| Type | Description | Example |
|---|---|---|
| Haloalkanes | Halogen attached to sp³ carbon | CH₃Cl, CH₃CH₂Br |
| Haloarenes | Halogen attached to sp² carbon of aromatic ring | C₆H₅Cl, C₆H₅Br |
| Primary (1°) | Halogen on carbon attached to one carbon | CH₃CH₂Cl |
| Secondary (2°) | Halogen on carbon attached to two carbons | (CH₃)₂CHBr |
| Tertiary (3°) | Halogen on carbon attached to three carbons | (CH₃)₃CCl |
| Method | Reaction | Notes |
|---|---|---|
| From Alcohols | R-OH + HX → R-X + H₂O R-OH + PCl₅ → R-Cl + POCl₃ + HCl R-OH + SOCl₂ → R-Cl + SO₂ + HCl | HX reactivity: HI > HBr > HCl SOCl₂ = Thionyl chloride (best method) |
| Halogenation of Alkanes | R-H + X₂ → R-X + HX (UV light) | Free radical mechanism |
| Addition to Alkenes | CH₂=CH₂ + HBr → CH₃CH₂Br | Follows Markovnikov's rule |
| Haloarenes from Benzene | C₆H₆ + Cl₂ → C₆H₅Cl + HCl (FeCl₃) | Electrophilic substitution |
| Sandmeyer's Reaction | C₆H₅N₂⁺Cl⁻ + CuCl → C₆H₅Cl + N₂ | From diazonium salts |
| Reaction Type | Details |
|---|---|
| SN1 Mechanism | • Two-step mechanism • Rate = k[R-X] • Carbocation intermediate • Racemization occurs • Favored by 3° > 2° > 1° alkyl halides • Polar protic solvents |
| SN2 Mechanism | • One-step mechanism • Rate = k[R-X][Nu⁻] • Transition state (no intermediate) • Inversion of configuration (Walden inversion) • Favored by 1° > 2° > 3° alkyl halides • Polar aprotic solvents |
| Reaction | Equation | Product |
|---|---|---|
| With KOH (aq) | R-X + KOH (aq) → R-OH + KX | Alcohol |
| With KOH (alc) | R-CH₂-CH₂-X + KOH (alc) → R-CH=CH₂ | Alkene (Elimination, follows Saytzeff rule) |
| With AgNO₃ (alc) | R-X + AgNO₃ → R-ONO₂ + AgX | Nitrite |
| With KCN | R-X + KCN → R-CN + KX | Nitrile (cyanide) |
| With AgCN | R-X + AgCN → R-NC + AgX | Isocyanide |
| With NH₃ | R-X + NH₃ → R-NH₂ + HX | Amine (Hoffmann ammonolysis) |
| With Na (Wurtz) | 2R-X + 2Na → R-R + 2NaX | Alkane (coupling) |
| With Mg (Grignard) | R-X + Mg → R-MgX (dry ether) | Grignard reagent |
| Reduction | R-X + Zn/HCl → R-H + ZnX₂ | Alkane |
| Compound | Formula | Uses/Properties |
|---|---|---|
| Chloroform | CHCl₃ | Anesthetic, solvent; oxidizes to phosgene (COCl₂) - poisonous |
| Iodoform | CHI₃ | Antiseptic; yellow precipitate (iodoform test) |
| CCl₄ | Carbon tetrachloride | Fire extinguisher, solvent |
| Freons (CFCs) | CCl₂F₂ | Refrigerants; deplete ozone layer |
| DDT | (ClC₆H₄)₂CH(CCl₃) | Insecticide; non-biodegradable |
| 1. What are haloalkanes and how are they classified? | ![]() |
| 2. What are the physical properties of haloalkanes? | ![]() |
| 3. Describe the reactivity of haloalkanes. | ![]() |
| 4. What are haloarenes and how do they differ from haloalkanes? | ![]() |
| 5. What are the common methods for the preparation of haloalkanes? | ![]() |