Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Textbook Question
Chapter 15, Problem 27P
Starting with aniline, outline a synthesis of each of the following:
(a) p-Bromoaniline
(b) o-Bromoaniline
(c) 2-Bromo-4-nitroaniline
(d) 4-Bromo-2-nitroaniline
(e) 2,4,6-Tribromoaniline
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Chapter 15 Solutions
Organic Chemistry
Ch. 15 - PRACTICE PROBLEM 15.1
Show how loss of a proton...Ch. 15 - Prob. 2PPCh. 15 - PRACTICE PROBLEM 15.3
Outline all steps in a...Ch. 15 - PRACTICE PROBLEM 15.4 Provide a mechanism that...Ch. 15 - Prob. 5PPCh. 15 - Prob. 6PPCh. 15 - Prob. 7PPCh. 15 - PRACTICE PROBLEM 15.8 Write resonance structures...Ch. 15 - PRACTICE PROBLEM 15.9
Provide a mechanism for the...Ch. 15 - PRACTICE PROBLEM 15.10 The trifluoromethyl group...
Ch. 15 - PRACTICE PROBLEM 15.11
Predict the major products...Ch. 15 - PRACTICE PROBLEM 15.12 Predict the major product...Ch. 15 - PRACTICE PROBLEM 15.13
Write mechanisms for the...Ch. 15 - Prob. 14PPCh. 15 - PRACTICE PROBLEM 15.15
Suppose you needed to...Ch. 15 - PRACTICE PROBLEM 15.16 1-Fluoro-2,4-dinitrobenzene...Ch. 15 - Prob. 17PPCh. 15 - PRACTICE PROBLEM 15.18
When...Ch. 15 - PRACTICE PROBLEM 15.19 Birch reduction of toluene...Ch. 15 - Prob. 20PCh. 15 - Prob. 21PCh. 15 - What monobromination product (or products) would...Ch. 15 - 15.23 Predict the major products of the following...Ch. 15 - Prob. 24PCh. 15 - 15.25 Starting with styrene, outline a synthesis...Ch. 15 - Prob. 26PCh. 15 - 15.27 Starting with aniline, outline a synthesis...Ch. 15 - Prob. 28PCh. 15 - Propose structures for compounds GI:Ch. 15 - 2,6-Dichlorophenol has been isolated from the...Ch. 15 - Prob. 31PCh. 15 - 15.32 Give structures (including stereochemistry...Ch. 15 - Provide a detailed mechanism for each of the...Ch. 15 - 15.34 Provide a detailed mechanism for the...Ch. 15 - Prob. 35PCh. 15 - Many polycyclic aromatic compounds have been...Ch. 15 - Prob. 37PCh. 15 - Prob. 38PCh. 15 - Prob. 39PCh. 15 - Prob. 40PCh. 15 - Predict the product of the following reaction.Ch. 15 - 15.42 When m-chlorotoluene is treated with sodium...Ch. 15 - Prob. 43PCh. 15 - Prob. 44PCh. 15 - Prob. 45PCh. 15 - Prob. 46PCh. 15 - 15.47 Provide structures for compounds A and B:
Ch. 15 - Prob. 48PCh. 15 - 15.49 Treating cyclohexene with acetyl chloride...Ch. 15 - 15.50 The tert-butyl group can be used as a...Ch. 15 - 15.51 When toluene is sulfonated (concentrated )...Ch. 15 - Prob. 52PCh. 15 - 2-Methylnaphthalene can be synthesized from...Ch. 15 - Prob. 54PCh. 15 - Prob. 55PCh. 15 - Prob. 56PCh. 15 - Prob. 57PCh. 15 - Prob. 58PCh. 15 - Furan undergoes electrophilic aromatic...Ch. 15 - A C-D bond is harder to break than a C-H bond,...Ch. 15 - 15.61 Acetanilide was subjected to the following...Ch. 15 - Prob. 62PCh. 15 - Prob. 63PCh. 15 - Prob. 64PCh. 15 - When compound C, which is often used to model a...Ch. 15 - Open the molecular model file for benzyne and...Ch. 15 - The structure of thyroxine, a thyroid hormone that...Ch. 15 - Prob. 2LGPCh. 15 - 3. Deduce the structures of compounds E–L in the...
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- Show how to prepare the following aromatic amines by aromatic nitration, followed by reduction. You may use benzene andtoluene as your aromatic starting materials. (c) m-bromoaniline (d) m-aminobenzoic acidarrow_forwardShow how to prepare the following aromatic amines by aromatic nitration, followed by reduction. You may use benzene andtoluene as your aromatic starting materials.(a) anilinarrow_forwardWrite a balanced chemical equation for each of the following reactions: (a) Phenol + sodium hydroxide (b) Product of part (a) + ethyl bromide (c) Product of part (a) + butyl p-toluenesulfonate (d) Product of part (a) + acetic anhydride (e) o-Cresol + benzoyl chloride (f) m-Cresol + ethylene oxide (g) 2,6-Dichlorophenol + bromine (h) p-Cresol + excess aqueous bromine (i) Isopropyl phenyl ether + excess hydrogen bromide + heatarrow_forward
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- Write a structural formula for each of the following compounds: (a) m-Chlorobenzoyl chloride (b) Trifluoroacetic anhydride (c) cis-1,2-Cyclopropanedicarboxylic anhydride (d) Ethyl cycloheptanecarboxylate (e) 1-Phenylethyl acetate (f) 2-Phenylethyl acetate (g) p-Ethylbenzamide (h) N-Ethylbenzamide (i) 2-Methylhexanenitrilearrow_forwardEach of the following is a much weaker base than aniline. Present a resonance argument to explain the effect of the substituent in each case. (a) o-Cyanoaniline (c) p-Aminoacetophenonearrow_forwardShow how to synthesize the following amines from the indicated starting materials byacylation–reduction.(a) N-butylpiperidine from piperidinearrow_forward
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