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