Organic Chemistry
Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 18, Problem 18.16P
Interpretation Introduction

(a)

Interpretation: The products formed when given compound is treated with HNO3 and H2SO4 are to be drawn. Whether the reaction occurs faster or slower than a similar reaction with benzene is to be stated.

Concept introduction: Benzene undergoes electrophile substitution. The kinetics of the electrophilic substitution reaction depends upon the nature of substituent present on the benzene ring. Electron releasing groups activates the ring towards the electrophilic substitution reaction while electron withdrawing groups deactivates the ring towards the electrophilic substitution reaction.

Expert Solution
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Answer to Problem 18.16P

The product formed by the reaction of given compound with HNO3 and H2SO4 is,

Organic Chemistry, Chapter 18, Problem 18.16P , additional homework tip  1

The reaction occurs slower because benzene ring contains deactivating group.

Explanation of Solution

Electron withdrawing groups deactivates the ring towards the electrophilic substitution reaction.

The substituent present in the given compound is electron withdrawing group. Thus, it directs the electrophile to meta position and deactivates the ring towards the electrophilic substitution reaction. Hence, the given compound reacts slower than benzene. The reaction is shown below.

Organic Chemistry, Chapter 18, Problem 18.16P , additional homework tip  2

Figure 1

Conclusion

The product formed by the reaction of given compound with HNO3 and H2SO4 is shown in Figure 1. The reaction occurs slower because benzene ring contains deactivating group.

Interpretation Introduction

(b)

Interpretation: The products formed when given compound is treated with HNO3 and H2SO4 are to be drawn. Whether the reaction occurs faster or slower than a similar reaction with benzene is to be stated.

Concept introduction: Benzene undergoes electrophile substitution. The kinetics of the electrophilic substitution reaction depends upon the nature of substituent present on the benzene ring. Electron releasing groups activates the ring towards the electrophilic substitution reaction while electron withdrawing groups deactivates the ring towards the electrophilic substitution reaction.

Expert Solution
Check Mark

Answer to Problem 18.16P

The product formed by the reaction of given compound with HNO3 and H2SO4 is,

Organic Chemistry, Chapter 18, Problem 18.16P , additional homework tip  3

The reaction occurs slower because benzene ring contains deactivating group.

Explanation of Solution

Electron withdrawing groups deactivates the ring towards the electrophilic substitution reaction.

The substituent present in the given compound is electron withdrawing group. Thus it directs the electrophile to meta position and deactivates the ring towards the electrophilic substitution reaction. Hence, the given compound reacts slower than benzene. The reaction is shown below.

Organic Chemistry, Chapter 18, Problem 18.16P , additional homework tip  4

Figure 2

Conclusion

The product formed by the reaction of given compound with HNO3 and H2SO4 is shown in Figure 2. The reaction occurs slower because benzene ring contains deactivating group.

Interpretation Introduction

(c)

Interpretation: The products formed when given compound is treated with HNO3 and H2SO4. is to be drawn. The reaction occurs faster or slower than a similar reaction with benzene is to be stated.

Concept introduction: Benzene undergoes electrophile substitution. The kinetics of the electrophile substitution reaction depends upon the nature of substituent present on the benzene ring. Electron releasing groups activates the ring towards the electrophilic substitution reaction while electron withdrawing groups deactivates the ring towards the electrophilic substitution reaction.

Expert Solution
Check Mark

Answer to Problem 18.16P

The product formed by the reaction of given compound with HNO3 and H2SO4 are,

Organic Chemistry, Chapter 18, Problem 18.16P , additional homework tip  5

Organic Chemistry, Chapter 18, Problem 18.16P , additional homework tip  6

The reaction occurs faster because benzene ring contains activating group.

Explanation of Solution

Electron releasing group directs the electrophile to ortho and para position.

The substituent present in the given compound is electron donating group. Thus, it directs the electrophile to ortho and para position and activates the ring towards the electrophilic substitution reaction. Hence, the given compound reacts faster than benzene. The reaction is shown below.

Organic Chemistry, Chapter 18, Problem 18.16P , additional homework tip  7

Figure 3

Conclusion

The product formed by the reaction of given compound with HNO3 and H2SO4 is shown in Figure 3. The reaction occurs faster because benzene ring contains activating group.

Interpretation Introduction

(d)

Interpretation: The products formed when given compound is treated with HNO3 and H2SO4 is to be drawn. The reaction occurs faster or slower than a similar reaction with benzene is to be stated.

Concept introduction: Benzene undergoes electrophile substitution. The kinetics of the electrophilic substitution reaction depends upon the nature of substituent present on the benzene ring. Electron releasing groups activates the ring towards the electrophilic substitution reaction while electron withdrawing groups deactivates the ring towards the electrophilic substitution reaction.

Expert Solution
Check Mark

Answer to Problem 18.16P

The products formed by the reaction of given compound with HNO3 and H2SO4 are,

Organic Chemistry, Chapter 18, Problem 18.16P , additional homework tip  8

Organic Chemistry, Chapter 18, Problem 18.16P , additional homework tip  9

The reaction occurs slower benzene ring because benzene ring contains deactivating group.

Explanation of Solution

The substituent present in the given compound is Cl. It contains lone pairs which participate in resonance as it shows mesomeric effect. The chlorine is more electronegative than carbon atom. It shows negative inductive effect.

Among these two cases, mesomeric effect predominates over inductive effect. Hence, chlorine on benzene ring acts as releasing group but deactivates the benzene ring due to its I effect.

Thus, it directs the electrophile to ortho and para position and deactivates the ring towards the electrophilic substitution reaction. Hence, the given compound reacts slower than benzene. The reaction is shown below.

Organic Chemistry, Chapter 18, Problem 18.16P , additional homework tip  10

Figure 4

Conclusion

The product formed by the reaction of given compound with HNO3 and H2SO4 is shown in Figure 4. The reaction occurs slower because benzene ring contains deactivating group.

Interpretation Introduction

(e)

Interpretation: The products formed when given compound is treated with HNO3 and H2SO4 is to be drawn. The reaction occurs faster or slower than a similar reaction with benzene is to be stated.

Concept introduction: Benzene undergoes electrophile substitution. The kinetics of the electrophile substitution reaction depends upon the nature of substituent present on the benzene ring. Electron releasing groups activates the ring towards the electrophilic substitution reaction while electron withdrawing groups deactivates the ring towards the electrophilic substitution reaction.

Expert Solution
Check Mark

Answer to Problem 18.16P

The products formed by the reaction of given compound with HNO3 and H2SO4 are,

Organic Chemistry, Chapter 18, Problem 18.16P , additional homework tip  11

Organic Chemistry, Chapter 18, Problem 18.16P , additional homework tip  12

The reaction occurs higher because benzene ring contains activating group.

Explanation of Solution

Electron releasing group directs the electrophile to ortho and para positions.

The substituent present in the given compound is electron withdrawing group. Thus it directs the electrophile to ortho and para positions and activates the ring towards the electrophilic substitution reaction. Hence, the given compound reacts faster than benzene. The reaction is shown below.

Organic Chemistry, Chapter 18, Problem 18.16P , additional homework tip  13

Figure 5

Conclusion

The product formed by the reaction of given compound with HNO3 and H2SO4 is shown in Figure 5. The reaction occurs faster because benzene ring contains activating group.

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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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