Orgo I Test 4

cis addition of OH to an alkene
OsO4 + catalytic peroxide
nonselective addition of OH to an alkene
KMnO4 + NaOH/H2O
problem of addition with KMnO4
oxidative cleavage
1 yne -> 2 enes
KMnO4, H2O/neutral
R-(triple bond)-R’ -> R-carboxylic acid + R’-carboxylic acid
ozonolysis (O3, H2O)
2 steps 1 yne to 1 ene
1) Sia2.BH
2) H2O2/NaOH
increasing hindrance of alcohol
decreasing reactivity
addition to carbonyls (always adds H)
R-,M+ OR AlH4
oxidation state
electrons to most electronegative atom in bond, then subtract the number it has from the number it should have
oxidation (reduction of alcohol)
H2CrO4 + Jones (acetone, H2O, H2SO4)
oxidation of 1′ alcohol
carboxylic acid
oxidation of 2′ alcohol
non-Jones oxidation of 2′ alcohol
“deoxidize” alcohol
Ms-Cl + pyridine
nonselective halide formation
halide formation with inversion
halide formation with retention
H2SO4 or O=Cl,-CH3
ethers accept/donate H bonds
ethers solvate…
ONLY cations and Lewis acids
end: ether + halide
acid cleavage (HBr, AlCl3)
oxidation of thioether (O double bond S)
alkylation of thioether (S(+)-I(-))
formation of epoxide
Cl2 + H2O
end: more substituted ether
acid-catalyzed opening of epoxide
end: less substituted ether
base-catalyzed opening of epoxide (or organometallic opening)
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