Answered: Provide Examples of dehydrohalogenation…

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

Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions

Section: Chapter Questions

Problem 20.42P: Bicyclo-2,5-heptadiene can be prepared in two steps from cyclopentadiene and vinyl chloride. Provide...

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Question

Provide Examples of dehydrohalogenation of dihalides to afford alkynes ?

Expert Solution

Step 1

Alkynes-

Unsaturated hydrocarbon containing carbon carbon triple bond is known as alkyne.
Alkynes have more electron density so they are highly reactive towards chemical species.
Alkynes can be easily converted into so many products by using a various chemical reactions in order to obtain the desired products.
Alkyne consists of ‘sp’ hybridization hence hydrogen attached to triply bonded carbon are most acidic in nature.
Alkyne is produce from dehydrhalogenation of germinal dihalides and vicinal dihalides.

E₂ mechanism- is type of elimination reaction in which two substituents is removed from molecule. It is called bimolecular elimination.

Step 2

Answer of given question:

Alkyne for example 2-butyne is prepared as follows:

When 1, 2 di bromo butane undergo E₂ elimination in presence of NaNH₂ in excess produce 2-butyne.

In this reaction from dihaloge, removal of halogen along with hydrogen produce alkyne is known as dehydrohalogenation.

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