9 Alkyne - Based on McMurrys Organic Chemistry , 8 th...

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Unformatted text preview: Based on McMurrys Organic Chemistry , 8 th edition Alkynes Hydrocarbons that contain carbon-carbon triple bonds Acetylene, the simplest alkyne is produced industrially from methane and steam at high temperature Our study of alkynes provides an introduction to organic synthesis, the preparation of organic molecules from simpler organic molecules 2 Why this chapter? We will use alkyne chemistry to begin looking at general strategies used in organic synthesis 3 Electronic Structure of Alkynes Carbon-carbon triple bond results from sp orbital on each C forming a sigma bond and unhybridized p X and p y orbitals forming bonds. The remaining sp orbitals form bonds to other atoms at 180 to C-C triple bond. The bond is shorter and stronger than single or double Breaking a bond in acetylene (HCCH) requires 318 kJ/mole (in ethylene it is 268 kJ/mole) 4 9.1 Naming Alkynes General hydrocarbon rules apply with - yne as a suffix indicating an alkyne Numbering of chain with triple bond is set so that the smallest number possible for the first carbon of the triple bond 5 6 7 8 9.2 Preparation of Alkynes: Elimination Reactions of Dihalides Treatment of a 1,2-dihalidoalkane with KOH or NaOH produces a two-fold elimination of HX Vicinal dihalides are available from addition of bromine or chlorine to an alkene Intermediate is a vinyl halide 9 10 9.3 Reactions of Alkynes: Addition of HX and X 2 Addition reactions of alkynes are similar to those of alkenes Intermediate alkene reacts further with excess reagent Regiospecificity according to Markovnikov 11 Addition of Bromine and Chlorine Initial addition gives trans intermediate Product with excess reagent is tetrahalide 12 Addition of HX to Alkynes Involves Vinylic Carbocations 13 14 Addition of H-X to alkyne should produce a vinylic carbocation intermediate Secondary vinyl carbocations form less readily than primary alkyl...
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9 Alkyne - Based on McMurrys Organic Chemistry , 8 th...

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