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14 Cards in this Set
- Front
- Back
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dehydrohalogenation
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*Alkyl Halide + KOH
*Alkene, H2O, KX |
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Dehydration
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*Alcohol in HSO4 + THF
* Alkene, H2O |
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halogenation
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*Alkene + X2
* Dilhalides *Markovnikov + Antistereochem |
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Halohydrins
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*Alkene + X2 in H20, can also use hypohalous acid, NBS used for Br transfer
* An alcohol + HX *Anti-stereochem, markovnikov *H20 attacks MORE substituted carbon, bromonium ion formation |
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Oxymercuration/demurcuration
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*1) alkene, Hg(OAc)2 followed by 2)NaBH4
*alcohol(one OH group) *markovnikov *Mercurinum ion intermediate |
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Hydration
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Alkene + HA catalyst
*alcohol, H30+ *markovnikov *1 -OH group only, Carbocation intermediate |
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Hydroboration
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*alkene + 1)BH3,THF followed by 2) H2O2, OH-
*alcohol *anti-markovnikov, Syn stereochem *1 -OH group only, organoborane intermediate, boron attaches to LESS substituted carbon |
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Epoxidation
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*alkene + RCOH3(Peroxyacid)
* epoxides *syn stereochem * oxygen farthest from carbonyl group transferred |
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Epoxidation via halohydrins
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* halohydrin in HB(NaOH) +H2O
*halohydrins + HB(NaOH) *syn stereochem |
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Epoxidation via acid catalyst
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epoxide + Acid
forms 1,2-diols |
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Hydroxylation
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*alkene + 1)OsO4, NMO followed by 2) NaHSO3, H2O
*di-alcohol +OsO4 *syn stereochem *-OH added from same side, cyclic osmate intermediate |
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Cleavage via ozone
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* alkene + O3 followed by Zn, H3O+
*2 carbonyl compounds *tetrasubbed = 2 ketones trisubbed = 1 ketone, 1 aldehyde *if alkene is a ring then a single dicarbonyl compound is made |
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cleavage via potassium permanganate
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*alkene +KmNO4 then H3O+
*2 carbonyl compounds *2 H's on same carbon = CO2 formation, H's present on dbl bond = carboxylic acids formed |
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Cleavage of 1,2-diols
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*1,2 diols + HIO4 followed by H2O, THF
*carbonyl compounds *open chain diol = 2 carbonyls ring diol = 1 dicarbonyl compound |
