First 8 Ochem Mechanisms

Hydrogen Halide (e.g. HBr)

Regioselectivity: Markovnikov

Stereoselectivity: N/A – only one stereocenter is generated

H added to least substituted carbon, Br added to most substituted carbon

Acid-Catalyzed Hydration (e.g. H2O and H2SO4)

Regioselectivity: Markovnikov

Stereoselectivity: N/A – only one stereocenter is generated

H added to least substituted carbon, OH added to most substituted carbon

Halogenation (e.g. Br2)

Regioselectivity: N/A

Stereoselectivity: Anti

Br added to both sides of where double bond was; one wedge, one dash

Halohydrin Formation (e.g. H2O and Br2)

Regioselectivity: Markovnikov

Stereoselectivity: Anti

OH added to most substituted carbon, Br added to least substituted carbon

Hydroboration-Oxidation (1. R2BH (hydroboration), 2. H2O2, NaOH (oxidation))

Regioselectivity: Non-Markovnikov

Stereoselectivity: Syn

H added to must substituted carbon, OH added to least substituted carbon

Oxidation of Alkenes (Diol Formation — OsO4)

Regioselectivity: N/A

Stereoselectivity: Syn

2 OH’s added on wedges to ends where double bond was

Ozonolysis (O3 and something like Me2S)

Regioselectivity: N/A

Stereoselectivity: N/A

Just split in half and add oxygens where double bond was

Hydrogenation (e.g. Pd but really any transition metal)

Regioselectivity: N/A

Stereoselectivity: Syn

Just get rid of the double bond