addition reactions

Halogenation

-addition of X2

-Cl2 or Br2 in CH2CL2 (non-participating solvent)

-stereochemistry: anti

-regioselectivity: mark

Halohydrin

-addition of ROH

-X2 in H2O

-Stereochemistry: anti

-Regioselectivity: mark

Acid-Catalyzed Hydration

-addition of an OH on the more substituted side

-carbocation formation

-H2O & H2SO4

-regioselectivity: mark

Oxymercuration-Demercuration  

-addition of an OH on the more substituted side

-two steps

-1. Hg(OAc)2, H2O/THF

-2. NaBH4

-avoid carbocation rearrangement

-regio: mark

-stereo: anti

Hydroboration-Oxidation

-addition of -OH to less substituted side

-2 steps

-1. BH3/THF

-2. H2O2, NaOH, H2O

-stereo: syn

-regio: anti-mark

Hydrogenation

-saturated alkane product

-H2 w/ Pd/C or PtO2

-stereo: syn

-Alkenes reduced

-Aromatic rings & carbonyls cannot be reduced