Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 18, Problem 18.64P

Synthesize each compound from benzene and any other organic or inorganic reagents.

a. o butylchlorobenzene

b. m bromonitrobenzene

c. Chapter 18, Problem 18.64P, Synthesize each compound from benzene and any other organic or inorganic reagents. a. , example  1 d. Chapter 18, Problem 18.64P, Synthesize each compound from benzene and any other organic or inorganic reagents. a. , example  2 e. Chapter 18, Problem 18.64P, Synthesize each compound from benzene and any other organic or inorganic reagents. a. , example  3 f. Chapter 18, Problem 18.64P, Synthesize each compound from benzene and any other organic or inorganic reagents. a. , example  4 g. Chapter 18, Problem 18.64P, Synthesize each compound from benzene and any other organic or inorganic reagents. a. , example  5

Expert Solution
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Interpretation Introduction

(a)

Interpretation: The synthesis of given compound from benzene and any other organic or inorganic reagent is to be stated.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron deficient chemical species that contains positive charge are known as electrophile. In electrophilic aromatic substitution reaction, electrophile takes the position of hydrogen atom by attacking the electron rich carbon atom of benzene.

Answer to Problem 18.64P

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown below:

Organic Chemistry, Chapter 18, Problem 18.64P , additional homework tip  1

Explanation of Solution

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 1.

Organic Chemistry, Chapter 18, Problem 18.64P , additional homework tip  2

Figure 1

The first step in the synthesis is the chlorination of benzene. The next step is the Friedel-Craft acylation in which chlorobenzene reacts with butnoyl chloride. The last step is the clemmensen reduction to form the desired product.

Conclusion

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 1.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The synthesis of given compound from benzene and any other organic or inorganic reagent is to be stated.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron deficient chemical species that contains positive charge are known as electrophile. In electrophilic aromatic substitution reaction, electrophile takes the position of hydrogen atom by attacking the electron rich carbon atom of benzene.

Answer to Problem 18.64P

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown below:

Organic Chemistry, Chapter 18, Problem 18.64P , additional homework tip  3

Explanation of Solution

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 2.

Organic Chemistry, Chapter 18, Problem 18.64P , additional homework tip  4

Figure 2

The first step in the synthesis is the formation of nitrobenzene. The next step is the reaction of nitrobenzene with bromine in the presence of aluminum chloride to give the final product.

Conclusion

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 2.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The synthesis of given compound from benzene and any other organic or inorganic reagent is to be stated.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron deficient chemical species that contains positive charge are known as electrophile. In electrophilic aromatic substitution reaction, electrophile takes the position of hydrogen atom by attacking the electron rich carbon atom of benzene.

Answer to Problem 18.64P

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown below.

Organic Chemistry, Chapter 18, Problem 18.64P , additional homework tip  5

Explanation of Solution

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 3.

Organic Chemistry, Chapter 18, Problem 18.64P , additional homework tip  6

Figure 3

The first step in the synthesis is the conversion of benzene into toluene. The next step is the reaction of toluene with concentrated sulfuric acid which results the addition of sulphonyl group at ortho position. The last step is the oxidation of methyl group into acid in the presence of potassium permanganate to give the final product.

Conclusion

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 3.

Expert Solution
Check Mark
Interpretation Introduction

(d)

Interpretation: The synthesis of given compound from benzene and any other organic or inorganic reagent is to be stated.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron deficient chemical species that contains positive charge are known as electrophile. In electrophilic aromatic substitution reaction, electrophile takes the position of hydrogen atom by attacking the electron rich carbon atom of benzene.

Answer to Problem 18.64P

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown below:

Organic Chemistry, Chapter 18, Problem 18.64P , additional homework tip  7

Explanation of Solution

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 4.

Organic Chemistry, Chapter 18, Problem 18.64P , additional homework tip  8

Figure 4

The first step in the synthesis is the conversion of benzene into toluene. The next step is the oxidation of methyl group into acid in the presence of potassium permanganate to give benzoic acid followed by the reaction with methanol to form methyl benzoate. The reaction of nitric acid in the presence of sulphuric acid results in the formation of final product.

Conclusion

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 4.

Expert Solution
Check Mark
Interpretation Introduction

(e)

Interpretation: The synthesis of given compound from benzene and any other organic or inorganic reagent is to be stated.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron deficient chemical species that contains positive charge are known as electrophile. In electrophilic aromatic substitution reaction, electrophile takes the position of hydrogen atom by attacking the electron rich carbon atom of benzene.

Answer to Problem 18.64P

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown below:

Organic Chemistry, Chapter 18, Problem 18.64P , additional homework tip  9

Explanation of Solution

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 5.

Organic Chemistry, Chapter 18, Problem 18.64P , additional homework tip  10

Figure 5

The first step in the synthesis is the conversion of benzene into toluene. The next step is the reaction of toluene with bromine in the presence of aluminum chloride. The last step is the oxidation of methyl group into acid in the presence of potassium permanganate to give the final product.

Conclusion

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 5.

Expert Solution
Check Mark
Interpretation Introduction

(f)

Interpretation: The synthesis of given compound from benzene and any other organic or inorganic reagent is to be stated.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron deficient chemical species that contains positive charge are known as electrophile. In electrophilic aromatic substitution reaction, electrophile takes the position of hydrogen atom by attacking the electron rich carbon atom of benzene.

Answer to Problem 18.64P

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown below:

Organic Chemistry, Chapter 18, Problem 18.64P , additional homework tip  11

Explanation of Solution

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 6.

Organic Chemistry, Chapter 18, Problem 18.64P , additional homework tip  12

Figure 6

The synthesis of given compound take place in four steps: Friedel-Craft alkylation, sulfonation, chlorination and at last oxidation.

Conclusion

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 6.

Expert Solution
Check Mark
Interpretation Introduction

(g)

Interpretation: The synthesis of given compound from benzene and any other organic or inorganic reagent is to be stated.

Concept introduction: The replacement or substitution of one functional group with another different functional group in any chemical reaction is termed as substitution reaction. The electron deficient chemical species that contains positive charge are known as electrophile. In electrophilic aromatic substitution reaction, electrophile takes the position of hydrogen atom by attacking the electron rich carbon atom of benzene.

Answer to Problem 18.64P

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown below:

Organic Chemistry, Chapter 18, Problem 18.64P , additional homework tip  13

Explanation of Solution

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 3.

Organic Chemistry, Chapter 18, Problem 18.64P , additional homework tip  14

Figure 7

The first, second, third and fourth step involved in the synthesis of given compound is chlorination, Friedel-Craft acylation, Wittig reaction and nitration, respectively.

Conclusion

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 7.

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Chapter 18 Solutions

Organic Chemistry

Ch. 18 - Prob. 18.11PCh. 18 - Prob. 18.12PCh. 18 - Problem 18.14 Draw all resonance structures for...Ch. 18 - Classify each substituent as electron donating or...Ch. 18 - Prob. 18.15PCh. 18 - Label each compound as more or less reactive than...Ch. 18 - Rank the following compounds in order of...Ch. 18 - Problem 18.18 Rank the following compounds in...Ch. 18 - Prob. 18.19PCh. 18 - Problem 18.20 Draw the products of each...Ch. 18 - Prob. 18.21PCh. 18 - Prob. 18.22PCh. 18 - Devise a synthesis of each compound from the...Ch. 18 - Problem 18.24 Draw the products of each...Ch. 18 - Problem 18.25 Draw a stepwise mechanism for the...Ch. 18 - Problem 18.26 Draw the products of each...Ch. 18 - Prob. 18.27PCh. 18 - Prob. 18.28PCh. 18 - Problem 18.29 How could you use ethylbenzene to...Ch. 18 - Prob. 18.30PCh. 18 - Problem 18.31 What steps are needed to convert...Ch. 18 - Problem 18.32 Synthesize each compound from...Ch. 18 - Synthesize each compound from benzene.Ch. 18 - Prob. 18.34PCh. 18 - 18.35 What is the major product formed by an...Ch. 18 - Draw the products formed when phenol (C6H5OH) is...Ch. 18 - Prob. 18.37PCh. 18 - Draw the products of each reaction. a. e. i. b. f....Ch. 18 - What products are formed when benzene is treated...Ch. 18 - Draw the products of each reaction. a.d. b.e. c.f.Ch. 18 - You have learned two ways to make an alkyl...Ch. 18 - Prob. 18.42PCh. 18 - Prob. 18.43PCh. 18 - 18.45 Explain why each of the following reactions...Ch. 18 - Prob. 18.45PCh. 18 - 18.47 For each of the following substituted...Ch. 18 - Which benzene ring in each compound is more...Ch. 18 - 18.49 For each N-substituted benzene, predict...Ch. 18 - Explain each statement in detail using resonance...Ch. 18 - Prob. 18.50PCh. 18 - Explain why the meta product is formed in the...Ch. 18 - 18.53 Rank the aryl halides in each group in order...Ch. 18 - Prob. 18.53PCh. 18 - 18.54 Draw a stepwise mechanism for the following...Ch. 18 - Prob. 18.55PCh. 18 - 18.56 Draw a stepwise, detailed mechanism for the...Ch. 18 - Prob. 18.57PCh. 18 - 18.58 Draw a stepwise mechanism for the following...Ch. 18 - Draw a stepwise mechanism for the following...Ch. 18 - Prob. 18.60PCh. 18 - Draw a stepwise mechanism for the following...Ch. 18 - Prob. 18.62PCh. 18 - Prob. 18.63PCh. 18 - Synthesize each compound from benzene and any...Ch. 18 - Synthesize each compound from benzene and any...Ch. 18 - Synthesize each compound from toluene (C6H5CH3)...Ch. 18 - Prob. 18.67PCh. 18 - Use the reactions in this chapter along with those...Ch. 18 - Prob. 18.69PCh. 18 - Prob. 18.70PCh. 18 - Problem 18.69 Identify the structures of isomers A...Ch. 18 - Prob. 18.72PCh. 18 - Problem 18.71 Compound X (molecular formula ) was...Ch. 18 - Prob. 18.74PCh. 18 - The NMR spectrum of phenol () shows three...Ch. 18 - Explain the reactivity and orientation effects...Ch. 18 - Prob. 18.77PCh. 18 - Prob. 18.78PCh. 18 - Prob. 18.79PCh. 18 - Prob. 18.80P
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