(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 18.78P

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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Q5: Label each chiral carbon in the following molecules as R or S. Make sure the stereocenter to which each of your R/S assignments belong is perfectly clear to the grader. (8pts) R OCH 3 CI H S 2pts for each R/S HO R H !!! I OH CI HN CI R H

Calculate the proton and carbon chemical shifts for this structure

A. B. b. Now consider the two bicyclic molecules A. and B. Note that A. is a dianion and B. is a neutral molecule. One of these molecules is a highly reactive compound first characterized in frozen noble gas matrices, that self-reacts rapidly at temperatures above liquid nitrogen temperature. The other compound was isolated at room temperature in the early 1960s, and is a stable ligand used in organometallic chemistry. Which molecule is the more stable molecule, and why?

Answer 2

Question

Chapter 18, Problem 18.78P

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 18.78P

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 18.78P

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 18.78P

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 18.78P

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 18.78P

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 - Prob. 18.6P Ch. 18 - Prob. 18.7P Ch. 18 - Prob. 18.8P Ch. 18 - Problem 18.9 Draw the product of each reaction a....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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Chapter 18 Solutions