Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 15, Problem 18PP
PRACTICE PROBLEM
1-Chloro-3-methyl-2-butene undergoes hydrolysis in a mixture of water and dioxane at a rate that is more than a thousand times that of 1-chloro-2-butene.
(a) What factor accounts for the difference in reactivity?
(b) What products would you expect to obtain? [Dioxane is a cyclic ether (below) that is miscible with water in all proportions and is a useful cosolvent for conducting reactions like these. Dioxane is carcinogenic (i.e., cancer causing), however, and like most ethers, it tends to form peroxides.]
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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 - PRACTICE PROBLEM
15.6 Explain how the percentages...Ch. 15 - PRACTICE PROBLEM
15.7
Predict the major products...Ch. 15 - Prob. 8PPCh. 15 - Prob. 9PPCh. 15 - Prob. 10PP
Ch. 15 - PRACTICE PROBLEM 15.8 Write resonance structures...Ch. 15 - PRACTICE PROBLEM 15.9
Provide a mechanism for the...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 Predict the major product...Ch. 15 - PRACTICE PROBLEM Account for the following...Ch. 15 - PRACTICE PROBLEM 1-Chloro-3-methyl-2-butene...Ch. 15 - Prob. 19PPCh. 15 - PRACTICE PROBLEM
15.20 The following chlorides (Ph...Ch. 15 - Prob. 21PPCh. 15 - Provide a detailed mechanism for each of the...Ch. 15 - 15.34 Provide a detailed mechanism for the...Ch. 15 - Prob. 24PCh. 15 - Many polycyclic aromatic compounds have been...Ch. 15 - Prob. 26PCh. 15 - Prob. 27PCh. 15 - Predict the major product (or products) formed...Ch. 15 - Prob. 29PCh. 15 - Prob. 30PCh. 15 - Predict the major products of the following...Ch. 15 - Prob. 32PCh. 15 - Prob. 33PCh. 15 - Prob. 34PCh. 15 - Starting with aniline, outline a synthesis of each...Ch. 15 - Prob. 36PCh. 15 - 15.37 Propose structures for compounds G–I:
Ch. 15 - 2,6-Dichlorophenol has been isolated from the...Ch. 15 - 2-Methylnaphthalene can be synthesized from...Ch. 15 - Show how you might synthesize each of the...Ch. 15 - Prob. 41PCh. 15 - Prob. 42PCh. 15 - 15.47 Provide structures for compounds A and B:
Ch. 15 - Prob. 44PCh. 15 - Prob. 45PCh. 15 - Treating cyclohexene with acetyl chloride and...Ch. 15 - 15.47 The tert-butyl group can be used as a...Ch. 15 - When toluene is sulfonated (concentrated H2SO4) at...Ch. 15 - Prob. 49PCh. 15 - 15.50 Heating 1,1,1-triphenylmethanol with ethanol...Ch. 15 - 15.51
(a) Which of the following halides would you...Ch. 15 - Furan undergoes electrophilic aromatic...Ch. 15 - 15.61 Acetanilide was subjected to the following...Ch. 15 - Prob. 54PCh. 15 - When compound C, which is often used to model a...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...Ch. 15 - Which of the following compounds would be most...Ch. 15 - 15.2 Which of the following is not a...Ch. 15 - Prob. 3QCh. 15 - Complete the following syntheses.
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