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Orgo I Test 4
alcohols, ethers, alkynes, epoxides
26
Chemistry
Undergraduate 2
12/07/2008

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Cards

Term
cis addition of OH to an alkene
Definition
OsO4 + catalytic peroxide
Term
nonselective addition of OH to an alkene
Definition
KMnO4 + NaOH/H2O
Term
problem of addition with KMnO4
Definition
oxidative cleavage
Term
1 yne -> 2 enes
Definition
KMnO4, H2O/neutral
Term
R-(triple bond)-R' -> R-carboxylic acid + R'-carboxylic acid
Definition
ozonolysis (O3, H2O)
Term
2 steps 1 yne to 1 ene
Definition
1) Sia2.BH
2) H2O2/NaOH
Term
increasing hindrance of alcohol
Definition
decreasing reactivity
Term
addition to carbonyls (always adds H)
Definition
R-,M+ OR AlH4
Term
oxidation state
Definition
electrons to most electronegative atom in bond, then subtract the number it has from the number it should have
Term
oxidation (reduction of alcohol)
Definition
H2CrO4 + Jones (acetone, H2O, H2SO4)
Term
oxidation of 1' alcohol
Definition
carboxylic acid
Term
oxidation of 2' alcohol
Definition
ketone/aldehyde
Term
non-Jones oxidation of 2' alcohol
Definition
DMSO/O=-Cl,-CH3/pyridine
Term
"deoxidize" alcohol
Definition
Ms-Cl + pyridine
Term
nonselective halide formation
Definition
HBr
Term
halide formation with inversion
Definition
PBr3
Term
halide formation with retention
Definition
SOCl2
Term
esterification
Definition
H2SO4 or O=Cl,-CH3
Term
ethers accept/donate H bonds
Definition
accept
Term
ethers solvate...
Definition
ONLY cations and Lewis acids
Term
end: ether + halide
Definition
acid cleavage (HBr, AlCl3)
Term
oxidation of thioether (O double bond S)
Definition
MCPBA
Term
alkylation of thioether (S(+)-I(-))
Definition
CH3I
Term
formation of epoxide
Definition
Cl2 + H2O
Term
end: more substituted ether
Definition
acid-catalyzed opening of epoxide
Term
end: less substituted ether
Definition
base-catalyzed opening of epoxide (or organometallic opening)
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