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