a) Interpretation: The product of the reaction in which actophenone reacts with HNO 3 and H 2 SO 4 is to be predicted. The observed regiochemistry is to be explained by drawing the resonance structures of the intermediates. Concept introduction: The carbonyl group is an electron withdrawing group. Hence in aromatic electrophilic substitution reactions, the keto group will deactivate the ring and orient the electrophile to the meta position. To predict: The product of the reaction in which actophenone reacts with HNO 3 and H 2 SO 4 . To explain: The observed regiochemistry by drawing the resonance structures of the intermediates.

Question

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Answer 1

Question

Chapter 16.SE, Problem 77AP

Interpretation Introduction

a)

Interpretation:

The product of the reaction in which actophenone reacts with HNO₃ and H₂SO₄ is to be predicted. The observed regiochemistry is to be explained by drawing the resonance structures of the intermediates.

Concept introduction:

The carbonyl group is an electron withdrawing group. Hence in aromatic electrophilic substitution reactions, the keto group will deactivate the ring and orient the electrophile to the meta position.

To predict:

The product of the reaction in which actophenone reacts with HNO₃ and H₂SO₄.

To explain:

The observed regiochemistry by drawing the resonance structures of the intermediates.

Expert Solution

Answer to Problem 77AP

Actophenone reacts with HNO₃ and H₂SO₄ to produce m-nitroacetophenone.

Explanation of Solution

The electrophile, NO₂⁺, attacks the aromatic ring in the first step to produce a resonance stabilized carbocation (sigma complex). In the second step the carbocation deprotonates to yield the product. For the meta attack the intermediate is more stabilized as shown.

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 2

For ortho and para attack one of the resonance forms will be unstable as there will be a positive charge on the carbon to which the carbonyl group is attached.

Conclusion

Actophenone reacts with HNO₃ and H₂SO₄ to produce m-nitroacetophenone.

Interpretation Introduction

b)

Interpretation:

The product of the reaction in which toluene reacts with isopropyl chloride in the presence of AlCl₃ is to be predicted. The observed regiochemistry is to be explained by drawing the resonance structures of the intermediates.

Concept introduction:

Alkyl groups are an electron releasing groups. Hence during aromatic electrophilic substitution reactions the alkyl groups will activate the ring and orient the electrophile to the ortho and para positions.

To predict:

The product of the reaction in which toluene reacts with isopropyl chloride in the presence of AlCl₃.

To explain:

The observed regiochemistry by drawing the resonance structures of the intermediates.

Expert Solution

Answer to Problem 77AP

When toluene reacts with isopropyl chloride in the presence of AlCl₃ the products obtained are o- and p-isopropylbenzenes. The p-isomer will predominate.

Explanation of Solution

The electrophile, (CH₃)₂CH⁺, attacks the aromatic ring in the first step to produce a resonance stabilized carbocation (sigma complex). In the second step the carbocation deprotonates to yield the product. For the ortho and para attacks, one of the the resonance structures has a positive charge on a carbon adjacent to the methyl group. This form is stabilized by electron release from the methyl group. Such stabilization is not possible for the meta attack. Hence a mixture of ortho-para products is produced in which the p-isomer predominates.

For ortho attack:

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 4

For para attack:

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 5

Conclusion

When toluene reacts with isopropyl chloride in the presence of AlCl₃ the products obtained are o- and p-isopropylbenzenes. The p-isomer will predominate.

Interpretation Introduction

c)

Interpretation:

The product of the reaction in which benzonitrile reacts with chlorine in the presence of FeCl₃ is to be predicted. The observed regiochemistry is to be explained by drawing the resonance structures of the intermediates.

Concept introduction:

The nitrile group is an electron withdrawing group. Hence in aromatic electrophilic substitution reactions the nitrile group will deactivate the ring and orient the electrophile to the meta position.

To predict:

The product of the reaction in which benzonitrile reacts with chlorine in the presence of FeCl₃.

To explain:

The observed regiochemistry by drawing the resonance structures of the intermediates.

Expert Solution

Answer to Problem 77AP

When benzonitrile reacts with chlorine in the presence of FeCl₃ meta chlorobenzonitrile will be produced.

Explanation of Solution

The electrophile, Cl⁺, attacks the aromatic ring in the first step to produce a resonance stabilized carbocation (sigma complex). In the second step the carbocation deprotonates to yield the product. For the meta attack the intermediate is more stabilized as shown.

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 7

For ortho and para attack one of the resonance forms will be unstable as there will be a positive charge on the carbon to which the nitrile group is attached.

Conclusion

When benzonitrile reacts with chlorine in the presence of FeCl₃ meta chlorobenzonitrile will be produced.

Interpretation Introduction

d)

Interpretation:

The product of the reaction in which methoxy benzene reacts with iodine in the presence of CuCl₂ is to be predicted. The observed regiochemistry is to be explained by drawing the resonance structures of the intermediates.

Concept introduction:

Methoxy group is an electron releasing group. Hence during aromatic electrophilic substitution reactions the methoxy group will activate the ring and orient the electrophile to the ortho and para positions.

To predict:

The product of the reaction in which benzene reacts with iodine in the presence of CuCl₂.

To explain:

The observed regiochemistry by drawing the resonance structures of the intermediates.

Expert Solution

Answer to Problem 77AP

When methoxybenzene reacts with iodine in the presence of CuCl₂, the products obtained are o- and p-iodobenzenes.

Explanation of Solution

Iodine itself is unreactive toward aromatic rings. CuCl₂ accelerate the iodination reaction by oxidizing iodine to a more powerful by electrophilic species that reacts like I⁺.

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 9

The electrophile, I⁺, attacks the aromatic ring in the first step to produce a resonance stabilized carbocation (sigma complex). In the second step the carbocation deprotonates to yield the product. For the ortho and para attacks, one of the the resonance structures has a positive charge on a carbon adjacent to the methoxy group. This form is stabilized by electron release from the methoxy group. Such stabilization is not possible for the meta attack. Hence a mixture of ortho-para products is produced.

Ortho attack:

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 10

Meta attack:

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 11

Conclusion

When methoxybenzene reacts with iodine in the presence of CuCl₂, the products obtained are o- and p-iodobenzenes.

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Answer 2

Question

Chapter 16.SE, Problem 77AP

Interpretation Introduction

a)

Interpretation:

The product of the reaction in which actophenone reacts with HNO₃ and H₂SO₄ is to be predicted. The observed regiochemistry is to be explained by drawing the resonance structures of the intermediates.

Concept introduction:

The carbonyl group is an electron withdrawing group. Hence in aromatic electrophilic substitution reactions, the keto group will deactivate the ring and orient the electrophile to the meta position.

To predict:

The product of the reaction in which actophenone reacts with HNO₃ and H₂SO₄.

To explain:

The observed regiochemistry by drawing the resonance structures of the intermediates.

Expert Solution

Answer to Problem 77AP

Actophenone reacts with HNO₃ and H₂SO₄ to produce m-nitroacetophenone.

Explanation of Solution

The electrophile, NO₂⁺, attacks the aromatic ring in the first step to produce a resonance stabilized carbocation (sigma complex). In the second step the carbocation deprotonates to yield the product. For the meta attack the intermediate is more stabilized as shown.

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 2

For ortho and para attack one of the resonance forms will be unstable as there will be a positive charge on the carbon to which the carbonyl group is attached.

Conclusion

Actophenone reacts with HNO₃ and H₂SO₄ to produce m-nitroacetophenone.

Interpretation Introduction

b)

Interpretation:

The product of the reaction in which toluene reacts with isopropyl chloride in the presence of AlCl₃ is to be predicted. The observed regiochemistry is to be explained by drawing the resonance structures of the intermediates.

Concept introduction:

Alkyl groups are an electron releasing groups. Hence during aromatic electrophilic substitution reactions the alkyl groups will activate the ring and orient the electrophile to the ortho and para positions.

To predict:

The product of the reaction in which toluene reacts with isopropyl chloride in the presence of AlCl₃.

To explain:

The observed regiochemistry by drawing the resonance structures of the intermediates.

Expert Solution

Answer to Problem 77AP

When toluene reacts with isopropyl chloride in the presence of AlCl₃ the products obtained are o- and p-isopropylbenzenes. The p-isomer will predominate.

Explanation of Solution

The electrophile, (CH₃)₂CH⁺, attacks the aromatic ring in the first step to produce a resonance stabilized carbocation (sigma complex). In the second step the carbocation deprotonates to yield the product. For the ortho and para attacks, one of the the resonance structures has a positive charge on a carbon adjacent to the methyl group. This form is stabilized by electron release from the methyl group. Such stabilization is not possible for the meta attack. Hence a mixture of ortho-para products is produced in which the p-isomer predominates.

For ortho attack:

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 4

For para attack:

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 5

Conclusion

When toluene reacts with isopropyl chloride in the presence of AlCl₃ the products obtained are o- and p-isopropylbenzenes. The p-isomer will predominate.

Interpretation Introduction

c)

Interpretation:

The product of the reaction in which benzonitrile reacts with chlorine in the presence of FeCl₃ is to be predicted. The observed regiochemistry is to be explained by drawing the resonance structures of the intermediates.

Concept introduction:

The nitrile group is an electron withdrawing group. Hence in aromatic electrophilic substitution reactions the nitrile group will deactivate the ring and orient the electrophile to the meta position.

To predict:

The product of the reaction in which benzonitrile reacts with chlorine in the presence of FeCl₃.

To explain:

The observed regiochemistry by drawing the resonance structures of the intermediates.

Expert Solution

Answer to Problem 77AP

When benzonitrile reacts with chlorine in the presence of FeCl₃ meta chlorobenzonitrile will be produced.

Explanation of Solution

The electrophile, Cl⁺, attacks the aromatic ring in the first step to produce a resonance stabilized carbocation (sigma complex). In the second step the carbocation deprotonates to yield the product. For the meta attack the intermediate is more stabilized as shown.

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 7

For ortho and para attack one of the resonance forms will be unstable as there will be a positive charge on the carbon to which the nitrile group is attached.

Conclusion

When benzonitrile reacts with chlorine in the presence of FeCl₃ meta chlorobenzonitrile will be produced.

Interpretation Introduction

d)

Interpretation:

The product of the reaction in which methoxy benzene reacts with iodine in the presence of CuCl₂ is to be predicted. The observed regiochemistry is to be explained by drawing the resonance structures of the intermediates.

Concept introduction:

Methoxy group is an electron releasing group. Hence during aromatic electrophilic substitution reactions the methoxy group will activate the ring and orient the electrophile to the ortho and para positions.

To predict:

The product of the reaction in which benzene reacts with iodine in the presence of CuCl₂.

To explain:

The observed regiochemistry by drawing the resonance structures of the intermediates.

Expert Solution

Answer to Problem 77AP

When methoxybenzene reacts with iodine in the presence of CuCl₂, the products obtained are o- and p-iodobenzenes.

Explanation of Solution

Iodine itself is unreactive toward aromatic rings. CuCl₂ accelerate the iodination reaction by oxidizing iodine to a more powerful by electrophilic species that reacts like I⁺.

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 9

The electrophile, I⁺, attacks the aromatic ring in the first step to produce a resonance stabilized carbocation (sigma complex). In the second step the carbocation deprotonates to yield the product. For the ortho and para attacks, one of the the resonance structures has a positive charge on a carbon adjacent to the methoxy group. This form is stabilized by electron release from the methoxy group. Such stabilization is not possible for the meta attack. Hence a mixture of ortho-para products is produced.

Ortho attack:

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 10

Meta attack:

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 11

Conclusion

When methoxybenzene reacts with iodine in the presence of CuCl₂, the products obtained are o- and p-iodobenzenes.

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Answer 3

Question

Chapter 16.SE, Problem 77AP

Interpretation Introduction

a)

Interpretation:

The product of the reaction in which actophenone reacts with HNO₃ and H₂SO₄ is to be predicted. The observed regiochemistry is to be explained by drawing the resonance structures of the intermediates.

Concept introduction:

The carbonyl group is an electron withdrawing group. Hence in aromatic electrophilic substitution reactions, the keto group will deactivate the ring and orient the electrophile to the meta position.

To predict:

The product of the reaction in which actophenone reacts with HNO₃ and H₂SO₄.

To explain:

The observed regiochemistry by drawing the resonance structures of the intermediates.

Expert Solution

Answer to Problem 77AP

Actophenone reacts with HNO₃ and H₂SO₄ to produce m-nitroacetophenone.

Explanation of Solution

The electrophile, NO₂⁺, attacks the aromatic ring in the first step to produce a resonance stabilized carbocation (sigma complex). In the second step the carbocation deprotonates to yield the product. For the meta attack the intermediate is more stabilized as shown.

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 2

For ortho and para attack one of the resonance forms will be unstable as there will be a positive charge on the carbon to which the carbonyl group is attached.

Conclusion

Actophenone reacts with HNO₃ and H₂SO₄ to produce m-nitroacetophenone.

Interpretation Introduction

b)

Interpretation:

The product of the reaction in which toluene reacts with isopropyl chloride in the presence of AlCl₃ is to be predicted. The observed regiochemistry is to be explained by drawing the resonance structures of the intermediates.

Concept introduction:

Alkyl groups are an electron releasing groups. Hence during aromatic electrophilic substitution reactions the alkyl groups will activate the ring and orient the electrophile to the ortho and para positions.

To predict:

The product of the reaction in which toluene reacts with isopropyl chloride in the presence of AlCl₃.

To explain:

The observed regiochemistry by drawing the resonance structures of the intermediates.

Expert Solution

Answer to Problem 77AP

When toluene reacts with isopropyl chloride in the presence of AlCl₃ the products obtained are o- and p-isopropylbenzenes. The p-isomer will predominate.

Explanation of Solution

The electrophile, (CH₃)₂CH⁺, attacks the aromatic ring in the first step to produce a resonance stabilized carbocation (sigma complex). In the second step the carbocation deprotonates to yield the product. For the ortho and para attacks, one of the the resonance structures has a positive charge on a carbon adjacent to the methyl group. This form is stabilized by electron release from the methyl group. Such stabilization is not possible for the meta attack. Hence a mixture of ortho-para products is produced in which the p-isomer predominates.

For ortho attack:

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 4

For para attack:

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 5

Conclusion

When toluene reacts with isopropyl chloride in the presence of AlCl₃ the products obtained are o- and p-isopropylbenzenes. The p-isomer will predominate.

Interpretation Introduction

c)

Interpretation:

The product of the reaction in which benzonitrile reacts with chlorine in the presence of FeCl₃ is to be predicted. The observed regiochemistry is to be explained by drawing the resonance structures of the intermediates.

Concept introduction:

The nitrile group is an electron withdrawing group. Hence in aromatic electrophilic substitution reactions the nitrile group will deactivate the ring and orient the electrophile to the meta position.

To predict:

The product of the reaction in which benzonitrile reacts with chlorine in the presence of FeCl₃.

To explain:

The observed regiochemistry by drawing the resonance structures of the intermediates.

Expert Solution

Answer to Problem 77AP

When benzonitrile reacts with chlorine in the presence of FeCl₃ meta chlorobenzonitrile will be produced.

Explanation of Solution

The electrophile, Cl⁺, attacks the aromatic ring in the first step to produce a resonance stabilized carbocation (sigma complex). In the second step the carbocation deprotonates to yield the product. For the meta attack the intermediate is more stabilized as shown.

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 7

For ortho and para attack one of the resonance forms will be unstable as there will be a positive charge on the carbon to which the nitrile group is attached.

Conclusion

When benzonitrile reacts with chlorine in the presence of FeCl₃ meta chlorobenzonitrile will be produced.

Interpretation Introduction

d)

Interpretation:

The product of the reaction in which methoxy benzene reacts with iodine in the presence of CuCl₂ is to be predicted. The observed regiochemistry is to be explained by drawing the resonance structures of the intermediates.

Concept introduction:

Methoxy group is an electron releasing group. Hence during aromatic electrophilic substitution reactions the methoxy group will activate the ring and orient the electrophile to the ortho and para positions.

To predict:

The product of the reaction in which benzene reacts with iodine in the presence of CuCl₂.

To explain:

The observed regiochemistry by drawing the resonance structures of the intermediates.

Expert Solution

Answer to Problem 77AP

When methoxybenzene reacts with iodine in the presence of CuCl₂, the products obtained are o- and p-iodobenzenes.

Explanation of Solution

Iodine itself is unreactive toward aromatic rings. CuCl₂ accelerate the iodination reaction by oxidizing iodine to a more powerful by electrophilic species that reacts like I⁺.

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 9

The electrophile, I⁺, attacks the aromatic ring in the first step to produce a resonance stabilized carbocation (sigma complex). In the second step the carbocation deprotonates to yield the product. For the ortho and para attacks, one of the the resonance structures has a positive charge on a carbon adjacent to the methoxy group. This form is stabilized by electron release from the methoxy group. Such stabilization is not possible for the meta attack. Hence a mixture of ortho-para products is produced.

Ortho attack:

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 10

Meta attack:

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 11

Conclusion

When methoxybenzene reacts with iodine in the presence of CuCl₂, the products obtained are o- and p-iodobenzenes.

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Answer 4

Question

Chapter 16.SE, Problem 77AP

Interpretation Introduction

a)

Interpretation:

The product of the reaction in which actophenone reacts with HNO₃ and H₂SO₄ is to be predicted. The observed regiochemistry is to be explained by drawing the resonance structures of the intermediates.

Concept introduction:

The carbonyl group is an electron withdrawing group. Hence in aromatic electrophilic substitution reactions, the keto group will deactivate the ring and orient the electrophile to the meta position.

To predict:

The product of the reaction in which actophenone reacts with HNO₃ and H₂SO₄.

To explain:

The observed regiochemistry by drawing the resonance structures of the intermediates.

Expert Solution

Answer to Problem 77AP

Actophenone reacts with HNO₃ and H₂SO₄ to produce m-nitroacetophenone.

Explanation of Solution

The electrophile, NO₂⁺, attacks the aromatic ring in the first step to produce a resonance stabilized carbocation (sigma complex). In the second step the carbocation deprotonates to yield the product. For the meta attack the intermediate is more stabilized as shown.

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 2

For ortho and para attack one of the resonance forms will be unstable as there will be a positive charge on the carbon to which the carbonyl group is attached.

Conclusion

Actophenone reacts with HNO₃ and H₂SO₄ to produce m-nitroacetophenone.

Interpretation Introduction

b)

Interpretation:

The product of the reaction in which toluene reacts with isopropyl chloride in the presence of AlCl₃ is to be predicted. The observed regiochemistry is to be explained by drawing the resonance structures of the intermediates.

Concept introduction:

Alkyl groups are an electron releasing groups. Hence during aromatic electrophilic substitution reactions the alkyl groups will activate the ring and orient the electrophile to the ortho and para positions.

To predict:

The product of the reaction in which toluene reacts with isopropyl chloride in the presence of AlCl₃.

To explain:

The observed regiochemistry by drawing the resonance structures of the intermediates.

Expert Solution

Answer to Problem 77AP

When toluene reacts with isopropyl chloride in the presence of AlCl₃ the products obtained are o- and p-isopropylbenzenes. The p-isomer will predominate.

Explanation of Solution

The electrophile, (CH₃)₂CH⁺, attacks the aromatic ring in the first step to produce a resonance stabilized carbocation (sigma complex). In the second step the carbocation deprotonates to yield the product. For the ortho and para attacks, one of the the resonance structures has a positive charge on a carbon adjacent to the methyl group. This form is stabilized by electron release from the methyl group. Such stabilization is not possible for the meta attack. Hence a mixture of ortho-para products is produced in which the p-isomer predominates.

For ortho attack:

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 4

For para attack:

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 5

Conclusion

When toluene reacts with isopropyl chloride in the presence of AlCl₃ the products obtained are o- and p-isopropylbenzenes. The p-isomer will predominate.

Interpretation Introduction

c)

Interpretation:

The product of the reaction in which benzonitrile reacts with chlorine in the presence of FeCl₃ is to be predicted. The observed regiochemistry is to be explained by drawing the resonance structures of the intermediates.

Concept introduction:

The nitrile group is an electron withdrawing group. Hence in aromatic electrophilic substitution reactions the nitrile group will deactivate the ring and orient the electrophile to the meta position.

To predict:

The product of the reaction in which benzonitrile reacts with chlorine in the presence of FeCl₃.

To explain:

The observed regiochemistry by drawing the resonance structures of the intermediates.

Expert Solution

Answer to Problem 77AP

When benzonitrile reacts with chlorine in the presence of FeCl₃ meta chlorobenzonitrile will be produced.

Explanation of Solution

The electrophile, Cl⁺, attacks the aromatic ring in the first step to produce a resonance stabilized carbocation (sigma complex). In the second step the carbocation deprotonates to yield the product. For the meta attack the intermediate is more stabilized as shown.

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 7

For ortho and para attack one of the resonance forms will be unstable as there will be a positive charge on the carbon to which the nitrile group is attached.

Conclusion

When benzonitrile reacts with chlorine in the presence of FeCl₃ meta chlorobenzonitrile will be produced.

Interpretation Introduction

d)

Interpretation:

The product of the reaction in which methoxy benzene reacts with iodine in the presence of CuCl₂ is to be predicted. The observed regiochemistry is to be explained by drawing the resonance structures of the intermediates.

Concept introduction:

Methoxy group is an electron releasing group. Hence during aromatic electrophilic substitution reactions the methoxy group will activate the ring and orient the electrophile to the ortho and para positions.

To predict:

The product of the reaction in which benzene reacts with iodine in the presence of CuCl₂.

To explain:

The observed regiochemistry by drawing the resonance structures of the intermediates.

Expert Solution

Answer to Problem 77AP

When methoxybenzene reacts with iodine in the presence of CuCl₂, the products obtained are o- and p-iodobenzenes.

Explanation of Solution

Iodine itself is unreactive toward aromatic rings. CuCl₂ accelerate the iodination reaction by oxidizing iodine to a more powerful by electrophilic species that reacts like I⁺.

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 9

The electrophile, I⁺, attacks the aromatic ring in the first step to produce a resonance stabilized carbocation (sigma complex). In the second step the carbocation deprotonates to yield the product. For the ortho and para attacks, one of the the resonance structures has a positive charge on a carbon adjacent to the methoxy group. This form is stabilized by electron release from the methoxy group. Such stabilization is not possible for the meta attack. Hence a mixture of ortho-para products is produced.

Ortho attack:

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 10

Meta attack:

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 11

Conclusion

When methoxybenzene reacts with iodine in the presence of CuCl₂, the products obtained are o- and p-iodobenzenes.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!

Answer 5

Chapter 16.SE, Problem 77AP

Interpretation Introduction

a)

Interpretation:

The product of the reaction in which actophenone reacts with HNO₃ and H₂SO₄ is to be predicted. The observed regiochemistry is to be explained by drawing the resonance structures of the intermediates.

Concept introduction:

The carbonyl group is an electron withdrawing group. Hence in aromatic electrophilic substitution reactions, the keto group will deactivate the ring and orient the electrophile to the meta position.

To predict:

The product of the reaction in which actophenone reacts with HNO₃ and H₂SO₄.

To explain:

The observed regiochemistry by drawing the resonance structures of the intermediates.

Expert Solution

Answer to Problem 77AP

Actophenone reacts with HNO₃ and H₂SO₄ to produce m-nitroacetophenone.

Explanation of Solution

The electrophile, NO₂⁺, attacks the aromatic ring in the first step to produce a resonance stabilized carbocation (sigma complex). In the second step the carbocation deprotonates to yield the product. For the meta attack the intermediate is more stabilized as shown.

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 2

For ortho and para attack one of the resonance forms will be unstable as there will be a positive charge on the carbon to which the carbonyl group is attached.

Conclusion

Actophenone reacts with HNO₃ and H₂SO₄ to produce m-nitroacetophenone.

Interpretation Introduction

b)

Interpretation:

The product of the reaction in which toluene reacts with isopropyl chloride in the presence of AlCl₃ is to be predicted. The observed regiochemistry is to be explained by drawing the resonance structures of the intermediates.

Concept introduction:

Alkyl groups are an electron releasing groups. Hence during aromatic electrophilic substitution reactions the alkyl groups will activate the ring and orient the electrophile to the ortho and para positions.

To predict:

The product of the reaction in which toluene reacts with isopropyl chloride in the presence of AlCl₃.

To explain:

The observed regiochemistry by drawing the resonance structures of the intermediates.

Expert Solution

Answer to Problem 77AP

When toluene reacts with isopropyl chloride in the presence of AlCl₃ the products obtained are o- and p-isopropylbenzenes. The p-isomer will predominate.

Explanation of Solution

The electrophile, (CH₃)₂CH⁺, attacks the aromatic ring in the first step to produce a resonance stabilized carbocation (sigma complex). In the second step the carbocation deprotonates to yield the product. For the ortho and para attacks, one of the the resonance structures has a positive charge on a carbon adjacent to the methyl group. This form is stabilized by electron release from the methyl group. Such stabilization is not possible for the meta attack. Hence a mixture of ortho-para products is produced in which the p-isomer predominates.

For ortho attack:

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 4

For para attack:

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 5

Conclusion

When toluene reacts with isopropyl chloride in the presence of AlCl₃ the products obtained are o- and p-isopropylbenzenes. The p-isomer will predominate.

Interpretation Introduction

c)

Interpretation:

The product of the reaction in which benzonitrile reacts with chlorine in the presence of FeCl₃ is to be predicted. The observed regiochemistry is to be explained by drawing the resonance structures of the intermediates.

Concept introduction:

The nitrile group is an electron withdrawing group. Hence in aromatic electrophilic substitution reactions the nitrile group will deactivate the ring and orient the electrophile to the meta position.

To predict:

The product of the reaction in which benzonitrile reacts with chlorine in the presence of FeCl₃.

To explain:

The observed regiochemistry by drawing the resonance structures of the intermediates.

Expert Solution

Answer to Problem 77AP

When benzonitrile reacts with chlorine in the presence of FeCl₃ meta chlorobenzonitrile will be produced.

Explanation of Solution

The electrophile, Cl⁺, attacks the aromatic ring in the first step to produce a resonance stabilized carbocation (sigma complex). In the second step the carbocation deprotonates to yield the product. For the meta attack the intermediate is more stabilized as shown.

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 7

For ortho and para attack one of the resonance forms will be unstable as there will be a positive charge on the carbon to which the nitrile group is attached.

Conclusion

When benzonitrile reacts with chlorine in the presence of FeCl₃ meta chlorobenzonitrile will be produced.

Interpretation Introduction

d)

Interpretation:

The product of the reaction in which methoxy benzene reacts with iodine in the presence of CuCl₂ is to be predicted. The observed regiochemistry is to be explained by drawing the resonance structures of the intermediates.

Concept introduction:

Methoxy group is an electron releasing group. Hence during aromatic electrophilic substitution reactions the methoxy group will activate the ring and orient the electrophile to the ortho and para positions.

To predict:

The product of the reaction in which benzene reacts with iodine in the presence of CuCl₂.

To explain:

The observed regiochemistry by drawing the resonance structures of the intermediates.

Expert Solution

Answer to Problem 77AP

When methoxybenzene reacts with iodine in the presence of CuCl₂, the products obtained are o- and p-iodobenzenes.

Explanation of Solution

Iodine itself is unreactive toward aromatic rings. CuCl₂ accelerate the iodination reaction by oxidizing iodine to a more powerful by electrophilic species that reacts like I⁺.

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 9

The electrophile, I⁺, attacks the aromatic ring in the first step to produce a resonance stabilized carbocation (sigma complex). In the second step the carbocation deprotonates to yield the product. For the ortho and para attacks, one of the the resonance structures has a positive charge on a carbon adjacent to the methoxy group. This form is stabilized by electron release from the methoxy group. Such stabilization is not possible for the meta attack. Hence a mixture of ortho-para products is produced.

Ortho attack:

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 10

Meta attack:

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 11

Conclusion

When methoxybenzene reacts with iodine in the presence of CuCl₂, the products obtained are o- and p-iodobenzenes.

Answer 6

Chapter 16.SE, Problem 77AP

Interpretation Introduction

a)

Interpretation:

The product of the reaction in which actophenone reacts with HNO₃ and H₂SO₄ is to be predicted. The observed regiochemistry is to be explained by drawing the resonance structures of the intermediates.

Concept introduction:

The carbonyl group is an electron withdrawing group. Hence in aromatic electrophilic substitution reactions, the keto group will deactivate the ring and orient the electrophile to the meta position.

To predict:

The product of the reaction in which actophenone reacts with HNO₃ and H₂SO₄.

To explain:

The observed regiochemistry by drawing the resonance structures of the intermediates.

Expert Solution

Answer to Problem 77AP

Actophenone reacts with HNO₃ and H₂SO₄ to produce m-nitroacetophenone.

Explanation of Solution

The electrophile, NO₂⁺, attacks the aromatic ring in the first step to produce a resonance stabilized carbocation (sigma complex). In the second step the carbocation deprotonates to yield the product. For the meta attack the intermediate is more stabilized as shown.

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 2

For ortho and para attack one of the resonance forms will be unstable as there will be a positive charge on the carbon to which the carbonyl group is attached.

Conclusion

Actophenone reacts with HNO₃ and H₂SO₄ to produce m-nitroacetophenone.

Answer 7

Chapter 16.SE, Problem 77AP

Interpretation Introduction

a)

Interpretation:

The product of the reaction in which actophenone reacts with HNO₃ and H₂SO₄ is to be predicted. The observed regiochemistry is to be explained by drawing the resonance structures of the intermediates.

Concept introduction:

The carbonyl group is an electron withdrawing group. Hence in aromatic electrophilic substitution reactions, the keto group will deactivate the ring and orient the electrophile to the meta position.

To predict:

The product of the reaction in which actophenone reacts with HNO₃ and H₂SO₄.

To explain:

The observed regiochemistry by drawing the resonance structures of the intermediates.

Answer 8

Expert Solution

Answer to Problem 77AP

Actophenone reacts with HNO₃ and H₂SO₄ to produce m-nitroacetophenone.

Answer 9

Expert Solution

Answer 10

Expert Solution

Answer 11

Expert Solution

Answer 12

Explanation of Solution

The electrophile, NO₂⁺, attacks the aromatic ring in the first step to produce a resonance stabilized carbocation (sigma complex). In the second step the carbocation deprotonates to yield the product. For the meta attack the intermediate is more stabilized as shown.

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 2

For ortho and para attack one of the resonance forms will be unstable as there will be a positive charge on the carbon to which the carbonyl group is attached.

Answer 13

Conclusion

Actophenone reacts with HNO₃ and H₂SO₄ to produce m-nitroacetophenone.

Answer 14

Interpretation Introduction

b)

Interpretation:

The product of the reaction in which toluene reacts with isopropyl chloride in the presence of AlCl₃ is to be predicted. The observed regiochemistry is to be explained by drawing the resonance structures of the intermediates.

Concept introduction:

Alkyl groups are an electron releasing groups. Hence during aromatic electrophilic substitution reactions the alkyl groups will activate the ring and orient the electrophile to the ortho and para positions.

To predict:

The product of the reaction in which toluene reacts with isopropyl chloride in the presence of AlCl₃.

To explain:

The observed regiochemistry by drawing the resonance structures of the intermediates.

Expert Solution

Answer to Problem 77AP

When toluene reacts with isopropyl chloride in the presence of AlCl₃ the products obtained are o- and p-isopropylbenzenes. The p-isomer will predominate.

Explanation of Solution

The electrophile, (CH₃)₂CH⁺, attacks the aromatic ring in the first step to produce a resonance stabilized carbocation (sigma complex). In the second step the carbocation deprotonates to yield the product. For the ortho and para attacks, one of the the resonance structures has a positive charge on a carbon adjacent to the methyl group. This form is stabilized by electron release from the methyl group. Such stabilization is not possible for the meta attack. Hence a mixture of ortho-para products is produced in which the p-isomer predominates.

For ortho attack:

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 4

For para attack:

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 5

Conclusion

When toluene reacts with isopropyl chloride in the presence of AlCl₃ the products obtained are o- and p-isopropylbenzenes. The p-isomer will predominate.

Answer 15

Interpretation Introduction

b)

Interpretation:

The product of the reaction in which toluene reacts with isopropyl chloride in the presence of AlCl₃ is to be predicted. The observed regiochemistry is to be explained by drawing the resonance structures of the intermediates.

Concept introduction:

Alkyl groups are an electron releasing groups. Hence during aromatic electrophilic substitution reactions the alkyl groups will activate the ring and orient the electrophile to the ortho and para positions.

To predict:

The product of the reaction in which toluene reacts with isopropyl chloride in the presence of AlCl₃.

To explain:

The observed regiochemistry by drawing the resonance structures of the intermediates.

Answer 16

Expert Solution

Answer to Problem 77AP

When toluene reacts with isopropyl chloride in the presence of AlCl₃ the products obtained are o- and p-isopropylbenzenes. The p-isomer will predominate.

Answer 17

Expert Solution

Answer 18

Expert Solution

Answer 19

Expert Solution

Answer 20

Explanation of Solution

The electrophile, (CH₃)₂CH⁺, attacks the aromatic ring in the first step to produce a resonance stabilized carbocation (sigma complex). In the second step the carbocation deprotonates to yield the product. For the ortho and para attacks, one of the the resonance structures has a positive charge on a carbon adjacent to the methyl group. This form is stabilized by electron release from the methyl group. Such stabilization is not possible for the meta attack. Hence a mixture of ortho-para products is produced in which the p-isomer predominates.

For ortho attack:

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 4

For para attack:

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 5

Answer 21

Conclusion

When toluene reacts with isopropyl chloride in the presence of AlCl₃ the products obtained are o- and p-isopropylbenzenes. The p-isomer will predominate.

Answer 22

Interpretation Introduction

c)

Interpretation:

The product of the reaction in which benzonitrile reacts with chlorine in the presence of FeCl₃ is to be predicted. The observed regiochemistry is to be explained by drawing the resonance structures of the intermediates.

Concept introduction:

The nitrile group is an electron withdrawing group. Hence in aromatic electrophilic substitution reactions the nitrile group will deactivate the ring and orient the electrophile to the meta position.

To predict:

The product of the reaction in which benzonitrile reacts with chlorine in the presence of FeCl₃.

To explain:

The observed regiochemistry by drawing the resonance structures of the intermediates.

Expert Solution

Answer to Problem 77AP

When benzonitrile reacts with chlorine in the presence of FeCl₃ meta chlorobenzonitrile will be produced.

Explanation of Solution

The electrophile, Cl⁺, attacks the aromatic ring in the first step to produce a resonance stabilized carbocation (sigma complex). In the second step the carbocation deprotonates to yield the product. For the meta attack the intermediate is more stabilized as shown.

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 7

For ortho and para attack one of the resonance forms will be unstable as there will be a positive charge on the carbon to which the nitrile group is attached.

Conclusion

When benzonitrile reacts with chlorine in the presence of FeCl₃ meta chlorobenzonitrile will be produced.

Answer 23

Interpretation Introduction

c)

Interpretation:

The product of the reaction in which benzonitrile reacts with chlorine in the presence of FeCl₃ is to be predicted. The observed regiochemistry is to be explained by drawing the resonance structures of the intermediates.

Concept introduction:

The nitrile group is an electron withdrawing group. Hence in aromatic electrophilic substitution reactions the nitrile group will deactivate the ring and orient the electrophile to the meta position.

To predict:

The product of the reaction in which benzonitrile reacts with chlorine in the presence of FeCl₃.

To explain:

The observed regiochemistry by drawing the resonance structures of the intermediates.

Answer 24

Expert Solution

Answer to Problem 77AP

When benzonitrile reacts with chlorine in the presence of FeCl₃ meta chlorobenzonitrile will be produced.

Answer 25

Expert Solution

Answer 26

Expert Solution

Answer 27

Expert Solution

Answer 28

Explanation of Solution

The electrophile, Cl⁺, attacks the aromatic ring in the first step to produce a resonance stabilized carbocation (sigma complex). In the second step the carbocation deprotonates to yield the product. For the meta attack the intermediate is more stabilized as shown.

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 7

For ortho and para attack one of the resonance forms will be unstable as there will be a positive charge on the carbon to which the nitrile group is attached.

Answer 29

Conclusion

When benzonitrile reacts with chlorine in the presence of FeCl₃ meta chlorobenzonitrile will be produced.

Answer 30

Interpretation Introduction

d)

Interpretation:

The product of the reaction in which methoxy benzene reacts with iodine in the presence of CuCl₂ is to be predicted. The observed regiochemistry is to be explained by drawing the resonance structures of the intermediates.

Concept introduction:

Methoxy group is an electron releasing group. Hence during aromatic electrophilic substitution reactions the methoxy group will activate the ring and orient the electrophile to the ortho and para positions.

To predict:

The product of the reaction in which benzene reacts with iodine in the presence of CuCl₂.

To explain:

The observed regiochemistry by drawing the resonance structures of the intermediates.

Expert Solution

Answer to Problem 77AP

When methoxybenzene reacts with iodine in the presence of CuCl₂, the products obtained are o- and p-iodobenzenes.

Explanation of Solution

Iodine itself is unreactive toward aromatic rings. CuCl₂ accelerate the iodination reaction by oxidizing iodine to a more powerful by electrophilic species that reacts like I⁺.

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 9

The electrophile, I⁺, attacks the aromatic ring in the first step to produce a resonance stabilized carbocation (sigma complex). In the second step the carbocation deprotonates to yield the product. For the ortho and para attacks, one of the the resonance structures has a positive charge on a carbon adjacent to the methoxy group. This form is stabilized by electron release from the methoxy group. Such stabilization is not possible for the meta attack. Hence a mixture of ortho-para products is produced.

Ortho attack:

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 10

Meta attack:

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 11

Conclusion

When methoxybenzene reacts with iodine in the presence of CuCl₂, the products obtained are o- and p-iodobenzenes.

Answer 31

Interpretation Introduction

d)

Interpretation:

The product of the reaction in which methoxy benzene reacts with iodine in the presence of CuCl₂ is to be predicted. The observed regiochemistry is to be explained by drawing the resonance structures of the intermediates.

Concept introduction:

Methoxy group is an electron releasing group. Hence during aromatic electrophilic substitution reactions the methoxy group will activate the ring and orient the electrophile to the ortho and para positions.

To predict:

The product of the reaction in which benzene reacts with iodine in the presence of CuCl₂.

To explain:

The observed regiochemistry by drawing the resonance structures of the intermediates.

Answer 32

Expert Solution

Answer to Problem 77AP

When methoxybenzene reacts with iodine in the presence of CuCl₂, the products obtained are o- and p-iodobenzenes.

Answer 33

Expert Solution

Answer 34

Expert Solution

Answer 35

Expert Solution

Answer 36

Explanation of Solution

Iodine itself is unreactive toward aromatic rings. CuCl₂ accelerate the iodination reaction by oxidizing iodine to a more powerful by electrophilic species that reacts like I⁺.

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 9

The electrophile, I⁺, attacks the aromatic ring in the first step to produce a resonance stabilized carbocation (sigma complex). In the second step the carbocation deprotonates to yield the product. For the ortho and para attacks, one of the the resonance structures has a positive charge on a carbon adjacent to the methoxy group. This form is stabilized by electron release from the methoxy group. Such stabilization is not possible for the meta attack. Hence a mixture of ortho-para products is produced.

Ortho attack:

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 10

Meta attack:

Organic Chemistry - With Access (Custom), Chapter 16.SE, Problem 77AP , additional homework tip 11