Organic Chemistry: Principles and Mechanisms (Second Edition)
Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
Question
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Chapter 23, Problem 23.55P
Interpretation Introduction

(a)

Interpretation:

How to synthesize the given trisubstituted benzene from the disubstituted benzene is to be shown.

Concept introduction:

If multiple substituents are attached to a phenyl ring, their activating/deactivating qualities are additive, and the regiochemistry tends to be governed by the most activating of those substituents.

The alkyl group is ortho/para director whereas NO2 group is meta director.

Expert Solution
Check Mark

Answer to Problem 23.55P

The disubstituted benzene used to synthesize the given trisubstituted benzene is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 23, Problem 23.55P , additional homework tip  1

Explanation of Solution

The given trisubstituted target molecule is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 23, Problem 23.55P , additional homework tip  2

In the above molecule, CH3 is an ortho/para director, and NO2 is ortho to one CH3 and para to another, that is, NO2 group is added via electrophilic addition reaction.

This reaction can be carried out using addition of nitric acid (NO2+) to the disubstituted benzene with two alkyl group as substituents.

Therefore, the product could be produced by nitrating 1, 3-dimethylbenzene:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 23, Problem 23.55P , additional homework tip  3

Conclusion

The disubstituted benzene used to synthesize the given trisubstituted benzene is shown on the basis of the directing nature of the substituents present at the benzene ring on the target molecule (given trisubstituted benzene).

Interpretation Introduction

(b)

Interpretation:

How to synthesize the given trisubstituted benzene from the disubstituted benzene is to be shown.

Concept introduction:

If multiple substituents are attached to a phenyl ring, their activating/deactivating qualities are additive, and the regiochemistry tends to be governed by the most activating of those substituents.

Expert Solution
Check Mark

Answer to Problem 23.55P

The disubstituted benzene used to synthesize the given trisubstituted benzene is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 23, Problem 23.55P , additional homework tip  4

Explanation of Solution

The given trisubstituted target molecule is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 23, Problem 23.55P , additional homework tip  5

In the above molecule, OH is an ortho/para director, and CH3C=O is a meta director. The Cl is ortho to the OH and meta to the CH3C=O. Thus, the Cl group is added via electrophilic addition reaction.

Thus, the product could be produced by chlorinating the disubstituted benzene using Cl2/AlCl3 as shown below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 23, Problem 23.55P , additional homework tip  6

Conclusion

The disubstituted benzene used to synthesize the given trisubstituted benzene is shown on the basis of the directing nature of the substituents present at the benzene ring on the target molecule (given trisubstituted benzene).

Interpretation Introduction

(c)

Interpretation:

How to synthesize the given trisubstituted benzene from the disubstituted benzene is to be shown.

Concept introduction:

If multiple substituents are attached to a phenyl ring, their activating/deactivating qualities are additive, and the regiochemistry tends to be governed by the most activating of those substituents.

Expert Solution
Check Mark

Answer to Problem 23.55P

The disubstituted benzene used to synthesize the given trisubstituted benzene is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 23, Problem 23.55P , additional homework tip  7

Explanation of Solution

The given trisubstituted target molecule is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 23, Problem 23.55P , additional homework tip  8

In the above molecule, CH3 is an ortho/para director (activator), and NO2 is a meta director (deactivator). The SO3H substituent is ortho to the CH3 and para to the NO2. These groups are in disagreement, but the CH3 group-activator directs the regiochemistry.

Therefore, the product could be produced by sulfonating the disubstituted benzene using fuming H2SO4, which is added to the deactivated disubstituted benzene with CH3 and NO2, as shown below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 23, Problem 23.55P , additional homework tip  9

Conclusion

The disubstituted benzene used to synthesize the given trisubstituted benzene is shown on the basis of the directing nature of the substituents present at the benzene ring on the target molecule (given trisubstituted benzene).

Interpretation Introduction

(d)

Interpretation:

How to synthesize the given trisubstituted benzene from the disubstituted benzene is to be shown.

Concept introduction:

If multiple substituents are attached to a phenyl ring, their activating/deactivating qualities are additive, and the regiochemistry tends to be governed by the most activating of those substituents.

Expert Solution
Check Mark

Answer to Problem 23.55P

The disubstituted benzene used to synthesize the given trisubstituted benzene is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 23, Problem 23.55P , additional homework tip  10

Explanation of Solution

The given trisubstituted target molecule is

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 23, Problem 23.55P , additional homework tip  11

Here, both Cl and CH3O are ortho/para directors. The Br is ortho to the Cl and para to the CH3O. Thus, the Br atom is added via electrophilic substitution reaction to the disubstituted benzene with Cl and CH3O groups as two substituents.

Therefore, the target molecule could be produced by brominating the disubstituted benzene using Br2/FeBr3, as shown below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 23, Problem 23.55P , additional homework tip  12

Conclusion

The disubstituted benzene used to synthesize the given trisubstituted benzene is shown on the basis of the directing nature of the substituents present at the benzene ring on the target molecule (given trisubstituted benzene).

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Chapter 23 Solutions

Organic Chemistry: Principles and Mechanisms (Second Edition)

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. 23.44PCh. 23 - Prob. 23.45PCh. 23 - Prob. 23.46PCh. 23 - Prob. 23.47PCh. 23 - Prob. 23.48PCh. 23 - Prob. 23.49PCh. 23 - Prob. 23.50PCh. 23 - Prob. 23.51PCh. 23 - Prob. 23.52PCh. 23 - Prob. 23.53PCh. 23 - Prob. 23.54PCh. 23 - Prob. 23.55PCh. 23 - Prob. 23.56PCh. 23 - Prob. 23.57PCh. 23 - Prob. 23.58PCh. 23 - Prob. 23.59PCh. 23 - Prob. 23.60PCh. 23 - Prob. 23.61PCh. 23 - Prob. 23.62PCh. 23 - Prob. 23.63PCh. 23 - Prob. 23.64PCh. 23 - Prob. 23.65PCh. 23 - Prob. 23.66PCh. 23 - Prob. 23.67PCh. 23 - Prob. 23.68PCh. 23 - Prob. 23.69PCh. 23 - Prob. 23.70PCh. 23 - Prob. 23.71PCh. 23 - Prob. 23.72PCh. 23 - Prob. 23.73PCh. 23 - Prob. 23.74PCh. 23 - Prob. 23.75PCh. 23 - Prob. 23.76PCh. 23 - Prob. 23.77PCh. 23 - Prob. 23.78PCh. 23 - Prob. 23.79PCh. 23 - Prob. 23.80PCh. 23 - Prob. 23.81PCh. 23 - Prob. 23.82PCh. 23 - Prob. 23.83PCh. 23 - Prob. 23.84PCh. 23 - Prob. 23.85PCh. 23 - Prob. 23.86PCh. 23 - Prob. 23.87PCh. 23 - Prob. 23.88PCh. 23 - Prob. 23.89PCh. 23 - Prob. 23.90PCh. 23 - Prob. 23.91PCh. 23 - Prob. 23.92PCh. 23 - Prob. 23.93PCh. 23 - Prob. 23.94PCh. 23 - Prob. 23.95PCh. 23 - Prob. 23.96PCh. 23 - Prob. 23.97PCh. 23 - Prob. 23.1YTCh. 23 - Prob. 23.2YTCh. 23 - Prob. 23.3YTCh. 23 - Prob. 23.4YTCh. 23 - Prob. 23.5YTCh. 23 - Prob. 23.6YTCh. 23 - Prob. 23.7YTCh. 23 - Prob. 23.8YTCh. 23 - Prob. 23.9YTCh. 23 - Prob. 23.10YTCh. 23 - Prob. 23.11YTCh. 23 - Prob. 23.12YTCh. 23 - Prob. 23.13YTCh. 23 - Prob. 23.14YT
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