Unformatted text preview: _..___. singly o: cupicd p orl riQiiéizléé 2‘5! Mikkel R at: / R 1‘?er
carbon M) Methyl radical is planar, which suggests that carbon is sp2 hybridized and that the
unpaired electron is in a p orbital.
The order of stability of free radicals is the same as for carbocations. Ethyl radical Isopropyl radical tert—Butyl radical Methyl radical (primary) (secondary) (tertiary)
H\C./H H\C'/CH3 H\c'/CH3 r~13c\_C /CH3
J. J. (La (La
least stable most stable The order of stability of free radicals can be determined by measuring bond strengths. By "bond strength" we mean the energy required to break a covalent bond.
A chemical bond can be broken in two different ways—~heterolytically or homolytically. O in a We bond cleavage, the two electrons in
the bond are divided equally between the two atoms. One electron goes wit one atom, the second with the other atom. tieterollatio
—-’ in a heterolﬁjg cleavage, one atom retains both
electrons. ﬂ l7 ...
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- Summer '08
- Organic chemistry