EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
9th Edition
ISBN: 9780100591318
Author: McMurry
Publisher: YUZU
Question
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Chapter 18.3, Problem 7P
Interpretation Introduction

a)

EBK ORGANIC CHEMISTRY, Chapter 18.3, Problem 7P , additional homework tip  1

Interpretation:

The product of the reaction shown is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by SN1 or SN2 mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN2 mechanism. The Br- or I- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or an allylic group cleave either by SN1 or E1 mechanism as these can produce stable carbocations yielding alkenes and alcohols.

To give:

The product of the reaction shown.

Interpretation Introduction

b)

EBK ORGANIC CHEMISTRY, Chapter 18.3, Problem 7P , additional homework tip  2

Interpretation:

The product of the reaction shown is to be given.

Concept introduction:

Ethers are cleaved by strong acids. The cleavage takes place either by SN1 or SN2 mechanisms, depending upon the structure of the substrate. Ethers with only primary and secondary alkyl groups react by SN2 mechanism. The Br- or I- attacks the protonated ether at the less hindered side to yield a single alcohol and a single alkyl halide. Ethers with a tertiary, benzylic or a allylic group cleave either by SN1 or E1 mechanism because these can produce a stable carbocation yielding alkenes and alcohols.

To give:

The product of the reaction shown.

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Chapter 18 Solutions

EBK ORGANIC CHEMISTRY

Ch. 18.5 - Prob. 11PCh. 18.6 - Predict the major product of each of the following...Ch. 18.6 - Prob. 13PCh. 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 - Prob. 16PCh. 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 - Prob. 21VCCh. 18.SE - Treatment of the following alkene with a...Ch. 18.SE - Prob. 23MPCh. 18.SE - Prob. 24MPCh. 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 - Prob. 29MPCh. 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 - Prob. 34MPCh. 18.SE - Prob. 35MPCh. 18.SE - Aldehydes and ketones undergo acid-catalyzed...Ch. 18.SE - Propose a mechanism to account for the following...Ch. 18.SE - Prob. 38APCh. 18.SE - Prob. 39APCh. 18.SE - How would you prepare the following ethers?Ch. 18.SE - Prob. 41APCh. 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 - Prob. 45APCh. 18.SE - Prob. 46APCh. 18.SE - Write the mechanism of the hydrolysis of cis-5,...Ch. 18.SE - Prob. 48APCh. 18.SE - Acid-catalyzed hydrolysis of a 1,...Ch. 18.SE - Prob. 50APCh. 18.SE - Epoxides are reduced by treatment with lithium...Ch. 18.SE - Prob. 52APCh. 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 - Prob. 56GPCh. 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 - Prob. 60GPCh. 18.SE - Prob. 61GPCh. 18.SE - The Zeisel method is an old analytical procedure...Ch. 18.SE - Prob. 63GPCh. 18.SE - Prob. 64GPCh. 18.SE - Prob. 65GPCh. 18.SE - Identify the reagents a-e in the following scheme:Ch. 18.SE - Propose structures for compounds that have the...Ch. 18.SE - Prob. 68GPCh. 18.SE - Prob. 69GPCh. 18.SE - Predict the product(s) if the starting materials...
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