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Haloalkanes and Haloarenes - Polyhalogen compounds

Grade 12ICSEChemistry

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

🔑Concepts

Dichloromethane (CH2Cl2CH_2Cl_2), also known as methylene chloride, is widely used as a solvent in paint strippers, as a propellant in aerosols, and as a process solvent in the pharmaceutical industry. High levels in air can cause dizziness and nausea.

Trichloromethane (CHCl3CHCl_3), commonly known as chloroform, was historically used as an anesthetic. It is stored in closed, dark-colored bottles to prevent its oxidation by air in the presence of light into the poisonous gas carbonyl chloride, or phosgene (COCl2COCl_2).

Triiodomethane (CHI3CHI_3), or iodoform, is a yellow crystalline solid. It was used as an antiseptic, though its efficacy is due to the liberation of free iodine (I2I_2) rather than the molecule itself. It has a characteristic unpleasant odor.

Tetrachloromethane (CCl4CCl_4), known as carbon tetrachloride, is used in the manufacture of refrigerants and propellants for aerosol cans. It was also used as a fire extinguisher under the trade name 'Pyrene'. It is highly toxic to the liver and is a known greenhouse gas.

Freons are chlorofluorocarbon (CFCCFC) compounds of methane and ethane. They are extremely stable, unreactive, non-toxic, and non-corrosive. Freon-12 (CCl2F2CCl_2F_2) is one of the most common. They are notorious for causing ozone (O3O_3) depletion in the stratosphere.

DDT (p,pp, p'-Dichlorodiphenyltrichloroethane) was the first chlorinated organic insecticide. While effective against mosquitoes and lice, it is chemically stable and fat-soluble, leading to biomagnification in the food chain. Many countries have banned its use due to ecological impacts.

📐Formulae

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

CHI3+3AgΔReaction with Ag powder yields Ethyne: 2CHCl3+6AgHCCH+6AgClCHI_3 + 3Ag \xrightarrow{\Delta} \text{Reaction with Ag powder yields Ethyne: } 2CHCl_3 + 6Ag \rightarrow HC \equiv CH + 6AgCl

CCl4+2H2O500CCO2+4HClCCl_4 + 2H_2O \xrightarrow{500^{\circ}C} CO_2 + 4HCl

3CCl4+2SbF3SbCl53CCl2F2+2SbCl3 (Swarts Reaction)3CCl_4 + 2SbF_3 \xrightarrow{SbCl_5} 3CCl_2F_2 + 2SbCl_3 \text{ (Swarts Reaction)}

CCl3CHO+2C6H5Clconc.H2SO4(ClC6H4)2CHCCl3+H2O (DDT Synthesis)CCl_3CHO + 2C_6H_5Cl \xrightarrow{conc. H_2SO_4} (ClC_6H_4)_2CHCCl_3 + H_2O \text{ (DDT Synthesis)}

💡Examples

Problem 1:

Why is 1%1\% ethyl alcohol (C2H5OHC_2H_5OH) added to chloroform bottles?

Solution:

COCl2+2C2H5OH(C2H5)2CO3+2HClCOCl_2 + 2C_2H_5OH \rightarrow (C_2H_5)_2CO_3 + 2HCl

Explanation:

Ethyl alcohol is added to convert any poisonous phosgene (COCl2COCl_2) formed by oxidation into a non-toxic compound called diethyl carbonate ((C2H5)2CO3)((C_2H_5)_2CO_3).

Problem 2:

How is Chloroform converted to Ethyne (Acetylene)?

Solution:

2CHCl3+6AgHeatCHCH+6AgCl2CHCl_3 + 6Ag \xrightarrow{\text{Heat}} CH \equiv CH + 6AgCl

Explanation:

When chloroform is heated with silver powder, dehalogenation occurs to produce ethyne gas and silver chloride.

Problem 3:

What is the IUPAC name and structure of DDT?

Solution:

2,2-bis(4-chlorophenyl)-1,1,1-trichloroethane

Explanation:

DDT is formed by the condensation of chloral (CCl3CHOCCl_3CHO) with two molecules of chlorobenzene in the presence of concentrated sulfuric acid (H2SO4H_2SO_4).

Polyhalogen compounds - Revision Notes & Key Formulas | ICSE Class 12 Chemistry