Organic Chemistry Study Guide and Solutions
Organic Chemistry Study Guide and Solutions
6th Edition
ISBN: 9781936221868
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 23, Problem 23.45AP
Interpretation Introduction

(a)

Interpretation:

The product obtained in the reaction of Nmethylaniline with Br2 is to be stated.

Concept introduction:

Amines are the organic compounds that are formed by replacement of hydrogen from ammonia with a substituent. It may be alkyl or aryl group. Amines are basic in nature because the nitrogen can donate its lone pairs and also the ability of the nitrogen to accept the proton in water. The replacement of hydrogen atom attached to a carbon atom of electron-rich benzene ring by an incoming electrophile is known as electrophilic aromatic substitution reaction.

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Answer to Problem 23.45AP

The product 2,4,6tribromoNmethylaniline is obtained in the reaction of Nmethylaniline with Br2. The chemical reaction is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 23, Problem 23.45AP , additional homework tip  1

Explanation of Solution

When Nmethylaniline undergo electrophilic substitution reaction with a molecule of Br2, it results in the formation of 2,4,6tribromoNmethylaniline. It is a similar reaction which happens with phenol. The reaction is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 23, Problem 23.45AP , additional homework tip  2

Figure 1

Conclusion

The product obtained in the reaction of Nmethylaniline with Br2 is 2,4,6tribromoNmethylaniline and its reaction is shown in Figure.1.

Interpretation Introduction

(b)

Interpretation:

The product obtained in the reaction of Nmethylaniline with benzoyl chloride is to be stated.

Concept introduction:

Amines are the organic compounds that are formed by replacement of hydrogen from ammonia with a substituent. It may be alkyl or aryl group. Amines are basic in nature because the nitrogen can donate its lone pairs and also the ability of the nitrogen to accept the proton in water. The replacement of hydrogen atom attached to a carbon atom of electron-rich benzene ring by an incoming electrophile is known as electrophilic aromatic substitution reaction.

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Answer to Problem 23.45AP

The product obtained in the reaction of Nmethylaniline with benzoyl chloride is NmethylNphenylbenzamide. The reaction is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 23, Problem 23.45AP , additional homework tip  3

Explanation of Solution

When Nmethylaniline undergoes acylation reaction with benzoyl chloride, it results in the formation of amide that is NmethylNphenylbenzamide. The reaction is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 23, Problem 23.45AP , additional homework tip  4

Figure 2

Conclusion

The product obtained in the reaction of Nmethylaniline with benzoyl chloride is NmethylNphenylbenzamide and its reaction is shown in Figure.2.

Interpretation Introduction

(c)

Interpretation:

The product obtained in the reaction of Nmethylaniline with benzyl chloride (excess), then dilute OH is to be stated.

Concept introduction:

Amines are the organic compounds that are formed by replacement of hydrogen from ammonia with a substituent. It may be alkyl or aryl group. Amines are basic in nature because the nitrogen can donate its lone pairs and also the ability of the nitrogen to accept the proton in water.

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Answer to Problem 23.45AP

The product N,NdibenzylNmethylbenzeneaminiumhydroxide is obtained in the reaction of Nmethylaniline with benzyl chloride (excess), then dilute OH. The reaction is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 23, Problem 23.45AP , additional homework tip  5

Explanation of Solution

When Nmethylaniline reacts with an excess of benzyl chloride followed by dilute OH then SN2 nucleophilic substitution reaction takes place which results in the formation of N,NdibenzylNmethylbenzenaminiumhydroxide. The reaction is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 23, Problem 23.45AP , additional homework tip  6

Figure 3

Conclusion

The product obtained in the reaction of Nmethylaniline with benzoyl chloride (excess), then dilute OH is N,NdibenzylNmethylbenzenaminiumhydroxide and its reaction is shown in Figure 3.

Interpretation Introduction

(d)

Interpretation:

The product obtained in the reaction of Nmethylaniline with ptoluenesulfonic acid is to be stated.

Concept introduction:

Amines are the organic compounds that are formed by replacement of hydrogen from ammonia with a substituent. It may be alkyl or aryl group. Amines are basic in nature because the nitrogen can donate its lone pairs and also the ability of the nitrogen to accept the proton in water.

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Answer to Problem 23.45AP

The product N,4methylNphenylbenzenesulphonamide is obtained in the reaction of Nmethylaniline with ptoluenesulfonic acid. The reaction is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 23, Problem 23.45AP , additional homework tip  7

Explanation of Solution

When Nmethylaniline reacts with ptoluenesulfonic acid, it results in the formation of sulfamide and product is known to be N,4methylNphenylbenzenesulphonamide. The reaction is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 23, Problem 23.45AP , additional homework tip  8

Figure 4

Conclusion

The product obtained in the reaction of Nmethylaniline with ptoluenesulfonic acid is N,4methylNphenylbenzenesulphonamide and its reaction is shown in Figure 4.

Interpretation Introduction

(e)

Interpretation:

The product obtained in the reaction of Nmethylaniline with NaNO2 and HCl is to be stated.

Concept introduction:

Amines are the organic compounds that are formed by replacement of hydrogen from ammonia with a substituent. It may be alkyl or aryl group. Amines are basic in nature because the nitrogen can donate its lone pairs and also the ability of the nitrogen to accept the proton in water.

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Answer to Problem 23.45AP

The product 2hydroxy1methyl1phenyldiazen1ium is obtained in the diazotization reaction of Nmethylaniline. The reaction is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 23, Problem 23.45AP , additional homework tip  9

Explanation of Solution

The reagents, NaNO2 and HCl are combined to form diazonium reagent but Nmethylaniline is secondary amine which does not undergo diazonium reaction. Therefore, the product obtained is N-nitroso N-methylaniline. The reaction is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 23, Problem 23.45AP , additional homework tip  10

Figure 5

Conclusion

The product obtained in the reaction of Nmethylaniline with NaNO2, HCl is 2hydroxy1methyl1phenyldiazen1ium and its reaction is shown in Figure 5.

Interpretation Introduction

(f)

Interpretation:

The product obtained in the reaction of Nmethylaniline with excess CH3I, heat, then Ag2O is to be stated.

Concept introduction:

Amines are the organic compounds that are formed by replacement of hydrogen from ammonia with a substituent. It may be alkyl or aryl group. Hofmann elimination reaction occurs as an anti-elimination reaction. In this reaction, the starting material is quaternary ammonium hydroxide. When quaternary ammonium hydroxide is heated, β elimination occurs to form an alkene, amines act as a leaving group.

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Answer to Problem 23.45AP

The product N,N,Ntrimethylbenzeneaminiumhydroxide is obtained in the reaction with excess CH3I, heat, then Ag2O. The reaction is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 23, Problem 23.45AP , additional homework tip  11

Explanation of Solution

Hofmann elimination reaction occurs as an anti-elimination reaction. In this reaction, the starting material is quaternary ammonium hydroxide. In the given case, when Nmethylaniline undergoes Hofmann elimination reaction, it results in the formation of N,N,Ntrimethylbenzeneaminiumhydroxide. The reaction is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 23, Problem 23.45AP , additional homework tip  12

Figure 6

Conclusion

The product obtained in the reaction of Nmethylaniline with excess CH3I, heat, then Ag2O is N,N,Ntrimethylbenzeneaminiumhydroxide and its reaction is shown in Figure 6.

Interpretation Introduction

(g)

Interpretation:

The product obtained in the reaction of Nmethylaniline with CH3CH=O, NaBH(OAc)2, and HOAc in ClCH2CH2Cl, then KOH is to be stated.

Concept introduction:

Amines are the organic compounds that are formed by replacement of hydrogen from ammonia with a substituent. It may be alkyl or aryl group. Amines are basic in nature because the nitrogen can donate its lone pairs and also the ability of the nitrogen to accept the proton in water. Reductive amination reaction is the conversion of the carbonyl group to the amine or it converts one amine to newer amine.

Expert Solution
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Answer to Problem 23.45AP

The product, NethylNmethylaniline is obtained in the reaction of Nmethylaniline with CH3CH=O, NaBH(OAc)2, and HOAc in ClCH2CH2Cl, then KOH. The reaction is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 23, Problem 23.45AP , additional homework tip  13

Explanation of Solution

Reductive amination reaction is the conversion of the carbonyl group to the amine or it converts one amine to new amine. In the given case, when Nmethylaniline undergoes reductive amination reaction, it results in the formation of NethylNmethylaniline. The reaction is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 23, Problem 23.45AP , additional homework tip  14

Figure 7

Conclusion

The product obtained in the reaction of Nmethylaniline with CH3CH=O, NaBH(OAc)2, and HOAc in ClCH2CH2Cl, then KOH is NethylNmethylaniline and its reaction is shown in Figure 7.

Interpretation Introduction

(h)

Interpretation:

The product obtained in the reaction of Nmethylaniline with chlorobenzene, K+tBuO, and a Pd(0) catalyst is to be stated.

Concept introduction:

Amines are the organic compounds that are formed by replacement of hydrogen from ammonia with a substituent. It may be alkyl or aryl group. Amines are basic in nature because the nitrogen can donate its lone pairs and also the ability of the nitrogen to accept the proton in water.

Expert Solution
Check Mark

Answer to Problem 23.45AP

The product NmethylNphenylaniline is obtained in the reaction of Nmethylaniline with chlorobenzene, K+tBuO, and a Pd(0) catalyst. The reaction is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 23, Problem 23.45AP , additional homework tip  15

Explanation of Solution

When Nmethylaniline undergoes Buchwald Hartwig reaction that is used for CN bond formation through palladium-catalyzed reaction, it results in the formation of NmethylNphenylaniline. The reaction is shown below.

Organic Chemistry Study Guide and Solutions, Chapter 23, Problem 23.45AP , additional homework tip  16

Figure 8

Conclusion

The product obtained in the reaction of Nmethylaniline with chlorobenzene, K+tBuO, and a Pd(0) catalyst is NmethylNphenylaniline and its reaction is shown in Figure 8.

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Chapter 23 Solutions

Organic Chemistry Study Guide and Solutions

Ch. 23 - Prob. 23.11PCh. 23 - Prob. 23.12PCh. 23 - Prob. 23.13PCh. 23 - Prob. 23.14PCh. 23 - Prob. 23.15PCh. 23 - Prob. 23.16PCh. 23 - Prob. 23.17PCh. 23 - Prob. 23.18PCh. 23 - Prob. 23.19PCh. 23 - Prob. 23.20PCh. 23 - Prob. 23.21PCh. 23 - Prob. 23.22PCh. 23 - Prob. 23.23PCh. 23 - Prob. 23.24PCh. 23 - Prob. 23.25PCh. 23 - Prob. 23.26PCh. 23 - Prob. 23.27PCh. 23 - Prob. 23.28PCh. 23 - Prob. 23.29PCh. 23 - Prob. 23.30PCh. 23 - Prob. 23.31PCh. 23 - Prob. 23.32PCh. 23 - Prob. 23.33PCh. 23 - Prob. 23.34PCh. 23 - Prob. 23.35PCh. 23 - Prob. 23.36PCh. 23 - Prob. 23.37PCh. 23 - Prob. 23.38PCh. 23 - Prob. 23.39PCh. 23 - Prob. 23.40PCh. 23 - Prob. 23.41PCh. 23 - Prob. 23.42PCh. 23 - Prob. 23.43PCh. 23 - Prob. 23.44APCh. 23 - Prob. 23.45APCh. 23 - Prob. 23.46APCh. 23 - Prob. 23.47APCh. 23 - Prob. 23.48APCh. 23 - Prob. 23.49APCh. 23 - Prob. 23.50APCh. 23 - Prob. 23.51APCh. 23 - Prob. 23.52APCh. 23 - Prob. 23.53APCh. 23 - Prob. 23.54APCh. 23 - Prob. 23.55APCh. 23 - Prob. 23.56APCh. 23 - Prob. 23.57APCh. 23 - Prob. 23.58APCh. 23 - Prob. 23.59APCh. 23 - Prob. 23.60APCh. 23 - Prob. 23.61APCh. 23 - Prob. 23.62APCh. 23 - Prob. 23.63APCh. 23 - Prob. 23.64APCh. 23 - Prob. 23.65APCh. 23 - Prob. 23.66APCh. 23 - Prob. 23.67APCh. 23 - Prob. 23.68APCh. 23 - Prob. 23.69APCh. 23 - Prob. 23.70APCh. 23 - Prob. 23.71APCh. 23 - Prob. 23.72APCh. 23 - Prob. 23.73APCh. 23 - Prob. 23.74APCh. 23 - Prob. 23.75APCh. 23 - Prob. 23.76APCh. 23 - Prob. 23.77APCh. 23 - Prob. 23.78APCh. 23 - Prob. 23.79APCh. 23 - Prob. 23.80APCh. 23 - Prob. 23.81AP
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