REACTIONS OF HYDROCARBONS
2. Substitution (with halides)
alkane + halogen haloalkane +hydrogen halide
CH4 + Cl2 CH3Cl + HCl
CH3Cl + Cl2 CH2Cl2 + HCl
1. Combustion (Extreme Oxidation)
Alkane + O2 CO2 + H2O
ALKANES
heat/UV Lightheat/UV Light
Incomplete combustion
Alkane + O2 CO + H2 O
ALKENES
1. Addition Reactions (breaking of the double bond)
A) Halogenation (adding halides)
alkene + halogen haloalkane
B) Hydrogenation (adding hydrogen)
alkene + hydrogen alkane
CH2=CH2 + H2 CH3CH3
PtPtPtPt
H2C CH2 + Cl2 C C
H
Cl
H
Cl
H
HCCl4
C) Hydrohalogenation (adding hydrogen halides)
alkene + hydrogen halide haloalkane
Hydrohalogenation and hydration follow Markovnikov’s Rule which states that the hydrogen is added to the carbon with the most hydrogen atoms originally bonded to it.
H2C CHCH3 + HCl C C
H
Cl
C
H
H
H
H
H
H
D) Hydration (adding water)alkene + water alcohol
H2C CHCH3 + H2O C C
H
OH
C
H
H
H
H
H
H
2. Combustion (extreme oxidation)
Alkene + O2 CO2 + H2O
3. Polymerization (forming long chains from small subunits)
C C
H
H H
H
n C C*
H
H
H
H
*
n
*Polymerization will be addressed later
ALKYNES1. Addition Reactions (breaking of the multiple bond)
A) Halogenation (adding halides)
alkyne + 2 halogens haloalkane
alkyne + 1 halogen haloalkene
CH CH + 2 Br2 C C
Br
H
Br Br
Br
H
CH CH + 2 Br2 C C
Br
H
Br Br
Br
H
B) Hydrogenation (adding hydrogen) alkyne + 2 hydrogen alkane
C) Hydrohalogenation (adding hydrogen halides)
alkyne + 2 hydrogen halides haloalkane
CH CH + 2 HCl C C
H
H
H Cl
Cl
H
Reactions of Aromatics1. Substitution
A) With Halogens
benzene + halogen halobenzene + hydrogen halide
Note: Due to reduced reactivity of the ring bonds compared with double bonds, aromatics due not undergo addition reactions under normal conditions.
Br
+ Br2
FeBr3
+ HBr
2. With Alkyl Halides ( not mentioned in textbook)
benzene + alkyl halide alkyl benzene + hydrogen halide
3. With Nitric Acid ( not mentioned in textbook)
benzene + nitric acid nitrobenzene + water
CH3CH2
+ CH3CH2ClAlCl3
+ HCl
NO2
+ HNO3 (aq)H2SO4
+ H2O
nitrobenzene
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