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.

Question

Treatment of cis-4-bromocyclohexanol with HO– affords compound A and cyclohex-3-en-1-ol. Treatment of trans-4- bromocyclohexanol under the same conditions forms compound B and cyclohex-3-en-1-ol. A and B contain different functional groups and are not isomers of each other. Propose structures for A and B and offer an explanation for their formation.

Answer 1

Question

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.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Students have asked these similar questions

Treatment of cis-4-bromocyclohexanol with HO– affords compound A and cyclohex-3-en-1-ol. Treatment of trans-4- bromocyclohexanol under the same conditions forms compound B and cyclohex-3-en-1-ol. A and B contain different functional groups and are not isomers of each other. Propose structures for A and B and offer an explanation for their formation.

A synthetic organic molecule, G, which contains both aldehyde and ether functional groups, is subjected to a series of reactions in a multi-step synthesis pathway. In the first step, G undergoes a Wittig reaction, leading to the formation of an alkene, H. Subsequently, H is treated with an ozone (O3) reagent followed by a reducing agent in an ozonolysis reaction, resulting in the formation of two different products, I and J. Considering the functional groups present in G and the nature of the reactions involved, what are the most probable structures or functional groups present in products I and J? A. I contains a carboxylic acid group, and J contains an aldehyde group. B. I contains a ketone group, and J contains an alcohol group. C. I and J both contain aldehyde groups. D. I contains an ester group, and J contains a ketone group. Don't use chat gpt.

Describe how 3-methyl-1-phenyl-3-pentanol can be prepared from benzene. You can use any inorganic reagents and solvents, and any organic reagents provided they contain no more than two carbons.