BuyFind

Organic Chemistry

9th Edition
John E. McMurry
Publisher: Cengage Learning
ISBN: 9781305080485
BuyFind

Organic Chemistry

9th Edition
John E. McMurry
Publisher: Cengage Learning
ISBN: 9781305080485

Solutions

Chapter 18.SE, Problem 68GP
Textbook Problem

We saw in Section 17-4 that ketones react with NaBH4 to yield alcohols. We’ll also see in Section 22-3 that ketones react with Br2 to yield α-bromo ketones. Perhaps surprisingly, treatment with NaBH4 of the α -bromo ketone from acetophenone yields an epoxide rather than a bromo alcohol. Show the structure of the epoxide, and explain its formation.

Chapter 18.SE, Problem 68GP, We saw in Section 17-4 that ketones react with NaBH4 to yield alcohols. We’ll also see in Section

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Chapter 18 Solutions

Organic Chemistry
Ch. 18.5 - Reaction of cis-2-butene with...Ch. 18.6 - Predict the major product of each of the following...Ch. 18.6 - How would you prepare the following diols?Ch. 18.6 - Predict the major product of the following...Ch. 18.7 - 15-Crown-5 and 12-crown-4 ethers complex Na+ and...Ch. 18.8 - Name the following compounds:Ch. 18.8 - 2-Butene-l-thiol is one component of skunk spray....Ch. 18.9 - The 1H NMR spectrum shown is that of a cyclic...Ch. 18.SE - Give IUPAC names for the following compounds...Ch. 18.SE - Show the product, including stereochemistry, that...Ch. 18.SE - Show the product, including stereochemistry, of...Ch. 18.SE - Treatment of the following alkene with a...Ch. 18.SE - Predict the product(s) and provide the mechanism...Ch. 18.SE - Predict the product(s) and provide the mechanism...Ch. 18.SE - Predict the product(s) and provide the mechanism...Ch. 18.SE - The alkoxymercuration of alkenes involves the...Ch. 18.SE - Predict the product(s) and provide the mechanism...Ch. 18.SE - Predict the product(s) and provide the mechanism...Ch. 18.SE - In the formation of the prepolymer used to make...Ch. 18.SE - Ethers undergo an acid-catalyzed cleavage reaction...Ch. 18.SE - Treatment of 1, 1-diphenyl-l, 2-epoxyethane with...Ch. 18.SE - Fluoxetine, a heavily prescribed antidepressant...Ch. 18.SE - When 2-methyl-2, 5-pentanediol is treated with...Ch. 18.SE - Methyl aryl ethers, such as anisole, are cleaved...Ch. 18.SE - The herbicide acifluorfen can be prepared by a...Ch. 18.SE - Aldehydes and ketones undergo acid-catalyzed...Ch. 18.SE - Propose a mechanism to account for the following...Ch. 18.SE - Draw structures corresponding to the following...Ch. 18.SE - Give IUPAC names for the following structures:Ch. 18.SE - How would you prepare the following ethers?Ch. 18.SE - How would you prepare the following compounds from...Ch. 18.SE - tert-Butyl ethers can be prepared by the reaction...Ch. 18.SE - Treatment of trans-2-chlorocyclohexanol with NaOH...Ch. 18.SE - Predict the products of the following ether...Ch. 18.SE - How would you carry out the following...Ch. 18.SE - What product would you expect from cleavage of...Ch. 18.SE - Write the mechanism of the hydrolysis of cis-5,...Ch. 18.SE - What is the stereochemistry of the product from...Ch. 18.SE - Acid-catalyzed hydrolysis of a 1,...Ch. 18.SE - Imagine that you have treated (2R, 3R)-2,...Ch. 18.SE - Epoxides are reduced by treatment with lithium...Ch. 18.SE - Show the structure and stereochemistry of the...Ch. 18.SE - The red fox (Vulpes vulpes) uses a chemical...Ch. 18.SE - Anethole, C10H12O, a major constituent of the oil...Ch. 18.SE - Propose structures for compounds that have the...Ch. 18.SE - Predict the products of the following reactions:Ch. 18.SE - How would you synthesize anethole (Problem 18-54)...Ch. 18.SE - How could you prepare benzyl phenyl ether from...Ch. 18.SE - Meerwein's reagent, triethyloxonium...Ch. 18.SE - Safrole, a substance isolated from oil of...Ch. 18.SE - Grignard reagents react with oxetane, a...Ch. 18.SE - The Zeisel method is an old analytical procedure...Ch. 18.SE - Disparlure, C19H38O, is a sex attractant released...Ch. 18.SE - How would you synthesize racemic disparlure...Ch. 18.SE - How would you prepare o-hydroxyphenylacetaldehyde...Ch. 18.SE - Identify the reagents a-e in the following scheme:Ch. 18.SE - Propose structures for compounds that have the...Ch. 18.SE - We saw in Section 17-4 that ketones react with...Ch. 18.SE - In nature, the enzyme chorismate mutase catalyzes...Ch. 18.SE - Predict the product(s) if the starting materials...

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