front 1 KMnO4/NaOH, cold or OSO4 cat/NMO | back 1 Syn-Dihydroxylation -> Adds OH & OH CIS |
front 2 1. Hg(OAc)2, H2O/ 2. NaBH4 | back 2 Oxymercuration-Demercuration -> Adds H and OH, OH to MORE substituted position |
front 3 1. BH3 * THF/ 2. H2O2, NaOH | back 3 Hydroboration-Oxidation -> Adds H and OH, OH LESS substituted position |
front 4 HBr/ROOR | back 4 Hydrohalogenation -> Adds H and X, X to LESS substituted position |
front 5 Br2/ CCl4 | back 5 Halogenation -> Adds X & X, ANTI |
front 6 H3O+ or H2SO4 cat./H2O | back 6 Acid-Catalyzed Hydration -> Adds H & OH, OH on MORE substituted position, rearrangement is possible |
front 7 HCl | back 7 Hydrohalogenation -> H & X, X in MORE substituted position, rearrangement is possible |
front 8 Br2/H2O | back 8 Halohydrin Formation -> Adds X & OH, ANTI, OH in MORE substituted position |
front 9 H2, Pt (Pd, Ni) | back 9 Catalytic Hydrogenation -> Adds H & H, CIS, (murder double bond) |
front 10 1. RCO3H/ 2. H3O+ or 1. MCPBA / H3O+, H2O | back 10 Anti-Dihydroxylation -> Adds OH and OH, ANTI |
front 11 1. O3/ 2. DMS or 1. O3 / 2. Zn/H2O | back 11 Ozonolysis -> Cut double bond in half and add O's |
front 12 Na (s) / NH3 (l) | back 12 Dissolving Metal Reduction of Alkynes -> TRANS ALKENE |
front 13 H2 / Metal (Pt, Pd, Ni) | back 13 Reduction of Alkynes Catalytic Hydrogenation -> ALKANE (murders all PI bonds) |
front 14 H2/ Lindlar's catalyst | back 14 Reduction of Alkynes Catalytic Hydrogenation -> CIS-ALKENE |
front 15 1. O3 / 2. H2O | back 15 Ozonolysis of an Alkyne -> Internal: 2 Carboxylic acids Terminal: Carboxylic acid + CO2 |
front 16 xs X2 / CCl4 | back 16 Halogenation of Alkynes -> Adds 4 X's (tetrahalide), VINCINAL |
front 17 X2 / CCl4 (1 eq) | back 17 Halogenation of Alkynes -> Adds 2 X's, ANTI |
front 18 HX (1 eq) | back 18 Hydrohalogenation of Alkynes -> Adds H & X, X in MORE substituted position |
front 19 xs HX | back 19 Hydrohalogenation of Alkynes -> Add's 2 X's & H, geminal dihalide, X's in MORE substituted position |
front 20 1. NANH2 / 2. Alkane with leave in group | back 20 Alkylation of Terminal Alkynes -> Sticks alkane onto end of triple bond |
front 21 NaNH2 / NH3 | back 21 Preparation of Alkynes -> Internal Alkyne |
front 22 1. xs NaNH2/NH3 / 2. H2O | back 22 Preparation of Alkynes -> Terminal Alkyne |