Free Radical Halogenation

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Initiation

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Formation of a reactive intermediate

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Propagation

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Reactive intermediate reacts with stable molecule to produce another reactive intermediate or a product molecule

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22 Terms

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Initiation

Formation of a reactive intermediate

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Propagation

Reactive intermediate reacts with stable molecule to produce another reactive intermediate or a product molecule

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Termination

Side reactions that destroy the reactive intermediates, often resulting in nonradical product

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Free Radicals

Species with odd numbers of electrons, stability determined by compound structure

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Homolytic Cleavage

Bond cleavage resulting in free radicals, with electrons going to different atoms

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Heterolytic Cleavage

Bond cleavage resulting in ions, with electrons going to the same atom

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Primary

Halide bonded to a carbon atom bonded to only one other carbon atom, weak and least preferred

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Secondary

Halide bonded to a carbon atom bonded to two other carbon atoms, slightly more stable

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Tertiary

Halide bonded to a carbon atom bonded to three other carbon atoms, highly stable and preferred

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Resonance

Increases stability of intermediate, preferred when exhibiting resonance

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Exothermic Reaction

Weak bonds broken/strong bonds formed, releases energy

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Endothermic Reaction

Strong bonds broken/weak bonds formed, requires input of energy

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Chlorination Process

Highly exothermic process

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Transition States

Highest position on the graph, where reactants change into products

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Activation Energy

Difference between starting reactants energy and transition states energy

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Rate-Limiting Step

Hump in the graph with highest energy, determines the overall reaction rate

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Electronegativities

Higher values lead to quicker reactions, inversely proportional to size

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Bond Dissociation Energy (+BDE)

Energy input required, useful in assessing energetics of a chemical reaction

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Bond Formation Energy (-BDE)

Energy released, useful in assessing energetics of a chemical reaction

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Hammond's Postulate

Related species similar in energy must be similar in structure, transition state resembles nearest stable molecule

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Bromination

Highly selective reaction

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Chlorination

Non-selective reaction