Free-radical addition

A reaction in which a free radical adds across a multiple bond, forming a new radical that can propagate a chain reaction.

Radical chain reaction: A chain reaction in which radical intermediates carry successive reaction steps. Free-radical addition is a propagation step within this broader reaction pattern.
Free radical: An atom, molecule, or ion with one or more unpaired electrons. The unpaired electron enables the species that initiates addition and carries its chain forward.
Polyethylene: A polymer of ethylene produced by chain-growth polymerization or other catalytic processes. High-pressure production uses radical addition to grow polyethylene chains.
Electrophilic addition: Addition to a multiple bond initiated by an electrophile, often through a carbocation intermediate. It provides a common ionic alternative to radical addition across alkenes.
Radical initiation: The formation of reactive radicals that starts a radical chain reaction. Initiation supplies the radical that first adds to the multiple bond.
Alkene: An unsaturated hydrocarbon containing at least one carbon–carbon double bond. Its double bond is a common target for radical addition.
Polystyrene: A synthetic polymer made from styrene, with phenyl groups attached to its carbon-chain backbone. Radical addition polymerization converts styrene double bonds into polystyrene.
Nucleophilic addition: Addition of a nucleophile to an electron-deficient atom, often a carbonyl carbon. Unlike radical addition, it proceeds through nucleophilic attack and typically targets polarized bonds.
Radical propagation: A chain-reaction stage in which a reactive intermediate produces another reactive intermediate. Addition creates a new radical that continues the chain through propagation.
Carbon–carbon double bond: A covalent bond between two carbon atoms consisting of one sigma bond and one pi bond. Addition consumes the pi bond while forming new sigma bonds.

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