Alkyne Electrophilic Addition
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Alkyne Addition Reactions by Increasing Electronegativity of Added Reagent

Atoms Added Name Reagents Regiochemistry Stereochemistry Subsequent Reactions
B, H Hydroboration dicyclohexylborane anti-Markovnikov syn Oxidation (H2O2, NaOH)
Net anti-Markovnikov Addition of Water, Tautomerization of Enol to Aldehydes for Terminal Alkynes
H, H Hydrogenation hydrogen, transition metal n/a syn double addition to make alkanes
H, H Hydrogenation hydrogen, transition metal, barium sulfate, quinoline (Lindlar Poison Catalyst) n/a syn single addition to internal alkynes makes cis-alkenes
H, H Sodium Reduction sodium in ammonia n/a anti single addition to internal alkynes makes trans-alkenes
Hg, O Oxymercuration Hg2+ Markovnikov? anti Demercuration with NaBH4 or hydronium workup,
Net Markovnikov Addition of Water,
Tautomerization of Enol to Methyl Ketone for Terminal Alkynes
H, X Hydrohalogenation mineral acid Markovnikov n/a double addition to make gem-dihalides
Br., H. Bromine Radical Addition hydrogen bromide, peroxide anti-Markovnikov n/a n/a
X, X Halogenation halogen n/a anti double addition to make tetrahalides

 

 

 

 

 

 

 

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