By I Prigogine
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Extra info for Advances in Chemical Physics, Vol.2 (Interscience 1958)
38). As might be expected, an even larger stabilization effect on a radical center is achieved through an Oᮎ substituent, a better donor than a neutral oxygen atom. 2 Stability of Radicals E Hb 2pz s*C–H s*C–H (negligible interaction) H n 2pz 2pz sC–H sC–H (more important interaction) full conjugation energy localized MOs delocalized MOs Fig. 6. Stabilization by overlap of a singly occupied 2pz AO with vicinal nonorthogonal sC—H MOs. localized MO delocalization of the excess negative charge and thus reduces the Coulomb repulsion force.
39) to a glycol derivative. 7 Radical Halogenation of Hydrocarbons Many hydrocarbons can be halogenated with elemental chlorine or bromine while being heated and/or irradiated together: Csp 3 H + Cl 2 (Br2 ) hv or Δ Csp 3 – Cl (Br) + HCl (HBr) The result is simple or multiple halogenations. 1 Simple and Multiple Chlorinations You should already be familiar with the mechanism for the thermal chlorination of methane. 17 to review briefly the net equation, the initiation step, and the propagation steps of the monochlorination of methane.
2 1 Radical Substitution Reactions at the Saturated C Atom Rs p3 Rs p3 H Hal Rs p3 HgH pure substitution reactions Rs p3 Rs p3 Hal Rs p3 N NH Rs p3 H Rs p3 H substitutions by fragmentation Rs p3 H H S Rs p3 O C Rs p3 Het substitutions including a fragmentation H substitutions including an addition O Rs p3 H Rs p3 Rs p3 O OH S Het O S Rs p3 HgH Rs p3 HgH Rs p3 O C C CH Het substitutions including a fragmentation and an addition Fig. 2. Classification of substitution reactions via radical intermediates, according to the type of reaction(s) involved.
Advances in Chemical Physics, Vol.2 (Interscience 1958) by I Prigogine