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2nd semester 2011/2012

Hydrocarbons
Physical Properties:
,

--

Combustion
+
+
3CO2 + 4CO
4H2O2+ E

CH3CH2CH3 + 5O2

:
-1 F2, Cl2, Br2, I2
CH3Cl + CH2Cl2 + CHCl3 + CCl4 + HCl

CH4 + Cl2

-2
CH4 +HNO3

420-450 C

CH3-NO2 +H2O
3H2
CH3-NH2

HO - NO2
CH3 - CH2 - CH3
Propane

+
420

CH3 - CH2 - CH2- NO2

Nitro-Propane

CH3 - CH2 - CH3

2-NiroPropane

NO2
CH3 - CH2 - NO2

Niroethane

CH3 - NO2

Nitromethane

Note that: nitrite alkane will be unstable and will be degraded and produce two of
the above product(nitroethane and nitromethan).

Preparation of Alkanes
1-Catalytic hydrogenation
H2
CH3 - C

C - CH3

CH3 - CH2
Pt,Pd, Ni

2-Butyne

CH2 - CH3

Butane

Note that : in case of aromatic hydrocarbone hydrogenation happened on

the side chain and could not the benzene ring.
CH = CH2

CH2 - CH3

H2, Pd

2- Reduction with metal hydride

1.2- Lithium aluminum hydride ( LiAlH4)

Lithium aluminum hydride ( LiAlH4) reduce primary and secondary alkyl halide
to its alkane while reduce ter-alkyl halide to alkene as follows :
CH3Cl

CH4

LiAlH4

LiCl

AlH3

Methane

Methyl chloride
CH3 - CH - CH3

LiAlH4

CH3- CH2 - CH3

Cl
Propane

2 - chloropropane

CH3
CH3

C - Cl

CH3

LiAlH4

CH3 - C = CH2
CH3
Isobutene

Tert-butyl chloride

2- Reduction with metal hydride

2.2 Sodium borohydride ( NaBH4)

Sodium borohydride ( NaBH4) reduce secondary and ter-alkyl hailde to
alkane and could not reduce primary alkyl halide as follows
CH3Cl

No reduction

NaBH4

Methyl chloride
CH3 - CH - CH3

NaBH4

CH3- CH2 - CH3

Cl
Propane

2 - chloropropane

CH3
CH3

C - Cl

CH3

Tert-butyl chloride

NaBH4

CH3 - CH - CH3
CH3
2-methyl-propane

2- Reduction with metal hydride

3.2 Triphenyl tin hydride( Ph3SnH)

Triphenyl tin hydride( Ph3SnH) reduce primary ,
secondary and tertiary alkyl halide to alkane

3 Wurtz reaction
1 - Initiation
Na

Na
2 - Propagation
CH3 Cl +
3 - Termination

. .
.
CH3

CH3
_

Cl

_
e

_
e

CH3

Cl

Methyl radical

CH3 - CH3

..

Ethane

Cl

+
Na

NaCl

4 Water hydrolysis of Grignard

reagents:
CH3MgBr

+ H2O

Methyl magnisum chloride

CH4 +
Methane

MgBrOH