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Alkynes - Coggle Diagram

- - - - 1) xs NaNH2/NH3 2) H2O
      - Alkane to Alkyne
  - - - Alkyne to Alkane
      - H2/Pt (or Pd or Ni)
      - Syn addition
    - - Alkyne to Alkene
        
        Lindlar's catalyst
        
        Produces cis alkene
        
        P-2 (Ni2B complex)
        
        Produces cis alkene
        
        Dissolving metal reduction
        
        Produces trans alkene
        
        Does this is a radical anion that prefers trans geometry
        
        Na(s)/NH3(l)
    - - excess X2/CCl4
        
        Yields a tetrahalide
      - X2/CCl4
        
        yields anti and syn addition
    - - 1) O3 2)H2O
        
        With internal alkynes
        
        The split double bond grows an oxygen and an OH forms on the other bond (carboxylic acid)
        
        With terminal alkynes
        
        For one half, the molecule happens, and for the other half, a carbon dioxide forms
  - - - Markovnikov addition
      - HX
      - Excess HX affords a geminal dihalide
      - Anti-Markovnikov addition
      - HBr/ROOR
      - Creates both E and Z isomers
    - - Acid catalyzed
        
        H2SO4, H2O/HgSO4
        
        HgSO4 acts as a catalyst to speed up the reaction from vinylic carbocation
        
        The vinylic carbocation produces an unstable enol
        
        This undergoes tautomarization to form a ketone
        
        Markovnikov
      - Hydroboran-oxidation
        
        1) 9-BBN (or disiamylborane) 2)H2O2,NaOH
        
        anti-Markovnikov
        
        enol tautomerizes with aldehyde
- - - - Simplest possible alkyne
- - - - "Next door neighbors"
    - - On the same carbon