Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 18, Problem 18.15P
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
Check Mark

Answer to Problem 18.15P

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

Organic Chemistry, Chapter 18, Problem 18.15P , 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 18.15P , 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 18.15P

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

Organic Chemistry, Chapter 18, Problem 18.15P , 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 18.15P , 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 18.15P

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

Organic Chemistry, Chapter 18, Problem 18.15P , additional homework tip  5

Organic Chemistry, Chapter 18, Problem 18.15P , 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 18.15P , 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 18.15P

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

Organic Chemistry, Chapter 18, Problem 18.15P , additional homework tip  8

Organic Chemistry, Chapter 18, Problem 18.15P , 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 18.15P , 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 18.15P

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

Organic Chemistry, Chapter 18, Problem 18.15P , additional homework tip  11

Organic Chemistry, Chapter 18, Problem 18.15P , 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 18.15P , 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 - 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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