Orgo Exam 3 Alkene Reactions

HX

Markovnikov, adds a halogen (HBr, HCl, HI) to the more substituted carbon

HX/ROOR,H2O2

Anti-markovnikov, halogen (HBr, HCl, HI) added to the lesser substituted carbon

H3O+; 1. Hg(OAc)2, H2O/2. NaBH4

Markovnikov, addition of an OH to the more substituted carbon

1. BH3, THF/2. H2O2, NaOH

Anti-markovnikov, addition of an OH to the lesser substituted carbon with stereochemistry, plus enantiomer

H2/Pt,Pd,Ni

Removal of the double bond

Br2

Addition of Bromine on the more and less substituted carbons, anti-stereochemistry from each other, plus enantiomer

Br2/H2O

Adds Bromine to less substituted carbon and an OH to the more substituted carbon anti-stereochemistry to each other, plus enantiomer

RCO3H/H3O+;mCPBA/H2O

Addition of two OH groups on more and less substituted carbons anti-stereochemistry from each other, plus enantiomer

1.OsO4/2.NaHSO3,H2O; KMnO4/NaOH cold

Addition of two OH groups on the more and less substituted carbons both with the same stereochemistry, plus enantiomer

KMnO4/conc. heat; 1.O3 -78*C/2.DMS

Splits double bond and puts an oxygen on the end of the carbon where it was split