Organic Chemistry

7th Edition

ISBN: 9780321803221

Author: Paula Y. Bruice

Publisher: Prentice Hall

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Reactions of Ethers

Ethers (R-O-R’) are compounds formed by replacing hydrogen atoms of an alcohol (R-OH compound) or a phenol (C6H5OH) by an aryl/ acyl group (functional group after removing single hydrogen from an aromatic ring). In this section, reaction, preparation and…

Epoxides

Epoxides are a special class of cyclic ethers which are an important functional group in organic chemistry and generate reactive centers due to their unusual high reactivity. Due to their high reactivity, epoxides are considered to be toxic and mutagenic…

Williamson Ether Synthesis

An organic reaction in which an organohalide and a deprotonated alcohol forms ether is known as Williamson ether synthesis. Alexander Williamson developed the Williamson ether synthesis in 1850. The formation of ether in this synthesis is an SN2 reaction…

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Textbook Question

Chapter 11.7, Problem 25P

Would you expect the reactivity of a five-membered ring ether such as tetrahydrofuran (Table 10.2) to be more similar to the reactivity of an epoxide or to the reactivity of a noncyclic ether? Why?

Chapter 11.7, Problem 25P, Would you expect the reactivity of a five-membered ring ether such as tetrahydrofuran (Table 10.2)

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Chapter 11.7, Problem 24P

Chapter 11.7, Problem 26P

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Chapter 11 Solutions

Organic Chemistry

Ch. 11.1 - Why are NH3 and CH3NH2 no longer nucleophiles when...Ch. 11.1 - Prob. 2P Ch. 11.1 - Prob. 5P Ch. 11.2 - Prob. 7P Ch. 11.3 - Prob. 9P Ch. 11.3 - Show how 1-propanol can be converted into the...Ch. 11.4 - Which of the following alcohols dehydrates the...Ch. 11.4 - Prob. 12P Ch. 11.4 - Prob. 13P Ch. 11.4 - Propose a mechanism for each of the following...

Ch. 11.4 - Draw the product of each of the following...Ch. 11.4 - Explain why the following alcohols, when heated...Ch. 11.4 - What stereoisomers are formed in the following...Ch. 11.4 - Prob. 18P Ch. 11.4 - What alcohol would you treat with phosphorus...Ch. 11.5 - Prob. 20P Ch. 11.6 - Prob. 22P Ch. 11.7 - Prob. 24P Ch. 11.7 - Would you expect the reactivity of a five-membered...Ch. 11.7 - Prob. 26P Ch. 11.7 - What products are obtained from the reaction of...Ch. 11.7 - Prob. 28P Ch. 11.7 - Prob. 29P Ch. 11.7 - Prob. 30P Ch. 11.8 - Prob. 31P Ch. 11.8 - Prob. 32P Ch. 11.8 - How do the major products obtained from...Ch. 11.8 - Explain why the two arene oxides in Problem 38...Ch. 11.8 - Three arene oxides can be obtained from...Ch. 11.9 - Explain why the half-life (the time it takes for...Ch. 11.10 - Prob. 38P Ch. 11.10 - Prob. 39P Ch. 11.10 - Prob. 40P Ch. 11.10 - Prob. 41P Ch. 11.10 - Prob. 42P Ch. 11.11 - Using an alkyl halide and a thiol as starting...Ch. 11.11 - The following three nitrogen mustards were studied...Ch. 11.11 - Why is melphalan a good cancer drug?Ch. 11.11 - Prob. 47P Ch. 11 - Prob. 48P Ch. 11 - Which compound is more likely to be carcinogenic?Ch. 11 - Prob. 50P Ch. 11 - Prob. 51P Ch. 11 - Write the appropriate reagent over each arrow.Ch. 11 - What alkenes would you expect to be obtained from...Ch. 11 - Prob. 54P Ch. 11 - When heated with H2SO4, both...Ch. 11 - What is the major product obtained from the...Ch. 11 - When deuterated phenanthrene oxide undergoes a...Ch. 11 - An unknown alcohol with a molecular formula of...Ch. 11 - Prob. 59P Ch. 11 - Prob. 60P Ch. 11 - Propose a mechanism for the following reaction:Ch. 11 - What product would be formed if the four-membered...Ch. 11 - Which of the following ethers would be obtained in...Ch. 11 - Using the given starting material any necessary...Ch. 11 - Prob. 65P Ch. 11 - When 3-methyl-2-butanol is heated with...Ch. 11 - Propose a mechanism for each of the following...Ch. 11 - How could you synthesize isopropyl propyl ether,...Ch. 11 - When the following seven-membered ring alcohol is...Ch. 11 - Ethylene oxide reacts readily with HO because of...Ch. 11 - Prob. 71P Ch. 11 - Propose a mechanism for each of the following...Ch. 11 - Explain why the acid-catalyzed dehydration of an...Ch. 11 - Triethylene glycol is one of the products obtained...Ch. 11 - Prob. 75P Ch. 11 - Prob. 76P Ch. 11 - When ethyl ether is heated with excess HI for...Ch. 11 - Propose a mechanism for the following reaction:Ch. 11 - Prob. 79P Ch. 11 - An ion with a positively charged nitrogen atom in...Ch. 11 - Propose a mechanism for each of the following...Ch. 11 - Prob. 82P Ch. 11 - The following reaction takes place several times...Ch. 11 - A vicinal diol has OH groups on adjacent carbons....Ch. 11 - Prob. 85P Ch. 11 - Prob. 86P Ch. 11 - Two stereoisomers are obtained from the reaction...Ch. 11 - Propose a mechanism for each or the following...Ch. 11 - Triethylenemelamine (TEM) is an antitumor agent....

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Would you expect the reactivity of a five-membered ring ether such as tetrahydrofuran (Table 10.2) to be more similar to the reactivity of an epoxide or to the reactivity of a noncyclic ether? Why?

Solution Summary: The author explains that the reactivity of tetrahydrofuran should be comparatively explained with epoxide and noncyclic ethers.

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