a) Bromobenzene Interpretation: The major product(s) formed when bromobenzene is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated. Concept introduction: Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO 3 and H 2 SO 4 . Electron releasing substituent groups, excep halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituent groups are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituent groups are less reactive than benzene. To give: The major products formed when bromobenzene is nitrated and to state whether it will react faster or slower than benzene.

Question

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Answer 1

Question

Chapter 16.SE, Problem 47AP

Interpretation Introduction

a) Bromobenzene

Interpretation:

The major product(s) formed when bromobenzene is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, excep halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituent groups are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituent groups are less reactive than benzene.

To give:

The major products formed when bromobenzene is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major products formed when bromobenzene is nitrated are o-bromonitrobenzene and p-bromonitrobenzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 1

Bromobenzene will react slower than benzene.

Explanation of Solution

Bromine is an o- and p-directing group. It also has considerable electron withdrawing inductive effect which deactivates the ring. Hence bromobenzene is less reactive than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 2

Conclusion

The major products formed when bromobenzene is nitrated are o-bromonitrobenzene and p-bromonitrobenzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 3

Bromobenzene will react slower than benzene.

Interpretation Introduction

b) Benzonitrile

Interpretation:

The major product(s) formed when benzonitrile is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when benzonitrile is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major product formed when benzonitrile is nitrated is m-nitrobenzonitrile.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 4

Benzonitrile will react slower than benzene.

Explanation of Solution

The cyanide group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus benzonitrile reacts slower than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 5

Conclusion

The major product formed when benzonitrile is nitrated is m-nitrobenzonitrile.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 6

Benzonitrile will react slower than benzene.

Interpretation Introduction

c) Benzoic acid

Interpretation:

The major product(s) formed when benzoic acid is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when benzoic acid is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major product formed when benzoic acid is nitrated is m-nitrobenzoic acid.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 7

Benzoic acid will react slower than benzene.

Explanation of Solution

The C=O in carboxyl group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus benzoic acid reacts slower than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 8

Conclusion

The major product formed when benzoic acid is nitrated is m-nitrobenzoic acid.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 9

Benzoic acid will react slower than benzene.

Interpretation Introduction

d) Nitrobenzene

Interpretation:

The major product(s) formed when nitrobenzene is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when nitrobenzene is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major product formed when nitrobenzene is nitrated is m-dinitrobenzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 10

Nitrobenzene will react slower than benzene.

Explanation of Solution

The nitro group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus nitrobenzene reacts slower than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 11

Conclusion

The major product formed when nitrobenzene is nitrated is m-dinitrobenzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 12

Nitrobenzene will react slower than benzene.

Interpretation Introduction

e) Benzenesulfonic acid

Interpretation:

The major product(s) formed when benzenesulfonic acid is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when benzenesulfonic acid is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major product formed when benzenesulfonic acid is nitrated is m-nitro benzenesulfonic acid.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 13

Benzenesulfonic acid will react slower than benzene.

Explanation of Solution

The sulfonic acid group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus benzenesulfonic acid reacts slower than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 14

Conclusion

The major product formed when benzenesulfonic acid is nitrated is m-nitro benzenesulfonic acid.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 15

Benzenesulfonic acid will react slower than benzene.

Interpretation Introduction

f) Methoxybenzene

Interpretation:

The major product(s) formed when methoxybenzene is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when methoxybenzene is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major products formed when methoxybenzene is nitrated are o-nitromethoxybenene and p-nitromethoxybenene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 16

Methoxybenzene will react faster than benzene.

Explanation of Solution

The methoxy group is electron releasing in nature. Hence it is an o- and p-director. The attraction of electrons towards the ring increases the electron density in the ring. Thus methoxybenzene reacts faster than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 17

Conclusion

The major products formed when methoxybenzene is nitrated are o-nitromethoxybenene and p-nitromethoxybenene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 18

Methoxybenzene will react faster than benzene.

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Answer 2

Question

Chapter 16.SE, Problem 47AP

Interpretation Introduction

a) Bromobenzene

Interpretation:

The major product(s) formed when bromobenzene is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, excep halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituent groups are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituent groups are less reactive than benzene.

To give:

The major products formed when bromobenzene is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major products formed when bromobenzene is nitrated are o-bromonitrobenzene and p-bromonitrobenzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 1

Bromobenzene will react slower than benzene.

Explanation of Solution

Bromine is an o- and p-directing group. It also has considerable electron withdrawing inductive effect which deactivates the ring. Hence bromobenzene is less reactive than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 2

Conclusion

The major products formed when bromobenzene is nitrated are o-bromonitrobenzene and p-bromonitrobenzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 3

Bromobenzene will react slower than benzene.

Interpretation Introduction

b) Benzonitrile

Interpretation:

The major product(s) formed when benzonitrile is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when benzonitrile is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major product formed when benzonitrile is nitrated is m-nitrobenzonitrile.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 4

Benzonitrile will react slower than benzene.

Explanation of Solution

The cyanide group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus benzonitrile reacts slower than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 5

Conclusion

The major product formed when benzonitrile is nitrated is m-nitrobenzonitrile.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 6

Benzonitrile will react slower than benzene.

Interpretation Introduction

c) Benzoic acid

Interpretation:

The major product(s) formed when benzoic acid is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when benzoic acid is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major product formed when benzoic acid is nitrated is m-nitrobenzoic acid.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 7

Benzoic acid will react slower than benzene.

Explanation of Solution

The C=O in carboxyl group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus benzoic acid reacts slower than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 8

Conclusion

The major product formed when benzoic acid is nitrated is m-nitrobenzoic acid.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 9

Benzoic acid will react slower than benzene.

Interpretation Introduction

d) Nitrobenzene

Interpretation:

The major product(s) formed when nitrobenzene is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when nitrobenzene is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major product formed when nitrobenzene is nitrated is m-dinitrobenzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 10

Nitrobenzene will react slower than benzene.

Explanation of Solution

The nitro group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus nitrobenzene reacts slower than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 11

Conclusion

The major product formed when nitrobenzene is nitrated is m-dinitrobenzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 12

Nitrobenzene will react slower than benzene.

Interpretation Introduction

e) Benzenesulfonic acid

Interpretation:

The major product(s) formed when benzenesulfonic acid is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when benzenesulfonic acid is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major product formed when benzenesulfonic acid is nitrated is m-nitro benzenesulfonic acid.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 13

Benzenesulfonic acid will react slower than benzene.

Explanation of Solution

The sulfonic acid group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus benzenesulfonic acid reacts slower than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 14

Conclusion

The major product formed when benzenesulfonic acid is nitrated is m-nitro benzenesulfonic acid.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 15

Benzenesulfonic acid will react slower than benzene.

Interpretation Introduction

f) Methoxybenzene

Interpretation:

The major product(s) formed when methoxybenzene is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when methoxybenzene is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major products formed when methoxybenzene is nitrated are o-nitromethoxybenene and p-nitromethoxybenene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 16

Methoxybenzene will react faster than benzene.

Explanation of Solution

The methoxy group is electron releasing in nature. Hence it is an o- and p-director. The attraction of electrons towards the ring increases the electron density in the ring. Thus methoxybenzene reacts faster than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 17

Conclusion

The major products formed when methoxybenzene is nitrated are o-nitromethoxybenene and p-nitromethoxybenene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 18

Methoxybenzene will react faster than benzene.

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Answer 3

Question

Chapter 16.SE, Problem 47AP

Interpretation Introduction

a) Bromobenzene

Interpretation:

The major product(s) formed when bromobenzene is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, excep halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituent groups are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituent groups are less reactive than benzene.

To give:

The major products formed when bromobenzene is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major products formed when bromobenzene is nitrated are o-bromonitrobenzene and p-bromonitrobenzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 1

Bromobenzene will react slower than benzene.

Explanation of Solution

Bromine is an o- and p-directing group. It also has considerable electron withdrawing inductive effect which deactivates the ring. Hence bromobenzene is less reactive than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 2

Conclusion

The major products formed when bromobenzene is nitrated are o-bromonitrobenzene and p-bromonitrobenzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 3

Bromobenzene will react slower than benzene.

Interpretation Introduction

b) Benzonitrile

Interpretation:

The major product(s) formed when benzonitrile is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when benzonitrile is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major product formed when benzonitrile is nitrated is m-nitrobenzonitrile.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 4

Benzonitrile will react slower than benzene.

Explanation of Solution

The cyanide group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus benzonitrile reacts slower than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 5

Conclusion

The major product formed when benzonitrile is nitrated is m-nitrobenzonitrile.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 6

Benzonitrile will react slower than benzene.

Interpretation Introduction

c) Benzoic acid

Interpretation:

The major product(s) formed when benzoic acid is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when benzoic acid is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major product formed when benzoic acid is nitrated is m-nitrobenzoic acid.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 7

Benzoic acid will react slower than benzene.

Explanation of Solution

The C=O in carboxyl group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus benzoic acid reacts slower than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 8

Conclusion

The major product formed when benzoic acid is nitrated is m-nitrobenzoic acid.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 9

Benzoic acid will react slower than benzene.

Interpretation Introduction

d) Nitrobenzene

Interpretation:

The major product(s) formed when nitrobenzene is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when nitrobenzene is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major product formed when nitrobenzene is nitrated is m-dinitrobenzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 10

Nitrobenzene will react slower than benzene.

Explanation of Solution

The nitro group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus nitrobenzene reacts slower than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 11

Conclusion

The major product formed when nitrobenzene is nitrated is m-dinitrobenzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 12

Nitrobenzene will react slower than benzene.

Interpretation Introduction

e) Benzenesulfonic acid

Interpretation:

The major product(s) formed when benzenesulfonic acid is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when benzenesulfonic acid is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major product formed when benzenesulfonic acid is nitrated is m-nitro benzenesulfonic acid.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 13

Benzenesulfonic acid will react slower than benzene.

Explanation of Solution

The sulfonic acid group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus benzenesulfonic acid reacts slower than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 14

Conclusion

The major product formed when benzenesulfonic acid is nitrated is m-nitro benzenesulfonic acid.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 15

Benzenesulfonic acid will react slower than benzene.

Interpretation Introduction

f) Methoxybenzene

Interpretation:

The major product(s) formed when methoxybenzene is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when methoxybenzene is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major products formed when methoxybenzene is nitrated are o-nitromethoxybenene and p-nitromethoxybenene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 16

Methoxybenzene will react faster than benzene.

Explanation of Solution

The methoxy group is electron releasing in nature. Hence it is an o- and p-director. The attraction of electrons towards the ring increases the electron density in the ring. Thus methoxybenzene reacts faster than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 17

Conclusion

The major products formed when methoxybenzene is nitrated are o-nitromethoxybenene and p-nitromethoxybenene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 18

Methoxybenzene will react faster than benzene.

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Answer 4

Question

Chapter 16.SE, Problem 47AP

Interpretation Introduction

a) Bromobenzene

Interpretation:

The major product(s) formed when bromobenzene is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, excep halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituent groups are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituent groups are less reactive than benzene.

To give:

The major products formed when bromobenzene is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major products formed when bromobenzene is nitrated are o-bromonitrobenzene and p-bromonitrobenzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 1

Bromobenzene will react slower than benzene.

Explanation of Solution

Bromine is an o- and p-directing group. It also has considerable electron withdrawing inductive effect which deactivates the ring. Hence bromobenzene is less reactive than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 2

Conclusion

The major products formed when bromobenzene is nitrated are o-bromonitrobenzene and p-bromonitrobenzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 3

Bromobenzene will react slower than benzene.

Interpretation Introduction

b) Benzonitrile

Interpretation:

The major product(s) formed when benzonitrile is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when benzonitrile is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major product formed when benzonitrile is nitrated is m-nitrobenzonitrile.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 4

Benzonitrile will react slower than benzene.

Explanation of Solution

The cyanide group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus benzonitrile reacts slower than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 5

Conclusion

The major product formed when benzonitrile is nitrated is m-nitrobenzonitrile.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 6

Benzonitrile will react slower than benzene.

Interpretation Introduction

c) Benzoic acid

Interpretation:

The major product(s) formed when benzoic acid is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when benzoic acid is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major product formed when benzoic acid is nitrated is m-nitrobenzoic acid.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 7

Benzoic acid will react slower than benzene.

Explanation of Solution

The C=O in carboxyl group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus benzoic acid reacts slower than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 8

Conclusion

The major product formed when benzoic acid is nitrated is m-nitrobenzoic acid.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 9

Benzoic acid will react slower than benzene.

Interpretation Introduction

d) Nitrobenzene

Interpretation:

The major product(s) formed when nitrobenzene is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when nitrobenzene is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major product formed when nitrobenzene is nitrated is m-dinitrobenzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 10

Nitrobenzene will react slower than benzene.

Explanation of Solution

The nitro group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus nitrobenzene reacts slower than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 11

Conclusion

The major product formed when nitrobenzene is nitrated is m-dinitrobenzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 12

Nitrobenzene will react slower than benzene.

Interpretation Introduction

e) Benzenesulfonic acid

Interpretation:

The major product(s) formed when benzenesulfonic acid is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when benzenesulfonic acid is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major product formed when benzenesulfonic acid is nitrated is m-nitro benzenesulfonic acid.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 13

Benzenesulfonic acid will react slower than benzene.

Explanation of Solution

The sulfonic acid group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus benzenesulfonic acid reacts slower than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 14

Conclusion

The major product formed when benzenesulfonic acid is nitrated is m-nitro benzenesulfonic acid.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 15

Benzenesulfonic acid will react slower than benzene.

Interpretation Introduction

f) Methoxybenzene

Interpretation:

The major product(s) formed when methoxybenzene is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when methoxybenzene is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major products formed when methoxybenzene is nitrated are o-nitromethoxybenene and p-nitromethoxybenene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 16

Methoxybenzene will react faster than benzene.

Explanation of Solution

The methoxy group is electron releasing in nature. Hence it is an o- and p-director. The attraction of electrons towards the ring increases the electron density in the ring. Thus methoxybenzene reacts faster than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 17

Conclusion

The major products formed when methoxybenzene is nitrated are o-nitromethoxybenene and p-nitromethoxybenene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 18

Methoxybenzene will react faster than benzene.

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Answer 5

Chapter 16.SE, Problem 47AP

Interpretation Introduction

a) Bromobenzene

Interpretation:

The major product(s) formed when bromobenzene is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, excep halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituent groups are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituent groups are less reactive than benzene.

To give:

The major products formed when bromobenzene is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major products formed when bromobenzene is nitrated are o-bromonitrobenzene and p-bromonitrobenzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 1

Bromobenzene will react slower than benzene.

Explanation of Solution

Bromine is an o- and p-directing group. It also has considerable electron withdrawing inductive effect which deactivates the ring. Hence bromobenzene is less reactive than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 2

Conclusion

The major products formed when bromobenzene is nitrated are o-bromonitrobenzene and p-bromonitrobenzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 3

Bromobenzene will react slower than benzene.

Interpretation Introduction

b) Benzonitrile

Interpretation:

The major product(s) formed when benzonitrile is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when benzonitrile is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major product formed when benzonitrile is nitrated is m-nitrobenzonitrile.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 4

Benzonitrile will react slower than benzene.

Explanation of Solution

The cyanide group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus benzonitrile reacts slower than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 5

Conclusion

The major product formed when benzonitrile is nitrated is m-nitrobenzonitrile.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 6

Benzonitrile will react slower than benzene.

Interpretation Introduction

c) Benzoic acid

Interpretation:

The major product(s) formed when benzoic acid is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when benzoic acid is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major product formed when benzoic acid is nitrated is m-nitrobenzoic acid.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 7

Benzoic acid will react slower than benzene.

Explanation of Solution

The C=O in carboxyl group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus benzoic acid reacts slower than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 8

Conclusion

The major product formed when benzoic acid is nitrated is m-nitrobenzoic acid.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 9

Benzoic acid will react slower than benzene.

Interpretation Introduction

d) Nitrobenzene

Interpretation:

The major product(s) formed when nitrobenzene is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when nitrobenzene is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major product formed when nitrobenzene is nitrated is m-dinitrobenzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 10

Nitrobenzene will react slower than benzene.

Explanation of Solution

The nitro group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus nitrobenzene reacts slower than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 11

Conclusion

The major product formed when nitrobenzene is nitrated is m-dinitrobenzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 12

Nitrobenzene will react slower than benzene.

Interpretation Introduction

e) Benzenesulfonic acid

Interpretation:

The major product(s) formed when benzenesulfonic acid is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when benzenesulfonic acid is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major product formed when benzenesulfonic acid is nitrated is m-nitro benzenesulfonic acid.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 13

Benzenesulfonic acid will react slower than benzene.

Explanation of Solution

The sulfonic acid group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus benzenesulfonic acid reacts slower than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 14

Conclusion

The major product formed when benzenesulfonic acid is nitrated is m-nitro benzenesulfonic acid.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 15

Benzenesulfonic acid will react slower than benzene.

Interpretation Introduction

f) Methoxybenzene

Interpretation:

The major product(s) formed when methoxybenzene is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when methoxybenzene is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major products formed when methoxybenzene is nitrated are o-nitromethoxybenene and p-nitromethoxybenene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 16

Methoxybenzene will react faster than benzene.

Explanation of Solution

The methoxy group is electron releasing in nature. Hence it is an o- and p-director. The attraction of electrons towards the ring increases the electron density in the ring. Thus methoxybenzene reacts faster than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 17

Conclusion

The major products formed when methoxybenzene is nitrated are o-nitromethoxybenene and p-nitromethoxybenene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 18

Methoxybenzene will react faster than benzene.

Answer 6

Chapter 16.SE, Problem 47AP

Interpretation Introduction

a) Bromobenzene

Interpretation:

The major product(s) formed when bromobenzene is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, excep halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituent groups are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituent groups are less reactive than benzene.

To give:

The major products formed when bromobenzene is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major products formed when bromobenzene is nitrated are o-bromonitrobenzene and p-bromonitrobenzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 1

Bromobenzene will react slower than benzene.

Explanation of Solution

Bromine is an o- and p-directing group. It also has considerable electron withdrawing inductive effect which deactivates the ring. Hence bromobenzene is less reactive than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 2

Conclusion

The major products formed when bromobenzene is nitrated are o-bromonitrobenzene and p-bromonitrobenzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 3

Bromobenzene will react slower than benzene.

Answer 7

Chapter 16.SE, Problem 47AP

Interpretation Introduction

a) Bromobenzene

Interpretation:

The major product(s) formed when bromobenzene is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, excep halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituent groups are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituent groups are less reactive than benzene.

To give:

The major products formed when bromobenzene is nitrated and to state whether it will react faster or slower than benzene.

Answer 8

Expert Solution

Answer to Problem 47AP

The major products formed when bromobenzene is nitrated are o-bromonitrobenzene and p-bromonitrobenzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 1

Bromobenzene will react slower than benzene.

Answer 9

Expert Solution

Answer 10

Expert Solution

Answer 11

Expert Solution

Answer 12

Explanation of Solution

Bromine is an o- and p-directing group. It also has considerable electron withdrawing inductive effect which deactivates the ring. Hence bromobenzene is less reactive than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 2

Answer 13

Conclusion

The major products formed when bromobenzene is nitrated are o-bromonitrobenzene and p-bromonitrobenzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 3

Bromobenzene will react slower than benzene.

Answer 14

Interpretation Introduction

b) Benzonitrile

Interpretation:

The major product(s) formed when benzonitrile is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when benzonitrile is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major product formed when benzonitrile is nitrated is m-nitrobenzonitrile.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 4

Benzonitrile will react slower than benzene.

Explanation of Solution

The cyanide group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus benzonitrile reacts slower than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 5

Conclusion

The major product formed when benzonitrile is nitrated is m-nitrobenzonitrile.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 6

Benzonitrile will react slower than benzene.

Answer 15

Interpretation Introduction

b) Benzonitrile

Interpretation:

The major product(s) formed when benzonitrile is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when benzonitrile is nitrated and to state whether it will react faster or slower than benzene.

Answer 16

Expert Solution

Answer to Problem 47AP

The major product formed when benzonitrile is nitrated is m-nitrobenzonitrile.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 4

Benzonitrile will react slower than benzene.

Answer 17

Expert Solution

Answer 18

Expert Solution

Answer 19

Expert Solution

Answer 20

Explanation of Solution

The cyanide group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus benzonitrile reacts slower than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 5

Answer 21

Conclusion

The major product formed when benzonitrile is nitrated is m-nitrobenzonitrile.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 6

Benzonitrile will react slower than benzene.

Answer 22

Interpretation Introduction

c) Benzoic acid

Interpretation:

The major product(s) formed when benzoic acid is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when benzoic acid is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major product formed when benzoic acid is nitrated is m-nitrobenzoic acid.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 7

Benzoic acid will react slower than benzene.

Explanation of Solution

The C=O in carboxyl group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus benzoic acid reacts slower than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 8

Conclusion

The major product formed when benzoic acid is nitrated is m-nitrobenzoic acid.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 9

Benzoic acid will react slower than benzene.

Answer 23

Interpretation Introduction

c) Benzoic acid

Interpretation:

The major product(s) formed when benzoic acid is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when benzoic acid is nitrated and to state whether it will react faster or slower than benzene.

Answer 24

Expert Solution

Answer to Problem 47AP

The major product formed when benzoic acid is nitrated is m-nitrobenzoic acid.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 7

Benzoic acid will react slower than benzene.

Answer 25

Expert Solution

Answer 26

Expert Solution

Answer 27

Expert Solution

Answer 28

Explanation of Solution

The C=O in carboxyl group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus benzoic acid reacts slower than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 8

Answer 29

Conclusion

The major product formed when benzoic acid is nitrated is m-nitrobenzoic acid.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 9

Benzoic acid will react slower than benzene.

Answer 30

Interpretation Introduction

d) Nitrobenzene

Interpretation:

The major product(s) formed when nitrobenzene is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when nitrobenzene is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major product formed when nitrobenzene is nitrated is m-dinitrobenzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 10

Nitrobenzene will react slower than benzene.

Explanation of Solution

The nitro group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus nitrobenzene reacts slower than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 11

Conclusion

The major product formed when nitrobenzene is nitrated is m-dinitrobenzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 12

Nitrobenzene will react slower than benzene.

Answer 31

Interpretation Introduction

d) Nitrobenzene

Interpretation:

The major product(s) formed when nitrobenzene is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when nitrobenzene is nitrated and to state whether it will react faster or slower than benzene.

Answer 32

Expert Solution

Answer to Problem 47AP

The major product formed when nitrobenzene is nitrated is m-dinitrobenzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 10

Nitrobenzene will react slower than benzene.

Answer 33

Expert Solution

Answer 34

Expert Solution

Answer 35

Expert Solution

Answer 36

Explanation of Solution

The nitro group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus nitrobenzene reacts slower than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 11

Answer 37

Conclusion

The major product formed when nitrobenzene is nitrated is m-dinitrobenzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 12

Nitrobenzene will react slower than benzene.

Answer 38

Interpretation Introduction

e) Benzenesulfonic acid

Interpretation:

The major product(s) formed when benzenesulfonic acid is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when benzenesulfonic acid is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major product formed when benzenesulfonic acid is nitrated is m-nitro benzenesulfonic acid.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 13

Benzenesulfonic acid will react slower than benzene.

Explanation of Solution

The sulfonic acid group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus benzenesulfonic acid reacts slower than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 14

Conclusion

The major product formed when benzenesulfonic acid is nitrated is m-nitro benzenesulfonic acid.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 15

Benzenesulfonic acid will react slower than benzene.

Answer 39

Interpretation Introduction

e) Benzenesulfonic acid

Interpretation:

The major product(s) formed when benzenesulfonic acid is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when benzenesulfonic acid is nitrated and to state whether it will react faster or slower than benzene.

Answer 40

Expert Solution

Answer to Problem 47AP

The major product formed when benzenesulfonic acid is nitrated is m-nitro benzenesulfonic acid.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 13

Benzenesulfonic acid will react slower than benzene.

Answer 41

Expert Solution

Answer 42

Expert Solution

Answer 43

Expert Solution

Answer 44

Explanation of Solution

The sulfonic acid group is strongly electron withdrawing in nature. Hence it is a meta director. The attraction of electrons away from the ring reduces the electron density in the ring. Thus benzenesulfonic acid reacts slower than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 14

Answer 45

Conclusion

The major product formed when benzenesulfonic acid is nitrated is m-nitro benzenesulfonic acid.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 15

Benzenesulfonic acid will react slower than benzene.

Answer 46

Interpretation Introduction

f) Methoxybenzene

Interpretation:

The major product(s) formed when methoxybenzene is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when methoxybenzene is nitrated and to state whether it will react faster or slower than benzene.

Expert Solution

Answer to Problem 47AP

The major products formed when methoxybenzene is nitrated are o-nitromethoxybenene and p-nitromethoxybenene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 16

Methoxybenzene will react faster than benzene.

Explanation of Solution

The methoxy group is electron releasing in nature. Hence it is an o- and p-director. The attraction of electrons towards the ring increases the electron density in the ring. Thus methoxybenzene reacts faster than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 17

Conclusion

The major products formed when methoxybenzene is nitrated are o-nitromethoxybenene and p-nitromethoxybenene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 18

Methoxybenzene will react faster than benzene.

Answer 47

Interpretation Introduction

f) Methoxybenzene

Interpretation:

The major product(s) formed when methoxybenzene is nitrated is to be given. Whether it will react faster or slower than benzene is also to be stated.

Concept introduction:

Monosubstituted benzenes can be nitrated using a mixture of Conc. HNO₃ and H₂SO₄. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p-positions. Compounds with these substituents are more reactive than benzene. Halogens are o- and p-directors but they deactivate the ring. Hence halobenzenes are less reactive than benzene. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m-position. Compounds with these substituents are less reactive than benzene.

To give:

The major products formed when methoxybenzene is nitrated and to state whether it will react faster or slower than benzene.

Answer 48

Expert Solution

Answer to Problem 47AP

The major products formed when methoxybenzene is nitrated are o-nitromethoxybenene and p-nitromethoxybenene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 16

Methoxybenzene will react faster than benzene.

Answer 49

Expert Solution

Answer 50

Expert Solution

Answer 51

Expert Solution

Answer 52

Explanation of Solution

The methoxy group is electron releasing in nature. Hence it is an o- and p-director. The attraction of electrons towards the ring increases the electron density in the ring. Thus methoxybenzene reacts faster than benzene.

Organic Chemistry, Chapter 16.SE, Problem 47AP , additional homework tip 17