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

Identify priority of the substituents: CH3

How many chiral carbons are in the molecule? OH F CI Br

A mixture of three compounds Phen-A, Acet-B and Rin-C was analyzed using TLC with 1:9 ethanol: hexane as the mobile phase. The TLC plate showed three spots of R, 0.1 and 0.2 and 0.3. Which of the three compounds (Phen-A; Acet-B or Rin-C) would have the highest (Blank 1), middle (Blank 2) and lowest (Blank 3) spot respectively? 0 CH: 0 CH, 0 H.C OH H.CN OH Acet-B Rin-C phen-A A A <

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