A mechanism for the given reaction is to be suggested. Concept Introduction: Aryl halides (halogens attached to the benzene ring) generally do not undergo nucleophilic aromatic substitution reaction, until and unless there are electronegative atoms present on the ring. An electron withdrawing atom or group attached to the benzene ring imposes the electron-attracting inductive effect and stabilizes the cyclohexadienyl anion intermediate which permits the reaction to proceed rapidly. Nucleophilic aromatic substitution reactions follow an addition-elimination mechanism. In the first step, addition of the nucleophile to aryl halide takes place to form a cyclohexadienyl anion intermediate. In the second step, the elimination of the halide group takes place. Strong electron withdrawing substituents in the aryl halide stabilizes the cyclohexadienyl anion intermediate. Nucleophilic aromatic substitution reactions follow the second order rate law in which the rate of the reaction depends on the concentration of aryl halide and the nucleophile. Presence of strongly electronegative (electron withdrawing) group(s) on the benzene ring activates it towards nucleophilic aromatic substitution.

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Answer 1

Question

Chapter 13, Problem 57P

Interpretation Introduction

Interpretation:

A mechanism for the given reaction is to be suggested.

Concept Introduction:

Aryl halides (halogens attached to the benzene ring) generally do not undergo nucleophilic aromatic substitution reaction, until and unless there are electronegative atoms present on the ring.

An electron withdrawing atom or group attached to the benzene ring imposes the electron-attracting inductive effect and stabilizes the cyclohexadienyl anion intermediate which permits the reaction to proceed rapidly.

Nucleophilic aromatic substitution reactions follow an addition-elimination mechanism.

In the first step, addition of the nucleophile to aryl halide takes place to form a cyclohexadienyl anion intermediate.

In the second step, the elimination of the halide group takes place.

Strong electron withdrawing substituents in the aryl halide stabilizes the cyclohexadienyl anion intermediate.

Nucleophilic aromatic substitution reactions follow the second order rate law in which the rate of the reaction depends on the concentration of aryl halide and the nucleophile.

Presence of strongly electronegative (electron withdrawing) group(s) on the benzene ring activates it towards nucleophilic aromatic substitution.

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Answer 2

Question

Chapter 13, Problem 57P

Interpretation Introduction

Interpretation:

A mechanism for the given reaction is to be suggested.

Concept Introduction:

Aryl halides (halogens attached to the benzene ring) generally do not undergo nucleophilic aromatic substitution reaction, until and unless there are electronegative atoms present on the ring.

An electron withdrawing atom or group attached to the benzene ring imposes the electron-attracting inductive effect and stabilizes the cyclohexadienyl anion intermediate which permits the reaction to proceed rapidly.

Nucleophilic aromatic substitution reactions follow an addition-elimination mechanism.

In the first step, addition of the nucleophile to aryl halide takes place to form a cyclohexadienyl anion intermediate.

In the second step, the elimination of the halide group takes place.

Strong electron withdrawing substituents in the aryl halide stabilizes the cyclohexadienyl anion intermediate.

Nucleophilic aromatic substitution reactions follow the second order rate law in which the rate of the reaction depends on the concentration of aryl halide and the nucleophile.

Presence of strongly electronegative (electron withdrawing) group(s) on the benzene ring activates it towards nucleophilic aromatic substitution.

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Answer 3

Question

Chapter 13, Problem 57P

Interpretation Introduction

Interpretation:

A mechanism for the given reaction is to be suggested.

Concept Introduction:

Aryl halides (halogens attached to the benzene ring) generally do not undergo nucleophilic aromatic substitution reaction, until and unless there are electronegative atoms present on the ring.

An electron withdrawing atom or group attached to the benzene ring imposes the electron-attracting inductive effect and stabilizes the cyclohexadienyl anion intermediate which permits the reaction to proceed rapidly.

Nucleophilic aromatic substitution reactions follow an addition-elimination mechanism.

In the first step, addition of the nucleophile to aryl halide takes place to form a cyclohexadienyl anion intermediate.

In the second step, the elimination of the halide group takes place.

Strong electron withdrawing substituents in the aryl halide stabilizes the cyclohexadienyl anion intermediate.

Nucleophilic aromatic substitution reactions follow the second order rate law in which the rate of the reaction depends on the concentration of aryl halide and the nucleophile.

Presence of strongly electronegative (electron withdrawing) group(s) on the benzene ring activates it towards nucleophilic aromatic substitution.

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Answer 4

Question

Chapter 13, Problem 57P

Interpretation Introduction

Interpretation:

A mechanism for the given reaction is to be suggested.

Concept Introduction:

Aryl halides (halogens attached to the benzene ring) generally do not undergo nucleophilic aromatic substitution reaction, until and unless there are electronegative atoms present on the ring.

An electron withdrawing atom or group attached to the benzene ring imposes the electron-attracting inductive effect and stabilizes the cyclohexadienyl anion intermediate which permits the reaction to proceed rapidly.

Nucleophilic aromatic substitution reactions follow an addition-elimination mechanism.

In the first step, addition of the nucleophile to aryl halide takes place to form a cyclohexadienyl anion intermediate.

In the second step, the elimination of the halide group takes place.

Strong electron withdrawing substituents in the aryl halide stabilizes the cyclohexadienyl anion intermediate.

Nucleophilic aromatic substitution reactions follow the second order rate law in which the rate of the reaction depends on the concentration of aryl halide and the nucleophile.

Presence of strongly electronegative (electron withdrawing) group(s) on the benzene ring activates it towards nucleophilic aromatic substitution.

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Answer 5

Chapter 13, Problem 57P

Interpretation Introduction

Interpretation:

A mechanism for the given reaction is to be suggested.

Concept Introduction:

Aryl halides (halogens attached to the benzene ring) generally do not undergo nucleophilic aromatic substitution reaction, until and unless there are electronegative atoms present on the ring.

An electron withdrawing atom or group attached to the benzene ring imposes the electron-attracting inductive effect and stabilizes the cyclohexadienyl anion intermediate which permits the reaction to proceed rapidly.

Nucleophilic aromatic substitution reactions follow an addition-elimination mechanism.

In the first step, addition of the nucleophile to aryl halide takes place to form a cyclohexadienyl anion intermediate.

In the second step, the elimination of the halide group takes place.

Strong electron withdrawing substituents in the aryl halide stabilizes the cyclohexadienyl anion intermediate.

Nucleophilic aromatic substitution reactions follow the second order rate law in which the rate of the reaction depends on the concentration of aryl halide and the nucleophile.

Presence of strongly electronegative (electron withdrawing) group(s) on the benzene ring activates it towards nucleophilic aromatic substitution.

Answer 6

Chapter 13, Problem 57P

Interpretation Introduction

Interpretation:

A mechanism for the given reaction is to be suggested.

Concept Introduction:

Aryl halides (halogens attached to the benzene ring) generally do not undergo nucleophilic aromatic substitution reaction, until and unless there are electronegative atoms present on the ring.

An electron withdrawing atom or group attached to the benzene ring imposes the electron-attracting inductive effect and stabilizes the cyclohexadienyl anion intermediate which permits the reaction to proceed rapidly.

Nucleophilic aromatic substitution reactions follow an addition-elimination mechanism.

In the first step, addition of the nucleophile to aryl halide takes place to form a cyclohexadienyl anion intermediate.

In the second step, the elimination of the halide group takes place.

Strong electron withdrawing substituents in the aryl halide stabilizes the cyclohexadienyl anion intermediate.

Nucleophilic aromatic substitution reactions follow the second order rate law in which the rate of the reaction depends on the concentration of aryl halide and the nucleophile.

Presence of strongly electronegative (electron withdrawing) group(s) on the benzene ring activates it towards nucleophilic aromatic substitution.

Answer 7

Chapter 13, Problem 57P

Interpretation Introduction

Interpretation:

A mechanism for the given reaction is to be suggested.

Concept Introduction:

Aryl halides (halogens attached to the benzene ring) generally do not undergo nucleophilic aromatic substitution reaction, until and unless there are electronegative atoms present on the ring.

An electron withdrawing atom or group attached to the benzene ring imposes the electron-attracting inductive effect and stabilizes the cyclohexadienyl anion intermediate which permits the reaction to proceed rapidly.

Nucleophilic aromatic substitution reactions follow an addition-elimination mechanism.

In the first step, addition of the nucleophile to aryl halide takes place to form a cyclohexadienyl anion intermediate.

In the second step, the elimination of the halide group takes place.

Strong electron withdrawing substituents in the aryl halide stabilizes the cyclohexadienyl anion intermediate.

Nucleophilic aromatic substitution reactions follow the second order rate law in which the rate of the reaction depends on the concentration of aryl halide and the nucleophile.

Presence of strongly electronegative (electron withdrawing) group(s) on the benzene ring activates it towards nucleophilic aromatic substitution.

Answer 8

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Answer 9

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Answer 10

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Answer 11

Ch. 13.2 - Based on Hammonds postulate which holds that the...Ch. 13.3 - Prob. 2P Ch. 13.3 - Using : O =N+= O : as the electrophile, write a...Ch. 13.4 - Prob. 4P Ch. 13.5 - Prob. 5P Ch. 13.6 - Prob. 6P Ch. 13.6 - Write a reasonable mechanism for the formation of...Ch. 13.6 - tert-Butylbenzene can be prepared by alkylation of...Ch. 13.6 - Prob. 9P Ch. 13.7 - The reaction shown gives a single product in 88...

Solution Summary: The author explains the mechanism of the nucleophilic aromatic substitution reaction, which proceeds as an intramolecular addition-elimination.

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