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Alkyne Reactions (Addition (Halogenation (1X2 (Dihalogenated alkene), 2X2…
Alkyne Reactions
Addition
Reduction
Alkanes
2H2 + Pt. Pd, or Ni
Alkenes
Cis
Lindlar's Catalyst
H2, Pd/BaSO4, quinoline
Trans
Na, NH3
Halogenation
Cl2 or Br2
1X2
Dihalogenated alkene
2X2
Tetrahalogenated alkane
Hydration
Markovnikov
HgSO4/H2SO4
ketone
Anti-Markovnikov
Hydroboration-oxidation
Sia2BH-THF, H2O2, NaOH
aldehyde
Hydrohalogenation
add H-X once - alkene
add twice - alkane
Markovnikov
Synthesis
Alkylation of Acetylide Ions
SN2 reaction with R-X and acetylide ion
Additions to carbonyl groups
Backside attack by acetylide ion pushes negative charge onto oxygen atom
Acid workup with H2O or H3O+ to protonate oxygen
Double Dehydrohalogenation of Alkyl Dihalides
KOH + heat
internal alkynes
NaNH2 + heat
terminal alkynes
Formation of Acetylide Ions
NaNH2
R-C---C- Na+ + NH3
R-Li
R-C---CLi + RH
R-MgX
R-C---CMgX + R-H
Oxidation
Oxidation to alpha-diketones
KMnO4, H2O, neutral
Oxidative Cleavage
KMnO4, KOH, heat; H+
forms carboxylic acids
O3, H2O
two carboxylic acids