KMnO4/NaOH, cold
or
OSO4 cat/NMO
Syn-Dihydroxylation -> Adds OH & OH CIS
1. Hg(OAc)2, H2O/ 2. NaBH4
Oxymercuration-Demercuration -> Adds H and OH, OH to MORE substituted position
1. BH3 * THF/ 2. H2O2, NaOH
Hydroboration-Oxidation -> Adds H and OH, OH LESS substituted position
HBr/ROOR
Hydrohalogenation -> Adds H and X, X to LESS substituted position
Br2/ CCl4
Halogenation -> Adds X & X, ANTI
H3O+
or
H2SO4 cat./H2O
Acid-Catalyzed Hydration -> Adds H & OH, OH on MORE substituted position, rearrangement is possible
HCl
Hydrohalogenation -> H & X, X in MORE substituted position, rearrangement is possible
Br2/H2O
Halohydrin Formation -> Adds X & OH, ANTI, OH in MORE substituted position
H2, Pt (Pd, Ni)
Catalytic Hydrogenation -> Adds H & H, CIS, (murder double bond)
1. RCO3H/ 2. H3O+
or
1. MCPBA / H3O+, H2O
Anti-Dihydroxylation -> Adds OH and OH, ANTI
1. O3/ 2. DMS
or
1. O3 / 2. Zn/H2O
Ozonolysis -> Cut double bond in half and add O's
Na (s) / NH3 (l)
Dissolving Metal Reduction of Alkynes -> TRANS ALKENE
H2 / Metal (Pt, Pd, Ni)
Reduction of Alkynes Catalytic Hydrogenation -> ALKANE (murders all PI bonds)
H2/ Lindlar's catalyst
Reduction of Alkynes Catalytic Hydrogenation -> CIS-ALKENE
1. O3 / 2. H2O
Ozonolysis of an Alkyne -> Internal: 2 Carboxylic acids
Terminal: Carboxylic acid + CO2
xs X2 / CCl4
Halogenation of Alkynes -> Adds 4 X's (tetrahalide), VINCINAL
X2 / CCl4 (1 eq)
Halogenation of Alkynes -> Adds 2 X's, ANTI
HX (1 eq)
Hydrohalogenation of Alkynes -> Adds H & X, X in MORE substituted position
xs HX
Hydrohalogenation of Alkynes -> Add's 2 X's & H, geminal dihalide, X's in MORE substituted position
1. NANH2 / 2. Alkane with leave in group
Alkylation of Terminal Alkynes -> Sticks alkane onto end of triple bond
NaNH2 / NH3
Preparation of Alkynes -> Internal Alkyne
1. xs NaNH2/NH3 / 2. H2O
Preparation of Alkynes -> Terminal Alkyne