ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Chapter 18, Problem 18.63P

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

a. Chapter 18, Problem 18.63P, 18.63 Synthesize each compound from benzene and any other organic or inorganic reagents.
	a. 	c. 	e. , example  1 c. Chapter 18, Problem 18.63P, 18.63 Synthesize each compound from benzene and any other organic or inorganic reagents.
	a. 	c. 	e. , example  2 e. Chapter 18, Problem 18.63P, 18.63 Synthesize each compound from benzene and any other organic or inorganic reagents.
	a. 	c. 	e. , example  3 g. Chapter 18, Problem 18.63P, 18.63 Synthesize each compound from benzene and any other organic or inorganic reagents.
	a. 	c. 	e. , example  4

b. Chapter 18, Problem 18.63P, 18.63 Synthesize each compound from benzene and any other organic or inorganic reagents.
	a. 	c. 	e. , example  5 d. Chapter 18, Problem 18.63P, 18.63 Synthesize each compound from benzene and any other organic or inorganic reagents.
	a. 	c. 	e. , example  6 f. Chapter 18, Problem 18.63P, 18.63 Synthesize each compound from benzene and any other organic or inorganic reagents.
	a. 	c. 	e. , example  7 h. Chapter 18, Problem 18.63P, 18.63 Synthesize each compound from benzene and any other organic or inorganic reagents.
	a. 	c. 	e. , example  8

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 18.63P

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

ORGANIC CHEMISTRY, Chapter 18, Problem 18.63P , 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 18.63P , additional homework tip  2

Figure 1

The synthesis of given compound takes place by chlorination of benzene, Friedel-Craft acylation and clemmensen reduction at last step.

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 18.63P

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

ORGANIC CHEMISTRY, Chapter 18, Problem 18.63P , 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 18.63P , additional homework tip  4

Figure 2

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 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 18.63P

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

ORGANIC CHEMISTRY, Chapter 18, Problem 18.63P , 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 18.63P , additional homework tip  6

Figure 3

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 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 18.63P

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

ORGANIC CHEMISTRY, Chapter 18, Problem 18.63P , 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 18.63P , additional homework tip  8

Figure 4

The first step of the synthesis is Friedel-Craft alkylation reaction. The product of this reaction undergoes nitration reaction. In next step, the CH3 group on reaction with KMnO4 changes to COOH group and NO2 group on reaction with Sn,HCl changes to NH2.

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 18.63P

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

ORGANIC CHEMISTRY, Chapter 18, Problem 18.63P , 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 18.63P , additional homework tip  10

Figure 5

Benzene undergoes nitration on reaction with conc.HNO3,H2SO4 and leads to the formation of nitrobenzene. The nitro group changes to NH2 on reaction with Sn,HCl. The product obtained by the bromination of aniline on Friedel-Craft acylation, followed by clemmensen reduction, leads to the formation of desired 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 18.63P

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

ORGANIC CHEMISTRY, Chapter 18, Problem 18.63P , 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 18.63P , additional homework tip  12

Figure 6

Benzene on Friedel-Craft alkylation with ethylchloride gives ethylbenzene. This product undergoes bromination in presence of light. The next step involves the abstraction of bromine on reaction with tertiary butoxide. This leads to the formation of C=C bond. The Friedel-Craft acylation followed by clemmensen reduction and chlorination of this product leads to the formation of given compound.

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 18.63P

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

ORGANIC CHEMISTRY, Chapter 18, Problem 18.63P , 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 7.

ORGANIC CHEMISTRY, Chapter 18, Problem 18.63P , additional homework tip  14

Figure 7

The first two steps involved in the synthesis of given compound are Friedel-Craft alkylation followed by chlorination in the presence of light. The chlorine group is replaced by hydroxyl group on reaction with KOH. This product undergoes reaction with CH3(CH2)3I in presence of NaH, followed by Friedel-Craft acylation and bromination.

Conclusion

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

Expert Solution
Check Mark
Interpretation Introduction

(h)

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 18.63P

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

ORGANIC CHEMISTRY, Chapter 18, Problem 18.63P , additional homework tip  15

Explanation of Solution

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 8.

ORGANIC CHEMISTRY, Chapter 18, Problem 18.63P , additional homework tip  16

Figure 8

Benzene on Friedel-Craft alkylation with ethylchloride gives ethylbenzene. This product undergoes bromination in presence of light. The next step involves the abstraction of bromine on reaction with tertiary butoxide. This leads to the formation of C=C bond. The product further reacts with OsO4 and gives rise to diol. The Friedel-Craft acylation and nitration of this product leads to the formation of given compound.

Conclusion

The synthesis of given compound from benzene and any other organic or inorganic reagent is shown in Figure 8.

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Chapter 18 Solutions

ORGANIC CHEMISTRY

Ch. 18 - Prob. 18.11PCh. 18 - Prob. 18.12PCh. 18 - Prob. 18.13PCh. 18 - Problem 18.14 Draw all resonance structures for...Ch. 18 - Problem 18.15 Classify each substituent as...Ch. 18 - Prob. 18.16PCh. 18 - Problem 18.17 Label each compound as more or less...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 - Problem 18.22 Draw the products formed when each...Ch. 18 - Problem 18.23 Devise a synthesis of each compound...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 - Problem 18.33 Synthesize each compound from...Ch. 18 - Prob. 18.34PCh. 18 - 18.35 What is the major product formed by an...Ch. 18 - 18.36 Draw the products formed when phenol is...Ch. 18 - Problem 18.37 Draw the products formed when each...Ch. 18 - 18.38 Draw the products of each reaction. a. d....Ch. 18 - 18.39 What products are formed when benzene is...Ch. 18 - 18.40 Draw the products of each reaction. c. d....Ch. 18 - 18.41 You have learned two ways to make an alkyl...Ch. 18 - 18.42 Draw the structure of A, an intermediate in...Ch. 18 - Prob. 18.43PCh. 18 - Prob. 18.44PCh. 18 - 18.45 Explain why each of the following reactions...Ch. 18 - Prob. 18.46PCh. 18 - 18.47 For each of the following substituted...Ch. 18 - 18.48 Consider the tetracyclic aromatic compound...Ch. 18 - 18.49 For each N-substituted benzene, predict...Ch. 18 - Prob. 18.50PCh. 18 - 18.51 Using resonance structures, explain why a...Ch. 18 - Prob. 18.52PCh. 18 - 18.53 Rank the aryl halides in each group in order...Ch. 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 - Prob. 18.59PCh. 18 - Prob. 18.60PCh. 18 - Prob. 18.61PCh. 18 - Prob. 18.62PCh. 18 - 18.63 Synthesize each compound from benzene and...Ch. 18 - Problem 18.64 Synthesize each compound from...Ch. 18 - Prob. 18.65PCh. 18 - Prob. 18.66PCh. 18 - Prob. 18.67PCh. 18 - Prob. 18.68PCh. 18 - Problem 18.69 Identify the structures of isomers A...Ch. 18 - Prob. 18.70PCh. 18 - Problem 18.71 Compound X (molecular formula ) was...Ch. 18 - 18.72 Reaction of p-cresol with two equivalents of...Ch. 18 - Prob. 18.73PCh. 18 - The NMR spectrum of phenol () shows three...Ch. 18 - Explain the reactivity and orientation effects...Ch. 18 - Prob. 18.76PCh. 18 - Prob. 18.77PCh. 18 - Prob. 18.78PCh. 18 - Prob. 18.79P
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