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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 |
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Alkene synthesis via alkyl halide dehydrohalogenation
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in ethanol, strong base solution
with heat 1,2 elimination |
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Addition of HX
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ether as solvent
Markovnikov regiochemistry mixed stereochemistry |
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Hydogenation
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uses Pt/Pd catalyst
in acid solution Hs add to same face |
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Hydration - oxymercuration
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Hg(Oac)/NaBH4 - mercurinium
Markovnikov regiochemistry nucleophilic H2O attacks more substituted C, then deprotonated anti addition, backdoor attack |
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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 |
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Addition of Br2
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in dichloromethane solution
Bromonium ion anti stereochemistry addition |
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Halohydrin formation
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addition of X2 in aqueous solution, water is nucleophile
Halonium ion, deprotonation of Nuc. anti stereochemistry Markovnikov regiochemistry |
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Dihydroxylation
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OsO4/KMnO4 + NaHSO4 in aqueous solution of pyridine
cyclic osmate syn addition |
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1, 2 diol oxidation
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OsO4 or HIO4 in acid solution or THF
dicarbonyl formed |
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Ozonolysis
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molozonide to ozonide
in aqueous acid Zn reduces to carbonyl |
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KMnO4 oxidation
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in acid solution
cleavage, gives mix of ketones vinylic H replaced by OH |
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Epoxide formation
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peroxyacid, R-CO3H in dichloromethane
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Simmons Smith reaction
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CH2I2 + Zn/Cu in ether
unhalogenated cyclopropane no carbene |
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Dichlorocarbene reaction
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HCCl3 in KOH (tBuK+ Kinstle)
dichlorocarbene formed halogenated cyclopropane formed |
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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 |