(a) Interpretation: The product of the [ 3 , 3 ] sigmatropic rearrangement for the given compound is to be drawn. Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product. Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.

Question

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Answer 1

Question

Chapter 27, Problem 27.45P

Interpretation Introduction

(a)

Interpretation: The product of the [3,3] sigmatropic rearrangement for the given compound is to be drawn.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.

Expert Solution

Answer to Problem 27.45P

The product of the [3,3] sigmatropic rearrangement for the given compound is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 1

Explanation of Solution

The product of the [3,3] sigmatropic rearrangement for the given compound is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 2 [a1]

Figure 1

The above diagram indicates that in the product, both the π bonds are rearranged. The old σ bond breaks at third carbon atom and simultaneously a new σ bond is formed at sixth carbon atom during the conversion of starting material into the product. Therefore, the product is formed with [3,3] sigmatropic rearrangement.

Thus, the name of product is 1−(3−methylcyclohex−3−enyl)ethanone.

Conclusion

The product of the [3,3] sigmatropic rearrangement for the given compound is 1−(3−methylcyclohex−3−enyl)ethanone.

Interpretation Introduction

(b)

Interpretation: The product of the [3,3] sigmatropic rearrangement for the given compound is to be drawn.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.

Expert Solution

Answer to Problem 27.45P

The product of the [3,3] sigmatropic rearrangement for the given compound is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 3

Explanation of Solution

The product of the [3,3] sigmatropic rearrangement for the given compound is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 4

Figure 2

The above diagram indicates that in the product, both the π bonds are rearranged. The old σ bond breaks at third carbon atom and simultaneously a new σ bond is formed at sixth carbon atom during the conversion of starting material into the product. Therefore, the product is formed with [3,3] sigmatropic rearrangement.

Thus, the name of product is 2,5,8−trimethylcyclonona−1,5−dienol.

Conclusion

The product of the [3,3] sigmatropic rearrangement for the given compound is 2,5,8−trimethylcyclonona−1,5−dienol.

Interpretation Introduction

(c)

Interpretation: The product of the [3,3] sigmatropic rearrangement for the given compound is to be drawn.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.

Expert Solution

Answer to Problem 27.45P

The product of the [3,3] sigmatropic rearrangement for the given compound is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 5

Explanation of Solution

The product of the [3,3] sigmatropic rearrangement for the given compound is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 6

Figure 3

The above diagram indicates that in the product, both the π bonds are rearranged. The old σ bond breaks at third carbon atom and simultaneously a new σ bond is formed at sixth carbon atom during the conversion of starting material into the product. Therefore, the product is formed with [3,3] sigmatropic rearrangement.

Thus, the name of product is 6-methyl-1, 2, 4a, 5, 8, 8a-hexahydronaphthalene.

Conclusion

The product of the [3,3] sigmatropic rearrangement for the given compound is 6-methyl-1, 2, 4a, 5, 8, 8a-hexahydronaphthalene.

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Answer 2

Question

Chapter 27, Problem 27.45P

Interpretation Introduction

(a)

Interpretation: The product of the [3,3] sigmatropic rearrangement for the given compound is to be drawn.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.

Expert Solution

Answer to Problem 27.45P

The product of the [3,3] sigmatropic rearrangement for the given compound is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 1

Explanation of Solution

The product of the [3,3] sigmatropic rearrangement for the given compound is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 2 [a1]

Figure 1

The above diagram indicates that in the product, both the π bonds are rearranged. The old σ bond breaks at third carbon atom and simultaneously a new σ bond is formed at sixth carbon atom during the conversion of starting material into the product. Therefore, the product is formed with [3,3] sigmatropic rearrangement.

Thus, the name of product is 1−(3−methylcyclohex−3−enyl)ethanone.

Conclusion

The product of the [3,3] sigmatropic rearrangement for the given compound is 1−(3−methylcyclohex−3−enyl)ethanone.

Interpretation Introduction

(b)

Interpretation: The product of the [3,3] sigmatropic rearrangement for the given compound is to be drawn.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.

Expert Solution

Answer to Problem 27.45P

The product of the [3,3] sigmatropic rearrangement for the given compound is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 3

Explanation of Solution

The product of the [3,3] sigmatropic rearrangement for the given compound is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 4

Figure 2

The above diagram indicates that in the product, both the π bonds are rearranged. The old σ bond breaks at third carbon atom and simultaneously a new σ bond is formed at sixth carbon atom during the conversion of starting material into the product. Therefore, the product is formed with [3,3] sigmatropic rearrangement.

Thus, the name of product is 2,5,8−trimethylcyclonona−1,5−dienol.

Conclusion

The product of the [3,3] sigmatropic rearrangement for the given compound is 2,5,8−trimethylcyclonona−1,5−dienol.

Interpretation Introduction

(c)

Interpretation: The product of the [3,3] sigmatropic rearrangement for the given compound is to be drawn.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.

Expert Solution

Answer to Problem 27.45P

The product of the [3,3] sigmatropic rearrangement for the given compound is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 5

Explanation of Solution

The product of the [3,3] sigmatropic rearrangement for the given compound is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 6

Figure 3

The above diagram indicates that in the product, both the π bonds are rearranged. The old σ bond breaks at third carbon atom and simultaneously a new σ bond is formed at sixth carbon atom during the conversion of starting material into the product. Therefore, the product is formed with [3,3] sigmatropic rearrangement.

Thus, the name of product is 6-methyl-1, 2, 4a, 5, 8, 8a-hexahydronaphthalene.

Conclusion

The product of the [3,3] sigmatropic rearrangement for the given compound is 6-methyl-1, 2, 4a, 5, 8, 8a-hexahydronaphthalene.

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Answer 3

Question

Chapter 27, Problem 27.45P

Interpretation Introduction

(a)

Interpretation: The product of the [3,3] sigmatropic rearrangement for the given compound is to be drawn.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.

Expert Solution

Answer to Problem 27.45P

The product of the [3,3] sigmatropic rearrangement for the given compound is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 1

Explanation of Solution

The product of the [3,3] sigmatropic rearrangement for the given compound is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 2 [a1]

Figure 1

The above diagram indicates that in the product, both the π bonds are rearranged. The old σ bond breaks at third carbon atom and simultaneously a new σ bond is formed at sixth carbon atom during the conversion of starting material into the product. Therefore, the product is formed with [3,3] sigmatropic rearrangement.

Thus, the name of product is 1−(3−methylcyclohex−3−enyl)ethanone.

Conclusion

The product of the [3,3] sigmatropic rearrangement for the given compound is 1−(3−methylcyclohex−3−enyl)ethanone.

Interpretation Introduction

(b)

Interpretation: The product of the [3,3] sigmatropic rearrangement for the given compound is to be drawn.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.

Expert Solution

Answer to Problem 27.45P

The product of the [3,3] sigmatropic rearrangement for the given compound is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 3

Explanation of Solution

The product of the [3,3] sigmatropic rearrangement for the given compound is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 4

Figure 2

The above diagram indicates that in the product, both the π bonds are rearranged. The old σ bond breaks at third carbon atom and simultaneously a new σ bond is formed at sixth carbon atom during the conversion of starting material into the product. Therefore, the product is formed with [3,3] sigmatropic rearrangement.

Thus, the name of product is 2,5,8−trimethylcyclonona−1,5−dienol.

Conclusion

The product of the [3,3] sigmatropic rearrangement for the given compound is 2,5,8−trimethylcyclonona−1,5−dienol.

Interpretation Introduction

(c)

Interpretation: The product of the [3,3] sigmatropic rearrangement for the given compound is to be drawn.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.

Expert Solution

Answer to Problem 27.45P

The product of the [3,3] sigmatropic rearrangement for the given compound is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 5

Explanation of Solution

The product of the [3,3] sigmatropic rearrangement for the given compound is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 6

Figure 3

The above diagram indicates that in the product, both the π bonds are rearranged. The old σ bond breaks at third carbon atom and simultaneously a new σ bond is formed at sixth carbon atom during the conversion of starting material into the product. Therefore, the product is formed with [3,3] sigmatropic rearrangement.

Thus, the name of product is 6-methyl-1, 2, 4a, 5, 8, 8a-hexahydronaphthalene.

Conclusion

The product of the [3,3] sigmatropic rearrangement for the given compound is 6-methyl-1, 2, 4a, 5, 8, 8a-hexahydronaphthalene.

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Answer 4

Question

Chapter 27, Problem 27.45P

Interpretation Introduction

(a)

Interpretation: The product of the [3,3] sigmatropic rearrangement for the given compound is to be drawn.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.

Expert Solution

Answer to Problem 27.45P

The product of the [3,3] sigmatropic rearrangement for the given compound is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 1

Explanation of Solution

The product of the [3,3] sigmatropic rearrangement for the given compound is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 2 [a1]

Figure 1

The above diagram indicates that in the product, both the π bonds are rearranged. The old σ bond breaks at third carbon atom and simultaneously a new σ bond is formed at sixth carbon atom during the conversion of starting material into the product. Therefore, the product is formed with [3,3] sigmatropic rearrangement.

Thus, the name of product is 1−(3−methylcyclohex−3−enyl)ethanone.

Conclusion

The product of the [3,3] sigmatropic rearrangement for the given compound is 1−(3−methylcyclohex−3−enyl)ethanone.

Interpretation Introduction

(b)

Interpretation: The product of the [3,3] sigmatropic rearrangement for the given compound is to be drawn.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.

Expert Solution

Answer to Problem 27.45P

The product of the [3,3] sigmatropic rearrangement for the given compound is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 3

Explanation of Solution

The product of the [3,3] sigmatropic rearrangement for the given compound is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 4

Figure 2

The above diagram indicates that in the product, both the π bonds are rearranged. The old σ bond breaks at third carbon atom and simultaneously a new σ bond is formed at sixth carbon atom during the conversion of starting material into the product. Therefore, the product is formed with [3,3] sigmatropic rearrangement.

Thus, the name of product is 2,5,8−trimethylcyclonona−1,5−dienol.

Conclusion

The product of the [3,3] sigmatropic rearrangement for the given compound is 2,5,8−trimethylcyclonona−1,5−dienol.

Interpretation Introduction

(c)

Interpretation: The product of the [3,3] sigmatropic rearrangement for the given compound is to be drawn.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.

Expert Solution

Answer to Problem 27.45P

The product of the [3,3] sigmatropic rearrangement for the given compound is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 5

Explanation of Solution

The product of the [3,3] sigmatropic rearrangement for the given compound is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 6

Figure 3

The above diagram indicates that in the product, both the π bonds are rearranged. The old σ bond breaks at third carbon atom and simultaneously a new σ bond is formed at sixth carbon atom during the conversion of starting material into the product. Therefore, the product is formed with [3,3] sigmatropic rearrangement.

Thus, the name of product is 6-methyl-1, 2, 4a, 5, 8, 8a-hexahydronaphthalene.

Conclusion

The product of the [3,3] sigmatropic rearrangement for the given compound is 6-methyl-1, 2, 4a, 5, 8, 8a-hexahydronaphthalene.

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Answer 5

Chapter 27, Problem 27.45P

Interpretation Introduction

(a)

Interpretation: The product of the [3,3] sigmatropic rearrangement for the given compound is to be drawn.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.

Expert Solution

Answer to Problem 27.45P

The product of the [3,3] sigmatropic rearrangement for the given compound is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 1

Explanation of Solution

The product of the [3,3] sigmatropic rearrangement for the given compound is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 2 [a1]

Figure 1

The above diagram indicates that in the product, both the π bonds are rearranged. The old σ bond breaks at third carbon atom and simultaneously a new σ bond is formed at sixth carbon atom during the conversion of starting material into the product. Therefore, the product is formed with [3,3] sigmatropic rearrangement.

Thus, the name of product is 1−(3−methylcyclohex−3−enyl)ethanone.

Conclusion

The product of the [3,3] sigmatropic rearrangement for the given compound is 1−(3−methylcyclohex−3−enyl)ethanone.

Interpretation Introduction

(b)

Interpretation: The product of the [3,3] sigmatropic rearrangement for the given compound is to be drawn.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.

Expert Solution

Answer to Problem 27.45P

The product of the [3,3] sigmatropic rearrangement for the given compound is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 3

Explanation of Solution

The product of the [3,3] sigmatropic rearrangement for the given compound is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 4

Figure 2

The above diagram indicates that in the product, both the π bonds are rearranged. The old σ bond breaks at third carbon atom and simultaneously a new σ bond is formed at sixth carbon atom during the conversion of starting material into the product. Therefore, the product is formed with [3,3] sigmatropic rearrangement.

Thus, the name of product is 2,5,8−trimethylcyclonona−1,5−dienol.

Conclusion

The product of the [3,3] sigmatropic rearrangement for the given compound is 2,5,8−trimethylcyclonona−1,5−dienol.

Interpretation Introduction

(c)

Interpretation: The product of the [3,3] sigmatropic rearrangement for the given compound is to be drawn.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.

Expert Solution

Answer to Problem 27.45P

The product of the [3,3] sigmatropic rearrangement for the given compound is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 5

Explanation of Solution

The product of the [3,3] sigmatropic rearrangement for the given compound is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 6

Figure 3

The above diagram indicates that in the product, both the π bonds are rearranged. The old σ bond breaks at third carbon atom and simultaneously a new σ bond is formed at sixth carbon atom during the conversion of starting material into the product. Therefore, the product is formed with [3,3] sigmatropic rearrangement.

Thus, the name of product is 6-methyl-1, 2, 4a, 5, 8, 8a-hexahydronaphthalene.

Conclusion

The product of the [3,3] sigmatropic rearrangement for the given compound is 6-methyl-1, 2, 4a, 5, 8, 8a-hexahydronaphthalene.

Answer 6

Chapter 27, Problem 27.45P

Interpretation Introduction

(a)

Interpretation: The product of the [3,3] sigmatropic rearrangement for the given compound is to be drawn.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.

Expert Solution

Answer to Problem 27.45P

The product of the [3,3] sigmatropic rearrangement for the given compound is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 1

Explanation of Solution

The product of the [3,3] sigmatropic rearrangement for the given compound is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 2 [a1]

Figure 1

The above diagram indicates that in the product, both the π bonds are rearranged. The old σ bond breaks at third carbon atom and simultaneously a new σ bond is formed at sixth carbon atom during the conversion of starting material into the product. Therefore, the product is formed with [3,3] sigmatropic rearrangement.

Thus, the name of product is 1−(3−methylcyclohex−3−enyl)ethanone.

Conclusion

The product of the [3,3] sigmatropic rearrangement for the given compound is 1−(3−methylcyclohex−3−enyl)ethanone.

Answer 7

Chapter 27, Problem 27.45P

Interpretation Introduction

(a)

Interpretation: The product of the [3,3] sigmatropic rearrangement for the given compound is to be drawn.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.

Answer 8

Expert Solution

Answer to Problem 27.45P

The product of the [3,3] sigmatropic rearrangement for the given compound is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 1

Answer 9

Expert Solution

Answer 10

Expert Solution

Answer 11

Expert Solution

Answer 12

Explanation of Solution

The product of the [3,3] sigmatropic rearrangement for the given compound is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 2 [a1]

Figure 1

The above diagram indicates that in the product, both the π bonds are rearranged. The old σ bond breaks at third carbon atom and simultaneously a new σ bond is formed at sixth carbon atom during the conversion of starting material into the product. Therefore, the product is formed with [3,3] sigmatropic rearrangement.

Thus, the name of product is 1−(3−methylcyclohex−3−enyl)ethanone.

Answer 13

Conclusion

The product of the [3,3] sigmatropic rearrangement for the given compound is 1−(3−methylcyclohex−3−enyl)ethanone.

Answer 14

Interpretation Introduction

(b)

Interpretation: The product of the [3,3] sigmatropic rearrangement for the given compound is to be drawn.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.

Expert Solution

Answer to Problem 27.45P

The product of the [3,3] sigmatropic rearrangement for the given compound is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 3

Explanation of Solution

The product of the [3,3] sigmatropic rearrangement for the given compound is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 4

Figure 2

The above diagram indicates that in the product, both the π bonds are rearranged. The old σ bond breaks at third carbon atom and simultaneously a new σ bond is formed at sixth carbon atom during the conversion of starting material into the product. Therefore, the product is formed with [3,3] sigmatropic rearrangement.

Thus, the name of product is 2,5,8−trimethylcyclonona−1,5−dienol.

Conclusion

The product of the [3,3] sigmatropic rearrangement for the given compound is 2,5,8−trimethylcyclonona−1,5−dienol.

Answer 15

Interpretation Introduction

(b)

Interpretation: The product of the [3,3] sigmatropic rearrangement for the given compound is to be drawn.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.

Answer 16

Expert Solution

Answer to Problem 27.45P

The product of the [3,3] sigmatropic rearrangement for the given compound is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 3

Answer 17

Expert Solution

Answer 18

Expert Solution

Answer 19

Expert Solution

Answer 20

Explanation of Solution

The product of the [3,3] sigmatropic rearrangement for the given compound is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 4

Figure 2

The above diagram indicates that in the product, both the π bonds are rearranged. The old σ bond breaks at third carbon atom and simultaneously a new σ bond is formed at sixth carbon atom during the conversion of starting material into the product. Therefore, the product is formed with [3,3] sigmatropic rearrangement.

Thus, the name of product is 2,5,8−trimethylcyclonona−1,5−dienol.

Answer 21

Conclusion

The product of the [3,3] sigmatropic rearrangement for the given compound is 2,5,8−trimethylcyclonona−1,5−dienol.

Answer 22

Interpretation Introduction

(c)

Interpretation: The product of the [3,3] sigmatropic rearrangement for the given compound is to be drawn.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.

Expert Solution

Answer to Problem 27.45P

The product of the [3,3] sigmatropic rearrangement for the given compound is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 5

Explanation of Solution

The product of the [3,3] sigmatropic rearrangement for the given compound is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 6

Figure 3

The above diagram indicates that in the product, both the π bonds are rearranged. The old σ bond breaks at third carbon atom and simultaneously a new σ bond is formed at sixth carbon atom during the conversion of starting material into the product. Therefore, the product is formed with [3,3] sigmatropic rearrangement.

Thus, the name of product is 6-methyl-1, 2, 4a, 5, 8, 8a-hexahydronaphthalene.

Conclusion

The product of the [3,3] sigmatropic rearrangement for the given compound is 6-methyl-1, 2, 4a, 5, 8, 8a-hexahydronaphthalene.

Answer 23

Interpretation Introduction

(c)

Interpretation: The product of the [3,3] sigmatropic rearrangement for the given compound is to be drawn.

Concept introduction: In the sigmatropic rearrangement, the rearrangement of pi bond and the breaking of sigma bond take place. This results in the generation of new sigma bond in the product. In this type of rearrangement, the number of pi bonds remains constant in the reactant as well as in the product.

Curved arrows aid in determining the movement and flow of electrons in the reaction. The electrons that take part in the chemical reactions are shown by the curved arrows.

Answer 24

Expert Solution

Answer to Problem 27.45P

The product of the [3,3] sigmatropic rearrangement for the given compound is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 5

Answer 25

Expert Solution

Answer 26

Expert Solution

Answer 27

Expert Solution

Answer 28

Explanation of Solution

The product of the [3,3] sigmatropic rearrangement for the given compound is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.45P , additional homework tip 6

Figure 3

The above diagram indicates that in the product, both the π bonds are rearranged. The old σ bond breaks at third carbon atom and simultaneously a new σ bond is formed at sixth carbon atom during the conversion of starting material into the product. Therefore, the product is formed with [3,3] sigmatropic rearrangement.

Thus, the name of product is 6-methyl-1, 2, 4a, 5, 8, 8a-hexahydronaphthalene.