Alkyne Reagents

Elimination

Reagents: 1) Excess NaNH2 2) H2O

A vicinal or geminal dibromide is converted to an alkyne

Hydrohalogenation (2 equivalents) : an alkyne undergoes Markovnikov (xs HX gives two addition reactions to give geminal dihalide)

Reagent: HX

Hydrohalogenation (one equivalent)

Reagent: HX

Acid-catalyzed hydration: a terminal Alkynes undergoes Markovnikov addition of H and OH to give an Enol, which quickly tautomerizes to give a ketone

Reagents: H2SO4, H2O, HgSO4

Hydroboration-oxidation: A terminal alkyne undergoes anti-Markovnikov addition of Hand OH to get an enol, then tautomerizes to give an aldehyde

Reagents: 1. R2BH 2. H2O2, NaOH

Halogenation

Reagent: X2, CCl4

Halogenation

Reagent: xs X2, CCl4

Ozoneolysis

Reagents: 1. O3 2. H2O

Alkylation

Reagents: 1. NaNH2 2. RX

Hydrogenation

Reagents: H2, Lindlar’s catalyst

Hydrogenation

Reagents: H2, Pt

Dissolving metal reduction

Reagents: Na, NH3 (l)