Na, NH3 H3C-C=C-CH3 CH3 H3C Alkynes are reduced to trans alkenes by a process called dissolving metal reduction. The reaction uses sodium or lithium metal as the reducing agent and liquid ammonia as the solvent. The method is specific in the formation of trans alkenes from alkynes. The method involves two successive transfers of single electrons from the alkali metal to the triple bond, with abstraction of protons from the ammonia solvent. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H CH3 H-NH2 CH3 H3C H3C°

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter21: Benzene And The Concept Of Aromaticity
Section: Chapter Questions
Problem 21.44P
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Na, NH3
H3C-C=C-CH3
CH3
H3C°
Alkynes are reduced to trans alkenes by a process called dissolving metal reduction. The reaction uses sodium or lithium metal as the reducing agent and liquid ammonia as the solvent. The
method is specific in the formation of trans alkenes from alkynes. The method involves two successive transfers of single electrons from the alkali metal to the triple bond, with abstraction of
protons from the ammonia solvent.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
.CH3 H-NH2
CH3
:NH2
H3C
H3C
Transcribed Image Text:Na, NH3 H3C-C=C-CH3 CH3 H3C° Alkynes are reduced to trans alkenes by a process called dissolving metal reduction. The reaction uses sodium or lithium metal as the reducing agent and liquid ammonia as the solvent. The method is specific in the formation of trans alkenes from alkynes. The method involves two successive transfers of single electrons from the alkali metal to the triple bond, with abstraction of protons from the ammonia solvent. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions .CH3 H-NH2 CH3 :NH2 H3C H3C
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