The methylanilines which can be formed by the reaction of m-bromotoluene with sodium amide in ammonia are to be determined. Concept introduction: Aryl halides in the presence of a strong base undergo substitution via elimination-addition mechanism. In the first step, the base abstracts a proton attached to the ring carbon atom which is adjacent to the halogen. The proton and the halogen from adjacent carbon atoms are eliminated, and triple bond is created. This intermediate formed is benzyne. The nucleophile then adds to any one of the triple bonded carbon atoms. If the ring has a substituent other than halogen, the position of the nucleophile with respect to the substituent can be at two different sites, thus producing two different isomers. In the overall reaction, the halogen is substituted by the nucleophile in product, and in the other product, the nucleophile gets attached to an adjacent carbon atom.

Question

Want to see the full answer?

Answer 1

Question

Chapter 13, Problem 61DSP

Interpretation Introduction

Interpretation:

The methylanilines which can be formed by the reaction of m-bromotoluene with sodium amide in ammonia are to be determined.

Concept introduction:

Aryl halides in the presence of a strong base undergo substitution via elimination-addition mechanism.

In the first step, the base abstracts a proton attached to the ring carbon atom which is adjacent to the halogen. The proton and the halogen from adjacent carbon atoms are eliminated, and triple bond is created. This intermediate formed is benzyne.

The nucleophile then adds to any one of the triple bonded carbon atoms.

If the ring has a substituent other than halogen, the position of the nucleophile with respect to the substituent can be at two different sites, thus producing two different isomers.

In the overall reaction, the halogen is substituted by the nucleophile in product, and in the other product, the nucleophile gets attached to an adjacent carbon atom.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Provide the reasonable steps to achieve the following synthesis.

Identify which compound is more acidic. Justify your choice.

Provide the reasonable steps to achieve the following synthesis.

Answer 2

Question

Chapter 13, Problem 61DSP

Interpretation Introduction

Interpretation:

The methylanilines which can be formed by the reaction of m-bromotoluene with sodium amide in ammonia are to be determined.

Concept introduction:

Aryl halides in the presence of a strong base undergo substitution via elimination-addition mechanism.

In the first step, the base abstracts a proton attached to the ring carbon atom which is adjacent to the halogen. The proton and the halogen from adjacent carbon atoms are eliminated, and triple bond is created. This intermediate formed is benzyne.

The nucleophile then adds to any one of the triple bonded carbon atoms.

If the ring has a substituent other than halogen, the position of the nucleophile with respect to the substituent can be at two different sites, thus producing two different isomers.

In the overall reaction, the halogen is substituted by the nucleophile in product, and in the other product, the nucleophile gets attached to an adjacent carbon atom.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 3

Question

Chapter 13, Problem 61DSP

Interpretation Introduction

Interpretation:

The methylanilines which can be formed by the reaction of m-bromotoluene with sodium amide in ammonia are to be determined.

Concept introduction:

Aryl halides in the presence of a strong base undergo substitution via elimination-addition mechanism.

In the first step, the base abstracts a proton attached to the ring carbon atom which is adjacent to the halogen. The proton and the halogen from adjacent carbon atoms are eliminated, and triple bond is created. This intermediate formed is benzyne.

The nucleophile then adds to any one of the triple bonded carbon atoms.

If the ring has a substituent other than halogen, the position of the nucleophile with respect to the substituent can be at two different sites, thus producing two different isomers.

In the overall reaction, the halogen is substituted by the nucleophile in product, and in the other product, the nucleophile gets attached to an adjacent carbon atom.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Chapter 13, Problem 61DSP

Interpretation Introduction

Interpretation:

The methylanilines which can be formed by the reaction of m-bromotoluene with sodium amide in ammonia are to be determined.

Concept introduction:

Aryl halides in the presence of a strong base undergo substitution via elimination-addition mechanism.

In the first step, the base abstracts a proton attached to the ring carbon atom which is adjacent to the halogen. The proton and the halogen from adjacent carbon atoms are eliminated, and triple bond is created. This intermediate formed is benzyne.

The nucleophile then adds to any one of the triple bonded carbon atoms.

If the ring has a substituent other than halogen, the position of the nucleophile with respect to the substituent can be at two different sites, thus producing two different isomers.

In the overall reaction, the halogen is substituted by the nucleophile in product, and in the other product, the nucleophile gets attached to an adjacent carbon atom.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 5

Chapter 13, Problem 61DSP

Interpretation Introduction

Interpretation:

The methylanilines which can be formed by the reaction of m-bromotoluene with sodium amide in ammonia are to be determined.

Concept introduction:

Aryl halides in the presence of a strong base undergo substitution via elimination-addition mechanism.

In the first step, the base abstracts a proton attached to the ring carbon atom which is adjacent to the halogen. The proton and the halogen from adjacent carbon atoms are eliminated, and triple bond is created. This intermediate formed is benzyne.

The nucleophile then adds to any one of the triple bonded carbon atoms.

If the ring has a substituent other than halogen, the position of the nucleophile with respect to the substituent can be at two different sites, thus producing two different isomers.

In the overall reaction, the halogen is substituted by the nucleophile in product, and in the other product, the nucleophile gets attached to an adjacent carbon atom.

Answer 6

Chapter 13, Problem 61DSP

Interpretation Introduction

Interpretation:

The methylanilines which can be formed by the reaction of m-bromotoluene with sodium amide in ammonia are to be determined.

Concept introduction:

Aryl halides in the presence of a strong base undergo substitution via elimination-addition mechanism.

In the first step, the base abstracts a proton attached to the ring carbon atom which is adjacent to the halogen. The proton and the halogen from adjacent carbon atoms are eliminated, and triple bond is created. This intermediate formed is benzyne.

The nucleophile then adds to any one of the triple bonded carbon atoms.

If the ring has a substituent other than halogen, the position of the nucleophile with respect to the substituent can be at two different sites, thus producing two different isomers.

In the overall reaction, the halogen is substituted by the nucleophile in product, and in the other product, the nucleophile gets attached to an adjacent carbon atom.

Answer 7

Chapter 13, Problem 61DSP

Interpretation Introduction

Interpretation:

The methylanilines which can be formed by the reaction of m-bromotoluene with sodium amide in ammonia are to be determined.

Concept introduction:

Aryl halides in the presence of a strong base undergo substitution via elimination-addition mechanism.

In the first step, the base abstracts a proton attached to the ring carbon atom which is adjacent to the halogen. The proton and the halogen from adjacent carbon atoms are eliminated, and triple bond is created. This intermediate formed is benzyne.

The nucleophile then adds to any one of the triple bonded carbon atoms.

If the ring has a substituent other than halogen, the position of the nucleophile with respect to the substituent can be at two different sites, thus producing two different isomers.

In the overall reaction, the halogen is substituted by the nucleophile in product, and in the other product, the nucleophile gets attached to an adjacent carbon atom.

Answer 8

Expert Solution & Answer

Answer 9

Expert Solution & Answer

Answer 10

Want to see the full answer?

Check out a sample textbook solution

See solution

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 that methylanilines can be formed by the reaction of m-bromotoluene with sodium amide in ammonia.

Concept explainers

Want to see the full answer?

Chapter 13 Solutions