Assuming that the nitrogen in enamine is sp? hybridized, explain why the double bond of an enamine is more nucleophilic than a typical alkene double bond. Propose the mechanism for the reaction below and use resonance structure to explain why the other regioisomer does not form. Br HBr OCH3 OCH3

Assuming that the nitrogen in enamine is sp? hybridized, explain why the double bond of an enamine is more nucleophilic than a typical alkene double bond. Propose the mechanism for the reaction below and use resonance structure to explain why the other regioisomer does not form. Br HBr OCH3 OCH3

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter14: Conjugated Compounds And Ultraviolet Spectroscopy

Section14.SE: Something Extra

Problem 65AP: The double bond of an enamine (alkene + amine) is much more nucleophilic than a typical alkene...

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Concept explainers

Diol

In chemistry there are so many chemical compounds that have a hydroxyl group but a chemical compound having two hydroxyl groups (-OH) is termed as a diol. It also implies the presence of two alcohols whereas polyols contain two or more than two hydroxyl groups (-OH). Glycol or 1,2-diol is an aliphatic diol that has two alcohol groups on adjacent carbon atoms. In industries, the most commonly used diol is ethylene glycol.

Question

Assuming that the nitrogen in enamine is sp hybridized, explain why the double bond of
an enamine is more nucleophilic than a typical alkene double bond.
Propose the mechanism for the reaction below and use resonance structure to explain
why the other regioisomer does not form.
Br
HBr
OCH3
OCH3

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