Organic Chemistry
Organic Chemistry
8th Edition
ISBN: 9781337516402
Author: Brown
Publisher: Cengage
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Chapter 11, Problem 11.28P
Interpretation Introduction

Interpretation:

Using Sharpless epoxidation, the allylic alcohol that can be used to prepare the given enantiomer has to be shown.

Concept Introduction:

Sharpless asymmetric epoxidation: Titanium-catalyzed asymmetric epoxidation of primary allylic alcohols is proposed by the Barry Sharpless known as Sharpless epoxidation. The reagent consists of tert-butyl hydroperoxide, titanium tetraisoproxide [Ti(O-iPr)4] and the diethyl tartrate.

Sharpless epoxidation is stereospecific based on the diethyl tartrate (DET) added. If the (DET) enantiomer is used, that catalyzes the reaction and delivers the epoxide Oxygen from the top face of the alkene; the +(DET) enantiomer is used, that delivers the epoxide where the oxygen is attached from the bottom of the alkene.

Organic Chemistry, Chapter 11, Problem 11.28P

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Chapter 11 Solutions

Organic Chemistry

Ch. 11.9 - Prob. CQCh. 11.9 - Prob. DQCh. 11 - Write names for these compounds. Where possible,...Ch. 11 - Prob. 11.11PCh. 11 - Each compound given in this problem is a common...Ch. 11 - Account for the fact that tetrahydrofuran (THF) is...Ch. 11 - Prob. 11.14PCh. 11 - Write equations to show a combination of reactants...Ch. 11 - Propose a mechanism for this reaction.Ch. 11 - Prob. 11.17PCh. 11 - Prob. 11.18PCh. 11 - Prob. 11.19PCh. 11 - Prob. 11.20PCh. 11 - Ethylene oxide is the starting material for the...Ch. 11 - Prob. 11.22PCh. 11 - Predict the structural formula of the major...Ch. 11 - The following equation shows the reaction of...Ch. 11 - Propose a mechanism to account for this...Ch. 11 - Acid-catalyzed hydrolysis of the following epoxide...Ch. 11 - Prob. 11.27PCh. 11 - Prob. 11.28PCh. 11 - Prob. 11.29PCh. 11 - Propose a mechanism for the following...Ch. 11 - Show reagents and experimental conditions to...Ch. 11 - Starting with cis-3-hexene, show how to prepare...Ch. 11 - Show reagents to convert cycloheptene to each of...Ch. 11 - Show reagents to convert bromocyclopentane to each...Ch. 11 - Prob. 11.35PCh. 11 - Starting with acetylene and ethylene oxide as the...Ch. 11 - Following are the steps in the industrial...Ch. 11 - Prob. 11.38PCh. 11 - Prob. 11.39PCh. 11 - Aldehydes and ketones react with one molecule of...Ch. 11 - Prob. 11.42PCh. 11 - Write the products of the following sequences of...Ch. 11 - Using your reaction roadmap as a guide, show how...Ch. 11 - Using your reaction roadmap as a guide, show how...Ch. 11 - Using your reaction roadmap as a guide, show how...Ch. 11 - During the synthesis of the antiasthmatic drug...Ch. 11 - Prob. 11.48P
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