REVISION MAP

Haloalkanes and Haloarenes

These are obtained by replacing H of hydrocarbons with halogen X,
e.g. C2H5Cl (chloroethane), C6H5Cl (chlorobenzene). Here, X = halogen = F, Cl, Br.

Monohalogen Derivatives Polyhalogen Derivatives

(contain more than one a-H-atoms)

Methods of Preparation Physical Properties

?
Their mp, bp and density increase with Dichloromethane (CH2Cl2)
increase in molecular mass. Prepared by free radical chlorination of CH4.
?
From Alcohols ?
Solubility and dipole moment decrease Used as solvent, propellant and refrigerant.
?
HX
—X + H2O with increase in molar mass. Harms CNS and leads to impaired hearing and
?
—OH
PCl5 or – Cl + POCl3 vision.
PCl3 + H3 PO3
SOCl2 + SO2+ HCl
Trichloromethane (CHCl3)
SOCl2 is the best reagent as
?
Also called chloroform.
?
by-products are gases. Chemical Reactions of Haloalkanes
In air, oxidises to give phosgene (COCl2).
?
Oxidation is checked by using dark coloured bottles
?
Nucleophilic Substitution and by adding 1% ethanol.
From Hydrocarbons
Reactions ? Used as a reagent, solvent and anaesthetic.
By free radical mechanism of
?
alkanes: Here, X is replaced by other nucleophile
– – –
Cl2 like CN , NO2 , OH .
R—H UV light
R—Cl Iodoform (CHI3)
Formed when —CHOH—CH3 or CH3CO— group
?
By alkenes
? containing compound reacts with alkali and I2.
SN1 Reactions
C C + HX Used as an antiseptic.
?
?
It is a two step reaction.
?
Involves the formation of carbocation
C C intermediate.
Carbon Tetrachloride (CCl4)
?
Involves the inversion of configuration as
H X Used as fire extinguisher (under the name pyrene)
?
well as retention, so give racemic
and cleaning fluid.
By electrophilic substitution of
? mixture if reactant is optically active.
? Leads to liver cancer, ozone depletion, etc.
benzene: X
SN2 Reactions Freons
FeCl3
+ X2 ?
It is one step reaction. These are chlorofluoro compounds of methane and
?
?
Involves the formation of transition state. ethane.
?
Favoured by less hindered alkyl halide ? These are non-toxic, unreactive, stable, non-corrosive.
and non-polar solvent. ? Used as refrigerant and coolant.
Finkelstein Reaction ?
Result in inversion of configuration if ? Leads to ozone layer depletion.
Acetone/D reactant is optically active.
RX + NaI RI + NaX
DDT
Elimination Reactions It is p, p-dichlorodiphenyl trichloroethane.
?
Swarts Reaction Formation of alkenes ? Prepared by treating chloral with 2 moles of
RBr + AgF RF + AgBr Alc. KOH chlorobenzene.
CH3CH2X HX
CH2 —
— CH2
? Used as an insecticide.
? Non-biodegradable so causes air pollution,
water pollution and soil pollution.