mechanisms

akene to haloalkane

reagents: HBr/HCl

products get: Br/Cl (and H)
HYDROHALOGENATION

alkene to alcohol (M)

reagents: HOH and H2SO4

products get: OH (and H)

HYDRATION

alkene to vicinal dihalide

reagents: Br2/Cl2
products: Br/Cl (anti)
HALOGENATION

alkene to halohydrin

reagents: Br2/Cl2 and H20 minus HCl

products: OH and X (anti)
HALOHYDRIN FORMATION

alkene to alcohol (NM)

reagents: 1) R2BH 2) H2O2 and NaOH
products: OH and H
HYDROBORATION OXI

alkene to vicinal diol

reagents: 1) OsO4 2) NaHSO3, H2O
products: OH and OH (syn)
DIOL FORMATION

alkene to 2 carbonyls

reagents: 1) O3 2) Me2S
OZONOLYSIS

alkene to alkane

reagents: H2/ Pd
products: alkane
HYDROGENATION

terminal alkyne to internal alkyne

reagents: 1) NaNH2 2) RX

products: internal alkyne

ALKYLATION

alkene to alkyne

Internal: 1) Br2 2) NaNH2 (2 eq)

Terminal: 1) Br2 2) NaNH2 3) H30+ (3 eq)
products: alkyne
Dehydrohalogenation (B- elim)

alkyne to tetrahaloalkane

reagents: Br2/ Cl2

products: tetrahaloalkane
HALOGENATION

alkyne to geminal dihalide

reagents: HX
products: X and X
Addition of Hydrogen Halide

alkyne to aldehyde or ketone (NM)

reagents: 1) R2BH 2) H2O2 and NaOH

products: ketone or aldehyde
Hydroboration oxidation

alkyne to ketone (M)

reagents: 1) H2SO4 2) H2O

products: ketone

Acid Catalyzed Hydration

alkyne to cis alkene

reagents: 1) H2 2) Lindlar’s

products: cis alkane

Hydrogenation to cis alkene

alkyne to trans alkene

reagents: 1) Li or Na 2) NH3
products: trans alkene

Hydrogenation to Trans alkene

alkyne to alkane

H2/Pd
alkane