Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 15, Problem 1LGP
The structure of thyroxine, a thyroid hormone that helps to regulate
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A common illicit synthesis of methamphetamine involves an interesting variation of the Birch reduction. A solution of ephedrine in alcohol is added to liquid ammonia, followed by several pieces of lithium metal. The Birch reduction usually reduces the aromatic ring, but in this case it eliminates the hydroxy group of ephedrine to give methamphetamine. Propose a mechanism, similar to that for the Birch reduction, to explain this unusual course of the reaction.
Carbonyl compounds can be protonated on the carbonyl oxygen. Protonation of the carbonyl oxygen gives a species whose positive charge is delocalized by resonance. Explain why acetic acid (ethanoic acid) is more readily protonated than acetone (propanone).
Starting with Benzene (or naphthalene or biphenyl) Show a sequence of 3 electrophilic aromatic substitution reactions. And the intermediates and products Each EAS reaction must introduce a different group on the ring
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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