Alkyne Reactions Flashcards
Hydration (acid catalyzed)
Reagents: HgSO4 / H2SO4, H2O Groups Added: H & OH or H & =O (ketone); Config: both syn & anti; Markovnikov; Stepwise
Hydroboration-Oxidation
Reagents: — Groups Added: H & OH or H & =O (ketone); Config: both syn & anti; Anti-Markovnikov (OH); Stepwise
Ozonolysis
Reagents: 1. O3 2. H2O; Groups Added: =O & CHO or OH & =O; Config: sp2; Markovnikov N/A; Concerted/Stepwise N/A
Allylic Bromination
Reagents: Br; Groups Added: —; Config: —; Markovnikov N/A; Concerted/Stepwise N/A
Dissolving metal reduction
Reagents: Na & NH3;
Groups Added: H & H;
Config: sp2;
Geo: E/trans Markovnikov N/A; Concerted/Stepwise N/A
Hydrohalogenation
Reagents: H–X or HX (xs); Groups Added: H & X or (xs) X + X; Config: sp2; (xs) = geminal placement; Markovnikov; Stepwise (carbocation rearrangement)
Catalytic Hydrogenation
Reagents: H2, Pd or Pt or Ni; Groups Added: H & H; Config: syn; Markovnikov N/A; Concerted/Stepwise N/A
Lindlar’s Catalyzed Hydrogenation
Reagents: H2, Lindlar’s Cat; Groups Added: H & H; Config: sp2; Geometry: Z/cis; Markovnikov N/A; Concerted/Stepwise N/A
Double Elimination
Alkyne formation; NaNH2 (xs) / NH3 or heat
Remove H+
Alkyne formation; NaNH2 / NH3
Add H+
NaNH2 / H2O
Full Alkyne reduction to alkane
H2 / Pd or Pr
Trans partial reduction
Na or Li / NH3 (l)
cis partial reduction
H2 / Lindlar’s catalyst (poisoned)
Aldehyde formation from alkyne
9-BBN / NaOH, H2O
