(a) Interpretation: The product formed when the given compound in Problem 27.6 undergoes photochemical electrocyclic ring opening or ring closure is to be predicted. The given process is to be labeled as conrotatory or disrotatory. The stereochemistry around tetrahedral stereogenic centers and double bonds is to be indicated. Concept introduction: Electrocyclic reactions involve the conversion of σ bonds into π bonds or π bonds into σ bonds. These reactions can take place in photochemical and as well as thermal conditions. The photochemical and thermal reactions take place in the presence of light and heat respectively. 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 27.8P

Interpretation Introduction

(a)

Interpretation: The product formed when the given compound in Problem 27.6 undergoes photochemical electrocyclic ring opening or ring closure is to be predicted. The given process is to be labeled as conrotatory or disrotatory. The stereochemistry around tetrahedral stereogenic centers and double bonds is to be indicated.

Concept introduction: Electrocyclic reactions involve the conversion of σ bonds into π bonds or π bonds into σ bonds. These reactions can take place in photochemical and as well as thermal conditions. The photochemical and thermal reactions take place in the presence of light and heat respectively.

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 27.8P

The product formed in the given photochemical electrocyclic ring closure reaction is trans−4,5− dimethylcyclohexa −2,6− diene-1,2-dibenzene. The formation of the product takes place by conrotatory process. The stereochemistry around tetrahedral stereogenic centers is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 1

Explanation of Solution

The thermal electrocyclic ring closure reaction is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 2

Figure 1

Electrocyclic reactions involve the conversion of σ bonds into π bonds or π bonds into σ bonds. In the product, the ring gets closed due to the rearrangement of π bonds and the formation of new σ bond. Therefore, the product formed in the given thermal electrocyclic ring closure reaction is cis−4,5− dimethylcyclohexa −2,6− diene-1,2-dibenzene.

Under photochemical condition, conrotatory process takes place in the given reaction. The orientation of substituents and stereochemistry around tetrahedral stereogenic centers and double bonds in the given reaction are shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 3

Figure 2

The conrotatory process involves the rotation of two orbitals in the same direction. The reaction in above figure implies that orbitals move in the same direction in the reactant molecule and the formation of trans product occurs. One methyl group is present above the plane and one methyl group is present below the plane in the product. Therefore, the product formed in the given photochemical electrocyclic ring closure reaction is trans−4,5− dimethylcyclohexa −2,6− diene-1,2-dibenzene.

Conclusion

The product formed in the given photochemical electrocyclic ring closure reaction is trans−4,5− dimethylcyclohexa −2,6− diene-1,2-dibenzene. The formation of the product takes place by conrotatory process. The stereochemistry around tetrahedral stereogenic centers is indicated in Figure 2.

Interpretation Introduction

(b)

Interpretation: The product formed when the given compound in Problem 27.6 undergoes photochemical electrocyclic ring opening or ring closure is to be predicted. The given process is to be labeled as conrotatory or disrotatory. The stereochemistry around tetrahedral stereogenic centers and double bonds is to be indicated.

Concept introduction: Electrocyclic reactions involve the conversion of σ bonds into π bonds or π bonds into σ bonds. These reactions can take place in photochemical and as well as thermal conditions. The photochemical and thermal reactions take place in the presence of light and heat respectively.

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 27.8P

The product formed in the given photochemical electrocyclic ring opening reaction is trans−3,4− dimethylhexa −2,4− diene. The formation of the product takes place by disrotatory process. The stereochemistry around tetrahedral stereogenic centers is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 4

Explanation of Solution

The thermal electrocyclic ring opening reaction is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 5

Figure 3

Electrocyclic reactions involve the conversion of σ bonds into π bonds or π bonds into σ bonds. In the product, the ring is opened due to the rearrangement of π bond and the breakdown of old σ bond. Therefore, the product formed in the given photochemical electrocyclic ring opening reaction is 3,4− dimethylhexa −2,4− diene.

Under photochemical condition, disrotatory process takes place in the given reaction. The movement of substituents and stereochemistry around tetrahedral stereogenic centers and double bonds in the given reaction are shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 6

Figure 4

The disrotatory process involves the rotation of two orbitals in the opposite direction. The reaction in above figure implies that orbitals move in the opposite direction in the reactant molecule and the formation of trans product occurs. One methyl group is present above the plane and one methyl group is present below the plane in the product shows the stereochemistry. Therefore, the product formed in the given photochemical electrocyclic ring opening reaction is trans−3,4− dimethylhexa −2,4− diene. The formation of the product takes place by disrotatory process. The stereochemistry around tetrahedral stereogenic centers is indicated in Figure 4.

Conclusion

The product formed in the given photochemical electrocyclic ring opening reaction is trans−3,4− dimethylhexa −2,4− diene. The formation of the product takes place by disrotatory process. The stereochemistry around tetrahedral stereogenic centers is indicated in Figure 4.

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Answer 2

Question

Chapter 27, Problem 27.8P

Interpretation Introduction

(a)

Interpretation: The product formed when the given compound in Problem 27.6 undergoes photochemical electrocyclic ring opening or ring closure is to be predicted. The given process is to be labeled as conrotatory or disrotatory. The stereochemistry around tetrahedral stereogenic centers and double bonds is to be indicated.

Concept introduction: Electrocyclic reactions involve the conversion of σ bonds into π bonds or π bonds into σ bonds. These reactions can take place in photochemical and as well as thermal conditions. The photochemical and thermal reactions take place in the presence of light and heat respectively.

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 27.8P

The product formed in the given photochemical electrocyclic ring closure reaction is trans−4,5− dimethylcyclohexa −2,6− diene-1,2-dibenzene. The formation of the product takes place by conrotatory process. The stereochemistry around tetrahedral stereogenic centers is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 1

Explanation of Solution

The thermal electrocyclic ring closure reaction is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 2

Figure 1

Electrocyclic reactions involve the conversion of σ bonds into π bonds or π bonds into σ bonds. In the product, the ring gets closed due to the rearrangement of π bonds and the formation of new σ bond. Therefore, the product formed in the given thermal electrocyclic ring closure reaction is cis−4,5− dimethylcyclohexa −2,6− diene-1,2-dibenzene.

Under photochemical condition, conrotatory process takes place in the given reaction. The orientation of substituents and stereochemistry around tetrahedral stereogenic centers and double bonds in the given reaction are shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 3

Figure 2

The conrotatory process involves the rotation of two orbitals in the same direction. The reaction in above figure implies that orbitals move in the same direction in the reactant molecule and the formation of trans product occurs. One methyl group is present above the plane and one methyl group is present below the plane in the product. Therefore, the product formed in the given photochemical electrocyclic ring closure reaction is trans−4,5− dimethylcyclohexa −2,6− diene-1,2-dibenzene.

Conclusion

The product formed in the given photochemical electrocyclic ring closure reaction is trans−4,5− dimethylcyclohexa −2,6− diene-1,2-dibenzene. The formation of the product takes place by conrotatory process. The stereochemistry around tetrahedral stereogenic centers is indicated in Figure 2.

Interpretation Introduction

(b)

Interpretation: The product formed when the given compound in Problem 27.6 undergoes photochemical electrocyclic ring opening or ring closure is to be predicted. The given process is to be labeled as conrotatory or disrotatory. The stereochemistry around tetrahedral stereogenic centers and double bonds is to be indicated.

Concept introduction: Electrocyclic reactions involve the conversion of σ bonds into π bonds or π bonds into σ bonds. These reactions can take place in photochemical and as well as thermal conditions. The photochemical and thermal reactions take place in the presence of light and heat respectively.

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 27.8P

The product formed in the given photochemical electrocyclic ring opening reaction is trans−3,4− dimethylhexa −2,4− diene. The formation of the product takes place by disrotatory process. The stereochemistry around tetrahedral stereogenic centers is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 4

Explanation of Solution

The thermal electrocyclic ring opening reaction is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 5

Figure 3

Electrocyclic reactions involve the conversion of σ bonds into π bonds or π bonds into σ bonds. In the product, the ring is opened due to the rearrangement of π bond and the breakdown of old σ bond. Therefore, the product formed in the given photochemical electrocyclic ring opening reaction is 3,4− dimethylhexa −2,4− diene.

Under photochemical condition, disrotatory process takes place in the given reaction. The movement of substituents and stereochemistry around tetrahedral stereogenic centers and double bonds in the given reaction are shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 6

Figure 4

The disrotatory process involves the rotation of two orbitals in the opposite direction. The reaction in above figure implies that orbitals move in the opposite direction in the reactant molecule and the formation of trans product occurs. One methyl group is present above the plane and one methyl group is present below the plane in the product shows the stereochemistry. Therefore, the product formed in the given photochemical electrocyclic ring opening reaction is trans−3,4− dimethylhexa −2,4− diene. The formation of the product takes place by disrotatory process. The stereochemistry around tetrahedral stereogenic centers is indicated in Figure 4.

Conclusion

The product formed in the given photochemical electrocyclic ring opening reaction is trans−3,4− dimethylhexa −2,4− diene. The formation of the product takes place by disrotatory process. The stereochemistry around tetrahedral stereogenic centers is indicated in Figure 4.

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Answer 3

Question

Chapter 27, Problem 27.8P

Interpretation Introduction

(a)

Interpretation: The product formed when the given compound in Problem 27.6 undergoes photochemical electrocyclic ring opening or ring closure is to be predicted. The given process is to be labeled as conrotatory or disrotatory. The stereochemistry around tetrahedral stereogenic centers and double bonds is to be indicated.

Concept introduction: Electrocyclic reactions involve the conversion of σ bonds into π bonds or π bonds into σ bonds. These reactions can take place in photochemical and as well as thermal conditions. The photochemical and thermal reactions take place in the presence of light and heat respectively.

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 27.8P

The product formed in the given photochemical electrocyclic ring closure reaction is trans−4,5− dimethylcyclohexa −2,6− diene-1,2-dibenzene. The formation of the product takes place by conrotatory process. The stereochemistry around tetrahedral stereogenic centers is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 1

Explanation of Solution

The thermal electrocyclic ring closure reaction is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 2

Figure 1

Electrocyclic reactions involve the conversion of σ bonds into π bonds or π bonds into σ bonds. In the product, the ring gets closed due to the rearrangement of π bonds and the formation of new σ bond. Therefore, the product formed in the given thermal electrocyclic ring closure reaction is cis−4,5− dimethylcyclohexa −2,6− diene-1,2-dibenzene.

Under photochemical condition, conrotatory process takes place in the given reaction. The orientation of substituents and stereochemistry around tetrahedral stereogenic centers and double bonds in the given reaction are shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 3

Figure 2

The conrotatory process involves the rotation of two orbitals in the same direction. The reaction in above figure implies that orbitals move in the same direction in the reactant molecule and the formation of trans product occurs. One methyl group is present above the plane and one methyl group is present below the plane in the product. Therefore, the product formed in the given photochemical electrocyclic ring closure reaction is trans−4,5− dimethylcyclohexa −2,6− diene-1,2-dibenzene.

Conclusion

The product formed in the given photochemical electrocyclic ring closure reaction is trans−4,5− dimethylcyclohexa −2,6− diene-1,2-dibenzene. The formation of the product takes place by conrotatory process. The stereochemistry around tetrahedral stereogenic centers is indicated in Figure 2.

Interpretation Introduction

(b)

Interpretation: The product formed when the given compound in Problem 27.6 undergoes photochemical electrocyclic ring opening or ring closure is to be predicted. The given process is to be labeled as conrotatory or disrotatory. The stereochemistry around tetrahedral stereogenic centers and double bonds is to be indicated.

Concept introduction: Electrocyclic reactions involve the conversion of σ bonds into π bonds or π bonds into σ bonds. These reactions can take place in photochemical and as well as thermal conditions. The photochemical and thermal reactions take place in the presence of light and heat respectively.

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 27.8P

The product formed in the given photochemical electrocyclic ring opening reaction is trans−3,4− dimethylhexa −2,4− diene. The formation of the product takes place by disrotatory process. The stereochemistry around tetrahedral stereogenic centers is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 4

Explanation of Solution

The thermal electrocyclic ring opening reaction is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 5

Figure 3

Electrocyclic reactions involve the conversion of σ bonds into π bonds or π bonds into σ bonds. In the product, the ring is opened due to the rearrangement of π bond and the breakdown of old σ bond. Therefore, the product formed in the given photochemical electrocyclic ring opening reaction is 3,4− dimethylhexa −2,4− diene.

Under photochemical condition, disrotatory process takes place in the given reaction. The movement of substituents and stereochemistry around tetrahedral stereogenic centers and double bonds in the given reaction are shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 6

Figure 4

The disrotatory process involves the rotation of two orbitals in the opposite direction. The reaction in above figure implies that orbitals move in the opposite direction in the reactant molecule and the formation of trans product occurs. One methyl group is present above the plane and one methyl group is present below the plane in the product shows the stereochemistry. Therefore, the product formed in the given photochemical electrocyclic ring opening reaction is trans−3,4− dimethylhexa −2,4− diene. The formation of the product takes place by disrotatory process. The stereochemistry around tetrahedral stereogenic centers is indicated in Figure 4.

Conclusion

The product formed in the given photochemical electrocyclic ring opening reaction is trans−3,4− dimethylhexa −2,4− diene. The formation of the product takes place by disrotatory process. The stereochemistry around tetrahedral stereogenic centers is indicated in Figure 4.

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Answer 4

Question

Chapter 27, Problem 27.8P

Interpretation Introduction

(a)

Interpretation: The product formed when the given compound in Problem 27.6 undergoes photochemical electrocyclic ring opening or ring closure is to be predicted. The given process is to be labeled as conrotatory or disrotatory. The stereochemistry around tetrahedral stereogenic centers and double bonds is to be indicated.

Concept introduction: Electrocyclic reactions involve the conversion of σ bonds into π bonds or π bonds into σ bonds. These reactions can take place in photochemical and as well as thermal conditions. The photochemical and thermal reactions take place in the presence of light and heat respectively.

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 27.8P

The product formed in the given photochemical electrocyclic ring closure reaction is trans−4,5− dimethylcyclohexa −2,6− diene-1,2-dibenzene. The formation of the product takes place by conrotatory process. The stereochemistry around tetrahedral stereogenic centers is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 1

Explanation of Solution

The thermal electrocyclic ring closure reaction is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 2

Figure 1

Electrocyclic reactions involve the conversion of σ bonds into π bonds or π bonds into σ bonds. In the product, the ring gets closed due to the rearrangement of π bonds and the formation of new σ bond. Therefore, the product formed in the given thermal electrocyclic ring closure reaction is cis−4,5− dimethylcyclohexa −2,6− diene-1,2-dibenzene.

Under photochemical condition, conrotatory process takes place in the given reaction. The orientation of substituents and stereochemistry around tetrahedral stereogenic centers and double bonds in the given reaction are shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 3

Figure 2

The conrotatory process involves the rotation of two orbitals in the same direction. The reaction in above figure implies that orbitals move in the same direction in the reactant molecule and the formation of trans product occurs. One methyl group is present above the plane and one methyl group is present below the plane in the product. Therefore, the product formed in the given photochemical electrocyclic ring closure reaction is trans−4,5− dimethylcyclohexa −2,6− diene-1,2-dibenzene.

Conclusion

The product formed in the given photochemical electrocyclic ring closure reaction is trans−4,5− dimethylcyclohexa −2,6− diene-1,2-dibenzene. The formation of the product takes place by conrotatory process. The stereochemistry around tetrahedral stereogenic centers is indicated in Figure 2.

Interpretation Introduction

(b)

Interpretation: The product formed when the given compound in Problem 27.6 undergoes photochemical electrocyclic ring opening or ring closure is to be predicted. The given process is to be labeled as conrotatory or disrotatory. The stereochemistry around tetrahedral stereogenic centers and double bonds is to be indicated.

Concept introduction: Electrocyclic reactions involve the conversion of σ bonds into π bonds or π bonds into σ bonds. These reactions can take place in photochemical and as well as thermal conditions. The photochemical and thermal reactions take place in the presence of light and heat respectively.

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 27.8P

The product formed in the given photochemical electrocyclic ring opening reaction is trans−3,4− dimethylhexa −2,4− diene. The formation of the product takes place by disrotatory process. The stereochemistry around tetrahedral stereogenic centers is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 4

Explanation of Solution

The thermal electrocyclic ring opening reaction is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 5

Figure 3

Electrocyclic reactions involve the conversion of σ bonds into π bonds or π bonds into σ bonds. In the product, the ring is opened due to the rearrangement of π bond and the breakdown of old σ bond. Therefore, the product formed in the given photochemical electrocyclic ring opening reaction is 3,4− dimethylhexa −2,4− diene.

Under photochemical condition, disrotatory process takes place in the given reaction. The movement of substituents and stereochemistry around tetrahedral stereogenic centers and double bonds in the given reaction are shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 6

Figure 4

The disrotatory process involves the rotation of two orbitals in the opposite direction. The reaction in above figure implies that orbitals move in the opposite direction in the reactant molecule and the formation of trans product occurs. One methyl group is present above the plane and one methyl group is present below the plane in the product shows the stereochemistry. Therefore, the product formed in the given photochemical electrocyclic ring opening reaction is trans−3,4− dimethylhexa −2,4− diene. The formation of the product takes place by disrotatory process. The stereochemistry around tetrahedral stereogenic centers is indicated in Figure 4.

Conclusion

The product formed in the given photochemical electrocyclic ring opening reaction is trans−3,4− dimethylhexa −2,4− diene. The formation of the product takes place by disrotatory process. The stereochemistry around tetrahedral stereogenic centers is indicated in Figure 4.

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Answer 5

Chapter 27, Problem 27.8P

Interpretation Introduction

(a)

Interpretation: The product formed when the given compound in Problem 27.6 undergoes photochemical electrocyclic ring opening or ring closure is to be predicted. The given process is to be labeled as conrotatory or disrotatory. The stereochemistry around tetrahedral stereogenic centers and double bonds is to be indicated.

Concept introduction: Electrocyclic reactions involve the conversion of σ bonds into π bonds or π bonds into σ bonds. These reactions can take place in photochemical and as well as thermal conditions. The photochemical and thermal reactions take place in the presence of light and heat respectively.

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 27.8P

The product formed in the given photochemical electrocyclic ring closure reaction is trans−4,5− dimethylcyclohexa −2,6− diene-1,2-dibenzene. The formation of the product takes place by conrotatory process. The stereochemistry around tetrahedral stereogenic centers is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 1

Explanation of Solution

The thermal electrocyclic ring closure reaction is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 2

Figure 1

Electrocyclic reactions involve the conversion of σ bonds into π bonds or π bonds into σ bonds. In the product, the ring gets closed due to the rearrangement of π bonds and the formation of new σ bond. Therefore, the product formed in the given thermal electrocyclic ring closure reaction is cis−4,5− dimethylcyclohexa −2,6− diene-1,2-dibenzene.

Under photochemical condition, conrotatory process takes place in the given reaction. The orientation of substituents and stereochemistry around tetrahedral stereogenic centers and double bonds in the given reaction are shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 3

Figure 2

The conrotatory process involves the rotation of two orbitals in the same direction. The reaction in above figure implies that orbitals move in the same direction in the reactant molecule and the formation of trans product occurs. One methyl group is present above the plane and one methyl group is present below the plane in the product. Therefore, the product formed in the given photochemical electrocyclic ring closure reaction is trans−4,5− dimethylcyclohexa −2,6− diene-1,2-dibenzene.

Conclusion

The product formed in the given photochemical electrocyclic ring closure reaction is trans−4,5− dimethylcyclohexa −2,6− diene-1,2-dibenzene. The formation of the product takes place by conrotatory process. The stereochemistry around tetrahedral stereogenic centers is indicated in Figure 2.

Interpretation Introduction

(b)

Interpretation: The product formed when the given compound in Problem 27.6 undergoes photochemical electrocyclic ring opening or ring closure is to be predicted. The given process is to be labeled as conrotatory or disrotatory. The stereochemistry around tetrahedral stereogenic centers and double bonds is to be indicated.

Concept introduction: Electrocyclic reactions involve the conversion of σ bonds into π bonds or π bonds into σ bonds. These reactions can take place in photochemical and as well as thermal conditions. The photochemical and thermal reactions take place in the presence of light and heat respectively.

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 27.8P

The product formed in the given photochemical electrocyclic ring opening reaction is trans−3,4− dimethylhexa −2,4− diene. The formation of the product takes place by disrotatory process. The stereochemistry around tetrahedral stereogenic centers is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 4

Explanation of Solution

The thermal electrocyclic ring opening reaction is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 5

Figure 3

Electrocyclic reactions involve the conversion of σ bonds into π bonds or π bonds into σ bonds. In the product, the ring is opened due to the rearrangement of π bond and the breakdown of old σ bond. Therefore, the product formed in the given photochemical electrocyclic ring opening reaction is 3,4− dimethylhexa −2,4− diene.

Under photochemical condition, disrotatory process takes place in the given reaction. The movement of substituents and stereochemistry around tetrahedral stereogenic centers and double bonds in the given reaction are shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 6

Figure 4

The disrotatory process involves the rotation of two orbitals in the opposite direction. The reaction in above figure implies that orbitals move in the opposite direction in the reactant molecule and the formation of trans product occurs. One methyl group is present above the plane and one methyl group is present below the plane in the product shows the stereochemistry. Therefore, the product formed in the given photochemical electrocyclic ring opening reaction is trans−3,4− dimethylhexa −2,4− diene. The formation of the product takes place by disrotatory process. The stereochemistry around tetrahedral stereogenic centers is indicated in Figure 4.

Conclusion

The product formed in the given photochemical electrocyclic ring opening reaction is trans−3,4− dimethylhexa −2,4− diene. The formation of the product takes place by disrotatory process. The stereochemistry around tetrahedral stereogenic centers is indicated in Figure 4.

Answer 6

Chapter 27, Problem 27.8P

Interpretation Introduction

(a)

Interpretation: The product formed when the given compound in Problem 27.6 undergoes photochemical electrocyclic ring opening or ring closure is to be predicted. The given process is to be labeled as conrotatory or disrotatory. The stereochemistry around tetrahedral stereogenic centers and double bonds is to be indicated.

Concept introduction: Electrocyclic reactions involve the conversion of σ bonds into π bonds or π bonds into σ bonds. These reactions can take place in photochemical and as well as thermal conditions. The photochemical and thermal reactions take place in the presence of light and heat respectively.

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 27.8P

The product formed in the given photochemical electrocyclic ring closure reaction is trans−4,5− dimethylcyclohexa −2,6− diene-1,2-dibenzene. The formation of the product takes place by conrotatory process. The stereochemistry around tetrahedral stereogenic centers is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 1

Explanation of Solution

The thermal electrocyclic ring closure reaction is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 2

Figure 1

Electrocyclic reactions involve the conversion of σ bonds into π bonds or π bonds into σ bonds. In the product, the ring gets closed due to the rearrangement of π bonds and the formation of new σ bond. Therefore, the product formed in the given thermal electrocyclic ring closure reaction is cis−4,5− dimethylcyclohexa −2,6− diene-1,2-dibenzene.

Under photochemical condition, conrotatory process takes place in the given reaction. The orientation of substituents and stereochemistry around tetrahedral stereogenic centers and double bonds in the given reaction are shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 3

Figure 2

The conrotatory process involves the rotation of two orbitals in the same direction. The reaction in above figure implies that orbitals move in the same direction in the reactant molecule and the formation of trans product occurs. One methyl group is present above the plane and one methyl group is present below the plane in the product. Therefore, the product formed in the given photochemical electrocyclic ring closure reaction is trans−4,5− dimethylcyclohexa −2,6− diene-1,2-dibenzene.

Conclusion

The product formed in the given photochemical electrocyclic ring closure reaction is trans−4,5− dimethylcyclohexa −2,6− diene-1,2-dibenzene. The formation of the product takes place by conrotatory process. The stereochemistry around tetrahedral stereogenic centers is indicated in Figure 2.

Answer 7

Chapter 27, Problem 27.8P

Interpretation Introduction

(a)

Interpretation: The product formed when the given compound in Problem 27.6 undergoes photochemical electrocyclic ring opening or ring closure is to be predicted. The given process is to be labeled as conrotatory or disrotatory. The stereochemistry around tetrahedral stereogenic centers and double bonds is to be indicated.

Concept introduction: Electrocyclic reactions involve the conversion of σ bonds into π bonds or π bonds into σ bonds. These reactions can take place in photochemical and as well as thermal conditions. The photochemical and thermal reactions take place in the presence of light and heat respectively.

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 27.8P

The product formed in the given photochemical electrocyclic ring closure reaction is trans−4,5− dimethylcyclohexa −2,6− diene-1,2-dibenzene. The formation of the product takes place by conrotatory process. The stereochemistry around tetrahedral stereogenic centers is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 1

Answer 9

Expert Solution

Answer 10

Expert Solution

Answer 11

Expert Solution

Answer 12

Explanation of Solution

The thermal electrocyclic ring closure reaction is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 2

Figure 1

Electrocyclic reactions involve the conversion of σ bonds into π bonds or π bonds into σ bonds. In the product, the ring gets closed due to the rearrangement of π bonds and the formation of new σ bond. Therefore, the product formed in the given thermal electrocyclic ring closure reaction is cis−4,5− dimethylcyclohexa −2,6− diene-1,2-dibenzene.

Under photochemical condition, conrotatory process takes place in the given reaction. The orientation of substituents and stereochemistry around tetrahedral stereogenic centers and double bonds in the given reaction are shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 3

Figure 2

The conrotatory process involves the rotation of two orbitals in the same direction. The reaction in above figure implies that orbitals move in the same direction in the reactant molecule and the formation of trans product occurs. One methyl group is present above the plane and one methyl group is present below the plane in the product. Therefore, the product formed in the given photochemical electrocyclic ring closure reaction is trans−4,5− dimethylcyclohexa −2,6− diene-1,2-dibenzene.

Answer 13

Conclusion

The product formed in the given photochemical electrocyclic ring closure reaction is trans−4,5− dimethylcyclohexa −2,6− diene-1,2-dibenzene. The formation of the product takes place by conrotatory process. The stereochemistry around tetrahedral stereogenic centers is indicated in Figure 2.

Answer 14

Interpretation Introduction

(b)

Interpretation: The product formed when the given compound in Problem 27.6 undergoes photochemical electrocyclic ring opening or ring closure is to be predicted. The given process is to be labeled as conrotatory or disrotatory. The stereochemistry around tetrahedral stereogenic centers and double bonds is to be indicated.

Concept introduction: Electrocyclic reactions involve the conversion of σ bonds into π bonds or π bonds into σ bonds. These reactions can take place in photochemical and as well as thermal conditions. The photochemical and thermal reactions take place in the presence of light and heat respectively.

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 27.8P

The product formed in the given photochemical electrocyclic ring opening reaction is trans−3,4− dimethylhexa −2,4− diene. The formation of the product takes place by disrotatory process. The stereochemistry around tetrahedral stereogenic centers is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 4

Explanation of Solution

The thermal electrocyclic ring opening reaction is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 5

Figure 3

Electrocyclic reactions involve the conversion of σ bonds into π bonds or π bonds into σ bonds. In the product, the ring is opened due to the rearrangement of π bond and the breakdown of old σ bond. Therefore, the product formed in the given photochemical electrocyclic ring opening reaction is 3,4− dimethylhexa −2,4− diene.

Under photochemical condition, disrotatory process takes place in the given reaction. The movement of substituents and stereochemistry around tetrahedral stereogenic centers and double bonds in the given reaction are shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 6

Figure 4

The disrotatory process involves the rotation of two orbitals in the opposite direction. The reaction in above figure implies that orbitals move in the opposite direction in the reactant molecule and the formation of trans product occurs. One methyl group is present above the plane and one methyl group is present below the plane in the product shows the stereochemistry. Therefore, the product formed in the given photochemical electrocyclic ring opening reaction is trans−3,4− dimethylhexa −2,4− diene. The formation of the product takes place by disrotatory process. The stereochemistry around tetrahedral stereogenic centers is indicated in Figure 4.

Conclusion

The product formed in the given photochemical electrocyclic ring opening reaction is trans−3,4− dimethylhexa −2,4− diene. The formation of the product takes place by disrotatory process. The stereochemistry around tetrahedral stereogenic centers is indicated in Figure 4.

Answer 15

Interpretation Introduction

(b)

Interpretation: The product formed when the given compound in Problem 27.6 undergoes photochemical electrocyclic ring opening or ring closure is to be predicted. The given process is to be labeled as conrotatory or disrotatory. The stereochemistry around tetrahedral stereogenic centers and double bonds is to be indicated.

Concept introduction: Electrocyclic reactions involve the conversion of σ bonds into π bonds or π bonds into σ bonds. These reactions can take place in photochemical and as well as thermal conditions. The photochemical and thermal reactions take place in the presence of light and heat respectively.

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 27.8P

The product formed in the given photochemical electrocyclic ring opening reaction is trans−3,4− dimethylhexa −2,4− diene. The formation of the product takes place by disrotatory process. The stereochemistry around tetrahedral stereogenic centers is,

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 4

Answer 17

Expert Solution

Answer 18

Expert Solution

Answer 19

Expert Solution

Answer 20

Explanation of Solution

The thermal electrocyclic ring opening reaction is shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 5

Figure 3

Electrocyclic reactions involve the conversion of σ bonds into π bonds or π bonds into σ bonds. In the product, the ring is opened due to the rearrangement of π bond and the breakdown of old σ bond. Therefore, the product formed in the given photochemical electrocyclic ring opening reaction is 3,4− dimethylhexa −2,4− diene.

Under photochemical condition, disrotatory process takes place in the given reaction. The movement of substituents and stereochemistry around tetrahedral stereogenic centers and double bonds in the given reaction are shown below.

ORGANIC CHEMISTRY, Chapter 27, Problem 27.8P , additional homework tip 6

Figure 4

The disrotatory process involves the rotation of two orbitals in the opposite direction. The reaction in above figure implies that orbitals move in the opposite direction in the reactant molecule and the formation of trans product occurs. One methyl group is present above the plane and one methyl group is present below the plane in the product shows the stereochemistry. Therefore, the product formed in the given photochemical electrocyclic ring opening reaction is trans−3,4− dimethylhexa −2,4− diene. The formation of the product takes place by disrotatory process. The stereochemistry around tetrahedral stereogenic centers is indicated in Figure 4.

Answer 21

Conclusion

The product formed in the given photochemical electrocyclic ring opening reaction is trans−3,4− dimethylhexa −2,4− diene. The formation of the product takes place by disrotatory process. The stereochemistry around tetrahedral stereogenic centers is indicated in Figure 4.

Answer 22

Ch. 27 - Prob. 27.1P Ch. 27 - Problem 27.2 For each molecular orbital in Figure...Ch. 27 - Problem 27.3 (a) Using Figure 27.2 as a guide,...Ch. 27 - Problem 27.4 (a) How many molecular orbitals are...Ch. 27 - Prob. 27.5P Ch. 27 - Prob. 27.6P Ch. 27 - Prob. 27.7P Ch. 27 - Prob. 27.8P Ch. 27 - Prob. 27.9P Ch. 27 - Prob. 27.10P

Solution Summary: The author explains the photochemical electrocyclic ring closure process and the stereochemistry around tetrahedral stereogenic centers and double bonds.

Concept explainers

Answer to Problem 27.8P

Explanation of Solution

Answer to Problem 27.8P

Explanation of Solution

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