π-bonds. However, there will be redistribution of six electrons as the characteristic of a pericyclic reaction. The numbering in the nomenclature of the shift indicates the formation of a new sigma bond in between the two numbered positions of any two allylic systems as shown in the following example:

Stereochemistry in [3,3]- Sigmatropic shift:

Two types of transition states are likely to occur in this shift such as chair-like and boat-like transition states. According to the Frontier-Molecular-Orbital theory, both the transition states are allowed transition states inspite of the stability difference. The product obtained from the chair-like transition state has trans-conformation whereas the product obtained from the boat-like transition state has cis-conformation.

(b)

Interpretation Introduction

Interpretation: The reason for why the products with boat-like conformation are formed to a lower extent than those with chair-like conformation.

Concept Introduction:

[3,3]- Sigmatropic shift:

It is a special class of pericyclic reaction in which a σ-bond moves on the phase of one or more π-bonds. However, there will be redistribution of six electrons as the characteristic of a pericyclic reaction. The numbering in the nomenclature of the shift indicates the formation of a new sigma bond in between the two numbered positions of any two allylic systems as shown in the following example:

Stereochemistry in [3,3]- Sigmatropic shift:

Two types of transition states are likely to occur in this shift such as chair-like and boat-like transition states. According to the Frontier-Molecular-Orbital theory, both the transition states are allowed transition states inspite of the stability difference. The product obtained from the chair-like transition state has trans-conformation whereas the product obtained from the boat-like transition state has cis-conformation.

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Answer 5

Chapter 20, Problem 20.48P

(a)

Interpretation Introduction

Interpretation: For the chair-like transition state of a [3,3]- Sigmatropic shift, the analogous pictures for an allowed boat-like reaction geometry have to be shown.

Concept Introduction:

[3,3]- Sigmatropic shift:

It is a special class of pericyclic reaction in which a σ-bond moves on the phase of one or more π-bonds. However, there will be redistribution of six electrons as the characteristic of a pericyclic reaction. The numbering in the nomenclature of the shift indicates the formation of a new sigma bond in between the two numbered positions of any two allylic systems as shown in the following example:

Stereochemistry in [3,3]- Sigmatropic shift:

Two types of transition states are likely to occur in this shift such as chair-like and boat-like transition states. According to the Frontier-Molecular-Orbital theory, both the transition states are allowed transition states inspite of the stability difference. The product obtained from the chair-like transition state has trans-conformation whereas the product obtained from the boat-like transition state has cis-conformation.

(b)

Interpretation Introduction

Interpretation: The reason for why the products with boat-like conformation are formed to a lower extent than those with chair-like conformation.

Concept Introduction:

[3,3]- Sigmatropic shift:

It is a special class of pericyclic reaction in which a σ-bond moves on the phase of one or more π-bonds. However, there will be redistribution of six electrons as the characteristic of a pericyclic reaction. The numbering in the nomenclature of the shift indicates the formation of a new sigma bond in between the two numbered positions of any two allylic systems as shown in the following example:

Stereochemistry in [3,3]- Sigmatropic shift:

Two types of transition states are likely to occur in this shift such as chair-like and boat-like transition states. According to the Frontier-Molecular-Orbital theory, both the transition states are allowed transition states inspite of the stability difference. The product obtained from the chair-like transition state has trans-conformation whereas the product obtained from the boat-like transition state has cis-conformation.

Answer 6

Chapter 20, Problem 20.48P

(a)

Interpretation Introduction

Interpretation: For the chair-like transition state of a [3,3]- Sigmatropic shift, the analogous pictures for an allowed boat-like reaction geometry have to be shown.

Concept Introduction:

[3,3]- Sigmatropic shift:

It is a special class of pericyclic reaction in which a σ-bond moves on the phase of one or more π-bonds. However, there will be redistribution of six electrons as the characteristic of a pericyclic reaction. The numbering in the nomenclature of the shift indicates the formation of a new sigma bond in between the two numbered positions of any two allylic systems as shown in the following example:

Stereochemistry in [3,3]- Sigmatropic shift:

Two types of transition states are likely to occur in this shift such as chair-like and boat-like transition states. According to the Frontier-Molecular-Orbital theory, both the transition states are allowed transition states inspite of the stability difference. The product obtained from the chair-like transition state has trans-conformation whereas the product obtained from the boat-like transition state has cis-conformation.

Answer 7

Chapter 20, Problem 20.48P

(a)

Interpretation Introduction

Interpretation: For the chair-like transition state of a [3,3]- Sigmatropic shift, the analogous pictures for an allowed boat-like reaction geometry have to be shown.

Concept Introduction:

[3,3]- Sigmatropic shift:

It is a special class of pericyclic reaction in which a σ-bond moves on the phase of one or more π-bonds. However, there will be redistribution of six electrons as the characteristic of a pericyclic reaction. The numbering in the nomenclature of the shift indicates the formation of a new sigma bond in between the two numbered positions of any two allylic systems as shown in the following example:

Stereochemistry in [3,3]- Sigmatropic shift:

Two types of transition states are likely to occur in this shift such as chair-like and boat-like transition states. According to the Frontier-Molecular-Orbital theory, both the transition states are allowed transition states inspite of the stability difference. The product obtained from the chair-like transition state has trans-conformation whereas the product obtained from the boat-like transition state has cis-conformation.

Answer 8

(b)

Interpretation Introduction

Interpretation: The reason for why the products with boat-like conformation are formed to a lower extent than those with chair-like conformation.

Concept Introduction:

[3,3]- Sigmatropic shift:

It is a special class of pericyclic reaction in which a σ-bond moves on the phase of one or more π-bonds. However, there will be redistribution of six electrons as the characteristic of a pericyclic reaction. The numbering in the nomenclature of the shift indicates the formation of a new sigma bond in between the two numbered positions of any two allylic systems as shown in the following example:

Stereochemistry in [3,3]- Sigmatropic shift:

Two types of transition states are likely to occur in this shift such as chair-like and boat-like transition states. According to the Frontier-Molecular-Orbital theory, both the transition states are allowed transition states inspite of the stability difference. The product obtained from the chair-like transition state has trans-conformation whereas the product obtained from the boat-like transition state has cis-conformation.

Answer 9

(b)

Interpretation Introduction

Interpretation: The reason for why the products with boat-like conformation are formed to a lower extent than those with chair-like conformation.

Concept Introduction:

[3,3]- Sigmatropic shift:

It is a special class of pericyclic reaction in which a σ-bond moves on the phase of one or more π-bonds. However, there will be redistribution of six electrons as the characteristic of a pericyclic reaction. The numbering in the nomenclature of the shift indicates the formation of a new sigma bond in between the two numbered positions of any two allylic systems as shown in the following example:

Stereochemistry in [3,3]- Sigmatropic shift:

Two types of transition states are likely to occur in this shift such as chair-like and boat-like transition states. According to the Frontier-Molecular-Orbital theory, both the transition states are allowed transition states inspite of the stability difference. The product obtained from the chair-like transition state has trans-conformation whereas the product obtained from the boat-like transition state has cis-conformation.

Answer 10

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Answer 13

Ch. 20.1 - Prob. 20.1P Ch. 20.1 - Estimate the stabilization gained as a result of...Ch. 20.2 - Predict the product(s) formed by addition of one...Ch. 20.3 - Prob. 20.4P Ch. 20.3 - Prob. 20.5P Ch. 20.4 - Prob. 20.6P Ch. 20.5 - Prob. 20.7P Ch. 20.5 - Prob. 20.8P Ch. 20.5 - Prob. 20.9P Ch. 20.6 - Prob. 20.10P

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