Organic Chemistry-Package(Custom)
Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 18, Problem 18.22P
Interpretation Introduction

(a)

Interpretation:

The products formed by the treatment of given compound with HNO3 and H2SO4 are to be drawn.

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.

Expert Solution
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Answer to Problem 18.22P

The products formed by the treatment of given compound with HNO3 and H2SO4 are drawn below.

Organic Chemistry-Package(Custom), Chapter 18, Problem 18.22P , additional homework tip  1

Explanation of Solution

The aromatic compound on reaction with HNO3 in presence of H2SO4 undergoes nitration reaction. The electron withdrawing groups present on a benzene ring direct NO2 group to meta position whereas electron donating groups direct it to ortho and para position.

The structure of given compound shows that benzene ring is substituted by OCH3 and CH3OC(O) groups. The OCH3 and CH3OC(O) groups are electron releasing and electron withdrawing, respectively. The nitration of given compound takes place ortho to OCH3 group and meta to CH3OC(O) group. The product formed by the treatment of given compound with HNO3 and H2SO4 is shown in Figure 1.

Organic Chemistry-Package(Custom), Chapter 18, Problem 18.22P , additional homework tip  2

Figure 1

Conclusion

The products formed by the treatment of given compound with HNO3 and H2SO4 are shown in Figure 1.

Interpretation Introduction

(b)

Interpretation:

The products formed by the treatment of given compound with HNO3 and H2SO4 are to be drawn.

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.

Expert Solution
Check Mark

Answer to Problem 18.22P

The products formed by the treatment of given compound with HNO3 and H2SO4 are drawn below.

Organic Chemistry-Package(Custom), Chapter 18, Problem 18.22P , additional homework tip  3

Explanation of Solution

The aromatic compound on reaction with HNO3 in presence of H2SO4 undergoes nitration reaction. The electron withdrawing groups present on a benzene ring direct NO2 group to meta position whereas electron donating groups direct it to ortho and para position.

The structure of given compound shows that benzene ring is substituted by OCH3 and Br groups. The OCH3 and Br groups are electron releasing and electron withdrawing, respectively. However, Br directs incoming nitro group to ortho and para position. The productd formed by the treatment of given compound with HNO3 and H2SO4 are shown in Figure 2.

Organic Chemistry-Package(Custom), Chapter 18, Problem 18.22P , additional homework tip  4

Figure 2

Conclusion

The products formed by the treatment of given compound with HNO3 and H2SO4 are shown in Figure 2.

Interpretation Introduction

(c)

Interpretation:

The products formed by the treatment of given compound with HNO3 and H2SO4 are to be drawn.

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.

Expert Solution
Check Mark

Answer to Problem 18.22P

The products formed by the treatment of given compound with HNO3 and H2SO4 are drawn below.

Organic Chemistry-Package(Custom), Chapter 18, Problem 18.22P , additional homework tip  5

Explanation of Solution

The aromatic compound on reaction with HNO3 in presence of H2SO4 undergoes nitration reaction. The electron withdrawing groups present on a benzene ring direct NO2 group to meta position whereas electron donating groups direct it to ortho and para position.

The structure of given compound shows that benzene ring is substituted by CH3 and NO2 groups. The CH3 and NO2 groups are electron releasing and electron withdrawing, respectively. The nitration of given compound takes place ortho and para to CH3 group and meta to NO2 group. The product formed by the treatment of given compound with HNO3 and H2SO4 is shown in Figure 3.

Organic Chemistry-Package(Custom), Chapter 18, Problem 18.22P , additional homework tip  6

Figure 3

Conclusion

The products formed by the treatment of given compound with HNO3 and H2SO4 are shown in Figure 3.

Interpretation Introduction

(d)

Interpretation:

The products formed by the treatment of given compound with HNO3 and H2SO4 are to be drawn.

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.

Expert Solution
Check Mark

Answer to Problem 18.22P

The products formed by the treatment of given compound with HNO3 and H2SO4 are drawn below.

Organic Chemistry-Package(Custom), Chapter 18, Problem 18.22P , additional homework tip  7

Explanation of Solution

The aromatic compound on reaction with HNO3 in presence of H2SO4 undergoes nitration reaction. The electron withdrawing groups present on a benzene ring direct NO2 group to meta position whereas electron donating groups direct it to ortho and para position.

The structure of given compound shows that benzene ring is substituted by Cl and Br groups. The Cl and Br groups are electron withdrawing groups. However, they directs the incoming nitro group to ortho and meta position. The products formed by the treatment of given compound with HNO3 and H2SO4 are shown in Figure 4.

Organic Chemistry-Package(Custom), Chapter 18, Problem 18.22P , additional homework tip  8

Figure 4

Conclusion

The products formed by the treatment of given compound with HNO3 and H2SO4 are shown in Figure 4.

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Chapter 18 Solutions

Organic Chemistry-Package(Custom)

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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