Organic Chemistry - With Access (Looseleaf) (Custom)
4th Edition
ISBN: 9781259726224
Author: SMITH
Publisher: MCG
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Chapter 18, Problem 18.80P
Interpretation Introduction
Interpretation: The stepwise mechanism for the given reaction is to be stated.
Concept introduction: The substitution reaction involves the replacement of one functional group by other functional group. In nucleophilic substitution an electron rich species attack the species that is deficient in electrons. The electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.
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The bicyclic heterocycles quinoline and indole undergo electrophilic aromatic substitution to give the products shown. (a) Explain why electrophilic substitution occurs on the ring without the N atom for quinoline, but occurs on the ring with the N atom in indole. (b) Explain why electrophilic substitution occurs more readily at C8 than C7 in quinoline. (c) Explain whyelectrophilic substitution occurs more readily at C3 rather than C2 of indole.
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meta director
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The bicyclic heterocycles quinoline and indole undergo electrophilic aromatic substitution to give the products shown. (a) Explain why electrophilic substitution occurs on the ring without the N atom for quinoline, but occurs on the ring with the N atom in indole. (b) Explain why electrophilic substitution occurs more readily at C8 than C7 in quinoline. (c) Explain why electrophilic substitution occurs more readily at C3 rather than C2 of indole.
Chapter 18 Solutions
Organic Chemistry - With Access (Looseleaf) (Custom)
Ch. 18 - Prob. 18.1PCh. 18 - Prob. 18.2PCh. 18 - Prob. 18.3PCh. 18 - Prob. 18.4PCh. 18 - Prob. 18.5PCh. 18 - What acid chloride would be needed to prepare each...Ch. 18 - Prob. 18.7PCh. 18 - Draw a stepwise mechanism for the following...Ch. 18 - Prob. 18.9PCh. 18 - Prob. 18.10P
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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