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.

Question

Want to see the full answer?

Answer 1

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

(c) (i) (ii) Explain what is meant by the trans effect. Using the trans effect, give a synthesis of trans-[PtCl₂(py)(PPhy)] from [PtCL]². [py = CsHsN = pyridine]

• 1. The HCo(CO)4 complex can catalyze the isomerization of pure cis-2-butene to a mixture of cis-2-butene, trans-2-butene, and 1-butene. Propose a mechanism. Carefully show the process using wedges and dashes to indicate stereochemistry of each intermediate.

3. It is required to introduce a halogen group to a five membered ring, thiophene. Discuss the reaction mechanism involved in the reaction by selecting a suitable halogen group and analyze why a particular substituted product obtained after the reaction is predominant over the other possible product(s) with the help of reactions. To meet the ever increasing demand of global population, the demand for textile products and consumption of dyes by these industries is increasing.

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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

Expert Solution & Answer

Answer 11

Expert Solution & Answer

Answer 12

Want to see the full answer?

Check out a sample textbook solution

See solution

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

Want to see the full answer?

Chapter 20 Solutions