Synthesis of 2-butyne from 2-butene

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SUMMARY

The synthesis of 2-butyne from 2-butene involves a halogenation step where Br2 is added to the double bond, followed by dehalogenation to form the triple bond. One equivalent of Br2 is sufficient for the reaction, as the addition of bromine facilitates the formation of a vicinal dibromide intermediate. A catalyst, such as zinc (Zn) or t-butoxide, is utilized in the dehalogenation step to promote the elimination of bromine atoms, resulting in the formation of the desired alkyne product. Understanding this mechanism is crucial for mastering alkyne synthesis in organic chemistry.

PREREQUISITES
  • Understanding of organic reaction mechanisms
  • Familiarity with halogenation reactions
  • Knowledge of alkyne formation and elimination reactions
  • Experience with using catalysts in organic synthesis
NEXT STEPS
  • Study the mechanism of halogenation reactions in detail
  • Learn about the role of zinc in dehalogenation processes
  • Research the use of t-butoxide as a base in organic reactions
  • Explore the synthesis of other alkynes from alkenes
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Chemistry students, organic chemists, and anyone interested in mastering the synthesis of alkynes and understanding reaction mechanisms in organic chemistry.

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Homework Statement


I'm having a hard time deciding exactly what the mechanism would be for
CH3CH=CHCH3→CH3C\equivCCH3


Homework Equations





The Attempt at a Solution


My professor only explained half of the mechanism quickly assuming the rest would be obvious, so I know that it will start with a halogenation breaking the double bond before reforming the triple bond. My problem is whether only one equivalent of Br2 is needed or two before you are able to dehalogenate and form the triple bond. I'm also having a hard time figuring out why the bromines have be be added in the first place only to be taken off again. Also it seems that after the bromination there is a second step adding a catalyst (?) of either Zn or something that looks like +o- (t-butoxide?). Does this have any effect on the whether we need 2 or 4 bromines on the molecule before reducing? And what exactly makes the bromines come off to form the triple bond?
 
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