Answered: 1. Ме,Culi Ether -78°С to -40°С 2. Н.О,…

Science

Chemistry

1. Ме,Culi Ether -78°С to -40°С 2. Н.О, НСI

Pushing Electrons

4th Edition

ISBN:9781133951889

Author:Weeks, Daniel P.

Publisher:Weeks, Daniel P.

Chapter3: Mechanisms

Section: Chapter Questions

Problem 107EQ

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Concept explainers

Reactions at the Alpha Carbon Atom

The position next to the ketone or aldehyde functional group is termed as alpha position and the reaction which occurs at alpha position is called alpha substitution reaction. In an alpha substitution reaction, the alpha proton atom is substituted by an electrophile by the formation of an enol intermediate or enolate ion intermediate. Most of the carbonyl compounds go through an alpha substitution reaction.

Question

The synthesis of carbohydrates can be particularly difficult because of the large number of chiral centers and OH functional groups present. Epoxides can be useful synthetic intermediates in carbohydrate syntheses. Draw the product of the following reaction of a Gilman reagent with each epoxide

1. Ме,Culi
Ether
-78°С to -40°С
2. Н.О, НСI

Definition Definition Group of atoms that shape the chemical characteristics of a molecule. The behavior of a functional group is uniform in undergoing comparable chemical reactions, regardless of the other constituents of the molecule. Functional groups aid in the classification and anticipation of reactivity of organic molecules.

Expert Solution

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$T h e G i l m a n r e a g e n t r e a c t s w i t h t h e e p o x i d e, w h i c h i s f o l l o w e d b y t h e a c i d g i v e s a l c o h o l s . H e r e, t h e G i l m a n r e a g e n t a t t a c k s a t t h e l e s s h i n d e r e d s i d e o f t h e e p o x i d e i n t h e p r e s e n c e o f a n a c i d .$

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