(a) Interpretation: How to synthesize the given compound using only a single nucleophilic aromatic substitution reaction is to be shown. Concept introduction: In a nucleophilic aromatic substitution reaction, the aromatic ring is attacked by a nucleophile. If these reactions are precedes though the benzyne intermediate formation, requires very extreme conditions like high temperature, a very strong base, or sometimes both. Since the benzyne intermediate is very highly unstable, undergoes a nucleophilic addition reaction with a nucleophile. If multiple substituents are attached to a phenyl ring, their activating/deactivating qualities govern mechanism of the reaction. The substituent ring with deactivating group precedes the reaction through benzyne intermediate formation. Methyl groups deactivate the ring towards nucleophilic addition reaction.

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Answer 1

Question

Chapter 23, Problem 23.79P

Interpretation Introduction

(a)

Interpretation:

How to synthesize the given compound using only a single nucleophilic aromatic substitution reaction is to be shown.

Concept introduction:

In a nucleophilic aromatic substitution reaction, the aromatic ring is attacked by a nucleophile. If these reactions are precedes though the benzyne intermediate formation, requires very extreme conditions like high temperature, a very strong base, or sometimes both. Since the benzyne intermediate is very highly unstable, undergoes a nucleophilic addition reaction with a nucleophile. If multiple substituents are attached to a phenyl ring, their activating/deactivating qualities govern mechanism of the reaction. The substituent ring with deactivating group precedes the reaction through benzyne intermediate formation. Methyl groups deactivate the ring towards nucleophilic addition reaction.

Interpretation Introduction

(b)

Interpretation:

How to synthesize the given compound using only a single nucleophilic aromatic substitution reaction is to be shown.

Concept introduction:

In a nucleophilic aromatic substitution reaction, the aromatic ring is attacked by a nucleophile. If these reactions are precedes though the benzyne intermediate formation, requires very extreme conditions like high temperature, a very strong base, or sometimes both. Since the benzyne intermediate is very highly unstable, undergoes a nucleophilic addition reaction with a nucleophile. If multiple substituents are attached to a phenyl ring, their activating/deactivating qualities govern the mechanism of the reaction. The substituent ring with a deactivating group precedes the reaction through benzyne intermediate formation.

Interpretation Introduction

(c)

Interpretation:

How to synthesize the given compound using only a single nucleophilic aromatic substitution reaction is to be shown.

Concept introduction:

In a nucleophilic aromatic substitution reaction, the aromatic ring is attacked by a nucleophile. If these reactions are precedes though the benzyne intermediate formation, requires very extreme conditions like high temperature, a very strong base, or sometimes both. Since the benzyne intermediate is very highly unstable, undergoes a nucleophilic addition reaction with a nucleophile. If multiple substituents are attached to a phenyl ring, their activating/deactivating qualities govern the mechanism of the reaction. The substituent ring with a deactivating group precedes the reaction through benzyne intermediate formation.

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Name the molecules & Identify any chiral center CH3CH2CH2CHCH₂CH₂CH₂CH₂ OH CH₂CHCH2CH3 Br CH3 CH3CHCH2CHCH2CH3 CH3

Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electrons-pushing arrows for the following reaction or mechanistic step(s).

Answer 2

Question

Chapter 23, Problem 23.79P

Interpretation Introduction

(a)

Interpretation:

How to synthesize the given compound using only a single nucleophilic aromatic substitution reaction is to be shown.

Concept introduction:

In a nucleophilic aromatic substitution reaction, the aromatic ring is attacked by a nucleophile. If these reactions are precedes though the benzyne intermediate formation, requires very extreme conditions like high temperature, a very strong base, or sometimes both. Since the benzyne intermediate is very highly unstable, undergoes a nucleophilic addition reaction with a nucleophile. If multiple substituents are attached to a phenyl ring, their activating/deactivating qualities govern mechanism of the reaction. The substituent ring with deactivating group precedes the reaction through benzyne intermediate formation. Methyl groups deactivate the ring towards nucleophilic addition reaction.

Interpretation Introduction

(b)

Interpretation:

How to synthesize the given compound using only a single nucleophilic aromatic substitution reaction is to be shown.

Concept introduction:

In a nucleophilic aromatic substitution reaction, the aromatic ring is attacked by a nucleophile. If these reactions are precedes though the benzyne intermediate formation, requires very extreme conditions like high temperature, a very strong base, or sometimes both. Since the benzyne intermediate is very highly unstable, undergoes a nucleophilic addition reaction with a nucleophile. If multiple substituents are attached to a phenyl ring, their activating/deactivating qualities govern the mechanism of the reaction. The substituent ring with a deactivating group precedes the reaction through benzyne intermediate formation.

Interpretation Introduction

(c)

Interpretation:

How to synthesize the given compound using only a single nucleophilic aromatic substitution reaction is to be shown.

Concept introduction:

In a nucleophilic aromatic substitution reaction, the aromatic ring is attacked by a nucleophile. If these reactions are precedes though the benzyne intermediate formation, requires very extreme conditions like high temperature, a very strong base, or sometimes both. Since the benzyne intermediate is very highly unstable, undergoes a nucleophilic addition reaction with a nucleophile. If multiple substituents are attached to a phenyl ring, their activating/deactivating qualities govern the mechanism of the reaction. The substituent ring with a deactivating group precedes the reaction through benzyne intermediate formation.

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Answer 3

Question

Chapter 23, Problem 23.79P

Interpretation Introduction

(a)

Interpretation:

How to synthesize the given compound using only a single nucleophilic aromatic substitution reaction is to be shown.

Concept introduction:

In a nucleophilic aromatic substitution reaction, the aromatic ring is attacked by a nucleophile. If these reactions are precedes though the benzyne intermediate formation, requires very extreme conditions like high temperature, a very strong base, or sometimes both. Since the benzyne intermediate is very highly unstable, undergoes a nucleophilic addition reaction with a nucleophile. If multiple substituents are attached to a phenyl ring, their activating/deactivating qualities govern mechanism of the reaction. The substituent ring with deactivating group precedes the reaction through benzyne intermediate formation. Methyl groups deactivate the ring towards nucleophilic addition reaction.

Interpretation Introduction

(b)

Interpretation:

How to synthesize the given compound using only a single nucleophilic aromatic substitution reaction is to be shown.

Concept introduction:

In a nucleophilic aromatic substitution reaction, the aromatic ring is attacked by a nucleophile. If these reactions are precedes though the benzyne intermediate formation, requires very extreme conditions like high temperature, a very strong base, or sometimes both. Since the benzyne intermediate is very highly unstable, undergoes a nucleophilic addition reaction with a nucleophile. If multiple substituents are attached to a phenyl ring, their activating/deactivating qualities govern the mechanism of the reaction. The substituent ring with a deactivating group precedes the reaction through benzyne intermediate formation.

Interpretation Introduction

(c)

Interpretation:

How to synthesize the given compound using only a single nucleophilic aromatic substitution reaction is to be shown.

Concept introduction:

In a nucleophilic aromatic substitution reaction, the aromatic ring is attacked by a nucleophile. If these reactions are precedes though the benzyne intermediate formation, requires very extreme conditions like high temperature, a very strong base, or sometimes both. Since the benzyne intermediate is very highly unstable, undergoes a nucleophilic addition reaction with a nucleophile. If multiple substituents are attached to a phenyl ring, their activating/deactivating qualities govern the mechanism of the reaction. The substituent ring with a deactivating group precedes the reaction through benzyne intermediate formation.

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Answer 4

Question

Chapter 23, Problem 23.79P

Interpretation Introduction

(a)

Interpretation:

How to synthesize the given compound using only a single nucleophilic aromatic substitution reaction is to be shown.

Concept introduction:

In a nucleophilic aromatic substitution reaction, the aromatic ring is attacked by a nucleophile. If these reactions are precedes though the benzyne intermediate formation, requires very extreme conditions like high temperature, a very strong base, or sometimes both. Since the benzyne intermediate is very highly unstable, undergoes a nucleophilic addition reaction with a nucleophile. If multiple substituents are attached to a phenyl ring, their activating/deactivating qualities govern mechanism of the reaction. The substituent ring with deactivating group precedes the reaction through benzyne intermediate formation. Methyl groups deactivate the ring towards nucleophilic addition reaction.

Interpretation Introduction

(b)

Interpretation:

How to synthesize the given compound using only a single nucleophilic aromatic substitution reaction is to be shown.

Concept introduction:

In a nucleophilic aromatic substitution reaction, the aromatic ring is attacked by a nucleophile. If these reactions are precedes though the benzyne intermediate formation, requires very extreme conditions like high temperature, a very strong base, or sometimes both. Since the benzyne intermediate is very highly unstable, undergoes a nucleophilic addition reaction with a nucleophile. If multiple substituents are attached to a phenyl ring, their activating/deactivating qualities govern the mechanism of the reaction. The substituent ring with a deactivating group precedes the reaction through benzyne intermediate formation.

Interpretation Introduction

(c)

Interpretation:

How to synthesize the given compound using only a single nucleophilic aromatic substitution reaction is to be shown.

Concept introduction:

In a nucleophilic aromatic substitution reaction, the aromatic ring is attacked by a nucleophile. If these reactions are precedes though the benzyne intermediate formation, requires very extreme conditions like high temperature, a very strong base, or sometimes both. Since the benzyne intermediate is very highly unstable, undergoes a nucleophilic addition reaction with a nucleophile. If multiple substituents are attached to a phenyl ring, their activating/deactivating qualities govern the mechanism of the reaction. The substituent ring with a deactivating group precedes the reaction through benzyne intermediate formation.

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Answer 5

Chapter 23, Problem 23.79P

Interpretation Introduction

(a)

Interpretation:

How to synthesize the given compound using only a single nucleophilic aromatic substitution reaction is to be shown.

Concept introduction:

In a nucleophilic aromatic substitution reaction, the aromatic ring is attacked by a nucleophile. If these reactions are precedes though the benzyne intermediate formation, requires very extreme conditions like high temperature, a very strong base, or sometimes both. Since the benzyne intermediate is very highly unstable, undergoes a nucleophilic addition reaction with a nucleophile. If multiple substituents are attached to a phenyl ring, their activating/deactivating qualities govern mechanism of the reaction. The substituent ring with deactivating group precedes the reaction through benzyne intermediate formation. Methyl groups deactivate the ring towards nucleophilic addition reaction.

Interpretation Introduction

(b)

Interpretation:

How to synthesize the given compound using only a single nucleophilic aromatic substitution reaction is to be shown.

Concept introduction:

In a nucleophilic aromatic substitution reaction, the aromatic ring is attacked by a nucleophile. If these reactions are precedes though the benzyne intermediate formation, requires very extreme conditions like high temperature, a very strong base, or sometimes both. Since the benzyne intermediate is very highly unstable, undergoes a nucleophilic addition reaction with a nucleophile. If multiple substituents are attached to a phenyl ring, their activating/deactivating qualities govern the mechanism of the reaction. The substituent ring with a deactivating group precedes the reaction through benzyne intermediate formation.

Interpretation Introduction

(c)

Interpretation:

How to synthesize the given compound using only a single nucleophilic aromatic substitution reaction is to be shown.

Concept introduction:

In a nucleophilic aromatic substitution reaction, the aromatic ring is attacked by a nucleophile. If these reactions are precedes though the benzyne intermediate formation, requires very extreme conditions like high temperature, a very strong base, or sometimes both. Since the benzyne intermediate is very highly unstable, undergoes a nucleophilic addition reaction with a nucleophile. If multiple substituents are attached to a phenyl ring, their activating/deactivating qualities govern the mechanism of the reaction. The substituent ring with a deactivating group precedes the reaction through benzyne intermediate formation.

Answer 6

Chapter 23, Problem 23.79P

Interpretation Introduction

(a)

Interpretation:

How to synthesize the given compound using only a single nucleophilic aromatic substitution reaction is to be shown.

Concept introduction:

In a nucleophilic aromatic substitution reaction, the aromatic ring is attacked by a nucleophile. If these reactions are precedes though the benzyne intermediate formation, requires very extreme conditions like high temperature, a very strong base, or sometimes both. Since the benzyne intermediate is very highly unstable, undergoes a nucleophilic addition reaction with a nucleophile. If multiple substituents are attached to a phenyl ring, their activating/deactivating qualities govern mechanism of the reaction. The substituent ring with deactivating group precedes the reaction through benzyne intermediate formation. Methyl groups deactivate the ring towards nucleophilic addition reaction.

Answer 7

Chapter 23, Problem 23.79P

Interpretation Introduction

(a)

Interpretation:

How to synthesize the given compound using only a single nucleophilic aromatic substitution reaction is to be shown.

Concept introduction:

In a nucleophilic aromatic substitution reaction, the aromatic ring is attacked by a nucleophile. If these reactions are precedes though the benzyne intermediate formation, requires very extreme conditions like high temperature, a very strong base, or sometimes both. Since the benzyne intermediate is very highly unstable, undergoes a nucleophilic addition reaction with a nucleophile. If multiple substituents are attached to a phenyl ring, their activating/deactivating qualities govern mechanism of the reaction. The substituent ring with deactivating group precedes the reaction through benzyne intermediate formation. Methyl groups deactivate the ring towards nucleophilic addition reaction.

Answer 8

Interpretation Introduction

(b)

Interpretation:

How to synthesize the given compound using only a single nucleophilic aromatic substitution reaction is to be shown.

Concept introduction:

In a nucleophilic aromatic substitution reaction, the aromatic ring is attacked by a nucleophile. If these reactions are precedes though the benzyne intermediate formation, requires very extreme conditions like high temperature, a very strong base, or sometimes both. Since the benzyne intermediate is very highly unstable, undergoes a nucleophilic addition reaction with a nucleophile. If multiple substituents are attached to a phenyl ring, their activating/deactivating qualities govern the mechanism of the reaction. The substituent ring with a deactivating group precedes the reaction through benzyne intermediate formation.

Answer 9

Interpretation Introduction

(b)

Interpretation:

How to synthesize the given compound using only a single nucleophilic aromatic substitution reaction is to be shown.

Concept introduction:

In a nucleophilic aromatic substitution reaction, the aromatic ring is attacked by a nucleophile. If these reactions are precedes though the benzyne intermediate formation, requires very extreme conditions like high temperature, a very strong base, or sometimes both. Since the benzyne intermediate is very highly unstable, undergoes a nucleophilic addition reaction with a nucleophile. If multiple substituents are attached to a phenyl ring, their activating/deactivating qualities govern the mechanism of the reaction. The substituent ring with a deactivating group precedes the reaction through benzyne intermediate formation.

Answer 10

Interpretation Introduction

(c)

Interpretation:

How to synthesize the given compound using only a single nucleophilic aromatic substitution reaction is to be shown.

Concept introduction:

In a nucleophilic aromatic substitution reaction, the aromatic ring is attacked by a nucleophile. If these reactions are precedes though the benzyne intermediate formation, requires very extreme conditions like high temperature, a very strong base, or sometimes both. Since the benzyne intermediate is very highly unstable, undergoes a nucleophilic addition reaction with a nucleophile. If multiple substituents are attached to a phenyl ring, their activating/deactivating qualities govern the mechanism of the reaction. The substituent ring with a deactivating group precedes the reaction through benzyne intermediate formation.

Answer 11

Interpretation Introduction

(c)

Interpretation:

How to synthesize the given compound using only a single nucleophilic aromatic substitution reaction is to be shown.

Concept introduction:

In a nucleophilic aromatic substitution reaction, the aromatic ring is attacked by a nucleophile. If these reactions are precedes though the benzyne intermediate formation, requires very extreme conditions like high temperature, a very strong base, or sometimes both. Since the benzyne intermediate is very highly unstable, undergoes a nucleophilic addition reaction with a nucleophile. If multiple substituents are attached to a phenyl ring, their activating/deactivating qualities govern the mechanism of the reaction. The substituent ring with a deactivating group precedes the reaction through benzyne intermediate formation.

Answer 12

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Answer 14

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Answer 15

Ch. 23 - Prob. 23.1P Ch. 23 - Prob. 23.2P Ch. 23 - Prob. 23.3P Ch. 23 - Prob. 23.4P Ch. 23 - Prob. 23.5P Ch. 23 - Prob. 23.6P Ch. 23 - Prob. 23.7P Ch. 23 - Prob. 23.8P Ch. 23 - Prob. 23.9P Ch. 23 - Prob. 23.10P

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