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Copyright © Tarek Kakhia. All rights reserved. http://tarek.kakhia.org Like the other halogens, chlorine participates in free-radical substitution reactions with hydrogen-containing organic compounds. This reaction is often — but not invariably — non -regioselective, and hence, may result in a mixture of isomeric products. It is often difficult to control the degree of substitution as well, so multiple substitutions are common. If the different reaction products are easily separated, e.g. by distillation, substitutive free-radical chlorination ( in some cases accompanied by concurrent thermal dehydro chlorination ) may be a useful synthetic route. Industrial examples of this are the production of methyl chloride, methylene chloride, chloroform and carbon tetrachloride from methane, allyl chloride from propylene, and trichloro ethylene and tetra chloro ethylene from 1 , 2 – dichloro ethane. Like the other halides, chlorine undergoes electrophilic additions reactions, most notably, the chlorination of alkenes and aromatic compounds with a Lewis acid catalyst. Organic chlorine compounds tend to be less reactive in nucleophilic substitution reactions than the corresponding bromine or iodine derivatives, but they tend to be cheaper. They may be activated for reaction by substituting with a tosylate group, or by the use of a catalytic amount of sodium iodide. Chlorine is used extensively in organic and inorganic chemistry as an oxidizing agent and in substitution reactions because chlorine often imparts many desired properties to an organic compound, due to its electronegativity. Chlorine compounds are used as intermediates in the production of a number of important commercial products that do not contain chlorine. Examples are: polycarbonates, polyurethanes, silicones, polytetrafluoroethylene, carboxymethyl cellulose and propylene oxide. 6 . 4 . Use as a Weapon Poison gas in World War I : 17PDF Image | Chlorine Characteristics
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