a) Interpretation: The major product(s) obtainable from sulfonation of fluorobenzene is/are to be predicted. Concept introduction: Aromatic rings can be sulfonated by using fuming sulfuric acid, a mixture of H 2 SO 4 and SO 3 . The electrophile is either SO 3 H + or SO 3 depending on the reaction conditions. Sulfonation is a reversible process. Sulfonation is favored in strong acid, but desulfonation is favored in hot, dilute aqueous acid. The substituents attached to the ring have a strong influence on the incoming electrophile. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p- positions. Halogens are o- and p- directors but they deactivate the ring. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m- position. To predict: The major products obtainable from sulfonation of fluorobenzene.

Question

Want to see more full solutions like this?

Answer 1

Question

Chapter 16.SE, Problem 51AP

Interpretation Introduction

a)

Interpretation:

The major product(s) obtainable from sulfonation of fluorobenzene is/are to be predicted.

Concept introduction:

Aromatic rings can be sulfonated by using fuming sulfuric acid, a mixture of H₂SO₄ and SO₃. The electrophile is either SO₃H⁺ or SO₃ depending on the reaction conditions. Sulfonation is a reversible process. Sulfonation is favored in strong acid, but desulfonation is favored in hot, dilute aqueous acid.

The substituents attached to the ring have a strong influence on the incoming electrophile. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p- positions. Halogens are o- and p- directors but they deactivate the ring. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m- position.

To predict:

The major products obtainable from sulfonation of fluorobenzene.

Expert Solution

Answer to Problem 51AP

The major products obtainable from sulfonation of fluorobenzene are o-flurobenzenesulfonic acid and p- flurobenzenesulfonic acid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 2

Explanation of Solution

Fluorine attached to an aromatic ring is an o- and p- directing deactivating group. Hence it directs the electrophile, SO₃H⁺ to these positions.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 3

Conclusion

The major products obtainable from sulfonation of fluorobenzene are o-flurobenzenesulfonic acid and p- flurobenzenesulfonic acid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 4

Interpretation Introduction

b)

Interpretation:

The major product(s) obtainable from sulfonation of m-bromophenol is/are to be predicted.

Concept introduction:

Electrophilic substitution of disubstituted benzenes follows three simple rules. (i) If the directing influence of both the substituents reinforce each other, a single product results. (ii) If the directing influences of both the substituent groups oppose each other, the most powerful activating group among them has the dominant influence but usually a mixture of products results. (iii) In meta disubstituted compounds, further substitution in between the groups occurs only rarely, due to steric reasons.

To predict:

The major product(s) obtainable from sulfonation of m-bromophenol.

Expert Solution

Answer to Problem 51AP

The major products produced during the sulfonation of m-bromophenol are 2-bromo-4-hydroxybenzenesulfonicacid (I) and 4-bromo-2-hydroxybenzenesulfonicacid (II).

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 6

Explanation of Solution

The Br is an ortho and para directing and deactivating group while -OH group is also an ortho and para directing and highly activating group. Hence the -OH group decides the position at which the electrophilic substitution reaction will occur. The electrophile, SO₃H⁺, enters into the ortho and para positions with respect to -OH group to produce 2-bromo-4-hydroxybenzenesulfonicacid (I) and 4-bromo-2-hydroxybenzenesulfonicacid (II).

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 7

Conclusion

The major products produced during the sulfonation of m-bromophenol are 2-bromo-4-hydroxybenzenesulfonicacid (I) and 4-bromo-2-hydroxybenzenesulfonicacid (II).

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 8

Interpretation Introduction

c)

Interpretation:

The major product(s) obtainable from sulfonation of m-dichlorobenzene is/are to be predicted.

Concept introduction:

Electrophilic substitution of disubstituted benzenes follows three simple rules. (i) If the directing influence of both the substituents reinforce each other, a single product results. (ii) If the directing influences of both the substituent groups oppose each other, the most powerful activating group among them has the dominant influence but usually a mixture of products results. (iii) In meta disubstituted compounds, further substitution in between the groups occurs only rarely, due to steric reasons.

To predict:

The major product(s) obtainable from sulfonation of m-dichlorobenzene.

Expert Solution

Answer to Problem 51AP

The major product produced during the sulfonation of m-dichlorobenzene is 2,4-dichlorobenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 10

Explanation of Solution

In electrophilic substitution reactions, Cl is an ortho and para directing and deactivating group. Hence the electrophile, SO₃H⁺, can enter into the ortho and para positions with respect to both Cl atoms. The ortho position in between the two Cl atoms is not favored for steric reasons. Hence the SO₃H gets substituted in the p-position to a Cl which happens to be the ortho position to another Cl to yield 2,4-dichlorobenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 11

Conclusion

The major product produced during the sulfonation of m-dichlorobenzene is 2,4-dichlorobenzenesulfonicacid(I).

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 12

Interpretation Introduction

d)

Interpretation:

The major product(s) obtainable from sulfonation of 2,4-dibromophenol is/are to be predicted.

Concept introduction:

Electrophilic substitution of di and trisubstituted benzenes follows three simple rules. (i) If the directing influence of both the substituents reinforce each other, a single product results. (ii) If the directing influences of both the substituent groups oppose each other, the most powerful activating group among them has the dominant influence but usually a mixture of products results. (iii) In meta disubstituted compounds, further substitution in between the groups occurs only rarely, due to steric reasons.

To predict:

The major product(s) obtainable from sulfonation of 2,4-dibromophenol.

Expert Solution

Answer to Problem 51AP

The major product produced during the sulfonation of 2,4-dibromophenol is 3,5-dibromo-2-hydroxybenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 14

Explanation of Solution

In aromatic electrophilic substitution reactions Br is an ortho and para directing and deactivating group while –OH group also though ortho and para directing is a highly activating group. Hence the –OH group decides the position at which the electrophilic substitution reaction will occur. The electrophile, SO₃H⁺, enters into the ortho and para positions with respect to –OH group. The para position and one ortho position to –OH are blocked by substituents. Hence the SO₃H⁺ enters into the another ortho position to –OH group available to produce 3,5-dibromo-2-hydroxybenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 15

Conclusion

The major product produced during the sulfonation of 2,4-dibromophenol is 3,5-dibromo-2-hydroxybenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 16

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!

Students have asked these similar questions

(11pts total) Consider the arrows pointing at three different carbon-carbon bonds in the molecule depicted below. Bond B Bond A Bond C a. (2pts) Which bond between A-C is weakest? Which is strongest? Place answers in appropriate boxes. Weakest Bond Strongest Bond b. (4pts) Consider the relative stability of all cleavage products that form when bonds A, B, AND C are homolytically cleaved/broken. Hint: cleavage products of bonds A, B, and C are all carbon radicals. i. Which ONE cleavage product is the most stable? A condensed or bond line representation is fine. ii. Which ONE cleavage product is the least stable? A condensed or bond line representation is fine. c. (5pts) Use principles discussed in lecture, supported by relevant structures, to succinctly explain the why your part b (i) radical is more stable than your part b(ii) radical. Written explanation can be no more than one-two succinct sentence(s)!

. 3°C with TH 12. (10pts total) Provide the major product for each reaction depicted below. If no reaction occurs write NR. Assume heat dissipation is carefully controlled in the fluorine reaction. 3H 24 total (30) 24 21 2h • 6H total ● 8H total 34 래 Br2 hv major product will be most Substituted 12 hv Br NR I too weak of a participate in P-1 F₂ hv Statistically most favored product will be major = most subst = thermo favored hydrogen atom abstractor to LL F

Five chemistry project topic that does not involve practical

Answer 2

Question

Chapter 16.SE, Problem 51AP

Interpretation Introduction

a)

Interpretation:

The major product(s) obtainable from sulfonation of fluorobenzene is/are to be predicted.

Concept introduction:

Aromatic rings can be sulfonated by using fuming sulfuric acid, a mixture of H₂SO₄ and SO₃. The electrophile is either SO₃H⁺ or SO₃ depending on the reaction conditions. Sulfonation is a reversible process. Sulfonation is favored in strong acid, but desulfonation is favored in hot, dilute aqueous acid.

The substituents attached to the ring have a strong influence on the incoming electrophile. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p- positions. Halogens are o- and p- directors but they deactivate the ring. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m- position.

To predict:

The major products obtainable from sulfonation of fluorobenzene.

Expert Solution

Answer to Problem 51AP

The major products obtainable from sulfonation of fluorobenzene are o-flurobenzenesulfonic acid and p- flurobenzenesulfonic acid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 2

Explanation of Solution

Fluorine attached to an aromatic ring is an o- and p- directing deactivating group. Hence it directs the electrophile, SO₃H⁺ to these positions.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 3

Conclusion

The major products obtainable from sulfonation of fluorobenzene are o-flurobenzenesulfonic acid and p- flurobenzenesulfonic acid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 4

Interpretation Introduction

b)

Interpretation:

The major product(s) obtainable from sulfonation of m-bromophenol is/are to be predicted.

Concept introduction:

Electrophilic substitution of disubstituted benzenes follows three simple rules. (i) If the directing influence of both the substituents reinforce each other, a single product results. (ii) If the directing influences of both the substituent groups oppose each other, the most powerful activating group among them has the dominant influence but usually a mixture of products results. (iii) In meta disubstituted compounds, further substitution in between the groups occurs only rarely, due to steric reasons.

To predict:

The major product(s) obtainable from sulfonation of m-bromophenol.

Expert Solution

Answer to Problem 51AP

The major products produced during the sulfonation of m-bromophenol are 2-bromo-4-hydroxybenzenesulfonicacid (I) and 4-bromo-2-hydroxybenzenesulfonicacid (II).

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 6

Explanation of Solution

The Br is an ortho and para directing and deactivating group while -OH group is also an ortho and para directing and highly activating group. Hence the -OH group decides the position at which the electrophilic substitution reaction will occur. The electrophile, SO₃H⁺, enters into the ortho and para positions with respect to -OH group to produce 2-bromo-4-hydroxybenzenesulfonicacid (I) and 4-bromo-2-hydroxybenzenesulfonicacid (II).

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 7

Conclusion

The major products produced during the sulfonation of m-bromophenol are 2-bromo-4-hydroxybenzenesulfonicacid (I) and 4-bromo-2-hydroxybenzenesulfonicacid (II).

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 8

Interpretation Introduction

c)

Interpretation:

The major product(s) obtainable from sulfonation of m-dichlorobenzene is/are to be predicted.

Concept introduction:

Electrophilic substitution of disubstituted benzenes follows three simple rules. (i) If the directing influence of both the substituents reinforce each other, a single product results. (ii) If the directing influences of both the substituent groups oppose each other, the most powerful activating group among them has the dominant influence but usually a mixture of products results. (iii) In meta disubstituted compounds, further substitution in between the groups occurs only rarely, due to steric reasons.

To predict:

The major product(s) obtainable from sulfonation of m-dichlorobenzene.

Expert Solution

Answer to Problem 51AP

The major product produced during the sulfonation of m-dichlorobenzene is 2,4-dichlorobenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 10

Explanation of Solution

In electrophilic substitution reactions, Cl is an ortho and para directing and deactivating group. Hence the electrophile, SO₃H⁺, can enter into the ortho and para positions with respect to both Cl atoms. The ortho position in between the two Cl atoms is not favored for steric reasons. Hence the SO₃H gets substituted in the p-position to a Cl which happens to be the ortho position to another Cl to yield 2,4-dichlorobenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 11

Conclusion

The major product produced during the sulfonation of m-dichlorobenzene is 2,4-dichlorobenzenesulfonicacid(I).

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 12

Interpretation Introduction

d)

Interpretation:

The major product(s) obtainable from sulfonation of 2,4-dibromophenol is/are to be predicted.

Concept introduction:

Electrophilic substitution of di and trisubstituted benzenes follows three simple rules. (i) If the directing influence of both the substituents reinforce each other, a single product results. (ii) If the directing influences of both the substituent groups oppose each other, the most powerful activating group among them has the dominant influence but usually a mixture of products results. (iii) In meta disubstituted compounds, further substitution in between the groups occurs only rarely, due to steric reasons.

To predict:

The major product(s) obtainable from sulfonation of 2,4-dibromophenol.

Expert Solution

Answer to Problem 51AP

The major product produced during the sulfonation of 2,4-dibromophenol is 3,5-dibromo-2-hydroxybenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 14

Explanation of Solution

In aromatic electrophilic substitution reactions Br is an ortho and para directing and deactivating group while –OH group also though ortho and para directing is a highly activating group. Hence the –OH group decides the position at which the electrophilic substitution reaction will occur. The electrophile, SO₃H⁺, enters into the ortho and para positions with respect to –OH group. The para position and one ortho position to –OH are blocked by substituents. Hence the SO₃H⁺ enters into the another ortho position to –OH group available to produce 3,5-dibromo-2-hydroxybenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 15

Conclusion

The major product produced during the sulfonation of 2,4-dibromophenol is 3,5-dibromo-2-hydroxybenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 16

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 3

Question

Chapter 16.SE, Problem 51AP

Interpretation Introduction

a)

Interpretation:

The major product(s) obtainable from sulfonation of fluorobenzene is/are to be predicted.

Concept introduction:

Aromatic rings can be sulfonated by using fuming sulfuric acid, a mixture of H₂SO₄ and SO₃. The electrophile is either SO₃H⁺ or SO₃ depending on the reaction conditions. Sulfonation is a reversible process. Sulfonation is favored in strong acid, but desulfonation is favored in hot, dilute aqueous acid.

The substituents attached to the ring have a strong influence on the incoming electrophile. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p- positions. Halogens are o- and p- directors but they deactivate the ring. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m- position.

To predict:

The major products obtainable from sulfonation of fluorobenzene.

Expert Solution

Answer to Problem 51AP

The major products obtainable from sulfonation of fluorobenzene are o-flurobenzenesulfonic acid and p- flurobenzenesulfonic acid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 2

Explanation of Solution

Fluorine attached to an aromatic ring is an o- and p- directing deactivating group. Hence it directs the electrophile, SO₃H⁺ to these positions.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 3

Conclusion

The major products obtainable from sulfonation of fluorobenzene are o-flurobenzenesulfonic acid and p- flurobenzenesulfonic acid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 4

Interpretation Introduction

b)

Interpretation:

The major product(s) obtainable from sulfonation of m-bromophenol is/are to be predicted.

Concept introduction:

Electrophilic substitution of disubstituted benzenes follows three simple rules. (i) If the directing influence of both the substituents reinforce each other, a single product results. (ii) If the directing influences of both the substituent groups oppose each other, the most powerful activating group among them has the dominant influence but usually a mixture of products results. (iii) In meta disubstituted compounds, further substitution in between the groups occurs only rarely, due to steric reasons.

To predict:

The major product(s) obtainable from sulfonation of m-bromophenol.

Expert Solution

Answer to Problem 51AP

The major products produced during the sulfonation of m-bromophenol are 2-bromo-4-hydroxybenzenesulfonicacid (I) and 4-bromo-2-hydroxybenzenesulfonicacid (II).

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 6

Explanation of Solution

The Br is an ortho and para directing and deactivating group while -OH group is also an ortho and para directing and highly activating group. Hence the -OH group decides the position at which the electrophilic substitution reaction will occur. The electrophile, SO₃H⁺, enters into the ortho and para positions with respect to -OH group to produce 2-bromo-4-hydroxybenzenesulfonicacid (I) and 4-bromo-2-hydroxybenzenesulfonicacid (II).

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 7

Conclusion

The major products produced during the sulfonation of m-bromophenol are 2-bromo-4-hydroxybenzenesulfonicacid (I) and 4-bromo-2-hydroxybenzenesulfonicacid (II).

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 8

Interpretation Introduction

c)

Interpretation:

The major product(s) obtainable from sulfonation of m-dichlorobenzene is/are to be predicted.

Concept introduction:

Electrophilic substitution of disubstituted benzenes follows three simple rules. (i) If the directing influence of both the substituents reinforce each other, a single product results. (ii) If the directing influences of both the substituent groups oppose each other, the most powerful activating group among them has the dominant influence but usually a mixture of products results. (iii) In meta disubstituted compounds, further substitution in between the groups occurs only rarely, due to steric reasons.

To predict:

The major product(s) obtainable from sulfonation of m-dichlorobenzene.

Expert Solution

Answer to Problem 51AP

The major product produced during the sulfonation of m-dichlorobenzene is 2,4-dichlorobenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 10

Explanation of Solution

In electrophilic substitution reactions, Cl is an ortho and para directing and deactivating group. Hence the electrophile, SO₃H⁺, can enter into the ortho and para positions with respect to both Cl atoms. The ortho position in between the two Cl atoms is not favored for steric reasons. Hence the SO₃H gets substituted in the p-position to a Cl which happens to be the ortho position to another Cl to yield 2,4-dichlorobenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 11

Conclusion

The major product produced during the sulfonation of m-dichlorobenzene is 2,4-dichlorobenzenesulfonicacid(I).

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 12

Interpretation Introduction

d)

Interpretation:

The major product(s) obtainable from sulfonation of 2,4-dibromophenol is/are to be predicted.

Concept introduction:

Electrophilic substitution of di and trisubstituted benzenes follows three simple rules. (i) If the directing influence of both the substituents reinforce each other, a single product results. (ii) If the directing influences of both the substituent groups oppose each other, the most powerful activating group among them has the dominant influence but usually a mixture of products results. (iii) In meta disubstituted compounds, further substitution in between the groups occurs only rarely, due to steric reasons.

To predict:

The major product(s) obtainable from sulfonation of 2,4-dibromophenol.

Expert Solution

Answer to Problem 51AP

The major product produced during the sulfonation of 2,4-dibromophenol is 3,5-dibromo-2-hydroxybenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 14

Explanation of Solution

In aromatic electrophilic substitution reactions Br is an ortho and para directing and deactivating group while –OH group also though ortho and para directing is a highly activating group. Hence the –OH group decides the position at which the electrophilic substitution reaction will occur. The electrophile, SO₃H⁺, enters into the ortho and para positions with respect to –OH group. The para position and one ortho position to –OH are blocked by substituents. Hence the SO₃H⁺ enters into the another ortho position to –OH group available to produce 3,5-dibromo-2-hydroxybenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 15

Conclusion

The major product produced during the sulfonation of 2,4-dibromophenol is 3,5-dibromo-2-hydroxybenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 16

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 4

Question

Chapter 16.SE, Problem 51AP

Interpretation Introduction

a)

Interpretation:

The major product(s) obtainable from sulfonation of fluorobenzene is/are to be predicted.

Concept introduction:

Aromatic rings can be sulfonated by using fuming sulfuric acid, a mixture of H₂SO₄ and SO₃. The electrophile is either SO₃H⁺ or SO₃ depending on the reaction conditions. Sulfonation is a reversible process. Sulfonation is favored in strong acid, but desulfonation is favored in hot, dilute aqueous acid.

The substituents attached to the ring have a strong influence on the incoming electrophile. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p- positions. Halogens are o- and p- directors but they deactivate the ring. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m- position.

To predict:

The major products obtainable from sulfonation of fluorobenzene.

Expert Solution

Answer to Problem 51AP

The major products obtainable from sulfonation of fluorobenzene are o-flurobenzenesulfonic acid and p- flurobenzenesulfonic acid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 2

Explanation of Solution

Fluorine attached to an aromatic ring is an o- and p- directing deactivating group. Hence it directs the electrophile, SO₃H⁺ to these positions.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 3

Conclusion

The major products obtainable from sulfonation of fluorobenzene are o-flurobenzenesulfonic acid and p- flurobenzenesulfonic acid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 4

Interpretation Introduction

b)

Interpretation:

The major product(s) obtainable from sulfonation of m-bromophenol is/are to be predicted.

Concept introduction:

Electrophilic substitution of disubstituted benzenes follows three simple rules. (i) If the directing influence of both the substituents reinforce each other, a single product results. (ii) If the directing influences of both the substituent groups oppose each other, the most powerful activating group among them has the dominant influence but usually a mixture of products results. (iii) In meta disubstituted compounds, further substitution in between the groups occurs only rarely, due to steric reasons.

To predict:

The major product(s) obtainable from sulfonation of m-bromophenol.

Expert Solution

Answer to Problem 51AP

The major products produced during the sulfonation of m-bromophenol are 2-bromo-4-hydroxybenzenesulfonicacid (I) and 4-bromo-2-hydroxybenzenesulfonicacid (II).

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 6

Explanation of Solution

The Br is an ortho and para directing and deactivating group while -OH group is also an ortho and para directing and highly activating group. Hence the -OH group decides the position at which the electrophilic substitution reaction will occur. The electrophile, SO₃H⁺, enters into the ortho and para positions with respect to -OH group to produce 2-bromo-4-hydroxybenzenesulfonicacid (I) and 4-bromo-2-hydroxybenzenesulfonicacid (II).

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 7

Conclusion

The major products produced during the sulfonation of m-bromophenol are 2-bromo-4-hydroxybenzenesulfonicacid (I) and 4-bromo-2-hydroxybenzenesulfonicacid (II).

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 8

Interpretation Introduction

c)

Interpretation:

The major product(s) obtainable from sulfonation of m-dichlorobenzene is/are to be predicted.

Concept introduction:

Electrophilic substitution of disubstituted benzenes follows three simple rules. (i) If the directing influence of both the substituents reinforce each other, a single product results. (ii) If the directing influences of both the substituent groups oppose each other, the most powerful activating group among them has the dominant influence but usually a mixture of products results. (iii) In meta disubstituted compounds, further substitution in between the groups occurs only rarely, due to steric reasons.

To predict:

The major product(s) obtainable from sulfonation of m-dichlorobenzene.

Expert Solution

Answer to Problem 51AP

The major product produced during the sulfonation of m-dichlorobenzene is 2,4-dichlorobenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 10

Explanation of Solution

In electrophilic substitution reactions, Cl is an ortho and para directing and deactivating group. Hence the electrophile, SO₃H⁺, can enter into the ortho and para positions with respect to both Cl atoms. The ortho position in between the two Cl atoms is not favored for steric reasons. Hence the SO₃H gets substituted in the p-position to a Cl which happens to be the ortho position to another Cl to yield 2,4-dichlorobenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 11

Conclusion

The major product produced during the sulfonation of m-dichlorobenzene is 2,4-dichlorobenzenesulfonicacid(I).

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 12

Interpretation Introduction

d)

Interpretation:

The major product(s) obtainable from sulfonation of 2,4-dibromophenol is/are to be predicted.

Concept introduction:

Electrophilic substitution of di and trisubstituted benzenes follows three simple rules. (i) If the directing influence of both the substituents reinforce each other, a single product results. (ii) If the directing influences of both the substituent groups oppose each other, the most powerful activating group among them has the dominant influence but usually a mixture of products results. (iii) In meta disubstituted compounds, further substitution in between the groups occurs only rarely, due to steric reasons.

To predict:

The major product(s) obtainable from sulfonation of 2,4-dibromophenol.

Expert Solution

Answer to Problem 51AP

The major product produced during the sulfonation of 2,4-dibromophenol is 3,5-dibromo-2-hydroxybenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 14

Explanation of Solution

In aromatic electrophilic substitution reactions Br is an ortho and para directing and deactivating group while –OH group also though ortho and para directing is a highly activating group. Hence the –OH group decides the position at which the electrophilic substitution reaction will occur. The electrophile, SO₃H⁺, enters into the ortho and para positions with respect to –OH group. The para position and one ortho position to –OH are blocked by substituents. Hence the SO₃H⁺ enters into the another ortho position to –OH group available to produce 3,5-dibromo-2-hydroxybenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 15

Conclusion

The major product produced during the sulfonation of 2,4-dibromophenol is 3,5-dibromo-2-hydroxybenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 16

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 51AP

Interpretation Introduction

a)

Interpretation:

The major product(s) obtainable from sulfonation of fluorobenzene is/are to be predicted.

Concept introduction:

Aromatic rings can be sulfonated by using fuming sulfuric acid, a mixture of H₂SO₄ and SO₃. The electrophile is either SO₃H⁺ or SO₃ depending on the reaction conditions. Sulfonation is a reversible process. Sulfonation is favored in strong acid, but desulfonation is favored in hot, dilute aqueous acid.

The substituents attached to the ring have a strong influence on the incoming electrophile. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p- positions. Halogens are o- and p- directors but they deactivate the ring. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m- position.

To predict:

The major products obtainable from sulfonation of fluorobenzene.

Expert Solution

Answer to Problem 51AP

The major products obtainable from sulfonation of fluorobenzene are o-flurobenzenesulfonic acid and p- flurobenzenesulfonic acid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 2

Explanation of Solution

Fluorine attached to an aromatic ring is an o- and p- directing deactivating group. Hence it directs the electrophile, SO₃H⁺ to these positions.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 3

Conclusion

The major products obtainable from sulfonation of fluorobenzene are o-flurobenzenesulfonic acid and p- flurobenzenesulfonic acid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 4

Interpretation Introduction

b)

Interpretation:

The major product(s) obtainable from sulfonation of m-bromophenol is/are to be predicted.

Concept introduction:

Electrophilic substitution of disubstituted benzenes follows three simple rules. (i) If the directing influence of both the substituents reinforce each other, a single product results. (ii) If the directing influences of both the substituent groups oppose each other, the most powerful activating group among them has the dominant influence but usually a mixture of products results. (iii) In meta disubstituted compounds, further substitution in between the groups occurs only rarely, due to steric reasons.

To predict:

The major product(s) obtainable from sulfonation of m-bromophenol.

Expert Solution

Answer to Problem 51AP

The major products produced during the sulfonation of m-bromophenol are 2-bromo-4-hydroxybenzenesulfonicacid (I) and 4-bromo-2-hydroxybenzenesulfonicacid (II).

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 6

Explanation of Solution

The Br is an ortho and para directing and deactivating group while -OH group is also an ortho and para directing and highly activating group. Hence the -OH group decides the position at which the electrophilic substitution reaction will occur. The electrophile, SO₃H⁺, enters into the ortho and para positions with respect to -OH group to produce 2-bromo-4-hydroxybenzenesulfonicacid (I) and 4-bromo-2-hydroxybenzenesulfonicacid (II).

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 7

Conclusion

The major products produced during the sulfonation of m-bromophenol are 2-bromo-4-hydroxybenzenesulfonicacid (I) and 4-bromo-2-hydroxybenzenesulfonicacid (II).

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 8

Interpretation Introduction

c)

Interpretation:

The major product(s) obtainable from sulfonation of m-dichlorobenzene is/are to be predicted.

Concept introduction:

Electrophilic substitution of disubstituted benzenes follows three simple rules. (i) If the directing influence of both the substituents reinforce each other, a single product results. (ii) If the directing influences of both the substituent groups oppose each other, the most powerful activating group among them has the dominant influence but usually a mixture of products results. (iii) In meta disubstituted compounds, further substitution in between the groups occurs only rarely, due to steric reasons.

To predict:

The major product(s) obtainable from sulfonation of m-dichlorobenzene.

Expert Solution

Answer to Problem 51AP

The major product produced during the sulfonation of m-dichlorobenzene is 2,4-dichlorobenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 10

Explanation of Solution

In electrophilic substitution reactions, Cl is an ortho and para directing and deactivating group. Hence the electrophile, SO₃H⁺, can enter into the ortho and para positions with respect to both Cl atoms. The ortho position in between the two Cl atoms is not favored for steric reasons. Hence the SO₃H gets substituted in the p-position to a Cl which happens to be the ortho position to another Cl to yield 2,4-dichlorobenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 11

Conclusion

The major product produced during the sulfonation of m-dichlorobenzene is 2,4-dichlorobenzenesulfonicacid(I).

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 12

Interpretation Introduction

d)

Interpretation:

The major product(s) obtainable from sulfonation of 2,4-dibromophenol is/are to be predicted.

Concept introduction:

Electrophilic substitution of di and trisubstituted benzenes follows three simple rules. (i) If the directing influence of both the substituents reinforce each other, a single product results. (ii) If the directing influences of both the substituent groups oppose each other, the most powerful activating group among them has the dominant influence but usually a mixture of products results. (iii) In meta disubstituted compounds, further substitution in between the groups occurs only rarely, due to steric reasons.

To predict:

The major product(s) obtainable from sulfonation of 2,4-dibromophenol.

Expert Solution

Answer to Problem 51AP

The major product produced during the sulfonation of 2,4-dibromophenol is 3,5-dibromo-2-hydroxybenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 14

Explanation of Solution

In aromatic electrophilic substitution reactions Br is an ortho and para directing and deactivating group while –OH group also though ortho and para directing is a highly activating group. Hence the –OH group decides the position at which the electrophilic substitution reaction will occur. The electrophile, SO₃H⁺, enters into the ortho and para positions with respect to –OH group. The para position and one ortho position to –OH are blocked by substituents. Hence the SO₃H⁺ enters into the another ortho position to –OH group available to produce 3,5-dibromo-2-hydroxybenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 15

Conclusion

The major product produced during the sulfonation of 2,4-dibromophenol is 3,5-dibromo-2-hydroxybenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 16

Answer 6

Chapter 16.SE, Problem 51AP

Interpretation Introduction

a)

Interpretation:

The major product(s) obtainable from sulfonation of fluorobenzene is/are to be predicted.

Concept introduction:

Aromatic rings can be sulfonated by using fuming sulfuric acid, a mixture of H₂SO₄ and SO₃. The electrophile is either SO₃H⁺ or SO₃ depending on the reaction conditions. Sulfonation is a reversible process. Sulfonation is favored in strong acid, but desulfonation is favored in hot, dilute aqueous acid.

The substituents attached to the ring have a strong influence on the incoming electrophile. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p- positions. Halogens are o- and p- directors but they deactivate the ring. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m- position.

To predict:

The major products obtainable from sulfonation of fluorobenzene.

Expert Solution

Answer to Problem 51AP

The major products obtainable from sulfonation of fluorobenzene are o-flurobenzenesulfonic acid and p- flurobenzenesulfonic acid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 2

Explanation of Solution

Fluorine attached to an aromatic ring is an o- and p- directing deactivating group. Hence it directs the electrophile, SO₃H⁺ to these positions.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 3

Conclusion

The major products obtainable from sulfonation of fluorobenzene are o-flurobenzenesulfonic acid and p- flurobenzenesulfonic acid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 4

Answer 7

Chapter 16.SE, Problem 51AP

Interpretation Introduction

a)

Interpretation:

The major product(s) obtainable from sulfonation of fluorobenzene is/are to be predicted.

Concept introduction:

Aromatic rings can be sulfonated by using fuming sulfuric acid, a mixture of H₂SO₄ and SO₃. The electrophile is either SO₃H⁺ or SO₃ depending on the reaction conditions. Sulfonation is a reversible process. Sulfonation is favored in strong acid, but desulfonation is favored in hot, dilute aqueous acid.

The substituents attached to the ring have a strong influence on the incoming electrophile. Electron releasing substituent groups, except halogens, activate the ring and direct the incoming electrophile to the o- and p- positions. Halogens are o- and p- directors but they deactivate the ring. Electron withdrawing substituent groups deactivate the ring and direct the incoming electrophile to the m- position.

To predict:

The major products obtainable from sulfonation of fluorobenzene.

Answer 8

Expert Solution

Answer to Problem 51AP

The major products obtainable from sulfonation of fluorobenzene are o-flurobenzenesulfonic acid and p- flurobenzenesulfonic acid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 2

Answer 9

Expert Solution

Answer 10

Expert Solution

Answer 11

Expert Solution

Answer 12

Explanation of Solution

Fluorine attached to an aromatic ring is an o- and p- directing deactivating group. Hence it directs the electrophile, SO₃H⁺ to these positions.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 3

Answer 13

Conclusion

The major products obtainable from sulfonation of fluorobenzene are o-flurobenzenesulfonic acid and p- flurobenzenesulfonic acid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 4

Answer 14

Interpretation Introduction

b)

Interpretation:

The major product(s) obtainable from sulfonation of m-bromophenol is/are to be predicted.

Concept introduction:

Electrophilic substitution of disubstituted benzenes follows three simple rules. (i) If the directing influence of both the substituents reinforce each other, a single product results. (ii) If the directing influences of both the substituent groups oppose each other, the most powerful activating group among them has the dominant influence but usually a mixture of products results. (iii) In meta disubstituted compounds, further substitution in between the groups occurs only rarely, due to steric reasons.

To predict:

The major product(s) obtainable from sulfonation of m-bromophenol.

Expert Solution

Answer to Problem 51AP

The major products produced during the sulfonation of m-bromophenol are 2-bromo-4-hydroxybenzenesulfonicacid (I) and 4-bromo-2-hydroxybenzenesulfonicacid (II).

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 6

Explanation of Solution

The Br is an ortho and para directing and deactivating group while -OH group is also an ortho and para directing and highly activating group. Hence the -OH group decides the position at which the electrophilic substitution reaction will occur. The electrophile, SO₃H⁺, enters into the ortho and para positions with respect to -OH group to produce 2-bromo-4-hydroxybenzenesulfonicacid (I) and 4-bromo-2-hydroxybenzenesulfonicacid (II).

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 7

Conclusion

The major products produced during the sulfonation of m-bromophenol are 2-bromo-4-hydroxybenzenesulfonicacid (I) and 4-bromo-2-hydroxybenzenesulfonicacid (II).

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 8

Answer 15

Interpretation Introduction

b)

Interpretation:

The major product(s) obtainable from sulfonation of m-bromophenol is/are to be predicted.

Concept introduction:

Electrophilic substitution of disubstituted benzenes follows three simple rules. (i) If the directing influence of both the substituents reinforce each other, a single product results. (ii) If the directing influences of both the substituent groups oppose each other, the most powerful activating group among them has the dominant influence but usually a mixture of products results. (iii) In meta disubstituted compounds, further substitution in between the groups occurs only rarely, due to steric reasons.

To predict:

The major product(s) obtainable from sulfonation of m-bromophenol.

Answer 16

Expert Solution

Answer to Problem 51AP

The major products produced during the sulfonation of m-bromophenol are 2-bromo-4-hydroxybenzenesulfonicacid (I) and 4-bromo-2-hydroxybenzenesulfonicacid (II).

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 6

Answer 17

Expert Solution

Answer 18

Expert Solution

Answer 19

Expert Solution

Answer 20

Explanation of Solution

The Br is an ortho and para directing and deactivating group while -OH group is also an ortho and para directing and highly activating group. Hence the -OH group decides the position at which the electrophilic substitution reaction will occur. The electrophile, SO₃H⁺, enters into the ortho and para positions with respect to -OH group to produce 2-bromo-4-hydroxybenzenesulfonicacid (I) and 4-bromo-2-hydroxybenzenesulfonicacid (II).

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 7

Answer 21

Conclusion

The major products produced during the sulfonation of m-bromophenol are 2-bromo-4-hydroxybenzenesulfonicacid (I) and 4-bromo-2-hydroxybenzenesulfonicacid (II).

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 8

Answer 22

Interpretation Introduction

c)

Interpretation:

The major product(s) obtainable from sulfonation of m-dichlorobenzene is/are to be predicted.

Concept introduction:

Electrophilic substitution of disubstituted benzenes follows three simple rules. (i) If the directing influence of both the substituents reinforce each other, a single product results. (ii) If the directing influences of both the substituent groups oppose each other, the most powerful activating group among them has the dominant influence but usually a mixture of products results. (iii) In meta disubstituted compounds, further substitution in between the groups occurs only rarely, due to steric reasons.

To predict:

The major product(s) obtainable from sulfonation of m-dichlorobenzene.

Expert Solution

Answer to Problem 51AP

The major product produced during the sulfonation of m-dichlorobenzene is 2,4-dichlorobenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 10

Explanation of Solution

In electrophilic substitution reactions, Cl is an ortho and para directing and deactivating group. Hence the electrophile, SO₃H⁺, can enter into the ortho and para positions with respect to both Cl atoms. The ortho position in between the two Cl atoms is not favored for steric reasons. Hence the SO₃H gets substituted in the p-position to a Cl which happens to be the ortho position to another Cl to yield 2,4-dichlorobenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 11

Conclusion

The major product produced during the sulfonation of m-dichlorobenzene is 2,4-dichlorobenzenesulfonicacid(I).

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 12

Answer 23

Interpretation Introduction

c)

Interpretation:

The major product(s) obtainable from sulfonation of m-dichlorobenzene is/are to be predicted.

Concept introduction:

Electrophilic substitution of disubstituted benzenes follows three simple rules. (i) If the directing influence of both the substituents reinforce each other, a single product results. (ii) If the directing influences of both the substituent groups oppose each other, the most powerful activating group among them has the dominant influence but usually a mixture of products results. (iii) In meta disubstituted compounds, further substitution in between the groups occurs only rarely, due to steric reasons.

To predict:

The major product(s) obtainable from sulfonation of m-dichlorobenzene.

Answer 24

Expert Solution

Answer to Problem 51AP

The major product produced during the sulfonation of m-dichlorobenzene is 2,4-dichlorobenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 10

Answer 25

Expert Solution

Answer 26

Expert Solution

Answer 27

Expert Solution

Answer 28

Explanation of Solution

In electrophilic substitution reactions, Cl is an ortho and para directing and deactivating group. Hence the electrophile, SO₃H⁺, can enter into the ortho and para positions with respect to both Cl atoms. The ortho position in between the two Cl atoms is not favored for steric reasons. Hence the SO₃H gets substituted in the p-position to a Cl which happens to be the ortho position to another Cl to yield 2,4-dichlorobenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 11

Answer 29

Conclusion

The major product produced during the sulfonation of m-dichlorobenzene is 2,4-dichlorobenzenesulfonicacid(I).

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 12

Answer 30

Interpretation Introduction

d)

Interpretation:

The major product(s) obtainable from sulfonation of 2,4-dibromophenol is/are to be predicted.

Concept introduction:

Electrophilic substitution of di and trisubstituted benzenes follows three simple rules. (i) If the directing influence of both the substituents reinforce each other, a single product results. (ii) If the directing influences of both the substituent groups oppose each other, the most powerful activating group among them has the dominant influence but usually a mixture of products results. (iii) In meta disubstituted compounds, further substitution in between the groups occurs only rarely, due to steric reasons.

To predict:

The major product(s) obtainable from sulfonation of 2,4-dibromophenol.

Expert Solution

Answer to Problem 51AP

The major product produced during the sulfonation of 2,4-dibromophenol is 3,5-dibromo-2-hydroxybenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 14

Explanation of Solution

In aromatic electrophilic substitution reactions Br is an ortho and para directing and deactivating group while –OH group also though ortho and para directing is a highly activating group. Hence the –OH group decides the position at which the electrophilic substitution reaction will occur. The electrophile, SO₃H⁺, enters into the ortho and para positions with respect to –OH group. The para position and one ortho position to –OH are blocked by substituents. Hence the SO₃H⁺ enters into the another ortho position to –OH group available to produce 3,5-dibromo-2-hydroxybenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 15

Conclusion

The major product produced during the sulfonation of 2,4-dibromophenol is 3,5-dibromo-2-hydroxybenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 16

Answer 31

Interpretation Introduction

d)

Interpretation:

The major product(s) obtainable from sulfonation of 2,4-dibromophenol is/are to be predicted.

Concept introduction:

Electrophilic substitution of di and trisubstituted benzenes follows three simple rules. (i) If the directing influence of both the substituents reinforce each other, a single product results. (ii) If the directing influences of both the substituent groups oppose each other, the most powerful activating group among them has the dominant influence but usually a mixture of products results. (iii) In meta disubstituted compounds, further substitution in between the groups occurs only rarely, due to steric reasons.

To predict:

The major product(s) obtainable from sulfonation of 2,4-dibromophenol.

Answer 32

Expert Solution

Answer to Problem 51AP

The major product produced during the sulfonation of 2,4-dibromophenol is 3,5-dibromo-2-hydroxybenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 14

Answer 33

Expert Solution

Answer 34

Expert Solution

Answer 35

Expert Solution

Answer 36

Explanation of Solution

In aromatic electrophilic substitution reactions Br is an ortho and para directing and deactivating group while –OH group also though ortho and para directing is a highly activating group. Hence the –OH group decides the position at which the electrophilic substitution reaction will occur. The electrophile, SO₃H⁺, enters into the ortho and para positions with respect to –OH group. The para position and one ortho position to –OH are blocked by substituents. Hence the SO₃H⁺ enters into the another ortho position to –OH group available to produce 3,5-dibromo-2-hydroxybenzenesulfonicacid.

Organic Chemistry, Chapter 16.SE, Problem 51AP , additional homework tip 15