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Preparation of Alkyl Halides
1. From alcohols: SOCl₂/pyridine (gaseous by-products SO₂ and HCl), PCl₅, PX₃ and HX/ZnCl₂ (Lucas) all convert R–OH to R–X.
2. Free radical halogenation of alkanes (light or high temperature). Reactivity F₂ > Cl₂ > Br₂ > I₂. The number of monochloro isomers equals the number of types of hydrogen.
3. Addition of HX to alkenes (Markovnikov): HI > HBr > HCl in reactivity.
4. Finkelstein reaction: R–Cl or R–Br + NaI in dry acetone gives R–I, because NaCl or NaBr is insoluble in acetone.
5. Swarts reaction: R–Cl or R–Br with AgF, Hg₂F₂, CoF₂ or SbF₃ gives R–F.
Reactions of Alkyl Halides
1. KCN gives a nitrile (attack through carbon); AgCN gives an isocyanide (attack through nitrogen). KNO₂ gives an alkyl nitrite (R–O–N=O); AgNO₂ gives a nitroalkane (R–NO₂).
2. Aqueous KOH gives the alcohol (substitution). Aryl, vinyl and bridgehead halides do not react in these substitutions.
3. Wurtz reaction: 2R–X + 2Na in dry ether gives R–R (even number of carbons, symmetrical). Wurtz-Fittig gives alkylbenzenes from aryl and alkyl halides.
4. Williamson synthesis: alkoxide + methyl or primary halide gives an ether; a tertiary halide mainly eliminates.
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