The following enamine reacts with electrophiles to afford exclusively the trans-product. 1. electrophile (El*) Me. El Me 2. H3O* Jse your knowledge of conformational analysis to explain this result by: a) Comparing the energies of the different conformations of the starting enamine.

The following enamine reacts with electrophiles to afford exclusively the trans-product. 1. electrophile (El) Me. El Me 2. H3O Jse your knowledge of conformational analysis to explain this result by: a) Comparing the energies of the different conformations of the starting enamine.

Pushing Electrons

4th Edition

ISBN:9781133951889

Author:Weeks, Daniel P.

Publisher:Weeks, Daniel P.

Chapter3: Mechanisms

Section: Chapter Questions

Problem 29EQ

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Concept explainers

Reactions of Ethers

Ethers (R-O-R’) are compounds formed by replacing hydrogen atoms of an alcohol (R-OH compound) or a phenol (C6H5OH) by an aryl/ acyl group (functional group after removing single hydrogen from an aromatic ring). In this section, reaction, preparation and behavior of ethers are discussed in the context of organic chemistry.

Epoxides

Epoxides are a special class of cyclic ethers which are an important functional group in organic chemistry and generate reactive centers due to their unusual high reactivity. Due to their high reactivity, epoxides are considered to be toxic and mutagenic.

Williamson Ether Synthesis

An organic reaction in which an organohalide and a deprotonated alcohol forms ether is known as Williamson ether synthesis. Alexander Williamson developed the Williamson ether synthesis in 1850. The formation of ether in this synthesis is an SN2 reaction.

Question

The following enamine reacts with electrophiles to afford exclusively the trans-product.
N.
1. electrophile (El*)
Ме.
.El
Ме.
2. H3O*
Use your knowledge of conformational analysis to explain this result by:
(a) Comparing the energies of the different conformations of the starting enamine.
(b) Comparing the energies of the transition states that lead to carbon-electrophile bond formation.

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