CHEMICAL REACTIONS OF ALKANES

Mechanism Reaction Reagent Condition Catalysts Product(s)

Free radical
Halogenation Cl2, Br2 UV light Haloalkane
substitution
Excess oxygen, O2 CO2 , H2O
- Combustion
Limited oxygen, O2 CO, C, H2O

Thermal
Free Radical
Cracking High temp
Substitution
(Pyrolysis) (600®C -
Alkane and
700®C)
alkenes
Carbocation Catalytic
Silica /
mechanism Cracking
Alumina
 CHEMICAL REACTIONS OF ALKENES
MECHANISM: Electrophilic Addition Mechanism

Reagent / Condition Condition Catalyst Product

Reaction
/ Catalysts
Catalytic
Room temp Pt, Pd
Hydrogenation: H2
140°C - 200°C Ni Alkane
Addition of H2

i. X2 in CCl4 Room temp,

Absence of
Dihaloalkane
Sunlight
Halogenation:
Haloalcohol
Addition of X2
ii. X2 + H2O (major)
(Halogen Water)
Dihaloalkane
(minor)

Hydrohalogenation: AlCl3
Addition of HX (g)
HX (g) Room temp
(only when using Haloalkane
Markonikov’s Rule HCl)

Hydration: H2O (g) : steam

300°C, 60 atm conc. H3PO4
Addition of H2O
Alcohol
Markonikov’s Rule H2O room temp conc. H2SO4

Combustion Excess oxygen, O2 CO2/ H2O

Epoxidation
Finely divided Diol
(followed by Acidic 200°C - 300°C
O2 silver, Ag Intermediate: Epoxy
Hydrolysis) Compound

< 20°C CCl4

O3 Ozonide

Ozonolysis
Reduction
Heat Zn / H+ (aq) Carbonyl
(reducing agent) Compound
 Cold KMnO4 / H+ or
OH- (aq) Cold Diol
Oxidation by KMnO4

Carbonyl
Compound,
Heat
Hot KMnO4 / H+ then Carboxylic
Acid

Polymerisation Polymer
-
 CHEMICAL REACTIONS OF BENZENE
MECHANISM: Electrophilic Aromatic Substitution Mechanism
Condition Catalyst Product
Reaction Reagent

Friedel-Crafts Haloalkane, RX Room temp AlCl3 (Lewis acid) Alkylbenzene

Alkylation

Friedel-Crafts Acyl Chloride, RCOCl 50°C - 80°C AlCl3 (Lewis acid) Phenylketone
Acylation

Halogenation Halogens (Cl2 / Br2) room temp Fe/ FeCl3 / FeBr3 Halobenzene
/ AlCl3 / AlBr3

(Lewis acid)

Nitration Conc. HNO3 < 55°C conc. H2SO4 Nitrobenzene

(yellow oily liquid
with almond smell)

Sulphonation Sulphur Trioxide, SO3 warm conc. H2SO4 Benzenesulphonic

Acid

Reaction with Alkene - - Alkylbenzene

Alkene

Reduction Hydrogen, H2 180°C Ni Cyclohexane

 CHEMICAL REACTIONS OF ALKYLBENZENE
MECHANISM: Electrophilic Aromatic Substitution Mechanism
Catalyst Product
Reaction Reagent Condition

Friedel-Crafts AlCl3 (Lewis

Haloalkane, RX Room temp
Alkylation acid) Dialkylbenzene

Friedel-Crafts Acyl Chloride, RCOCl AlCl3 (Lewis

50°C - 80°C
Acylation acid) Ketone

FeCl3 / FeBr3 /
Halogens (Cl2 / Br2)
room temp AlCl3 / AlBr3
Halogenation Haloalkylbenzene
(Lewis acid)

conc. HNO3 and

conc. H2SO4
room temp
Nitration Nitroalkylbenzene

Alkylbenzene
Sulphonation SO3
sulphonic acid

Hydrogenation Hydrogen, H2 150°C Ni Alkyl-cyclohexane

 CHEMICAL REACTIONS OF HALOALKANE
MECHANISM: Nucleophilic Substitution Mechanism
Catalyst Product
Reaction Reagent Condition

Hydrolysis NaOH (aq) Heat One X : Alcohol

KOH (aq) Two X : Aldehyde / Ketone
Three X : Carboxylic Acid

Formation of Nitrile KCN (aq) / ethanol Heat Nitrile

i. Hydrolysis 2H2O / H+ Heat Carboxylic Acid

H2O / OH- Heat Salt of Carboxylic Acid

ii. Reduction H2 180°C Ni Amine

Formation of Amine Ethanolic conc. NH3 Heat Amine

(aq)

Elimination Ethanolic NaOH (aq) Heat Alkene

 CHEMICAL REACTIONS OF CHLOROMETHYLBENZENE
MECHANISM: Nucleophilic OR Electrophilic Substitution Mechanism
Catalyst Product
Reaction Reagent Condition

Alkaline NaOH (aq) Heat Phenylmethanol

Hydrolysis

Reaction Free radical mechanism Light and Dichloromethylbenzene

with Heat
Chlorine Cl2

Tricholoromethylbenzene

Electrophilic room temp FeCl3 / Fe 2-chloro(chloromethyl) benzene

Substitution

Cl2
4-chloro(chloromethyl) benzene

Formation of KCN (aq) / ethanol Heat Benzyl cyanide

Nitriles

i. Reduction H2 180°C Ni Amine

ii. Acidic 2H2O / H+ Heat Carboxylic Acid

Hydrolysis

Formation of Ethanolic NH3 (aq) Heat Amine

Amine

Oxidation KMnO4 / H+ (aq) Heat Benzoid Acid

(white precipitate - solid)
K2Cr2O7 / H+ (aq)
 CHEMICAL REACTIONS OF CHLOROBENZENE
MECHANISM: Nucleophilic OR Electrophilic Substitution Mechanism

Catalyst Product
Reaction Reagent Condition

Alkaline NaOH (aq) 300°C Sodium phenoxide

Hydrolysis 200 atm

Nucleophilic
(Vigorous
condition)

Reaction with room temp FeCl3 1,2-chlorobenzene (ortho-)

Chlorine Cl2 and 1,4-chlorobenzene (para-)

Electrophilic

Reaction with CH3Cl room temp FeCl3 2- chloromethylbenzene

Chloromethane and 4- chloromethylbenzene

Electrophilic
USES OF HYDROCARBONS
Hydrocarbon Uses