(a) Interpretation: The reason as to why electrophilic substitution occurs on the ring without N atom for quinoline, but occurs on the ring with the N atom in indole is to be stated. Concept introduction: The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

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Answer 1

Question

Chapter 18, Problem 18.79P

Interpretation Introduction

(a)

Interpretation: The reason as to why electrophilic substitution occurs on the ring without N atom for quinoline, but occurs on the ring with the N atom in indole is to be stated.

Concept introduction: The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

Interpretation Introduction

(b)

Interpretation: The reason as to why electrophilic substitution occurs more readily at C8 than C7 in quinoline is to be stated.

Concept introduction: The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

Interpretation Introduction

(c)

Interpretation: The reason as to why electrophilic substitution occurs more readily at C3 rather than C2 of indole is to be stated.

Concept introduction: The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

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Consider the tetracyclic aromatic compound drawn below, with rings labeled as A, B, C, and D. (a) Which of the four rings is most reactive in electrophilic aromatic substitution? (b) Which of the four rings is least reactive in electrophilic aromatic substitution? (c) What are the major product(s) formed when this compound is treated with one equivalent of Br2?

The bicyclic heterocycles quinoline and indole undergo electrophilic aromatic substitution to give the products shown.(a) Explain why electrophilic substitution occurs on the ring without theN atom for quinoline, but occurs on the ring with the N atom in indole. (b)Explain why electrophilic substitution occurs more readily at C8 than C7in quinoline. (c) Explain why electrophilic substitution occurs morereadily at C3 rather than C2 of indole.

Consider the tetracyclic compound with rings labeled A–D. (a) Which ring is the most reactive in electrophilic aromatic substitution? (b) Which ring is the least reactive in electrophilic aromatic substitution?

Answer 2

Question

Chapter 18, Problem 18.79P

Interpretation Introduction

(a)

Interpretation: The reason as to why electrophilic substitution occurs on the ring without N atom for quinoline, but occurs on the ring with the N atom in indole is to be stated.

Concept introduction: The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

Interpretation Introduction

(b)

Interpretation: The reason as to why electrophilic substitution occurs more readily at C8 than C7 in quinoline is to be stated.

Concept introduction: The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

Interpretation Introduction

(c)

Interpretation: The reason as to why electrophilic substitution occurs more readily at C3 rather than C2 of indole is to be stated.

Concept introduction: The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

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Answer 3

Question

Chapter 18, Problem 18.79P

Interpretation Introduction

(a)

Interpretation: The reason as to why electrophilic substitution occurs on the ring without N atom for quinoline, but occurs on the ring with the N atom in indole is to be stated.

Concept introduction: The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

Interpretation Introduction

(b)

Interpretation: The reason as to why electrophilic substitution occurs more readily at C8 than C7 in quinoline is to be stated.

Concept introduction: The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

Interpretation Introduction

(c)

Interpretation: The reason as to why electrophilic substitution occurs more readily at C3 rather than C2 of indole is to be stated.

Concept introduction: The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

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Answer 4

Question

Chapter 18, Problem 18.79P

Interpretation Introduction

(a)

Interpretation: The reason as to why electrophilic substitution occurs on the ring without N atom for quinoline, but occurs on the ring with the N atom in indole is to be stated.

Concept introduction: The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

Interpretation Introduction

(b)

Interpretation: The reason as to why electrophilic substitution occurs more readily at C8 than C7 in quinoline is to be stated.

Concept introduction: The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

Interpretation Introduction

(c)

Interpretation: The reason as to why electrophilic substitution occurs more readily at C3 rather than C2 of indole is to be stated.

Concept introduction: The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

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Answer 5

Chapter 18, Problem 18.79P

Interpretation Introduction

(a)

Interpretation: The reason as to why electrophilic substitution occurs on the ring without N atom for quinoline, but occurs on the ring with the N atom in indole is to be stated.

Concept introduction: The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

Interpretation Introduction

(b)

Interpretation: The reason as to why electrophilic substitution occurs more readily at C8 than C7 in quinoline is to be stated.

Concept introduction: The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

Interpretation Introduction

(c)

Interpretation: The reason as to why electrophilic substitution occurs more readily at C3 rather than C2 of indole is to be stated.

Concept introduction: The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

Answer 6

Chapter 18, Problem 18.79P

Interpretation Introduction

(a)

Interpretation: The reason as to why electrophilic substitution occurs on the ring without N atom for quinoline, but occurs on the ring with the N atom in indole is to be stated.

Concept introduction: The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

Answer 7

Chapter 18, Problem 18.79P

Interpretation Introduction

(a)

Interpretation: The reason as to why electrophilic substitution occurs on the ring without N atom for quinoline, but occurs on the ring with the N atom in indole is to be stated.

Concept introduction: The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

Answer 8

Interpretation Introduction

(b)

Interpretation: The reason as to why electrophilic substitution occurs more readily at C8 than C7 in quinoline is to be stated.

Concept introduction: The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

Answer 9

Interpretation Introduction

(b)

Interpretation: The reason as to why electrophilic substitution occurs more readily at C8 than C7 in quinoline is to be stated.

Concept introduction: The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

Answer 10

Interpretation Introduction

(c)

Interpretation: The reason as to why electrophilic substitution occurs more readily at C3 rather than C2 of indole is to be stated.

Concept introduction: The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

Answer 11

Interpretation Introduction

(c)

Interpretation: The reason as to why electrophilic substitution occurs more readily at C3 rather than C2 of indole is to be stated.

Concept introduction: The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

Answer 12

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Answer 14

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Answer 15

Ch. 18 - Prob. 18.1P Ch. 18 - Prob. 18.2P Ch. 18 - Prob. 18.3P Ch. 18 - Prob. 18.4P Ch. 18 - Prob. 18.5P Ch. 18 - What acid chloride would be needed to prepare each...Ch. 18 - Prob. 18.7P Ch. 18 - Draw a stepwise mechanism for the following...Ch. 18 - Prob. 18.9P Ch. 18 - Prob. 18.10P

Solution Summary: The author explains that electrophilic substitution occurs on the ring without N atom for quinoline, but occurs in the resonance. The electron rich species attack the species that is deficient in electron

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