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Nucleophilic substitution with cyanide Haloalkane Free radical substitution STEP 1: INITIATION - a radical is created by using UV, starts the reaction. Br - Br → 2Br∙ STEP 2: PROPAGATION - a radical reacts, creating a new radical to continue the reaction. Br∙ + CH₄ → HBr + CH₃∙ CH₃∙+ Br₂ → CH₃Br + Br∙ STEP 3: TERMINATION - 2 radicals react stopping the chain reaction. Br∙ + Br∙→ Br₂ CH₃∙ + CH₃∙→ 2CH₃ CH₃∙ + Br∙ → CH₃Br Electrophilic addition Cyanide ions: NaCN & KCN Ethanolic Conditions Nitriles Hydrogen Halide Room temperature Nucleophilic substitution with ammonia Excess ammonia Ethanolic Conditions Amine Alkane Alcohol Elimination reaction Concentrated NaOH & KOH Ethanoic Conditions High temperature Elimination reaction: dehydration of alcohols into alkenes Reagent: Concentrated H₂SO₄ (also acts as a catalyst). Reflux Conditions Excess acid High temperature Alkene Nucleophilic substitution with hydroxides Hydroxides: NaOH & KOH Aqueous Conditions + Reflux