Chemical Properties Of Chloroform

The common reactions(chemical properties) shown by chloroform are listed below.

–)Air Oxidation:-
When Chloroform is left on open air in presence of sunlight,it gets decomposed to Carbonyl Chloride.

2CHCL3 + O2 –Sunlight–> COCL2 + HCl

-The so formed Carbonyl Chloride is highly poisonous gas which is also used as a chemical weapon.To prevent quality loss of Chloroform,it is always stored inside dark brown bottle with air tight lead.Otherwise Chloroform being light and air sensitive is oxidised into highly poisonous phosgene gas(Carbonyl Chloride).

-During storage of Chloroform, about 1% of ethanol is added to it which converts the poisonous Carbonyl Chloride(Phosgene Gas) into non-poisonous Diethyl Carbonate.

COCL2 + 2CH3CH2OH —-> (C2H5)2CO3 + 2HCl

–)Hydrolysis of CHCl3
Chloroform during hydrolysis with aq.NaOH is hydrolysed into Sodium Formate.

CHCL3 + aq.3NaOH –heat–> [ H-C(OH)3 ] + H2O

Here [ H-C(OH)3 ] is very unstable and it becomes methanoic acid and thus further reaction takes place as

Thus HCOONa is the final compound of this reaction.

–)Reaction with conc.HNO3
When Chloroform is heated with conc.HNO3,Tear Gas is produced.

CHCL3 + conc.HNO3 –Over Heat–> CCl3NO2 + H2O

–)Reaction with acetone ( CH3-CO-CH3)
When Chloroform is reacted with acetone,a sleep inducing/hypnotic drug named Chloretone( 1,1,1-trichloro-2-methylpropan-2-ol) is produced.

CHCL3 + CH3-CO-CH3 –aq.KOH+heat–> CCl3-C(CH2)2OH

–)Reaction with Silver powder.
When Chloroform is heated with silver powder then Ethyne or Acetylene is formed.

2CHCL3 + 6Ag –heat–>C2H2 + 6AgCl

–)Reaction with Primary amines.
Primary Amines= R-NH2 and Ar-NH2
When Chloroform is heated with primary amines at about 60C-70C then alkylisocyanide or alkylcarbylamine is produced which has offensive smell.This reaction is also known as Carbylamine reaction.

CHCL3 + R-NH2 + alc.3KOH –(60-70C)–> R-NC + 3KCl + 3H2O

For Example:-
Aniline:-C6H5NH2 reacts as –

CHCL3 + C6H5-NH2 + alc.3KOH –(60-70C)–> C6H5-NC + 3KCl + 3H2O

There are two types of reduction,Acidic reduction and Neutral reduction.

-Acidic Reduction

CHCL3 –Zn+c.HCl–> CH2CL2 + HCl

-Neutral Reduction(Strong Reduction)

CHCL3 –Zn+H2O–> CH4 + 3HCl

–)Chlorination of Chloroform.
When Chloroform is allowed to react with Chlorine in presence of diffused sunlight then Carbontetrachloride known as Pyrene(Fire Extinguisher for metallic firing) is produced.

CHCL3 + Cl2 —-> CCl4 + HCl




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