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16 Cards in this Set

  • Front
  • Back
Alkene synthesis via alcohol dehydrogenation
strong acid
-OH is protonated to make O+
H2O leaves, double bond forms, H3O+ restored
Alkene synthesis via alkyl halide dehydrohalogenation
in ethanol, strong base solution
with heat
1,2 elimination
Addition of HX
ether as solvent
Markovnikov regiochemistry
mixed stereochemistry
uses Pt/Pd catalyst
in acid solution
Hs add to same face
Hydration - oxymercuration
Hg(Oac)/NaBH4 - mercurinium
Markovnikov regiochemistry
nucleophilic H2O attacks more substituted C, then deprotonated
anti addition, backdoor attack
Hydration - hydroboration/oxidation
in tetrahydrofuran (THF)
concerted attition of B-H
anti-Markovnakov regiochemistry
empty p-obr on P acts as E+
syn stereochemistry addition
Addition of Br2
in dichloromethane solution
Bromonium ion
anti stereochemistry addition
Halohydrin formation
addition of X2 in aqueous solution, water is nucleophile
Halonium ion, deprotonation of Nuc. anti stereochemistry Markovnikov regiochemistry
OsO4/KMnO4 + NaHSO4 in aqueous solution of pyridine
cyclic osmate
syn addition
1, 2 diol oxidation
OsO4 or HIO4 in acid solution or THF
dicarbonyl formed
molozonide to ozonide
in aqueous acid
Zn reduces to carbonyl
KMnO4 oxidation
in acid solution
cleavage, gives mix of ketones
vinylic H replaced by OH
Epoxide formation
peroxyacid, R-CO3H in dichloromethane
Simmons Smith reaction
CH2I2 + Zn/Cu in ether
unhalogenated cyclopropane
no carbene
Dichlorocarbene reaction
HCCl3 in KOH (tBuK+ Kinstle)
dichlorocarbene formed
halogenated cyclopropane formed
Dechlorination via free-radical solution
– (nBu)3SnH with AIBN as R-initiator
Overall C-Cl + (nBu)3SnH C-H + (nBu)3SnCl