Ch_322a_10.04

Ch_322a_10.04 - Halogenation of Alkanes The Chlorination...

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Halogenation of Alkanes The Chlorination Reaction When a gaseous mixture of methane and chlorine (Cl 2 ) is heated or irradiated with ultraviolet light, chlorinated methane products and hydrogen chloride are produced. This reaction is called chlorination . CH 4 + Cl 2 CH 3 Cl + H Cl If sufficient Cl 2 is present, further chlorination occurs: CH 3 Cl + Cl 2 CH 2 Cl 2 + H Cl Eventually, all hydrogens are replaced to give tetrachloromethane , CCl 4 . The mixture of products may be adjusted by controlling the relative amounts of the reactants. With an excess of CH 4 over Cl 2 , only chloromethane, CH 3 Cl is produced.
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Chlorination of Higher Alkanes The chlorination of alkanes with multiple reaction sites tends to be unselective . There is only slight discrimination in the competition among primary, secondary and tertiary hydrogens. CH 3 CH 2 CH 3 + Cl 2 CH 3 CH 2 CH 2 Cl + CH 2 CHCH 3 Cl 1-chloropropane 2-chloropropane 50% 50% + HCl CH 3 CCH 3 CH 3 H + Cl 2 CH 3 CHCH 2 Cl CH 3 + CH 3 CCH 3 CH 3 Cl + HCl isobutyl chloride tert-butyl chloride 48% 29% An explanation for the poor selectivity in the chlorination of higher alkanes will emerge from an examination of the mechanism of this reaction.
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Observations on the Chlorination of Methane CH 4 + Cl 2 CH 3 Cl + HCl (A) The reaction does not occur in the dark at 25
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Ch_322a_10.04 - Halogenation of Alkanes The Chlorination...

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