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NOTES-Electrophilic_Addition_to_an_Alkyne - Addition...

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Addition Reactions to Alkynes Alkynes contain carbon-carbon triple bonds. The triple bond is an electron dense region and it should therefore not be surprising that it has good nucleophilic characteristics. In studying the reactions of alkynes, we will reason-through new transformations by drawing analogies to the mechanisms and concepts that we have previously learned. The success of applying established ways to a new class of compounds illustrates the power of the mechanism-based approach for studying reactivity. CH 3 CH 2 C CH + H–Br CH 3 CH 2 C C Br a vinylic cation intermediate CH 3 CH 2 C C Br H H H H [Ad E 2] [A E ] [A N ] http://wps.prenhall.com/wps/media/objects/724/742058/0019f.html
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The Vinylic Cation CH 3 CH 2 C CH 2 CH 3 CH 2 CH CH more stable less stable A two-EPD carbocation (sp-hybridized) R C H H RCH C–H primary alkyl cation primary vinylic cation 3-EPDs (sp 2 hybridized) 2-EPDs (sp hybridized) The vinylic cation possesses a positively charged carbon atom having only two electron pair domains (EPDs); the carbon bearing the positive charge is thus sp-hybridized. The addition of the
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NOTES-Electrophilic_Addition_to_an_Alkyne - Addition...

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