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

3. Consider the compounds below and determine if they are aromatic, antiaromatic, or non-aromatic. In case of aromatic or anti-aromatic, please indicate number of I electrons in the respective systems. (Hint: 1. Not all lone pair electrons were explicitly drawn and you should be able to tell that the bonding electrons and lone pair electrons should reside in which hybridized atomic orbital 2. You should consider ring strain- flexibility and steric repulsion that facilitates adoption of aromaticity or avoidance of anti- aromaticity) H H N N: NH2 N Aromaticity (Circle) Aromatic Aromatic Aromatic Aromatic Aromatic Antiaromatic Antiaromatic Antiaromatic Antiaromatic Antiaromatic nonaromatic nonaromatic nonaromatic nonaromatic nonaromatic aromatic TT electrons Me H Me Aromaticity (Circle) Aromatic Aromatic Aromatic Aromatic Aromatic Antiaromatic Antiaromatic Antiaromatic Antiaromatic Antiaromatic nonaromatic nonaromatic nonaromatic nonaromatic nonaromatic aromatic πT electrons H HH…

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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.

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