(a) Interpretation: The given compound can be produced from two different Diels-Alder reactions. The reactants that would be required for each reaction are to be drawn. Concept introduction: The Diels-Alder reaction (also known as [4+2] cycloaddition) joins a conjugated diene and a dienophile (an alkene or an alkyne ) via the formation of two new sigma bonds. The six membered ring of carbon atoms has formed as a product. If the double bonds in the diene are either both trans or both cis, then the substituents at the ends of the diene become cis to each other with respect to the plane of the ring in the product. Electron-withdrawing groups must be a part of a dienophile while electron-donating groups must be a part of the diene to facilitate the cycloaddition. The stereochemical configuration in the dienophile is conserved throughout a Diels-Alder reaction.

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Answer 1

Question

Chapter 24, Problem 24.46P

Interpretation Introduction

(a)

Interpretation:

The given compound can be produced from two different Diels-Alder reactions. The reactants that would be required for each reaction are to be drawn.

Concept introduction:

The Diels-Alder reaction (also known as [4+2] cycloaddition) joins a conjugated diene and a dienophile (an alkene or an alkyne) via the formation of two new sigma bonds. The six membered ring of carbon atoms has formed as a product.

If the double bonds in the diene are either both trans or both cis, then the substituents at the ends of the diene become cis to each other with respect to the plane of the ring in the product. Electron-withdrawing groups must be a part of a dienophile while electron-donating groups must be a part of the diene to facilitate the cycloaddition. The stereochemical configuration in the dienophile is conserved throughout a Diels-Alder reaction.

Interpretation Introduction

(b)

Interpretation:

Out of the two sets of reactants, which set would be a better choice is to be identified and exaplained.

Concept introduction:

The Diels-Alder reaction (also known as [4+2] cycloaddition) joins a conjugated diene and a dienophile (an alkene or an alkyne) via the formation of two new sigma bonds. The six membered ring of carbon atoms has formed as a product.

If the double bonds in the diene are either both trans or both cis, then the substituents at the ends of the diene become cis to each other with respect to the plane of the ring in the product. Electron-withdrawing groups must be a part of a dienophile while electron-donating groups must be a part of the diene to facilitate the cycloaddition. The stereochemical configuration in the dienophile is conserved throughout a Diels-Alder reaction.

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(SYN) The compound shown here can be produced from two different Diels–Alder reactions.(a) Draw the reactants that can be used for each Diels–Alder reaction.(b) Which would be the better route? Why?

(b) Addition of HBr to the alkene in the presence of peroxide form radical intermediates. Based on the following reaction, use the curved arrows to HBr B (preferred product) ROOR (i) show the initiation step of this reaction. (ii) draw the possible structures of the two radicals formed in the propagation step. (ii) explain the formation of the preferred product B.

Resveratrol is an antioxidant found in the skin of red grapes. Its anticancer, anti-inammatory, and various cardiovascular effects are under active investigation. (a) Draw all resonance structures for the radical that results from homolysis of the OH bond shown in red. (b) Explain why homolysis of this OH bond is preferred to homolysis of either OH bond in the other benzene ring.

Answer 2

Question

Chapter 24, Problem 24.46P

Interpretation Introduction

(a)

Interpretation:

The given compound can be produced from two different Diels-Alder reactions. The reactants that would be required for each reaction are to be drawn.

Concept introduction:

The Diels-Alder reaction (also known as [4+2] cycloaddition) joins a conjugated diene and a dienophile (an alkene or an alkyne) via the formation of two new sigma bonds. The six membered ring of carbon atoms has formed as a product.

If the double bonds in the diene are either both trans or both cis, then the substituents at the ends of the diene become cis to each other with respect to the plane of the ring in the product. Electron-withdrawing groups must be a part of a dienophile while electron-donating groups must be a part of the diene to facilitate the cycloaddition. The stereochemical configuration in the dienophile is conserved throughout a Diels-Alder reaction.

Interpretation Introduction

(b)

Interpretation:

Out of the two sets of reactants, which set would be a better choice is to be identified and exaplained.

Concept introduction:

The Diels-Alder reaction (also known as [4+2] cycloaddition) joins a conjugated diene and a dienophile (an alkene or an alkyne) via the formation of two new sigma bonds. The six membered ring of carbon atoms has formed as a product.

If the double bonds in the diene are either both trans or both cis, then the substituents at the ends of the diene become cis to each other with respect to the plane of the ring in the product. Electron-withdrawing groups must be a part of a dienophile while electron-donating groups must be a part of the diene to facilitate the cycloaddition. The stereochemical configuration in the dienophile is conserved throughout a Diels-Alder reaction.

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Answer 3

Question

Chapter 24, Problem 24.46P

Interpretation Introduction

(a)

Interpretation:

The given compound can be produced from two different Diels-Alder reactions. The reactants that would be required for each reaction are to be drawn.

Concept introduction:

The Diels-Alder reaction (also known as [4+2] cycloaddition) joins a conjugated diene and a dienophile (an alkene or an alkyne) via the formation of two new sigma bonds. The six membered ring of carbon atoms has formed as a product.

If the double bonds in the diene are either both trans or both cis, then the substituents at the ends of the diene become cis to each other with respect to the plane of the ring in the product. Electron-withdrawing groups must be a part of a dienophile while electron-donating groups must be a part of the diene to facilitate the cycloaddition. The stereochemical configuration in the dienophile is conserved throughout a Diels-Alder reaction.

Interpretation Introduction

(b)

Interpretation:

Out of the two sets of reactants, which set would be a better choice is to be identified and exaplained.

Concept introduction:

The Diels-Alder reaction (also known as [4+2] cycloaddition) joins a conjugated diene and a dienophile (an alkene or an alkyne) via the formation of two new sigma bonds. The six membered ring of carbon atoms has formed as a product.

If the double bonds in the diene are either both trans or both cis, then the substituents at the ends of the diene become cis to each other with respect to the plane of the ring in the product. Electron-withdrawing groups must be a part of a dienophile while electron-donating groups must be a part of the diene to facilitate the cycloaddition. The stereochemical configuration in the dienophile is conserved throughout a Diels-Alder reaction.

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Answer 4

Question

Chapter 24, Problem 24.46P

Interpretation Introduction

(a)

Interpretation:

The given compound can be produced from two different Diels-Alder reactions. The reactants that would be required for each reaction are to be drawn.

Concept introduction:

The Diels-Alder reaction (also known as [4+2] cycloaddition) joins a conjugated diene and a dienophile (an alkene or an alkyne) via the formation of two new sigma bonds. The six membered ring of carbon atoms has formed as a product.

If the double bonds in the diene are either both trans or both cis, then the substituents at the ends of the diene become cis to each other with respect to the plane of the ring in the product. Electron-withdrawing groups must be a part of a dienophile while electron-donating groups must be a part of the diene to facilitate the cycloaddition. The stereochemical configuration in the dienophile is conserved throughout a Diels-Alder reaction.

Interpretation Introduction

(b)

Interpretation:

Out of the two sets of reactants, which set would be a better choice is to be identified and exaplained.

Concept introduction:

The Diels-Alder reaction (also known as [4+2] cycloaddition) joins a conjugated diene and a dienophile (an alkene or an alkyne) via the formation of two new sigma bonds. The six membered ring of carbon atoms has formed as a product.

If the double bonds in the diene are either both trans or both cis, then the substituents at the ends of the diene become cis to each other with respect to the plane of the ring in the product. Electron-withdrawing groups must be a part of a dienophile while electron-donating groups must be a part of the diene to facilitate the cycloaddition. The stereochemical configuration in the dienophile is conserved throughout a Diels-Alder reaction.

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Answer 5

Chapter 24, Problem 24.46P

Interpretation Introduction

(a)

Interpretation:

The given compound can be produced from two different Diels-Alder reactions. The reactants that would be required for each reaction are to be drawn.

Concept introduction:

The Diels-Alder reaction (also known as [4+2] cycloaddition) joins a conjugated diene and a dienophile (an alkene or an alkyne) via the formation of two new sigma bonds. The six membered ring of carbon atoms has formed as a product.

If the double bonds in the diene are either both trans or both cis, then the substituents at the ends of the diene become cis to each other with respect to the plane of the ring in the product. Electron-withdrawing groups must be a part of a dienophile while electron-donating groups must be a part of the diene to facilitate the cycloaddition. The stereochemical configuration in the dienophile is conserved throughout a Diels-Alder reaction.

Interpretation Introduction

(b)

Interpretation:

Out of the two sets of reactants, which set would be a better choice is to be identified and exaplained.

Concept introduction:

The Diels-Alder reaction (also known as [4+2] cycloaddition) joins a conjugated diene and a dienophile (an alkene or an alkyne) via the formation of two new sigma bonds. The six membered ring of carbon atoms has formed as a product.

If the double bonds in the diene are either both trans or both cis, then the substituents at the ends of the diene become cis to each other with respect to the plane of the ring in the product. Electron-withdrawing groups must be a part of a dienophile while electron-donating groups must be a part of the diene to facilitate the cycloaddition. The stereochemical configuration in the dienophile is conserved throughout a Diels-Alder reaction.

Answer 6

Chapter 24, Problem 24.46P

Interpretation Introduction

(a)

Interpretation:

The given compound can be produced from two different Diels-Alder reactions. The reactants that would be required for each reaction are to be drawn.

Concept introduction:

The Diels-Alder reaction (also known as [4+2] cycloaddition) joins a conjugated diene and a dienophile (an alkene or an alkyne) via the formation of two new sigma bonds. The six membered ring of carbon atoms has formed as a product.

If the double bonds in the diene are either both trans or both cis, then the substituents at the ends of the diene become cis to each other with respect to the plane of the ring in the product. Electron-withdrawing groups must be a part of a dienophile while electron-donating groups must be a part of the diene to facilitate the cycloaddition. The stereochemical configuration in the dienophile is conserved throughout a Diels-Alder reaction.

Answer 7

Chapter 24, Problem 24.46P

Interpretation Introduction

(a)

Interpretation:

The given compound can be produced from two different Diels-Alder reactions. The reactants that would be required for each reaction are to be drawn.

Concept introduction:

The Diels-Alder reaction (also known as [4+2] cycloaddition) joins a conjugated diene and a dienophile (an alkene or an alkyne) via the formation of two new sigma bonds. The six membered ring of carbon atoms has formed as a product.

If the double bonds in the diene are either both trans or both cis, then the substituents at the ends of the diene become cis to each other with respect to the plane of the ring in the product. Electron-withdrawing groups must be a part of a dienophile while electron-donating groups must be a part of the diene to facilitate the cycloaddition. The stereochemical configuration in the dienophile is conserved throughout a Diels-Alder reaction.

Answer 8

Interpretation Introduction

(b)

Interpretation:

Out of the two sets of reactants, which set would be a better choice is to be identified and exaplained.

Concept introduction:

The Diels-Alder reaction (also known as [4+2] cycloaddition) joins a conjugated diene and a dienophile (an alkene or an alkyne) via the formation of two new sigma bonds. The six membered ring of carbon atoms has formed as a product.

If the double bonds in the diene are either both trans or both cis, then the substituents at the ends of the diene become cis to each other with respect to the plane of the ring in the product. Electron-withdrawing groups must be a part of a dienophile while electron-donating groups must be a part of the diene to facilitate the cycloaddition. The stereochemical configuration in the dienophile is conserved throughout a Diels-Alder reaction.

Answer 9

Interpretation Introduction

(b)

Interpretation:

Out of the two sets of reactants, which set would be a better choice is to be identified and exaplained.

Concept introduction:

The Diels-Alder reaction (also known as [4+2] cycloaddition) joins a conjugated diene and a dienophile (an alkene or an alkyne) via the formation of two new sigma bonds. The six membered ring of carbon atoms has formed as a product.

If the double bonds in the diene are either both trans or both cis, then the substituents at the ends of the diene become cis to each other with respect to the plane of the ring in the product. Electron-withdrawing groups must be a part of a dienophile while electron-donating groups must be a part of the diene to facilitate the cycloaddition. The stereochemical configuration in the dienophile is conserved throughout a Diels-Alder reaction.

Answer 10

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Answer 12

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Answer 13

Ch. 24 - Prob. 24.1P Ch. 24 - Prob. 24.2P Ch. 24 - Prob. 24.3P Ch. 24 - Prob. 24.4P Ch. 24 - Prob. 24.5P Ch. 24 - Prob. 24.6P Ch. 24 - Prob. 24.7P Ch. 24 - Prob. 24.8P Ch. 24 - Prob. 24.9P Ch. 24 - Prob. 24.10P

Solution Summary: The author explains that the compound can be produced from two different Diels-Alder reactions.

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Chapter 24 Solutions