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alkene + Br2 (any halide), H2O (halogenation)
add OH to most substituted C and Br to least subbed + enantiomer
alkene + Hg(OAc)2 + H2O + THF + NaBH4 (oxymercuration, demercuration)
adds OH to most substituted C + enantiomer / no ability to upgrade carbocation
alkene + HCl (or any halide) + (some sort of solvent)
add Cl (halide) to most substituted C + enantiomer
alkene + BH3 + THF + H2O2 + NaOH
add OH to least subbed and H to most subbed ADD SYN + enantiomer
alkene + H2SO4 + H2O
add OH to most subbed + enantiomer / has ability to upgrade carbocation to make more stable / if it can, it will
alkene + I2 (any halide) + (some sort of solvent)
add I to both sides of DB, add trans + enantiomer
alkene + O3 + H2O + Zn + CH3CO2H
cleave alkene at DB and add O at cleaved site on both molecules
alkene + MCPBA + CH2Cl2 (just a solvent)
makes epoxide ring (draw epoxide in plane first then add in substituents) C-C bond across from O is where the double bond would have been so use that as a guide as to where to correctly place the other groups + enantiomer
alkene + H2 + Pd/C
H's add syn to either side of DB + enantiomer
alkene + OsO4 + pyridine + NaHSO3 + H2O
adds OH syn to either side of DB
ALKYNE + H2, (Lindlar's catalyst --> quinoline, CaCO3)
gets rid of TB and rxn stops @ cis (Z) alkene
ALKYNE + H2 + Pd/C
hydroginizes alkyne COMPLETELY
ALKYNE + H2 + Pd / CaCO3 and quinoline
stops ALKYNE at cis (Z) alkene
ALKYNE + Na(0) + NH3(liquid)
hydrogenizes and stops ALKYNE at trans (E) alkene
ALKYNE + NaNH2
deprotonates ALKYNE
ALKYNE + NANH2 + CH3Br (or some other alkyl halide)
deprotonates ALKYNE and then adds everything attached to halide
alkyl halide + Li(0) + CuI + another alkyl halide
creates new bond between two alkyl halides, but halides are not present in product
Sn2
concerted / nucleophile must approach via opposite side of leaving group / stereochem switches / requires strong nuc./base / reacts best with methyl, 1, and 2 halides but not with 3 degree halides / rate determined by concentration of both nuc. and elctro.
Sn1
first step ALWAYS requires creation of carbocation / works best with 3 and 2 carbocations, but NO rxn with primary / works with weak nucleophiles / nucleophile attacks from either right or left and forms racemic mixture (rate determined by alkyl halide)
E1
requires secondary or tertiary halides / works best with weak base / creates double bond between alpha carbon and carbon with beta hydrogen but does not require antiperiplanarity / carbocation formed initially / works best with weak bases
E2
only sub / elim rxn that can work with all three; primary, secondary, AND tertiary halides / works best with stericallly hindered bases (tertbutoxide) and doesn't compete with Sn2 when bulky base used but does with something like -OH/ concerted / must have beta hydrogen that is antiperipl…

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