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Haloalkanes and Haloarenes - Polyhalogen Compounds

Grade 12CBSEChemistry

Review the key concepts, formulae, and examples before starting your quiz.

🔑Concepts

Polyhalogen compounds are carbon compounds containing more than one halogen atom. Many of these are industrially important but have significant environmental and health impacts.

Dichloromethane (CH2Cl2CH_2Cl_2): Widely used as a solvent in paint strippers, propellants in aerosols, and process solvent in pharmaceuticals. High levels in air cause dizziness, nausea, and numbness.

Trichloromethane (CHCl3CHCl_3): Also known as Chloroform. It was used as an anesthetic but is now primarily used in the production of Freon refrigerant R22R-22. It is oxidized by air in the presence of light to an extremely poisonous gas called Phosgene (COCl2COCl_2).

Triiodomethane (CHI3CHI_3): Also known as Iodoform. It is used as an antiseptic, though its antiseptic properties are due to the liberation of free iodine (I2I_2) rather than the CHI3CHI_3 molecule itself. It has a characteristic unpleasant smell.

Tetrachloromethane (CCl4CCl_4): Also known as Carbon tetrachloride. Used in the manufacture of refrigerants and as a cleaning fluid. It is a major contributor to ozone depletion and can cause liver cancer in humans.

Freons: Chlorofluorocarbon (CFCCFC) derivatives of methane and ethane. They are extremely stable, unreactive, non-toxic, and non-corrosive. CCl2F2CCl_2F_2 (Freon-12) is common. In the stratosphere, they trigger radical chain reactions that deplete the ozone layer.

p,p'-Dichlorodiphenyltrichloroethane (DDTDDT): The first chlorinated organic insecticide. It is highly effective against mosquitoes and lice but is chemically stable and fat-soluble, leading to bioaccumulation in the food chain and harmful effects on wildlife.

📐Formulae

2CHCl3+O2light2COCl2+2HCl2CHCl_3 + O_2 \xrightarrow{light} 2COCl_2 + 2HCl

CCl4+2HFSbCl5CCl2F2+2HClCCl_4 + 2HF \xrightarrow{SbCl_5} CCl_2F_2 + 2HCl

CH3COCH3+3I2+4NaOHCHI3+CH3COONa+3NaI+3H2OCH_3COCH_3 + 3I_2 + 4NaOH \rightarrow CHI_3 + CH_3COONa + 3NaI + 3H_2O

C14H9Cl5 (Molecular formula of DDT)C_{14}H_9Cl_5 \text{ (Molecular formula of DDT)}

💡Examples

Problem 1:

Why is Chloroform (CHCl3CHCl_3) stored in closed dark-coloured bottles completely filled to the brim?

Solution:

Chloroform is slowly oxidized by air in the presence of light to an extremely poisonous gas, carbonyl chloride, also known as Phosgene (COCl2COCl_2). To prevent this reaction, it is stored in dark bottles to cut off light and filled to the brim to exclude air.

Explanation:

The reaction is represented as: 2CHCl3+O2hv2COCl2+2HCl2CHCl_3 + O_2 \xrightarrow{hv} 2COCl_2 + 2HCl. Adding a small amount of ethanol (1%1\%) can also convert any formed phosgene into non-toxic diethyl carbonate.

Problem 2:

What is the structural formula of DDTDDT?

Solution:

The structure consists of a central ethane chain where one carbon has three chlorine atoms and the other has one hydrogen and two pp-chlorophenyl groups: (ClC6H4)2CHCCl3(Cl-C_6H_4)_2CH-CCl_3.

Explanation:

DDT is synthesized from chloral (CCl3CHOCCl_3CHO) and chlorobenzene (C6H5ClC_6H_5Cl) in the presence of concentrated H2SO4H_2SO_4.

Problem 3:

Which polyhalogen compound is used as a fire extinguisher under the name Pyrene?

Solution:

Carbon tetrachloride (CCl4CCl_4).

Explanation:

In the industrial and commercial sector, CCl4CCl_4 was used as a fire extinguisher because its heavy vapors form a non-combustible layer over the burning substance, cutting off the oxygen supply.

Polyhalogen Compounds - Revision Notes & Key Formulas | CBSE Class 12 Chemistry