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CHEM 261: Exam 3
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 antiperiplanar to LG |