CHEM12B Alkynes

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Author:
daynuhmay
ID:
203499
Filename:
CHEM12B Alkynes
Updated:
2013-02-26 03:52:33
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alkynes
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alkynes
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  1. NaNH2
    1 equivalent removes 1 H from a terminal alkyne
  2. 2NaH
    • double E2 rxn
    • creates alkyne from dihalide (alkane)
  3. synthesize alkyne from alkene
    • 1) dihalogenate
    • 2) 2 equiv. strong base (NaH, NaNH2)
  4. 2H2(g) + Pd catalyst
    alkyne -> alkane
  5. H2(g) + Lindler's catalyst
    alkyne -> cis-alkene
  6. Na metal + NH3(l), -33C
    alkyne -> trans-alkene
  7. Br2/Cl2 + CCl4
    • 1mol: alkyne -> dibrominated alkene (trans) 
    • 2mol: alkyne -> tetrabrominated alkane
  8. addition of H-X
    • dihalogenation of more hindered C of alkyne
    • alkyne -> alkane
  9. H+, H2O, Hg2+ cat
    • terminal alkyne -> ketone on more hindered C
    • -Markovnikov addition

    • internal alkyne -> ketone at both ends
    • -no Markovnikov rule
  10. 1) BH(sia)2; 2) NaOH, H2O2
    • terminal alkyne -> aldehyde at less hindered C
    • anti-Markovnikov addition
    • syn addition added to less hindered C
  11. nBuLi
    • strong base
    • removes H from alkyne

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