Show the relationship between E2 Reactions and Alkyne Synthesis ?

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 20.45P: Following is a retrosynthetic scheme for the synthesis of the tricyclic diene on the left. Show how...
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Show the relationship between E2 Reactions and Alkyne Synthesis ?

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Step 1

Interpretation: The relationship between E2 reactions and alkyne synthesis is to be shown.

Step 2

E2 reactions: 

In an E2 mechanism which refers to bimolecular elimination is basically a one-step mechanism.

Here, the carbon-hydrogen and carbon-halogen bonds mostly break off to form a new double bond.

However, in the E2 mechanism, a base is part of the rate-determining step and it has a huge influence on the mechanism.

General mechanism of E2 reaction is as shown below,

Chemistry homework question answer, step 2, image 1

Alkyne synthesis:

In general, chlorine or bromine is used with an inert halogenated solvent like chloromethane to create a vicinal dihalide from from an alkene. The vicinal dihalide formed is the reactant needed to produce the alkyne using double elimination.

Mechanism:

Chemistry homework question answer, step 2, image 2

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