Organic Chemistry: Chapter 8, Reactions of Alkenes

Halogenation

-Br2, Cl2, CCl4

-Trans

-Halogens go to both sides of the double bond in trans form

Halohydrin

-Cl2, Br2, H2O

-Trans

-Markonikov, OH goes to more substituted

-Halogens go to least substituted

Oxymercuration

-1.Hg,(OAC)2,THF

2. NaBH4

-OH goes to more substituted

Hydroboration

-1.BH3, THF

2. H2O2, OH-

-OH goes to least substituted

-Syn

Hyrdogenation

-H2, Pd/PtC

-Syn

Epoxidation

-MCPBA, CHCl3

-Syn or Cis Stereochemistry

-Results in a cyclic ether

Hydroxylation

-1.OSO4, pyridine

2. NaHSO3, H2O

-Syn OH

Dichlorocarbene

-CHCL3, KOH

-Triangle with Cl

Simon-Smith

-Zn(Cu), CH2I2

-Triangle with H's

Ozmolysis Ozone

-1.O3

2. Zn/H3O+

- R-C=O O=C-R

Ozmolysis KMNO4/H3O+

- C=OOH (Carboxylic Acid) + O=C-R

Addition of HBr, HCl, HI

-Markonikov: Cl, Br, I go to more substituted carbon

-H goes to least

HBr, HCl, HI In the Presence of Peroxides

-Anti-Mark: Cl, Br, I go to least substituted carbon

-H goes to most