16th_lecture_ReviewCh4_10_5_2011(1)

16th_lecture_ReviewCh4_10_5_2011(1) - Halogenation of...

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carried out at high temperature (400 °C) CH 4 + Cl 2 CH 3 Cl + HCl CH 3 Cl + Cl 2 CH 2 Cl 2 + HCl CH 2 Cl 2 + Cl 2 CHCl 3 + HCl CHCl 3 + Cl 2 CCl 4 + HCl This is an example of a radical reaction Chlorination of Methane 1 Halogenation of alkanes: RH + X 2 RX + HX
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C H H H . Methyl radical less stable than C H 3 C H H . Ethyl radical (primary) C H 3 C CH 3 H . Isopropyl radical (secondary) less stable than less stable than C H 3 C CH 3 CH 3 . tert -Butyl radical (tertiary) Alkyl Radicals 2
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The initiation step "gets the reaction going" by producing free radicals—chlorine atoms from chlorine molecules in this case. Initiation step is followed by propagation steps. Each propagation step consumes one : : .. .. Cl Cl .. .. : : Cl Cl .. .. : : .. .. .. .. Cl Cl .. .. : : . . : : Cl Cl .. .. .. .. . . + + Free-radical chain mechanism. Free-radical chain mechanism. Initiation step: Initiation step: Mechanism of Chlorination of Methane 3
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Cl Cl : : .. .. .. .. . . H H 3 C C : : H H H H : : Cl Cl : : .. .. .. .. H H 3 C C . . + + + + First propagation step: First propagation step: Second propagation step: Second propagation step: + + + + Cl Cl : : .. .. .. .. . . H H 3 C C . . : : .. .. Cl Cl .. .. : : Cl Cl .. .. : : .. .. H H 3 C C .. .. .. .. : : Cl Cl : : Mechanism of the Chlorination of Methane 4 + CH 4
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Cl Cl : : .. .. .. .. . . H H 3 C C : : H H H H : : Cl Cl : : .. .. .. .. H H 3 C C . . + + + + Second propagation step: Second propagation step: + + + + + + + + First propagation step: First propagation step: Cl Cl : : .. .. .. .. . . H H 3 C C . . : : .. .. Cl
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This note was uploaded on 02/15/2012 for the course ORGO 101 taught by Professor Staff during the Fall '11 term at Syracuse.

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16th_lecture_ReviewCh4_10_5_2011(1) - Halogenation of...

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