SYNTHESIS OF ALKANES

 Hydrogenation of Alkenes

 Reduction of Alkyl Halides

-add an organometallic reagent to water

Formation of Grignard Reagent:

R MgX + H O H R H + XMgOH

H2O
R X + 2 Li R Li + LiX R H + LiOH

 Reduction of Alkyl Halide by Metal and Acids

Zn
R X R H
CH3COOH

 Reduction of Alkyl Halide by Reducing Agents

LiAlH4
R X R H
 Coupling of Alkyl Halide with Organocopper Reagents

R X + Li R Li + CuX R CuLi

R CuLi + R'X R R' + RCu + LiX

Example:
CH3Br + Li CH3Li
bromomethane

CuX

CH3
CH3(CH2)4CH2Br + H3C Cu Li
1-bromohexane

CH3(CH2)4CH2CH3
heptane