CHEM 125A: FRESHMAN ORGANIC CHEMISTRY II - Lecture 3 - Professor J. Michael McBride
Rate and Selectivity in Radical-Chain Reactions
The reactivity-selectivity principle explains why bromine atoms are more
selective that chlorine atoms in abstracting hydrogen atoms from
carbon. A free-radical mechanism for adding HBr to alkenes explains its
anti-Markovnikov regiospecificity. Careful analysis is required to
understand kinetic order for reactions involving catalysts. Termination
of radical-chain reactions can make their rate half-order in the
initiator. Selectivity due to protonation of radicals and their
reaction partners illustrates the importance of ionic charge in
determining reaction rates.
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