Transcription of Reactions of Alkenes
1 Reactions of AlkenesProductType of Reaction (name)Reaction ConditionsRegiochemistryStereochemistryH alides(Ch ) electrophilic AdditionHX, organic solvent (anhydrous)Markovnikov AdditionNo stereochemical pref.(Ch. )Radical Chain HBr, H2O2, h Anti-Markovnikov No stereochemical addition_____Dihalides (Ch. ) electrophilic AdditionCl2, Br2, I2in CCl4solventMarkovnikov-likeAnti stereochemistry_____Halohydrin(Ch. ) electrophilic AdditionX2in H2O (X=Cl, Br, I)Markovnikov-likeAnti stereochemistryNBS or NCS in H2O/DMSOM arkovnikov-likeAnti stereochemistry_____Alcohol (Ch. ) electrophilic AdditionH3O+Markovnikov AdditionNo stereochemical pref.(hydration) (Ch. ) oxymercuration1. Hg(OAc)2, H2O, THF 2. NaBH4 Markovnikov AdditionNo stereochemical pref.(Ch. ) hydroboration1. BH3, THF 2. H2O2, NaOH, H2 OAnti-MarkovnikovSyn Stereochemistry_____CyclopropanesElectro philic AdditionCHCl3, NaOHSyn addition(Ch.)
2 Simmons-Smith ReactionCH2I2, Zu(Cu)Syn addition_____AlkanesReduction (Addition)H2, Pd (C), solventSyn stereochemistry(Ch. )catalytic hydrogenation_____1,2-Diols (glycols)Oxidation (Addition)1. OsO4, pyridine 2. NaHSO3 Syn addition(hydroxylation) (Ch. ) osmylation_____CarbonylsOxidative Cleavage(Ch. ) Ozonolysis1. O32. Zn, H3O+(Cleavage of Alkenes only to give aldehydes and/or ketones)(Ch. )HIO4, H2O, THF(Cleavage of 1,2-diols only to give aldehydes and/or ketones) Dunlaprevised: 3 October 1996
