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Reactions of Alkynes : Addition of a HX to an Internal Alkyne

المؤلف:  ..................

المصدر:  LibreTexts Project

الجزء والصفحة:  .................

20-7-2019

1797

Addition of a HX to an Internal Alkyne

As described in Figure 1, the π electrons will attack the hydrogen of the HBr and because this is a symmetric molecule it does not matter which carbon it adds to, but in an asymmetric molecule the hydrogen will covalently bond to the carbon with the most hydrogens. Once the hydrogen is covalently bonded to one of the carbons, you will get a carbocation intermediate (not shown, but will look the same as depicted in Figure 1) on the other carbon. Again, this is a symmetric molecule and if it were asymmetric, which carbon would have the positive charge?

The final step is the addition of the Bromine, which is a good nucleophile because it has electrons to donate or share. Bromine, therefore attacks the carbocation intermediate placing it on the highly substituted carbon. As a result, you get 2-bromobutene from your 2-butyne reactant, as shown below.

Now, what if you have excess HBr?