CH 9 - Alkyne Reactions
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12 Terms
Hydrohalogenation
Reagents = H - X (excess) (X = Cl, Br, I)
Markovnikov (if terminal)
--
Rearrange = yes
Acid-catalyzed hydration
Reagents = H2O and acid or H3O+
Markovnikov (if terminal)
--
--
Oxymercuration-demercuration
Reagents = 1. Hg(OAc)2 , H2O | 2. NaBH4
--
--
--
Oxymercuration-demercuration (terminal alkyne)
--
Markovnikov
--
--
Hydroboration-oxidation
Reagents = 1. BH3 , THF | 2. H2O2 , NaOH , H2O
--
Syn
--
Hydroboration-oxidation (terminal alkyne)
--
Anti-Markovnikov
Syn
--
Halogenation
Reagents = X2 (excess) (X = Cl, Br)
--
Anti
Rearrange = no
Hydrogenation
Reagents = H2 , Pd/C
--
Syn
Rearrange = no
Dissolving Metal Reduction
Reagents = Na , NH3
--
Anti
Rearrage = no
Hydrogenation with poisoned catalyst
Reagents = H2 , Lindlar Catalyst
--
Syn
No
Acetylide alkylation
Reagents = 1. NaNH2 | 2. R - CH2 - X (primary alkyl halide)
--
--
Rearrage = no
Alkyne Synthesis → Dihalide Elimination
Reagents = Strong base (KOH, NaNH2), excess
--
Anti (Eliimination)
Rearrange = no
Note 
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