The correct product should be identified for the given [1, 3] sigmatropic rearrangement reaction. Concept introduction: In a sigmatropic reaction “ one new sigma-bond is formed as another breaks.” Sigmatropic rearrangement reactions are designated with digits. For example a [1, 3] sigmatropic rearrangement describe a reaction in which the residue migrates from position 1 to position 3. [3,3] sigmatropic rearrangement of a 1,3-diene known as Cope rearrangement reaction . Woodward –Hoffmann rules are the set of rules used to vindicate or predict certain aspects of the stereo chemical outcome and activation energy of pericyclic reactions. Woodward – Hoffmann rules for sigmatropic rearrangement reactions are listed below S u m o f t h e n u m b e r o f b o n d s i n t h e r e a c t i n g s y t e m s o f b o t h r e a g e n t s Reaction conditions Allowed mode of bond formation Even number Thermal Antarafacial Photochemical Suprafacial Odd number Thermal Suprafacial Photochemical Antarafacial Carbon migrating with one lobe of its p orbital interacting Carbon migrating with both lobe of its p orbital interacting of configuration is the inversion of a chiral center in a molecule in a chemical reaction .

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Answer 1

Question

Chapter 28, Problem 32P

Interpretation Introduction

Interpretation:

The correct product should be identified for the given [1, 3] sigmatropic rearrangement reaction.

Concept introduction:

In a sigmatropic reaction “ one new sigma-bond is formed as another breaks.”

Sigmatropic rearrangement reactions are designated with digits. For example a [1, 3] sigmatropic rearrangement describe a reaction in which the residue migrates from position 1 to position 3.

[3,3] sigmatropic rearrangement of a 1,3-diene known as Cope rearrangement reaction.

Woodward –Hoffmann rules are the set of rules used to vindicate or predict certain aspects of the stereo chemical outcome and activation energy of pericyclic reactions.

Woodward – Hoffmann rules for sigmatropic rearrangement reactions are listed below

Sum of the number of bonds in the reacting sytems of both reagents Reaction conditionsAllowed mode of bond formationEven numberThermalAntarafacialPhotochemicalSuprafacialOdd numberThermalSuprafacialPhotochemicalAntarafacial

Carbon migrating with one lobe of its p orbital interacting

Carbon migrating with both lobe of its p orbital interacting

of configuration is the inversion of a chiral center in a molecule in a chemical reaction.

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Students have asked these similar questions

Given that an E2 reaction proceeds with anti periplanar stereochemistry, draw the products of each elimination. The alkyl halides in (a) and (b) are diastereomers of each other. How are the products of these two reactions related?

What are the intermediates J, K and L? What regiochemistry and stereochemistry is involved in each step? Why is M the only stereoisomer formed?

What product is formed by the [3,3] sigmatropic rearrangement of eachcompound?

Answer 2

Question

Chapter 28, Problem 32P

Interpretation Introduction

Interpretation:

The correct product should be identified for the given [1, 3] sigmatropic rearrangement reaction.

Concept introduction:

In a sigmatropic reaction “ one new sigma-bond is formed as another breaks.”

Sigmatropic rearrangement reactions are designated with digits. For example a [1, 3] sigmatropic rearrangement describe a reaction in which the residue migrates from position 1 to position 3.

[3,3] sigmatropic rearrangement of a 1,3-diene known as Cope rearrangement reaction.

Woodward –Hoffmann rules are the set of rules used to vindicate or predict certain aspects of the stereo chemical outcome and activation energy of pericyclic reactions.

Woodward – Hoffmann rules for sigmatropic rearrangement reactions are listed below

Sum of the number of bonds in the reacting sytems of both reagents Reaction conditionsAllowed mode of bond formationEven numberThermalAntarafacialPhotochemicalSuprafacialOdd numberThermalSuprafacialPhotochemicalAntarafacial

Carbon migrating with one lobe of its p orbital interacting

Carbon migrating with both lobe of its p orbital interacting

of configuration is the inversion of a chiral center in a molecule in a chemical reaction.

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Answer 3

Question

Chapter 28, Problem 32P

Interpretation Introduction

Interpretation:

The correct product should be identified for the given [1, 3] sigmatropic rearrangement reaction.

Concept introduction:

In a sigmatropic reaction “ one new sigma-bond is formed as another breaks.”

Sigmatropic rearrangement reactions are designated with digits. For example a [1, 3] sigmatropic rearrangement describe a reaction in which the residue migrates from position 1 to position 3.

[3,3] sigmatropic rearrangement of a 1,3-diene known as Cope rearrangement reaction.

Woodward –Hoffmann rules are the set of rules used to vindicate or predict certain aspects of the stereo chemical outcome and activation energy of pericyclic reactions.

Woodward – Hoffmann rules for sigmatropic rearrangement reactions are listed below

Sum of the number of bonds in the reacting sytems of both reagents Reaction conditionsAllowed mode of bond formationEven numberThermalAntarafacialPhotochemicalSuprafacialOdd numberThermalSuprafacialPhotochemicalAntarafacial

Carbon migrating with one lobe of its p orbital interacting

Carbon migrating with both lobe of its p orbital interacting

of configuration is the inversion of a chiral center in a molecule in a chemical reaction.

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Answer 4

Question

Chapter 28, Problem 32P

Interpretation Introduction

Interpretation:

The correct product should be identified for the given [1, 3] sigmatropic rearrangement reaction.

Concept introduction:

In a sigmatropic reaction “ one new sigma-bond is formed as another breaks.”

Sigmatropic rearrangement reactions are designated with digits. For example a [1, 3] sigmatropic rearrangement describe a reaction in which the residue migrates from position 1 to position 3.

[3,3] sigmatropic rearrangement of a 1,3-diene known as Cope rearrangement reaction.

Woodward –Hoffmann rules are the set of rules used to vindicate or predict certain aspects of the stereo chemical outcome and activation energy of pericyclic reactions.

Woodward – Hoffmann rules for sigmatropic rearrangement reactions are listed below

Sum of the number of bonds in the reacting sytems of both reagents Reaction conditionsAllowed mode of bond formationEven numberThermalAntarafacialPhotochemicalSuprafacialOdd numberThermalSuprafacialPhotochemicalAntarafacial

Carbon migrating with one lobe of its p orbital interacting

Carbon migrating with both lobe of its p orbital interacting

of configuration is the inversion of a chiral center in a molecule in a chemical reaction.

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Answer 5

Chapter 28, Problem 32P

Interpretation Introduction

Interpretation:

The correct product should be identified for the given [1, 3] sigmatropic rearrangement reaction.

Concept introduction:

In a sigmatropic reaction “ one new sigma-bond is formed as another breaks.”

Sigmatropic rearrangement reactions are designated with digits. For example a [1, 3] sigmatropic rearrangement describe a reaction in which the residue migrates from position 1 to position 3.

[3,3] sigmatropic rearrangement of a 1,3-diene known as Cope rearrangement reaction.

Woodward –Hoffmann rules are the set of rules used to vindicate or predict certain aspects of the stereo chemical outcome and activation energy of pericyclic reactions.

Woodward – Hoffmann rules for sigmatropic rearrangement reactions are listed below

Sum of the number of bonds in the reacting sytems of both reagents Reaction conditionsAllowed mode of bond formationEven numberThermalAntarafacialPhotochemicalSuprafacialOdd numberThermalSuprafacialPhotochemicalAntarafacial

Carbon migrating with one lobe of its p orbital interacting

Carbon migrating with both lobe of its p orbital interacting

of configuration is the inversion of a chiral center in a molecule in a chemical reaction.

Answer 6

Chapter 28, Problem 32P

Interpretation Introduction

Interpretation:

The correct product should be identified for the given [1, 3] sigmatropic rearrangement reaction.

Concept introduction:

In a sigmatropic reaction “ one new sigma-bond is formed as another breaks.”

Sigmatropic rearrangement reactions are designated with digits. For example a [1, 3] sigmatropic rearrangement describe a reaction in which the residue migrates from position 1 to position 3.

[3,3] sigmatropic rearrangement of a 1,3-diene known as Cope rearrangement reaction.

Woodward –Hoffmann rules are the set of rules used to vindicate or predict certain aspects of the stereo chemical outcome and activation energy of pericyclic reactions.

Woodward – Hoffmann rules for sigmatropic rearrangement reactions are listed below

Sum of the number of bonds in the reacting sytems of both reagents Reaction conditionsAllowed mode of bond formationEven numberThermalAntarafacialPhotochemicalSuprafacialOdd numberThermalSuprafacialPhotochemicalAntarafacial

Carbon migrating with one lobe of its p orbital interacting

Carbon migrating with both lobe of its p orbital interacting

of configuration is the inversion of a chiral center in a molecule in a chemical reaction.

Answer 7

Chapter 28, Problem 32P

Interpretation Introduction

Interpretation:

The correct product should be identified for the given [1, 3] sigmatropic rearrangement reaction.

Concept introduction:

In a sigmatropic reaction “ one new sigma-bond is formed as another breaks.”

Sigmatropic rearrangement reactions are designated with digits. For example a [1, 3] sigmatropic rearrangement describe a reaction in which the residue migrates from position 1 to position 3.

[3,3] sigmatropic rearrangement of a 1,3-diene known as Cope rearrangement reaction.

Woodward –Hoffmann rules are the set of rules used to vindicate or predict certain aspects of the stereo chemical outcome and activation energy of pericyclic reactions.

Woodward – Hoffmann rules for sigmatropic rearrangement reactions are listed below

Sum of the number of bonds in the reacting sytems of both reagents Reaction conditionsAllowed mode of bond formationEven numberThermalAntarafacialPhotochemicalSuprafacialOdd numberThermalSuprafacialPhotochemicalAntarafacial

Carbon migrating with one lobe of its p orbital interacting

Carbon migrating with both lobe of its p orbital interacting

of configuration is the inversion of a chiral center in a molecule in a chemical reaction.

Answer 8

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Answer 9

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Answer 10

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Answer 11

Ch. 28.1 - Prob. 1P Ch. 28.2 - Prob. 2P Ch. 28.2 - Prob. 3P Ch. 28.2 - Give a molecular orbital description for each of...Ch. 28.3 - Prob. 5P Ch. 28.3 - Prob. 6P Ch. 28.3 - Prob. 7P Ch. 28.3 - Prob. 8P Ch. 28.4 - Prob. 10P Ch. 28.4 - Prob. 11P

Solution Summary: The author explains that sigmatropic rearrangement reactions are designated with digits. Woodward – Hoffmann rules vindicate or predict certain aspects of the stereo chemical outcome and activation energy of pericyclic reactions

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Chapter 28 Solutions