7th Edition

ISBN: 9780133556186

Author: Bruice

Publisher: VST

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Organic synthesis is a branch of chemical synthesis that involves the planned construction of organic compounds/molecules from smaller units that possess functional groups. Friedrich Wöhler was the first scientist who designed the synthesis of an organic…

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Textbook Question

Chapter 11.4, Problem 17P

What stereoisomers are formed in the following reactions? Which stereoisomer is the major product?

a. the acid-catalyzed dehydration of 1-pentanol to 2-pentene
b. the acid-catalyzed dehydration of 3,4-dimethyl-3-hexanol to 3,4-dimethyl-3-hexene

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Chapter 11.4, Problem 16P

Chapter 11.4, Problem 18P

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Chapter 11 Solutions

EBK 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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What stereoisomers are formed in the following reactions? Which stereoisomer is the major product? a. the acid-catalyzed dehydration of 1-pentanol to 2-pentene b. the acid-catalyzed dehydration of 3,4-dimethyl-3-hexanol to 3,4-dimethyl-3-hexene

Solution Summary: The author explains that the major isomer product should be given from the reaction of acid-catalysed dehydration of 1-pentanol to 2-pentene.

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Chapter 11 Solutions